Pharmaceutical Reference Substances and Impurities from LGC Gmbh LR

Home , Adrenalone

Pharmaceutical reference substances and impurities from LGC GmbH For further information, or if you require substances or materials not currently listed please contact one of our local sales ofﬁces.

Brazil Hungary Russia Tel: +55 12 3302 5880 Tel: +36 (06) 26 314 891 Tel: +7 (812)935 1180 Email: [email protected] Email: [email protected] Email: [email protected] Countries served: Croatia, Hungary, Slovenia

Bulgaria Spain Tel: +359 (0)2 971 4955 Tel: +34 (0)93 308 4181 Email: [email protected] India Email: [email protected] Countries served: Tel: +91 (0)80 6701 2000 Countries served: Bulgaria, Macedonia (FYRM) Email: [email protected] Andorra, Latin America, Portugal, Spain Countries served: Bangladesh, India, Nepal, Pakistan

China Sweden Tel: +86 10 85324820 Tel: +46 (0)33 20 90 60 Email: [email protected] Ireland Email: [email protected] Countries served: Tel: +44 (0)28 7930 0078 Countries served: China, Hongkong, Macau, Taiwan Email: [email protected] Denmark, Estonia, Iceland, Latvia, Norway, Sweden

Czech Republic Italy Tel: +420 543 529 205 Tel: +39 02 2412 6830 Turkey Email: [email protected] Email: [email protected] Tel: +90 216 360 0870 Countries served: Email: [email protected] Czech Republic, Slovakia Netherlands Tel: +31 (0)643 775 422 Middle East Finland Email: [email protected] Tel: +971 555 570 664 Tel: +358 (0)2 233 9355 Email: [email protected] Email: [email protected] Countries served: Egypt, Sudan, UAE, Yemen Poland Tel: +48 (0)22 751 31 40 France Email: [email protected] Tel: +33 (0)3 88 04 82 82 Countries served: United Kingdom Email: [email protected] Armenia, Azerbaijan, Belarus, Georgia, Tel: +44 (0)20 8943 8480 Countries served: Kazakhstan, Kyrgizstan, Lithuania, Poland, Email: [email protected] Algeria, Belgium, France, Ivory Coast, Slovakia, Tajikistan, Turkmenistan, Ukraine, Countries served: Jordan, Lebanon, Libya, Madagascar, Uzbekistan Australia, Brunei, Channel Islands, Ireland, Morocco, Senegal, Syria, Tanzania, Kenya, Kuwait, Malta, New Zealand, Tunesia Philippines, Saudi Arabia, South Africa, United Kingdom Romania Tel: +40 364 116890 Germany Email: [email protected] Tel: +49 (0)281 9887 0 Countries served: Email: [email protected] USA + Canada Moldova, Romania, Serbia Tel: +44 (0)20 8943 8480 Countries served: Email: [email protected] Austria, Cyprus, Germany, Greece, Israel, Japan, Korea, Singapore, Switzerland, Thailand, Vietnam www.lgcstandards.com Contents Contents Introduction

Background 2

About LGC 2

Certification 2

Narcotics 3

Delivery time 3

Certificate of Accreditation according ISO Guide 34:2009 4

Certificate of Accreditation according DIN EN ISO/IEC 17025:2005 5

Certificate of analysis 6 Pharmaceutical impurities

List of products 10

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 1 Pharmaceutical impurities Pharmaceutical impurities Background The pharmacopeial monographs regulate the legal definition but also the analysis and the limits of impurities in a given substance. Impurities in a pharmaceutical substance can change the effects and side effects of a drug significantly. It is therefore important to have an accurate detection of impurities. The increasing importance of impurity reference materials is also becoming apparent in the registration of drugs, where an exact identification and quantification of susceptible impurities is required for an assured documentation. A wide range of known impurities is listed in individual pharmacopeial monographs. However, impurities that are still protected by a patent, as well as those that are only known to the manufacturer, are not listed. Guidelines and limits for impurities have been laid out in compendial monographs, in specifications from the manufacturer internally or in the International Conference on Harmonisation (ICH) Guidelines which have been agreed by Europe, Japan and the United States. The ICH conducted three guidelines on impurity issues:

ICH Q3A (R1): Impurities in New Drug Substances ICH Q3B (R2): Impurities in New Drug Products ICH Q3C (R3): Impurity Guidelines for Residual Solvents.

The full wording of the ICH guidelines is available at the official website of the ICH: www.ich.org.

About LGC The pharmaceutical impurities listed in this section are produced by LGC, whose Research & Technology Division acts as the designated UK National Measurement Institute for Chemical and Biochemical Measurements. LGC is an independent, science-based service company providing chemical, biochemical and DNA based analytical and diagnostic services, and reference standards. LGC is Europe's largest, independent analytical laboratory.Its services include analytical testing, research, consultancy, validation, training and knowledge transfer. LGC Standards, a division of LGC, provides the most comprehensive source of certified reference materials and standards, pharmaceutical reference substances and impurities, biomaterials, cell lines and high purity solvents to the scientific community worldwide. LGC Standards has successfully established a global reputation for the production of impurities and working standards, and as a single source for the supply of pharmacopeia reference materials. Our menu of custom services, including custom synthesis of impurities and metabolites, characterisation, certification, packaging and distribution, adds value to the scientific support we provide to our pharmaceutical customers. For more information about these services, please contact your local LGC Standards office.

Certification Each product is accompanied by a detailed certificate of analysis, which gives information on the identity and purity, together with the various analytical methods and their conditions. A sample of such a certificate is printed on the following pages. In the past, we received some inquiries from a few customers wondering why there is no declaration on the certificates of analysis (CofA) for LGC products stating that the substances are fulfilling the specifications for reagents, as described for example in chapter 4 of the European Pharmacopeia. The LGC impurity standards are thoroughly tested chemical reference substances and are used for reliable identification and quantification of impurities of pharmaceutical ingredients and products. The abbreviations EP, Pharmeuropa, BP and USP in the article description are indicating that the particular substance is mentioned as an impurity in that particular compendial publication. They do not indicate that certain specification of reagents or drug substances mentioned in the publications are fulfilled. The standards – where they are actually listed as reagents or drug substances – may fulfill this specification, but this is not the intention and is not certified on the CofA. LGC GmbH in Luckenwalde has reached the peak of the accreditation for the production of pharmaceutical reference substances. The accreditation according to ISO guide 34, which has been developed for producers of certified reference materials, completes the way from the ISO 9001 ff quality management and the confirmation of the accretitation body DQS that the company´s system respects the rules of "Good Manufacturing Practice (GMP)" via the EN ISO/IEC 17025 for their analytical laboratory. The company takes over Europe´s leading role for pharmaceutical reference substances of this high quality level and is the only one in Germany.

2 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Narcotics Some of the substances described in this section are subject to narcotics legislation. These are marked as [Controlled Substance]. Please contact your local LGC Standards office for information on the legal requirements in order to purchase these products.

Delivery time The majority of products mentioned in this section are available from stock; others may have a delivery time of approximately four weeks. For substances marked with "on request", longer delivery times may apply. For custom synthesis, the time is estimated from previous experience. Customers will be notified if unforeseen complications arise during the synthesis. In the unlikely event that a synthesis does not reach the expected result, LGC Standards reserves the right to cancel the order.

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 3

Pharmaceutical impurities

Products

Code Product Code Unit 4-Aminobenzoic Acid MM 0094.00 Imp. B (EP): Benzocaine O (A) 500 mg O

H2N MM 0093.17 Imp. C (EP) as Hydrochloride: Aniline Hydrochloride (B) 100 mg x HCl

H2N Acebutolol Hydrochloride

O MM 0435.00 Acebutolol Hydrochloride OH H (A) 500 mg O N O

N H x HCl MM 0435.01 Imp. A (EP): N-[3-Acetyl-4-[(2RS)-oxiran- O (A) 50 mg 2-ylmethoxy]phenyl]butanamide O O O

N H O MM 0435.02 Imp. B (EP) as Hydrochloride:N-[3-Acetyl-4-[(2RS)- OH (A) 100 mg H 2-hydroxy-3-[(1-methylethyl)amino]- O N propoxy]phenyl]acetamide Hydrochloride O x HCl (Diacetolol Hydrochloride) N H MM 0435.03 Imp. C (EP): N-(3-Acetyl-4-hydroxyphenyl)butanamide O (A) 100 mg OH O

N H O MM 0435.04 Imp. D (EP) as Hydrochloride: 1-[5-Amino-2- OH (A) 50 mg H [(2RS)-2-hydroxy-3-[(1-methylethyl)amino]- O N x 2 HCl propoxy]phenyl]ethanone Dihydrochloride

H2N OH MM 0435.05 Imp. E (EP) as Hydrochloride: N-[4-[(2RS)-2- H (A) 50 mg O N Hydroxy-3-[(1-methylethyl)amino]propoxy]- O x HCl

phenyl]butanamide Hydrochloride N H O MM 0435.06 Imp. F (EP): N-[3-Acetyl-4-[(2RS)- OH (A) 50 mg 2,3-dihydroxypropoxy]phenyl]butanamide O OH O

N H O O MM 0435.07 Imp. G (EP): N,N'-[[(1-Methylethyl)imino]- OH OH (A) 50 mg bis[(2-hydroxypropane-1,3-diyl)oxy(3-acetyl- O N O 1,4-phenylene)]]dibutanamide (Acebutolol Biamine) HN NH

O O O O MM 0435.08 Imp. H (EP): N,N'-[(2-Hydroxypropane- OH (A) 50 mg 1,3-diyl)bis[oxy(3-acetyl-1,4-phenylene)]]di- O O butanamide HN NH

O O O MM 0435.09 Imp. I (EP): N-[3-Acetyl-4-[(2RS)-3-(ethylamino)- OH (A) 50 mg H 2-hydroxypropoxy]-phenyl]butanamide O N O

N H O MM 0435.10 Imp. J (EP) as Hydrochloride: N-[3-Acetyl-4- OH (A) 50 mg H [(2RS)-2-hydroxy-3-[(1-methylethyl)amino]- O N O x HCl propoxy]phenyl]propanamide Hydrochloride N H O MM 0435.11 Imp. K (EP) as Hydrochloride: N-[3-Butanoyl- OH (A) 50 mg H 4-[(2RS)-2-hydroxy-3-[(1-methylethyl)amino]- O N x HCl propoxy]phenyl]butanamide Hydrochloride O N H

10 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Aceclofenac MM 0181.00 Aceclofenac O (A) 250 mg O OH O NH Cl Cl

MM 0006.20 Imp. A (EP): [2-[(2,6-Dichlorophenyl)amino]phenyl]acetic Acid OH (A) 100 mg (Diclofenac) O NH Cl Cl

MM 0006.10 Imp. B (EP): Methyl [2-[(2,6-Dichlorophenyl)amino]phenyl]acetate O (A) 100 mg O (Methyl Ester of Diclofenac) NH Cl Cl

MM 0006.11 Imp. C (EP): Ethyl 2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetate O (A) 100 mg O (Ethyl Ester of Diclofenac) NH Cl Cl

MM 0181.01 Imp. D (EP): Methyl [[[2-[(2,6-Dichloro- O (A) 100 mg O phenyl)amino]phenyl]acetyl]oxy]- O O acetate (Methyl Ester of Aceclofenac) NH Cl Cl

MM 0181.02 Imp. E (EP): Ethyl [[[2-[(2,6-Dichlorophenyl)amino]phenyl] O (A) 100 mg O acetyl]oxy]acetate (Ethyl Ester of Aceclofenac) O O NH Cl Cl

MM 0181.03 Imp. F (EP): Benzyl[[[2-[(2,6-Dichlorophenyl)amino]phenyl] O (A) 100 mg O acetyl]oxy]acetate (Benzyl Ester of Aceclofenac) O O NH Cl Cl

MM 0181.04 Imp. G (EP): [[[[[2-[(2,6-Dichlorophenyl)amino]phenyl]- O (A) 100 mg O OH acetyl]oxy]acetyl]oxy]acetic Acid (Acetic Aceclofenac) O O O NH Cl Cl

MM 0006.01 Imp. I (EP):1-(2,6-Dichlorophenyl)-1,3-dihydro-2H-indol-2-one (A) 100 mg O N Cl Cl

MM 0181.05 Imp. H (EP): [[[[[[[2-[(2,6-Dichlorophenyl)- O O (A) 50 mg O O amino]phenyl]acetyl]oxy]acetyl]oxy]acetyl]-oxy]acetic O OH Acid (Diacetic Aceclofenac) O O NH Cl Cl

MM 0181.06 Isopropyl [2-[(2,6-Dichlorophenyl)amino]phenyl]acetate O (A) 100 mg O (Isopropyl Ester of Diclofenac) NH Cl Cl

Acesulfame Potassium New MM 1093.01 Imp. A (EP): 3-Oxobutanamide (Acetylacetamide) O (A) 100 mg

NH2

O Acetazolamide

MM 0648.00 Acetazolamide H OO (A) 500 mg N S S NH2 O NN

H New MM 0648.04 Imp. A (EP): N-(5-Chloro-1,3,4-thiadiazol-2- Cl S N (A) 50 mg yl)acetamide N N O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 11 Pharmaceutical impurities

Code Product Code Unit H New MM 0648.01 Imp. B (EP): N-(1,3,4-Thiadiazol-2-yl)acetamide S N (A) 100 mg

N N O Acetylcysteine MM 0024.00 N-Acetyl-L-cysteine O (A) 500 mg HS OH HN

MM 0024.03 Imp. A (EP): L-Cystine NH2 O (B) 100 mg HO S SOH

O NH2 MM 0024.02 Imp. B (EP): L-Cysteine O (B) 100 mg HS OH

NH2 MM 0024.04 Imp. C (EP): N,N’-Diacetyl-L-cystine O (A) 100 mg NH O HO S SOH O HN

O MM 0024.01 Imp. D (EP): N,S-Diacetyl-L-cysteine O O (A) 100 mg SOH HN

O MM 0024.05 Sodium 2-Methyl-4,5-dihydro-1,3-thiazol-4-carboxylate O (A) 100 mg N ONa S MM 0024.06 N-Propionyl-L-cysteine O (A) 100 mg HS OH HN

O Acetylsalicylic Acid MM 0133.00 Acetylsalicylic Acid O O (A) 500 mg HO O

MM 0045.01 Imp. A (EP): 4-Hydroxybenzoic Acid O (B) 100 mg HO

OH MM 0045.02 Imp. B (EP): 4-Hydroxybenzene-1,3-dicarboxylic Acid O O (A) 100 mg (4-Hydroxyisophthalic Acid) HO OH OH MM 0045.00 Imp. C (EP): Salicylic Acid O (A) 500 mg OH

OH MM 0133.01 Imp. D (EP): 2-[[2-(Acetyloxy)benzoyl]oxy]benzoic Acid O (A) 100 mg (Acetylsalicylsalicylic Acid) OH O

O O

MM 0133.03 Imp. E (EP):2-[(2-Hydroxybenzoyl)oxy]benzoic Acid O (A) 100 mg (Salicylsalicylic Acid) OH

O OH

MM 0133.02 Imp. F (EP): 2-(Acetyloxy)benzoic Anhydride O (A) 100 mg (Acetylsalicylic Anhydride) O O O

12 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0133.04 2-(2,4-Dihydroxybenzoyl)benzoic Acid O (A) 100 mg OH O

OH N-Acetyltryptophan

H MM 1267.01 Imp. A (EP): Tryptophan N (A) 100 mg NH2 OH

O H MM 0172.03 Imp. D (EP): (S)-2-Amino-3-(5-hydroxy- N (A) 100 mg NH2 1H-indol-3-yl)propanoic Acid (5-Hydroxy- OH tryptophan) O HO Aciclovir MM 0061.00 Aciclovir O (A) 500 mg HN N OH N H2N N O MM 0061.01 Imp. A (EP): 2-[(2-Amino-6-oxo-1,6-dihydro-9H-purin- O (A) 100 mg N 9-yl)methoxy]ethyl Acetate HN O N O H2N N O O MM 0061.02 Imp. B (EP): 2-Amino-1,7-dihydro-6H-purin-6-one (Guanine) H (B) 100 mg N HN

N H2N N

MM 0061.04 Imp. D (EP): 2-[(2-Amino-6-oxo-1,6-dihydro-9H-purin- O (A) 100 mg 9-yl)methoxy]ethyl Benzoate N HN O N O H2N N O MM 0061.06 Imp. F (EP): N-[9-[(2-Hydroxyethoxy)methyl]-6-oxo- O (A) 100 mg N 6,9-dihydro-1H-purin-2-yl]acetamide O HN OH N N N H O MM 0061.07 Imp. G (EP): 2-[[(2-(Acetylamino)-6-oxo-1,6-dihydro-9H-purin- O (A) 100 mg O O HN N 9-yl]methoxy]ethyl Acetate O N N N H O

MM 0061.08 Imp. H (EP): 2-[[2-(Acetylamino)-6-oxo-1,6-dihydro-9H- O (A) 100 mg purin-9-yl]methoxy]ethyl Benzoate N O HN O N N N O H O MM 0061.10 2,6-Dichloropurine Cl (B) 100 mg N N

Cl N N H Adalapene New MM 0681.03 Imp. A (EP): 2,2'-Binaphthalene-6,6'-dicarboxylic Acid O (A) 50 mg HO

O New MM 0681.01 Imp. C (EP): 1-(2-Methoxyphenyl)tricyclo- O (A) 50 mg 3,7 [3.3.1.1 ]decane

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 13 Pharmaceutical impurities

Code Product Code Unit Adenosine

MM 0784.00 Adenosine NH2 (A) 500 mg N N HO N N O

OH OH

New MM 0784.01 Imp. A (EP) as Sulphate: 7H-Purin-6-amine NH2 (A) 100 mg N Sulphate (Adenine Sulphate) N x H2SO4

N N H 2 New MM 0784.02 Imp. F (EP): 1-i-D-Ribofuranosylpyrimidine- O (A) 100 mg 2,4(1H,3H)-dione (Uridine) HN

HO O N O

OH OH New MM 0784.03 Imp. G (EP): 9-i-D-Ribofuranosyl-1,9-dihydro- O (A) 100 mg N 6H-purin-6-one (Inosine) HN HO N N O

OH OH New MM 0784.04 Imp. H (EP): 2-Amino-9-i-D-ribofuranosyl- O (A) 100 mg N 1,9-dihydro-6H-purin-6-one (Guanosine) HN N H2N N HO O

OH OH Adiphenine Hydrochloride

MM 1172.00 Adiphenine Hydrochloride O (A) 250 mg N O x HCl

Adrenaline Tartrate

MM 0614.00 Adrenaline Tartrate OH H (A) 500 mg N OH O HO x OH HO O OH OH

MM 0614.02 L-Adrenaline OH H (A) 500 mg N

HO OH

O MM 0614.13 Imp. C (EP) as Hydrochloride: 1-(3,4-Di- H (A) 100 mg HO N hydroxyphenyl)-2-(methylamino)ethanone x HCl Hydrochloride (Adrenalone Hydrochloride) HO

SO3H MM 0614.01 (1R)-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanesulphonic Acid H (A) 100 mg (Adrenaline i-Sulphonate) N

HO OH Alanine

MM 0566.00 Alanine NH2 (A) 500 mg OH

O Albendazole

MM 0382.00 Albendazole H O (A) 500 mg N O NH S N

H MM 0382.01 Imp. A (EP): 5-(Propylsulphanyl)-1H-benzimidazol-2-amine N (A) 100 mg

NH2 S N

14 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit

MM 0382.02 Imp. B (EP): Methyl [5-Propylsulphinyl)-1H-benzimidazol- H O (A) 100 mg N O 2-yl]carbamate NH S N O

O MM 0382.03 Imp. C (EP): Methyl [5-Propylsulphonyl)-1H-benzimidazol- H (A) 100 mg N O 2-yl]carbamate NH S N O O

H MM 0382.04 Imp. D (EP): 5-(Propylsulphonyl)-1H-benzimidazol-2-amine N (A) 100 mg NH2 S N O O

O MM 2500.00 Imp. E (EP): Methyl (1H-Benzimidazol-2-yl)carbamate H (A) 100 mg N O (Carbendazim) NH N Alfuzosin Hydrochloride MM 0085.04 Imp. B (EP): 2-Chloro-6,7-dimethoxyquinazolin-4-amine O N Cl (A) 100 mg N O

NH2 New MM 1004.04 Imp. D (EP) as Dihydrochloride: N- (A) 50 mg O N N NH2 (4-Amino-6,7-dimethoxyquinazolin- x 2 HCl N 2-yl)-N-methylpropane-1,3- O

diamine Dihydrochloride NH2 Allobarbital

H MM 0899.00 Allobarbital O N O (A) 100 mg [Controlled Substance] NH

O Allopurinol MM 0034.00 Allopurinol O (A) 500 mg NH N N N H MM 0034.01 Imp. A (EP) as Hemisulphate: 5-Amino-1H-pyrazole- O (A) 100 mg

NH2 1 4-carboxamide Hemisulphate N x /2 H2SO4 N NH H 2 MM 0034.05 Imp. D (EP): Ethyl 5-Amino1H-pyrazole-4-carboxylate O (A) 100 mg O N N NH H 2 MM 0034.06 Imp. E (EP): Ethyl 5-(Formylamino)-1H-pyrazole-4-carboxylate O (A) 100 mg O N N N O H H MM 0034.07 Oxypurinol O (A) 100 mg NH N N N O H H Alprazolam

MM 0028.03 Imp. E (EP): (2-Amino-5-chlorophenyl)phenylmethanone NH2 (B) 100 mg O Cl

Alverine Citrate MM 0454.00 Alverine Citrate O (A) 250 mg OH

N OH x O OH OH O MM 0454.02 Imp. A (EP): 1-Chloro-3-phenyl-propane (A) 100 mg Cl MM 0454.03 Imp. B (EP): 3-Phenylpropan-1-ol (A) 100 mg OH

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 15 Pharmaceutical impurities

Code Product Code Unit

MM 0454.04 Imp. C (EP) as Hydrochloride: N-Ethyl- x HCl (A) 100 mg 3-phenylpropan-1-amine Hydrochloride NH

MM 0454.05 Imp. D (EP) as Hydrochloride: N-(3- x HCl (A) 100 mg Cyclohexylpropyl)-N-ethyl-3-phenyl- N propan-1-amine Hydrochloride MM 0454.06 Imp. E (EP) as Hydrochloride: 3-Phenyl- (A) 100 mg N,N-bis(3-phenylpropyl)propan-1-amine Hydrochloride x HCl

N Amantadine Hydrochloride

MM 0564.00 Amantadine Hydrochloride NH2 (A) 500 mg x HCl

Ambroxol Hydrochloride MM 0005.00 Ambroxol Hydrochloride OH (A) 500 mg Br N H x HCl NH2 Br

Br MM 0005.01 Imp. A (EP): (2-Amino-3,5-dibromophenyl)methanol OH (A) 100 mg

NH2 Br MM 0005.04 Imp. B (EP) as Hydrochloride: trans-4-(6,8-Dibromo- OH (A) 100 mg 1,4-dihydroquinazolin-3(2H)-yl)cyclohexanol Hydrochloride Br N x HCl N H Br MM 0005.03 Imp. C (EP): trans-4-[[(E)-2-Amino- OH (A) 100 mg Br 3,5-dibromobenzyliden]amino]cyclohexanol N

NH2 Br MM 0005.05 Imp. D (EP) as Hydrochloride: cis-4-[(2-Amino- OH (A) 100 mg Br 3,5-dibromobenzyl)amino]cyclohexanol Hydrochloride N H x HCl NH2 Br

Br MM 0005.02 Imp. E (EP): 2-Amino-3,5-dibromobenzaldehyde O (A) 100 mg

NH2 Br MM 0005.06 trans-4-Aminocyclohexanol Hydrochloride OH (A) 100 mg x HCl H2N MM 0005.07 cis-4-Aminocyclohexanol Hydrochloride OH (A) 100 mg x HCl H2N Amiloride Hydrochloride MM 0560.00 Amiloride Hydrochloride Dihydrate O NH (A) 500 mg Cl N N NH2 x HCl H x 2 H2O H2N N NH2 Aminocaproic Acid MM 0896.00 Aminocaproic Acid O (A) 500 mg H2N OH Amiodarone Hydrochloride MM 0697.00 Amiodarone Hydrochloride O (A) 250 mg I O x HCl N O I MM 0697.11 Imp. A (EP) as Oxalate: O (A) 100 mg (2-Butylbenzofuran-3-yl) HO O O x [4-[2-(diethylamino)ethoxy]- N O phenyl]methanone Oxalate HO O

16 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0697.03 Imp. B (EP) as Hydrochloride: O (D) 100 mg (2-Butylbenzofuran-3-yl)[4- I O H x HCl [2-(ethylamino)ethoxy]-3,5- N O diiodophenyl]methanone I Hydrochloride (Desethylamiodarone Hydrochloride) MM 0697.04 Imp. C (EP) as Hydrochloride: O (A) 100 mg (2-Butylbenzofuran- I O x HCl 3-yl)[4-[2-(diethylamino)ethoxy]- N O 3-iodophenyl]methanone Hydrochloride

MM 0697.05 Imp. D (EP): (2-Butylbenzofuran-3-yl)(4-hydroxy- O (A) 100 mg 3,5-diiodophenyl)methanone I O OH I MM 0697.06 Imp. E (EP): (2-Butylbenzofuran- O (A) 100 mg 3-yl)(4-hydroxyphenyl)methanone O OH

MM 0697.07 Imp. F (EP): (2-Butylbenzofuran-3-yl)(4-hydroxy- O (A) 100 mg 3-iodophenyl)methanone I O OH

MM 0697.09 Imp. H (EP) as Hydrochloride: 2-Chloro-N,N-diethylethanamine (C) 100 mg x HCl N Hydrochloride (2-Chlorotriethylamine Hydrochloride; Cl (2-Chloroethyl)diethylamine Hydrochloride) MM 0697.10 Amiodarone N-Oxide Hydrochloride O (A) 100 mg I O O x HCl N O I Amisulpride

MM 0051.01 Imp. A (EP): [(2RS)-1-Ethylpyrrolidin-2-yl]methanamine H2N (A) 100 mg N

New MM 0793.03 Imp. C (EP): 4-Amino-N-[[(2RS)-1-ethyl- O (A) 50 mg I pyrrolidin-2-yl]methyl]-5-iodo-2-methoxy- N H benzamide N H2N O

New MM 0793.04 Imp. D (EP): 4-Amino-N-[[(2RS)-1-ethyl- O O O (A) 50 mg S pyrrolidin-2-yl]methyl]-2-methoxy-5- N H (methylsulphonyl)benzamide N H2N O

New MM 0793.05 Imp. E (EP): 4-Amino-5-(ethylsulphonyl)- O O O (A) 100 mg S 2-methoxybenzoic Acid OH

H2N O Amitraz

MM 1018.01 Imp. A (BP): 2,4-Dimethylaniline NH2 (A) 100 mg (2,4-Xylidine)

H MM 1018.02 Imp. B (BP): Form-2',4'-xylidide N O (A) 100 mg

Amitriptyline Hydrochloride MM 0062.00 Amitriptyline Hydrochloride (A) 500 mg

N x HCl

MM 0062.01 Imp. A (EP): 10,11-Dihydro-5H-dibenzo- (B) 100 mg [a,d][7]annulen-5-one (Dibenzosuberone) O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 17 Pharmaceutical impurities

Code Product Code Unit MM 0062.02 Imp. B (EP) as Hydrochloride: 3-(5H-Dibenzo[a,d][7]annulen- (A) 100 mg 5-ylidene)-N,N-dimethylpropan-1-amine Hydrochloride (Cyclobenzaprine Hydrochloride) N x HCl

MM 0079.00 Imp. C (EP) as Hydrochloride: 3-(10,11-Dihydro-5H- (A) 500 mg dibenzo[a,d][7]annulen-5-ylidene)-N-methylpropan-1-amine N Hydrochloride (Nortriptyline Hydrochloride) H x HCl

MM 0062.03 Imp. D (EP): 5-[3-(Dimethylamino)propyl]-10,11-dihydro-5H- (A) 100 mg OH dibenzo[a,d][7]annulen-5-ol N

MM 0062.05 Imp. F (EP): (5EZ,10RS)-5-[3-(Dimethyl- (A) 100 mg amino)propylidene]-10,11-dihydro-5H- N dibenzo[a,d][7]annulen-10-ol

MM 0062.14 Imp. G (EP): 10,11-Dihydro-5H-dibenzo[a,d][7]annulen-5-ol (A) 100 mg (Dibenzosuberol) OH

MM 0062.12 Amitriptyline N-Oxide Hydrochloride (B) 10 mg

N O x HCl

MM 0062.13 10,11-Dihydro-5H-dibenzo[a,d]cycloheptene (Dibenzosuberane) (A) 100 mg

Amlodipine Besilate

H MM 0383.00 Amlodipine Besilate N NH2 (D) 100 mg O O O O O S OH

O O Cl x

H MM 0383.06 Amlodipine N NH (A) 100 mg O 2 O O

O O Cl

MM 0383.01 Imp. A (EP): 3-Ethyl-5-Methyl (4RS)-4-(2-Chlorophenyl)- O (D) 100 mg H 2-[[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethoxy]methyl]- N N O 6-methyl-1,4-dihydropyridine-3,5-dicarboxylate O O O

O O Cl

H H MM 0383.02 Imp. B (EP): 3-Ethyl 5-Methyl (4RS)- N N O (D) 100 mg 4-(2-Chlorophenyl)-6-methyl- O O O O 2-[[2-[[2-(methylcarbamoyl)benzoyl]amino]- N H ethoxy]methyl]-1,4-dihydropyridine-3,5-dicarboxylate O O Cl

H MM 0383.03 Ethyl Methyl (4RS)-2,6-Bis[(2-aminoethoxy)methyl]- H2N N NH2 (D) 100 mg 4-(2-chlorophenyl)-1,4-dihydropyridine- O O 3,5-dicarboxylate Dihydrochloride O O O O Cl x 2 HCl

N NH MM 0383.04 Imp. D (EP): 3-Ethyl-5-Methyl 2-[(2-Aminoethoxy)methyl]- O 2 (D) 100 mg 4-(2-chlorophenyl)-6-methylpyridine-3,5-dicarboxylate O O O O Cl

18 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit H MM 0383.10 Imp. E (EP): Diethyl (4RS)-2-[(2-Amino- N NH2 (D) 100 mg ethoxy)methyl]-4-(2-chlorophenyl)-6- O methyl-1,4-dihydropyridine-3,5-dicarboxylate O O O O Cl

H MM 0383.07 Imp. G (EP): Dimethyl 4-(2-Chlorophenyl)- N (A) 100 mg 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate O O

O O Cl

MM 0383.11 Imp. H (EP): 2-[[2-[[(4RS)-4-(2-Chlorophenyl)- (D) 100 mg H H N N 3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6- O methyl-1,4-dihydropyridin-2-yl]methoxy]ethyl]- O O O carbamoyl]benzoic Acid O OH O O Cl

MM 0383.05 Benzenesulfonic Acid O (B) 100 mg O S OH

Amlodipine Maleate

H MM 0631.00 Amlodipine Maleate N NH (D) 100 mg O 2 O O O OH x O O OH Cl O

Amlodipine Mesilate

H MM 0592.00 Amlodipine Mesilate N NH2 (D) 100 mg O

O O O O x S O O HO Cl

Amodiaquine Dihydrochloride Dihydrate MM 0617.00 Amodiaquine Dihydrochloride Dihydrate Cl N (A) 500 mg

N x 2 HCl HN x 2 H2O

OH MM 0617.01 4-Acetamido-2-diethylaminomethylphenol (A) 100 mg H N N

O OH MM 0617.02 7-Chloro-4-(4-hydroxyphenylamino)quinoline Cl N (A) 100 mg

OH MM0617.03 4,7-Dichloroquinoline Cl N (C) 100 mg

Cl MM 0617.04 Monodesethylamodiaquine Dihydrochloride Cl N (A) 100 mg

HN x 2 HCl HN

OH Amoxicillin Trihydrate

O MM 0232.00 Amoxicillin Trihydrate OH (A) 500 mg O NH2 N H N x 3 H2O S H O HO

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 19 Pharmaceutical impurities

Code Product Code Unit O MM 0026.04 Imp. A (EP): (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia- OH (B) 100 mg 1-azabicyclo[3.2.0]-heptane-2-carboxylic Acid O N (6-Aminopenicillanic Acid) S H2N H O New MM 0232.02 Imp. B (EP): (2S,5R,6R)-6-[[(2S)-2-Amino- OH (D) 100 mg 2-(4-hydroxyphenyl)acetyl]amino]-3,3- O NH2 N H dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]- N S heptane-2-carboxylic Acid (L-Amoxicillin) H O HO O MM 0232.03 Imp. C (EP): (4S)-2-[5-(4-Hydroxyphenyl)- OH (A) 100 mg 3,6-dioxopiperazin-2-yl]-5,5-dimethyl-thiazolidine- HN 4-carboxylic Acid (Amoxicillin Diketopiperazines) H O N S

N O H HO O MM 0232.04 Imp. D (EP) as Sodium Salt:(4S)-2-[[[(2R)-2-Amino- ONa (A) 100 mg 2-(4-hydroxyphenyl)acetyl]amino]-carboxymethyl]- NH2 HN 5,5-dimethylthiazolidine-4-carboxylic Acid Sodium Salt H N (Penicilloic Acids of Amoxicillin Sodium Salt) S O HO HO O O MM 0232.05 Imp. E (EP): (2RS,4S)-2-[[[(2R)-2-Amino- OH (A) 50 mg 2-(4-hydroxyphenyl)acetyl]amino]methyl]- NH2 HN 5,5-dimethylthiazolidine-4-carboxylic Acid H N (Penilloic Acids of Amoxicillin) S O HO MM 0232.06 Imp. F (EP): 3-(4-Hydroxyphenyl)pyrazin-2-ol HO N (A) 100 mg

HO MM 0232.08 Imp. H (EP): (2R)-2-[(2,2-Dimethylpropanoyl)amino]-2- O (A) 100 mg (4-hydroxyphenyl)acetic Acid NH OH

O HO MM 0232.09 Imp. I (EP): (2R)-2-Amino-2-(4-hydroxyphenyl)acetic Acid NH2 (B) 100 mg OH

O HO

MM 0232.12 (2R)-2-Amino-2-(4-hydroxyphenyl)acetamide NH2 (A) 100 mg NH2

O HO Ampicillin Sodium

O MM 0253.00 Ampicillin Sodium ONa (A) 500 mg O NH2 N H N S H O

O MM 0253.15 Ampicillin Trihydrate OH (A) 500 mg O NH2 N H x 3 H O N 2 S H O

O MM 0026.04 Imp. A (EP): (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia- OH (B) 100 mg 1-azabicyclo[3.2.0]-heptane-2-carboxylic Acid (6-Aminopenicillanic O N Acid) S H2N H O MM 0253.02 Imp. B (EP): (2S,5R,6R)-6-[[(2S)-2-Amino- OH (A) 100 mg 2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia- O NH2 N 1-azabicyclo[3.2.0]heptane-2-carboxylic Acid (L-Ampicillin) H N S H O

O MM 0253.03 Imp. C (EP): (4S)-2-(3,6-Dioxo-5-phenylpiperazin-2-yl)- OH (A) 100 mg 5,5-dimethylthiazolidine-4-carboxylic Acid (Diketopiperazines of HN Ampicillin) H O N S

N O H

20 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit O MM 0253.04 Imp. D (EP) as Sodium Salt: (4S)-2-[[[(2R)-2-Amino- ONa (A) 100 mg 2-phenylacetyl]amino]-carboxymethyl]- NH2 HN H 5,5-dimethylthiazolidine-4-carboxylic Acid Sodium Salt N (Penicilloic Acids of Ampicillin Sodium Salt) S O HO O O MM 0253.06 Imp. F (EP): (2RS,4S)-2-[[[(2R)-2-Amino- OH (A) 100 mg 2-phenylacetyl]amino]methyl]-5,5-dimethyl-thiazolidine- NH2 HN 4-carboxylic Acid (Penilloic Acids of Ampicillin) H N S

O MM 0253.11 Imp. K (EP): (2R)-2-[(2,2-Dimethylpropanoyl)amino]-2-phenylacetic O (A) 100 mg Acid NH OH

MM 0253.08 Imp. H (EP): 3-Phenylpyrazin-2-ol HO N (A) 100 mg

MM 0253.12 Imp. L (EP): (2R)-2-Amino-2-phenylacetic Acid NH2 (B) 100 mg (D-Phenylglycine) OH O

O MM 0253.16 Ampicillin, anhydrous OH (A) 500 mg O NH2 N H N S H O Androstanolone MM 0565.00 Androstanolone OH (A) 250 mg

O Anise Oil MM 0164.01 trans-Anethole (C) 100 mg

O MM 0164.02 Estragole (C) 100 mg

MM 0164.03 Anisaldehyde O (C) 100 mg

O MM 0164.05 Linalol (C) 100 mg

MM 0164.06 cis-Anethole (D) 100 mg

O Antazoline Hydrochloride MM 0171.00 Antazoline Hydrochloride (A) 500 mg

N x HCl N N H MM 0171.01 Imp. A (EP) as Dihydrochloride: N-(2-Aminoethyl)- (A) 100 mg 2-(benzylphenylamino)acetamide Dihydrochloride O x 2 HCl

N NH2 N H

MM 0171.03 N-Benzylaniline NH (B) 100 mg

MM 0171.04 Imp. B (Pharmeuropa) as Hydrochloride: 2-(Chloro- N (A) 100 mg x HCl methyl)-4,5-dihydro-1H-imidazole Hydrochloride N H Cl

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 21 Pharmaceutical impurities

Code Product Code Unit Antazoline Phosphate MM 0561.00 Antazoline Phosphate H (A) 500 mg N N N x H3PO4

Apomorphine Hydrochloride

MM 0562.00 Apomorphine Hydrochloride Hemihydrate OH (A) 250 mg HO x HCl x ½ H O N 2 H

MM 0037.00 Imp. B (EP) as Hydrochloride Trihydrate: Morphine N (A) 250 mg Hydrochloride Trihydrate x HCl [Controlled Substance] x 3 H2O

HO O OH Aprindine Hydrochloride

MM 0467.00 Aprindine Hydrochloride N on request

N HCl

Arginine

MM 0568.00 Arginine H NH2 (A) 500 mg H2N N OH

NH O Arginine Hydrochloride

MM 0569.00 Arginine Hydrochloride H NH2 (A) 500 mg H2N N OH x HCl

NH O Articaine Hydrochloride

O MM 0369.00 Articaine Hydrochloride O (A) 100 mg H N x HCl N S H O

O MM 0369.01 Imp. A (EP) as Hydrochloride: Methyl O H (A) 100 mg N x HCl 3-[[2-(Propylamino)acetyl]amino]-4-methylthiophene- N S 2-carboxylate Hydrochloride (Acetamidoarticaine O H Hydrochloride)

O MM 0369.02 Imp. B (EP) as Hydrochloride: 4-Methyl-3-[[(2RS)- HO H (A) 50 mg N x HCl 2-(propylamino)propanoyl]amino]thiophene-2-carboxylic N S Acid Hydrochloride (Articaine Acid Hydrochloride) O H

O MM 0369.03 Imp. C (EP) as Hydrochloride: 1-Methylethyl 4-Methyl- O H (A) 100 mg N x HCl 3-[[(2RS)-2-(propylamino)propanoyl]amino]thiophene- N S 2-carboxylate Hydrochloride (Articaine Isopropyl Ester O H Hydrochloride)

O MM 0369.04 Imp. D (EP) as Hydrochloride: Methyl 3-[[(2RS)- O H (B) 10 mg N x HCl 2-(Ethylamino)propanoyl]amino]-4-methylthiophene- N S 2-carboxylate Hydrochloride (Ethylarticaine Hydrochloride) O H

O MM 0369.05 Imp. E (EP) as Hydrochloride: Methyl 4-Methyl-3-[[(2RS)- O H (A) 100 mg N x HCl 2-[(1-methylethyl)amino]propanoyl]amino]thiophene- N S 2-carboxylate Hydrochloride (Isopropylarticaine O H Hydrochloride)

MM 0369.06 Imp. F (EP) as Hydrochloride: 4-Methyl-N-propyl- H O (A) 50 mg N H 3-[[(2RS)-2-(propylamino)propanoyl]amino]thiophene- N x HCl N S 2-carboxamide Hydrochloride (Articaine Acid O H Propionamide Hydrochloride)

O MM 0369.07 Imp. G (EP) as Hydrochloride: Methyl 3-[[(2RS)- O H (A) 100 mg N x HCl 2-(Butylamino)propanoyl]amino]-4-methylthiophene- N S 2-carboxylate Hydrochloride (Butylarticaine Hydrochloride) O H

O MM 0369.08 Imp. H (EP) as Hydrochloride: Methyl 3-[[(2RS)- O H (A) 100 mg N x HCl 2-(Dipropylamino)propanoyl]amino]-4-methylthiophene- N S 2-carboxylate Hydrochloride (Dipropylarticaine O Hydrochloride)

22 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit O MM 0369.09 Imp. I (EP): Methyl 3-Amino-4-methylthiophene-2-carboxylate O (C) 100 mg

(3-Aminoarticaine) NH2 S

O MM 0369.10 Imp. J (EP): Methyl 3-[[(2RS)-2-Bromopropanoyl]amino]- O H (B) 10 mg N 4-methylthiophene-2-carboxylate (Bromo Compound) Br S O Ascorbic Acid

OH MM 0166.00 L-Ascorbic Acid HO (A) 500 mg O O HO OH Asparagine Monohydrate

MM 0765.01 Phenylacetylasparagine O (C) 50 mg

O HN OH H2N O Aspartame

MM 0314.00 Aspartame O NH2 H O (A) 500 mg N HO O O

MM 0314.01 Imp. A (EP): 2-(5-Benzyl-3,6-dioxopiperazin-2-yl)acetic Acid O (A) 100 mg (Diketopiperazine) O HN NH HO O

MM 0314.02 Imp. B (EP): L-Aspartyl-L-phenylalanine O NH2 H O (A) 100 mg N HO OH O

MM 0314.03 Imp. C (EP): Phenylalanine O (B) 100 mg H2N OH

Aspartic Acid

MM 0567.00 Aspartic Acid O NH2 (A) 500 mg OH HO O New MM 0460.10 Imp. B (Pharmeuropa): (E)-Butenedioic Acid O (B) 100 mg HO (Fumaric Acid) OH O

New MM 0566.00 Imp. D (Pharmeuropa): (S)-2-Aminopropanoic NH2 (A) 500 mg Acid (Alanine) OH O

New MM 0169.00 Imp. F (Pharmeuropa): (2S)-2,5-Diamino-5- NH2 (A) 500 mg oxopentanoic Acid (L-Glutamine) H2N OH O O Astemizole

MM 0184.00 Astemizole F HN (A) 250 mg N N N O

MM 0184.13 Desmethyl Astemizole Hydrochloride F HN (B) 10 mg N N N OH

x HCl Atenolol

OH MM 0013.00 Atenolol H (A) 500 mg O N O

H2N

OH MM 0013.03 Imp. A (EP): 2-(4-Hydroxyphenyl)acetamide O (B) 100 mg

H2N

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 23 Pharmaceutical impurities

Code Product Code Unit MM 0013.05 Imp. B (EP): 2-[4-[(2RS)- OH (A) 100 mg O OH 2,3-Dihydroxypropoxy)phenyl]acetamide O

H2N

O MM 0013.01 2-[4-[[(2RS)-Oxiran-2-yl]methoxy]phenyl]acetamide O (A) 100 mg O

H2N MM 0013.06 Imp. D (EP): 2-[4-[(2RS)-3-Chloro- OH (A) 50 mg O Cl 2-hydroxypropoxy]phenyl]acetamide O

H2N MM 0013.07 Imp. E (EP): 2,2'-[(2-Hydroxypropane-1,3- OH (A) 50 mg O O diyl)bis(oxy-4,1-phenylene)]diacetamide O O

H2N NH2

MM 0013.02 Imp. F (EP): 2,2'-[[(1-Methylethyl)- OH OH (A) 50 mg O N O imino]bis[(2-hydroxypropane-3,1- O O diyl)oxy-4,1-phenylene]]diacetamide H2N NH2

OH MM 0013.04 Imp. G (EP): 2-[4-[(2RS)-2-Hydroxy- H (A) 50 mg O N 3-[(1-methylethyl)amino]propoxy]phenyl]acetic Acid O HO

OH MM 0013.08 Imp. H (EP): 2-[4-[(2RS)-2-Hydroxy- H (A) 100 mg O N 3-[(1-methylethyl)amino]propoxy]phenyl]acetonitrile N

OH MM 0013.13 4-Hydroxyphenylacetic Acid O (B) 100 mg

HO Atorvastatin Calcium MM 0400.00 Atorvastatin Calcium O (D) 100 mg - O OH O

N N OH H Ca2+

F 2 MM 0400.12 Imp. G (Pharmeuropa) as Calcium Salt: O (D) 100 mg - (3R,5R)-7-[2-(4-Fluorophenyl)-3-phenyl-4- O OH O (phenylcarbamoyl)-5-(propan-2-yl)-1H- N N O pyrrol-1-yl]-5-hydroxy-3-methoxyheptanoic H Ca2+ Acid Calcium Salt (3-O-Methylatorvastatin Calcium Salt)

F 2 MM 0400.16 Imp. G (Pharmeuropa) as Lithium Salt: (3R,5R)-7- O (D) 100 mg [2-(4-Fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)- O OH OLi

5-(propan-2-yl)-1H-pyrrol-1-yl]-5-hydroxy-3-methoxy- N N O heptanoic Acid Lithium Salt (3-O-Methylatorvastatin H Lithium Salt)

F MM 0400.01 Imp. H (Pharmeuropa): (2R,4R)-2-[2-[2-(4-Fluoro- O (D) 100 mg phenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan- O O

2-yl)-1H-pyrrol-1-yl]ethyl]-4-hydroxytetrahydro-2H- N N OH pyran-6-one (Atorvastatin Lactone) H

F MM 0400.04 1,1-Dimethylethyl (4R-cis)- (A) 100 mg 6-[2-[2-(4-Fluorophenyl)-5-(1-methylethyl)- O O O O 3-phenyl-4-[(phenylamino)carbonyl]-1-H-pyrrol- N N O H 1-yl]ethyl]-2,2-dimethyl-1,3-dioxane-4-acetate

F MM 0400.05 1,1-Dimethylethyl (4R-cis)-6-Aminoethyl-2,2-dimethyl- (A) 100 mg 1,3-dioxane-4-acetate O O O

H2N O

24 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0400.13 1-[2-[(2S)-3,6-Dihydro-6-oxo-2H-pyran-2-yl]-ethyl]- O (A) 100 mg 5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1H- O O

pyrrole-3-carboxamide (Atorvastatin eliminated Lactone) N N H

F Atracurium Besilate MM 0858.13 Imp. J (EP): Methyl Benzenesulphonate O O (A) 100 mg S O

Atropine MM 0289.18 Atropine H (A) 250 mg O H N O

OH H and enantiomer MM 0289.00 Atropine Sulphate H (A) 500 mg O H x H2SO4 N O x H2O and enantiomer OH H 2 MM 0289.01 Imp. A (EP) as Hydrochloride: (1R,3r,5S)-8-Methyl- H (D) 100 mg O 8-azabicyclo[3.2.1]oct-3-yl 2-Phenylpropenoate H N x HCl Hydrochloride O (Apoatropine Hydrochloride) H

MM 0601.03 Imp. C (EP): (2RS)-3-Hydroxy-2-phenylpropanoic Acid (Tropic Acid) O (A) 100 mg

OH MM 0546.00 Imp. F (EP) as Hydrobromide Trihydrate: Hyoscine H H (A) 500 mg O H x HBr Hydrobromide Trihydrate N O O x 3 H2O H OH H

MM 0289.03 Atropic Acid O (A) 100 mg

Avobenzone MM 0902.00 Avobenzone O O (A) 500 mg

Azelaic Acid MM 0687.00 Azelaic Acid O O (A) 500 mg HO OH Azelastine Hydrochloride

MM 0362.00 Azelastine Hydrochloride O (A) 100 mg N N N x HCl

Cl MM 0362.04 Imp. A (EP): Benzoyldiazane (Benzohydrazide) O (C) 100 mg NH

NH2 MM 0362.02 Imp. B (EP) as Hydrochloride: 1-Benzoyl-2-[(4RS)- (A) 100 mg H N 1-methylhexahydro-1H-azepin-4-yl]diazane Hydrochloride N x HCl N H O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 25 PRS - Pharmaceutical reference standards traceable to USP, EP, BP

The concept of secondary standards derived by direct comparison with pharmacopoeial reference standards is a proven one and acknowledged by all major regulation agencies and pharmacopoeias.

To source them from a dedicated provider instead of producing them on your own offers some more advantages.

Efficiency: You can focus your resources on value producing activities, rather than the routine. Risk Mitigation: These standards are supplied by an independent 3rd party Reference Material Producer accredited according to ISO 17025 & ISO Guide 34. Economical savings: Attractively priced over pharmacopeial reference standards or in-house standards. Generous Quantities: Product contains 2 - 20x the amount offered by the Pharmacopoeias, allowing multiple uses.

Furthermore, every current Pharmaceutical Reference Standard is re-certified after new pharmacopoeial lot or batch releases. Please contact your local LGC Standards office to obtain updated certificates for the materials purchased.

www.lgcstandards.com

No part of this publication may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, recording or any retrieval system, without the written permission of the copyright holder. © LGC Standards, 2010. All rights reserved. 2593/SR/0510 Pharmaceutical impurities

Code Product Code Unit MM 0362.05 Imp. C (EP): 2-[(4-Chlorophenyl)acetyl]benzoic Acid O (A) 100 mg OH O

Cl MM 0362.01 Imp. D (EP): 4-(4-Chlorobenzyl)phthalazin-1(2H)-one O (A) 100 mg NH N

Cl MM 0362.06 Imp. E (EP) Z-Isomer: (Z)-3-(4-Chlorobenzylidene)- O (A) 100 mg

isobenzofuran-1(3H)-one O

Cl MM 0362.03 1-Methylazepan-4-one Hydrochloride (A) 100 mg N x HCl O Azithromycin New MM 1075.00 Azithromycin N (A) 100 mg OH HO HO O O O OH N O O O O OH

H MM 1075.01 Imp. A (EP): 6-Demethylazithromycin N (D) 100 mg (Azaerythromycin A) OH HO HO OO

O N OH OO O OH O

Baclofen MM 1235.03 Imp. B (EP): (3RS)-5-Amino-3-(4-chlorophenyl)- O (A) 100 mg

5-oxopentanoic Acid H2N O

Cl MM 1235.01 3-(4-Chlorophenyl)glutaric Acid O (A) 100 mg HO O

Cl Bambuterol Hydrochloride MM 0773.04 Imp. D (EP): 5-[(1RS)-1-Hydroxyethyl]-1,3-phenylene OH (A) 100 mg Bis(dimethylcarbamate) N O O

N O

O MM 0773.05 Imp. E (EP): 5-Acetyl-1,3-phenylene Bis-(dimethylcarbamate) O (A) 100 mg N O

N O

O Basic Butylated Methacrylate Copolymer MM 0753.01 Imp. A (EP): Butyl Methacrylate O (A) 100 mg O

MM 0753.02 Imp. B (EP): Methyl Methacrylate O (A) 100 mg O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 27 Pharmaceutical impurities

Code Product Code Unit MM 0753.03 Imp. C (EP): 2-(Dimethylamino)ethyl Methacrylate O (A) 100 mg N O

Beclometasone Dipropionate MM 0199.00 Beclometasone Dipropionate O (A) 250 mg O O O HO O

Cl O MM 0199.02 Imp. A (EP): 9-Chloro-11i,17-dihydroxy-16i- O (A) 100 mg O methyl-3,20-dioxopregna-1,4-dien-21-yl O Propanoate (Beclometasone 21-Propionate) HO OH

Cl O MM 0199.06 Imp. B (EP): 21-(Acetyloxy)-9-chloro-11i- O (A) 100 mg O hydroxy-16i-methyl-3,20-dioxopregna-1,4- O O

dien-17-yl Propanoate (Beclometasone 21- HO Acetate 17-Propionate) O

Cl O MM 0199.05 Imp. C (EP): 9-Chloro-11i-hydroxy-16i-methyl- O (A) 100 mg O 3,20-dioxo-17-(propanoyloxy)-pregna-1,4-dien- O O 21-yl Butanoate (Beclometasone 21-Butyrate HO 17-Propionate) O

Cl O i i OH MM 0199.01 Imp. H (EP): 9-Chloro-11 ,21-dihydroxy-16 - O O (A) 100 mg

methyl-3,20-dioxopregna-1,4-dien-17-yl HO Propanoate (Beclometasone 17-Propionate) O

Cl O i i OH MM 0199.03 9-Chloro-11 ,17,21-trihydroxy-16 -methylpregna- O (A) 100 mg 1,4-diene-3,20-dione (Beclometasone) HO OH

Cl O Benazepril Hydrochloride

New MM 1229.00 Benazepril Hydrochloride O (A) 100 mg H OH N N x HCl O O O

Bendroflumethiazide

O O O O MM 0674.01 Imp. A (EP): 4-Amino-6-(trifluoromethyl)benzene-1,3-disulphonamide S S (A) 100 mg H2N NH2 F NH F 2 F Benfluorex Hydrochloride New MM 0278.01 Imp. C (EP): Benzoic Acid O (B) 100 mg HO

Benperidol MM 0113.00 Benperidol O (A) 100 mg NH N O N

F MM 0113.03 Imp. A (EP): 1-(Piperidin-4-yl)-1,3-dihydro-2H-benzimidazol-2-one O (A) 100 mg NH N

28 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0113.07 4-Chloro-4'-fluorobutyrophenone O (B) 100 mg Cl

F Benzalkonium Chloride

MM 0224.00 Benzalkonium Chloride Cl (A) 500 mg N n MM 0795.00 Imp. A (EP): Benzyl Alcohol (A) 500 mg OH

MM 0224.01 Benzyldimethyldodecylammonium Chloride Cl (A) 500 mg N 5

MM 0224.02 Benzyldimethyltetradecylammonium Chloride Cl (A) 500 mg N 6

MM 0224.03 Benzyldimethylhexadecylammonium Chloride Cl (A) 500 mg N 7 Benzbromarone MM 0456.00 Benzbromarone O (A) 500 mg Br O OH Br Benzocaine MM 0094.00 Benzocaine O (A) 500 mg O

H2N MM 0094.01 Benzocaine Acetylsalicylamide O (C) 50 mg O O

N H O

O MM 0094.02 N-Acetylbenzocaine O (A) 100 mg O O

N H MM 0094.03 4-Aminobenzoic Acid O (B) 100 mg OH

H2N MM 0094.04 Ethyl 4-Nitrobenzoate O (B) 100 mg O

O2N Benzydamine Hydrochloride MM 0142.00 Benzydamine Hydrochloride (A) 500 mg N N x HCl

MM 0142.04 Imp. C (BP): 1-Benzyl-1H-indazol-3-ol (A) 100 mg N N

OH MM 0142.08 Benzydamine N-Oxide Hydrochloride (A) 100 mg N N x HCl

ON O

MM 0290.02 1-Chloropropyl(dimethyl)amine Hydrochloride (N,N-Dimethyl- Cl N x HCl (B) 100 mg 3-chloropropylamine Hydrochloride) Benzyl Alcohol MM 0795.00 Benzyl Alcohol (A) 500 mg OH

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 29 Pharmaceutical impurities

Code Product Code Unit

MM 0795.02 Imp. B (EP): Cyclohexylmethanol OH (A) 100 mg

Benzyl Benzoate MM 0570.00 Benzyl Benzoate O (A) 500 mg O

Benzyl Nicotinate MM 0104.00 Benzyl Nicotinate O (A) 500 mg NO

MM 0553.00 Nicotinic Acid O (A) 500 mg NOH

Benzylpenicillin Benzathine

O MM 0513.00 Benzylpenicillin Benzathine OH (A) 500 mg H N O N x H N N S H H O 2

NH MM 0513.02 Imp. A (EP): Monobenzylethylendiamine HN 2 (C) 100 mg

MM 0160.03 Imp. B (EP): Phenylacetic Acid [Drug Precursor] OH (B) 100 mg O

O MM 0160.07 Imp. D (EP): (3S,7R,7aR)-5-Benzyl-2,2-dimethyl-2,3,7,7a- OH (A) 100 mg

tetrahydroimidazo[5,1-b]-thiazole-3,7-dicarboxylic Acid (Penillic Acid N N of Benzylpenicillin) S H HO O

O MM 0160.01 Imp. E (EP): (4S)-2-[Carboxy[(phenylacetyl)amino]methyl]- OH (A) 100 mg

5,5-dimethylthiazolidine-4-carboxylic Acid (Penicilloic Acids of HN H Benzylpenicillin) N S O OOH

O MM 0160.05 Imp. F (EP): (2RS,4S)-2-[[(Phenylacetyl)amino]methyl]- OH (A) 100 mg

5,5-dimethylthiazolidine-4-carboxylic Acid (Penilloic Acids of HN H Benzylpenicillin) N S O

MM 0513.01 N,N’-Dibenzylethylenediamine Diacetate (C) 100 mg H N O x HO N 2 H

Benzylpenicillin Potassium

O MM 0160.00 Benzylpenicillin Potassium OK (A) 250 mg O O N

N S H H

O MM 0026.04 Imp. A (EP): (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia- OH (B) 100 mg O 1-azabicyclo[3.2.0]-heptane-2-carboxylic Acid (6-Aminopenicillanic N

Acid) H N S 2 H

MM 0160.03 Imp. B (EP): Phenylacetic Acid [Drug Precursor] O (B) 100 mg

O MM 0160.07 Imp. D (EP): (3S,7R,7aR)-5-Benzyl-2,2-dimethyl-2,3,7,7a- OH (A) 100 mg

tetrahydroimidazo[5,1-b]-thiazole-3,7-dicarboxylic Acid N N (Penillic Acid of Benzylpenicillin) S H HO O

O MM 0160.01 Imp. E (EP): (4S)-2-[Carboxy[(phenylacetyl)amino]methyl]- OH (A) 100 mg

5,5-dimethyl-thiazolidine-4-carboxylic Acid (Penicilloic Acids of HN H Benzylpenicillin) N S O OOH

30 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit

O MM 0160.05 Imp. F (EP): (2RS,4S)-2-[[(Phenylacetyl)amino]methyl]- OH (A) 100 mg

5,5-dimethylthiazolidine-4-carboxylic Acid (Penilloic Acids of HN H Benzylpenicillin) N S O Benzylpenicillin Procaine MM 0094.03 Imp. A (EP): 4-Aminobenzoic Acid O (B) 100 mg OH

H2N O MM 0160.01 Imp. B (EP): (4S)-2-[Carboxy[(phenyl- OH (A) 100 mg acetyl)amino]methyl]-5,5-dimethyl- HN thiazolidine-4-carboxylic Acid H N (Penicilloic Acids of Benzylpenicillin) S O OOH O MM 0160.05 Imp. C (EP): (2RS,4S)-2-[[(Phenylacetyl)- OH (A) 100 mg amino]methyl]-5,5-dimethylthiazolidine-4- HN carboxylic Acid (Penilloic Acids of H N Benzylpenicillin) S O

O MM 0160.07 Imp. D (EP): (3S,7R,7aR)-5-Benzyl-2,2- OH (A) 100 mg dimethyl-2,3,7,7a-tetrahydroimidazo[5,1- N b]thiazole-3,7-dicarboxylic Acid (Penillic N S Acid of Benzylpenicillin) H HO O MM 0160.03 Imp. E (EP): Phenylacetic Acid [Drug Precursor] OH (B) 100 mg O Betahistine Dihydrochloride

H MM 0587.00 Betahistine Dihydrochloride N N (A) 500 mg x 2 HCl

MM 0587.01 Imp. A (EP): 2-Ethenylpyridine (2-Vinylpyridine) N (C) 100 mg

MM 0587.02 Imp. B (EP): 2-(Pyridin-2-yl)ethanol (2-(2-Hydroxyethyl)pyridine) NOH (B) 100 mg

MM 0587.03 Imp. C (EP) as Trihydrochloride: N-Methyl-2-(pyridin- (A) 100 mg NNN 2-yl)-N-[2-(pyridin-2-yl)ethyl]ethanamine Trihydrochloride x 3 HCl

MM 0587.04 Imp. C (EP) as Trimesilate: N-Methyl-2-(pyridin-2-yl)- (A) 100 mg NNN O O x 3 S N-[2-(pyridin-2-yl)ethyl]ethanamine Trimesilate OH

Betaine Hydrochloride MM 0611.00 Betaine Hydrochloride O (A) 500 mg N Cl OH Betamethasone MM 0200.00 Betamethasone O (A) 250 mg OH HO OH

F O MM 0213.00 Imp. A (EP): Dexamethasone O (A) 250 mg OH HO OH

F O MM 0200.01 Imp. B (EP): 21-Chloro-9-fluoro-11i,17-dihydroxy-16i- O (A) 100 mg Cl methylpregna-1,4-diene-3,20-dione (Clobetasol) HO OH

F O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 31 Pharmaceutical impurities

Code Product Code Unit Betamethasone Acetate MM 0201.00 Betamethasone Acetate O (A) 250 mg O O HO OH

F O

O MM 0200.00 Imp. A (EP): Betamethasone OH (A) 250 mg HO OH

F O MM 0445.00 Imp. B (EP): Dexamethasone Acetate O (A) 250 mg O O HO OH

F O

O MM 0201.03 Imp. C (EP): Betamethasone 11,21-Diacetate O O (A) 100 mg O O OH

F O Betamethasone Dipropionate

OH MM 0200.00 Imp. A (Pharmeuropa): 9-Fluoro-11i,17,21- O (A) 250 mg trihydroxy-16i-methylpregna-1,4-diene-3,20- HO OH dione (Betamethasone)

F O MM 0202.00 Betamethasone Dipropionate O (A) 250 mg O O O HO O

F O MM 0202.04 Imp. C (Pharmeuropa): 9-Fluoro-11i,17- O (A) 100 mg O dihydroxy-16i-methyl-3,20-dioxopregna- O

1,4-dien-21-yl Propanoate (Betamethasone HO 21-Propionate) OH

F O MM 0199.00 Imp. E (Pharmeuropa): 9-Chloro-11i-hydroxy- O (A) 250 mg O 16i-methyl-3,20-dioxopregna-1,4-diene-17,21- O O diyl Dipropanoate (Beclometasone Dipropionate) HO O

Cl O Betamethasone Sodium Phosphate MM 0303.00 Betamethasone Sodium Phosphate O on request OPONa O ONa HO OH

F O Betamethasone 17-Valerate MM 0203.00 Betamethasone 17-Valerate OH (A) 250 mg O O HO O

F O

OH MM 0200.00 Imp. A (EP): Betamethasone O (A) 250 mg

HO OH

F O

32 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Betaxolol Hydrochloride

OH MM 0436.01 Imp. A (EP) as Hydrochloride: (2RS)- H (A) 50 mg O N 1-(4-Ethylphenoxy)-3-[(1-methylethyl)amino]-propan- x HCl 2-ol Hydrochloride Imp. B (EP): (2RS)-1-[4-(2-Hydroxyethyl)phenoxy]- OH MM 0027.10 H (A) 100 mg 3-[(1-methylethyl)amino]propan-2-ol O N

MM 0436.03 Imp. C (EP): 2-[[4-[2-(Cyclopropylmethoxy)- O (A) 50 mg O ethyl]phenoxy]methyl]oxirane O

MM 0436.04 Imp. D (EP): 4-[2-(Cyclopropylmethoxy)ethyl]phenol OH (A) 50 mg

OH MM 0436.05 Imp. E (EP) as Hydrochloride: (2RS)- H (A) 50 mg 1-[4-(2-Butoxyethyl)phenoxy]- O N

3-[(1-methylethyl)amino]propan-2-ol Hydrochloride O x HCl OH New MM 0436.06 1-[4-(2-Cyclobutoxyethyl)phenoxy]- H (D) 50 mg 3-(isopropylamino)propan-2-ol Hydrochloride O N

O x HCl Bezafibrate MM 0063.00 Bezafibrate O (A) 500 mg O O OH

N H Cl

OH MM 0063.01 Imp. A (EP): 4-Chloro-N-[2-(4-hydroxyphenyl)ethyl]benzamide O (A) 100 mg

(4-Chlorobenzoyltyramine) N H Cl MM 0063.03 Imp. B (EP): 4-Chlorobenzoic Acid O (B) 100 mg OH

Cl MM 0063.04 Imp. C (EP): Methyl O (A) 100 mg O 2-[4-[2-[(4-Chlorobenzoyl)amino]ethyl]phenoxy]- O O 2-methylpropanoate N H Cl MM 0063.02 Imp. D (EP): Ethyl 2-[4-[2-[(4-Chlorobenzoyl)amino]- O (A) 100 mg O ethyl]phenoxy]-2-methylpropanoate O O N H Cl MM 0063.05 Imp. E (EP): Butyl 2-[4-[2-[(4-Chlorobenzoyl)amino]- O (A) 100 mg O ethyl]phenoxy]-2-methylpropanoate O O N H Cl MM 0063.06 Tyramine OH (B) 100 mg

H2N MM 0063.07 N,O-Bis-(4-chlorobenzoyl)tyramine Cl (A) 100 mg O O O N H Cl Bicalutamide

N MM 0894.00 Bicalutamide F (A) 100 mg O F S N H O O OH F F

O HO F F MM 0894.01 N-[4-Cyano-3-(trifluoromethyl)phenyl]- H (A) 50 mg S N 3-[(4-fluorophenyl)sulfinyl]-2-hydroxy- F O 2-methylpropanamide F N

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 33 Pharmaceutical impurities

Code Product Code Unit Bifonazole MM 0318.00 Bifonazole (A) 500 mg

N N

MM 0318.01 Imp. A (EP): (RS)-(Biphenyl-4-yl)phenylmethanol (A) 100 mg

H MM 0015.02 Imp. C (EP): 1H-Imidazole (Imidazole) N (B) 100 mg

N MM 0318.03 Imp. D (EP) as Chloride: 1,3-Bis[(biphenyl-4-yl)phenylmethyl]-1H- (D) 100 mg imidazolium Chloride

N+ Cl- N

Bisacodyl MM 0031.00 Bisacodyl O O (A) 500 mg O O

MM 0031.01 Imp. A (EP): 4,4'-(Pyridin-2-ylmethylene)diphenol HO OH (A) 100 mg

MM 0031.04 Imp. B (EP): 2-[(RS)-(4-Hydroxyphenyl)(pyridin-2-yl)methyl]phenol OH OH (A) 50 mg

MM 0031.02 Imp. C (EP): 4-[(RS)-(4-Hydroxyphenyl)(pyridin- HO O (A) 100 mg 2-yl)methyl]phenyl Acetate O

MM 0031.03 Imp. E (EP): 2-[(RS)-[4-(Acetyloxy)phenyl](pyridin- O (A) 50 mg 2-yl)methyl]phenyl Acetate O O

HO O ONa MM 0054.01 4-[(RS)-(4-Hydroxyphenyl)(pyridin-2-yl)- S (A) 100 mg methyl]phenyl Sodium Sulphate O O (4-[(Pyridin-2-yl)(4-hydroxyphenyl)methyl]- phenyl Sodium Sulphate) N

NaO O MM 0054.02 2-[(RS)-(Pyridin-2-yl)[4-(sulphonatooxy)- S (D) 50 mg phenyl]methyl]phenyl Disodium Sulphate O O (2,4'-[(Pyridin-2-yl)methylene]bisphenyl O ONa Bis(Sodium Sulphate)) N S O O

Bisoprolol Fumarate

MM 0460.00 Bisoprolol OH H (A) 100 mg O N

O O

OH OH MM 0460.08 Bisoprolol Fumarate H (A) 100 mg O N O x

O O O 2 HO

34 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit OH MM 0460.01 Imp. A (EP): (RS)-1-(4-Hydroxymethyl- H (A) 100 mg phenoxy)-3-isopropylaminopropan-2-ol O N

OH OH MM 0460.07 Imp. B (EP): (RS)-1-Isopropylamino-3-[4-(2- H (A) 100 mg propoxyethoxymethyl)phenoxy]propan-2-ol O N

O O OH OH MM 0460.15 Imp. C (EP): (RS)- H H (A) 100 mg 1-[4-[4-(2-Hydroxy- N O O N 3-isopropylaminopropoxy) benzyl]-phenoxy]- 3-isopropylaminopropan-2-ol OH MM 0460.21 Imp. G (EP): (2RS)-1-[4-[[(2-Isopropoxy- H (D) 100 mg ethoxy)methoxy]methyl]phenoxy]-3-iso- O N propylaminopropan-2-ol

O O O MM 0460.24 Imp. J (Pharmeuropa): (2RS)-3-[4-((2-Isopropoxy- OH (A) 100 mg O OH ethoxy)methyl)phenoxy]-1,2-propanediol O O

OH MM 0460.18 Imp. K (EP): 2-Isopropoxyethyl 4-[[(2RS)- H (A) 100 mg O N 2-Hydroxy-3-(isopropylamino)propyl]oxy]- O benzoate (Bisoprolol Ester) O

O Imp. L (EP) as Hydrochloride: 4-[[(2RS)-2- OH MM 0027.24 H (A) 100 mg Hydroxy-3-(isopropylamino)propyl]oxy]benz- O N aldehyde Hydrochloride (4-[(2RS)-2-Hydroxy- x HCl 3-[(1-methylethyl)amino]propoxy]benzaldehyde Hydrochloride) O MM 0460.02 Imp. M (Pharmeuropa): 4-[(2-Isopropoxyethoxy)methyl]phenol (A) 100 mg OH O O

OH MM 0460.25 Imp. N (EP): [(2RS)-1-[4-[(2-Ethoxyethoxy)- H (A) 100 mg O N methyl]phenoxy]-3-isopropylaminopropan-2-ol O O

OH MM 0460.05 Imp. Q (EP): (2RS)-1-(Isopropylamino)-3-[4-(2- H (A) 100 mg O N methoxyethoxy)methyl]phenoxypropan-2-ol O O

OH MM 0460.28 Imp. R (EP): (2RS)-1-(Isopropylamino)-3-(4- H (A) 50 mg methylphenoxy)propan-2-ol O N

MM 0460.14 Imp. S (EP): 4-Hydroxybenzaldehyde OH (C) 100 mg O MM 0460.17 Imp. T (EP): 4-[(3-Isopropyl-2-oxo-1,3-oxazolidin-5- O (A) 50 mg O yl)methoxy]benzaldehyde (Bisoprolol Oxazolidinone- N benzaldehyde) O

O OH MM 0460.27 (2RS)-4-[2-Hydroxy-3-(isopropylamino)propoxy]- H (A) 50 mg benzoic Acid Hydrochloride O N x HCl HO

O MM 0460.16 Imp. U (EP): 5-[[4-(Hydroxymethyl)phenoxy]- O (A) 50 mg O methyl]-3-isopropyl-1,3-oxazolidin-2-one N (Bisoprolol Oxazolidinonebenzylalcohol) O HO

O MM 0460.03 2-[4-(2-Isopropoxyethoxymethyl)phenoxymethyl]oxirane O (A) 100 mg

O O MM 0460.06 4-Hydroxybenzyl Alcohol OH (B) 100 mg HO

MM 0460.10 Fumaric Acid O (B) 100 mg HO OH O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 35 Pharmaceutical impurities

Code Product Code Unit New MM 0460.23 (2RS)-1-[4-((2-Hydroxyethoxy)methyl)phenoxy]-3-(isopropylamino)- O (A) 50 mg

2-propanol NH2

O Boldenone MM 0864.00 Boldenone OH (A) 100 mg

O Brimonidine Tartrate

N New MM 1324.00 Brimonidine Tartrate N OH O (A) 100 mg x HO N N N OH H H Br O OH Bromazepam

H O MM 0064.00 Bromazepam N (A) 100 mg [Controlled Substance] Br N

MM 0064.01 Imp. A (EP): (2-Amino-5-bromophenyl)(pyridin-2-yl)methanone NH2 (A) 100 mg O Br

O MM 0064.02 Imp. B (EP): N-[4-Bromo-2-(pyridin-2- Cl (A) 50 mg ylcarbonyl)phenyl]-2-chloroacetamide NH

O Br

H O MM 0064.09 Imp. C (EP): 7-Bromo-5-(6-methylpyridin-2-yl)-1,3-dihydro-2H- N (A) 50 mg 1,4-benzodiazepin-2-one Br N

H MM 0064.04 Imp. D (EP): 3-Amino-6-bromo-4-(pyridin- N O (A) 50 mg 2-yl)quinolin-2(1H)-one

Br NH2

O MM 0064.07 Imp. E (EP): 2-Bromo-N-[4-bromo-2-(pyridin- Br (A) 50 mg 2-ylcarbonyl)phenyl]acetamide NH

O Br

Bromhexine Hydrochloride MM 0065.00 Bromhexine Hydrochloride Br (A) 500 mg

x HCl N Br

NH2

Br MM 0005.01 Imp. A (EP): (2-Amino-3,5-dibromophenyl)methanol OH (A) 100 mg

NH2 Br

Br MM 0005.02 Imp. B (EP): 2-Amino-3,5-dibromobenzaldehyde O (A) 100 mg

NH2 Br MM 0065.02 Imp. C (EP): N-(2-Aminobenzyl)-N-methylcyclohexanamine (A) 100 mg N

NH2

36 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0065.03 Imp. D (EP) as Dihydrochloride: N-(2-Amino-5-bromobenzyl)-N- Br (A) 100 mg

methylcyclohexanamine Dihydrochloride x 2 HCl N

NH2 MM 0065.01 N-(2-Nitrobenzyl)-N-cyclohexyl-N-methylamine (A) 100 mg N

NO2 MM 0065.05 6,8-Dibromo-3-cyclohexyl-3,4-dihydro-2(1H)-quinazolinone Br (A) 100 mg

Br HN N

O MM 0065.09 Bromhexine N-Oxide Br (A) 100 mg

N Br O NH2 Bromisoval MM 1128.01 Ethyl 2-Bromoisovalerate O (A) 100 mg O Br Brompheniramine Maleate

MM 0060.00 Brompheniramine Maleate O (A) 500 mg N OH x OH N O Br

MM 0090.00 Imp. A (EP) as Maleate: Chlorphenamine Maleate O (A) 500 mg N OH x OH N O Cl

MM 1114.00 Imp. B (EP) as Maleate: Dexchlorpheniramine Maleate O (A) 100 mg N OH x OH N O Cl MM 0059.01 Imp. C (EP): (3RS)-N,N-Dimethyl-3-phenyl-3-(pyridin-2-yl)- (A) 100 mg propan-1-amine (Pheniramine) N

MM 0059.00 Imp. C (EP) as Maleate: (3RS)-N,N-Dimethyl- O (A) 100 mg N 3-phenyl-3-(pyridin-2-yl)propan-1-amine OH x Maleate (Pheniramine Maleate) OH N O MM 0060.12 Brompheniramine N-Oxide on request N

N O Br

MM 0060.16 Desmethylbrompheniramine Maleate O (A) 100 mg N OH x OH N H O Br Buclizine Hydrochloride MM 0380.04 Imp. A (BP): 1,4-Bis(4-chlorobenzhydryl)piperazine (A) 100 mg (1,4-Bis[(4-chlorophenyl)phenylmethyl]piperazine)

Cl N N Cl

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 37 Pharmaceutical impurities

Code Product Code Unit MM 0380.09 4-Chlorobenzhydrol Cl (B) 100 mg OH

MM 0380.10 4-Chlorobenzophenone Cl (B) 100 mg O

Cl MM 0380.01 1-(4-Chlorobenzhydryl)piperazine((RS)- NH (A) 100 mg 1-[(4-Chlorophenyl)phenylmethyl]piperazine) N

Budesonide MM 0204.01 Imp. A (EP): 11i,16h,17,21-Tetrahydroxy- O (A) 100 mg pregna-1,4-diene-3,20-dione (16h-Hydroxy- HO OH OH prednisolone) OH

O OH New MM 0204.02 Imp. B (EP): 16h,17-[(1RS)-Ethylidenebis(oxy)]- O (A) 50 mg i 11 ,21-dihydroxypregna-1,4-diene-3,20-dione HO O O

O Bufexamac

H MM 0179.00 Bufexamac N (A) 500 mg OH O O MM 0179.01 Imp. A (EP): 2-(4-Butoxyphenyl)acetic Acid OH (A) 100 mg O O MM 0179.02 Imp. B (EP): Methyl 2-(4-Butoxyphenyl)acetate O (A) 100 mg O O MM 0179.03 Imp. C (EP): Butyl 2-(4-Butoxyphenyl)acetate O (A) 100 mg O O

MM 0179.04 Imp. D (EP): 2-(4-Butoxyphenyl)acetamide NH2 (A) 100 mg O O MM 0179.05 4'-Butoxyacetophenone O (A) 100 mg

O MM 0179.06 Ethyl 2-(4-Butoxyphenyl)acetate O on request O O Buflomedil Hydrochloride

MM 0066.00 Buflomedil Hydrochloride O O (A) 500 mg N x HCl O O MM 0066.01 Imp. A (EP) as Hydrochloride: 4-(Pyrrolidin- OH O (A) 100 mg 1-yl)-1-(2-hydroxy-4,6-dimethoxyphenyl)- N x HCl butan-1-one Hydrochloride O O (o-Desmethyl-Buflomedil Hydrochloride)

MM 0066.02 Imp. B (EP) as Hydrochloride: 4-(Pyrrolidin-1-yl)- O O (A) 100 mg 1-(4-hydroxy-2,6-dimethoxyphenyl)butan-1-one Hydrochloride N x HCl (p-Desmethyl-Buflomedil Hydrochloride) HO O

MM 0066.03 4-(1-Pyrrolidino)butyronitrile N (C) 100 mg N

MM 0066.05 1,3,5-Trimethoxybenzene O (C) 100 mg

O O

38 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Bunolol Hydrochloride

OH MM 0642.00 Bunolol Hydrochloride H (A) 100 mg O N O x HCl

Buphenine Hydrochloride MM 0710.00 Buphenine Hydrochloride OH (A) 500 mg

x HCl HN HO

Bupivacaine Hydrochloride MM 0613.00 Bupivacaine Hydrochloride Monohydrate (A) 500 mg H N x HCl N x H2O O MM 0368.03 Imp. A (EP): N-(2,6-Dimethylphenyl)pyridine- (A) 100 mg H N 2-carboxamide N O

MM 0613.05 H (A) 50 mg Imp. E (EP) as Hydrochloride: 6-(Butylamino)-N- N N (2,6-dimethylphenyl)hexanamide Hydrochloride H O x HCl MM 0102.02 Imp. F (EP): 2,6-Dimethylaniline (B) 100 mg NH2

MM 0613.07 Bupivacaine N-Oxide (A) 100 mg H N N O O Bupropion Hydrochloride

O MM 0745.00 Bupropion Hydrochloride H (A) 100 mg Cl N x HCl

O MM 0745.02 2-(tert-Butylamino)-4'-chloropropiophenone Hydrochloride H (A) 100 mg N x HCl

O MM 0745.03 2-(tert-Butylamino)-3'-bromopropiophenone Hydrochloride H on request Br N x HCl

O MM 0745.05 2-(tert-Butylamino)propiophenone Hydrochloride H (A) 100 mg N x HCl

MM 0745.07 1-(3-Chlorophenyl)-1-hydroxy-2-propanone OH (D) 100 mg Cl O

MM 0745.08 3-Chloropropiophenone O (B) 100 mg Cl

Buspirone Hydrochloride

MM 0464.00 Buspirone Hydrochloride O N (A) 500 mg

N N N x HCl N O

MM 0464.02 Imp. A (EP) as Dihydrochloride: 2-(Piperazin- HN (A) 100 mg 1-yl)pyrimidine Dihydrochloride N N x 2 HCl

New MM 0464.04 Imp. C (EP): 2,2'-[Butane- N (A) 50 mg

1,4-diylbis(piperazine- N N 1,4-diyl)]dipyrimidine N N N N

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 39 Pharmaceutical impurities

Code Product Code Unit

New MM 0464.12 Imp. G (EP): 2,2'-(Piperazine-1,4-diyl)dipyrimidine N (A) 50 mg

N N N N

N New MM 0464.14 Imp. I (EP): 8-[4-[4-(5-Chloropyrimidin-2- O (A) 50 mg yl)-piperazin-1-yl]butyl]-8-azaspiro N [4.5]decane-7,9-dione N O N N

N Cl

MM 0464.08 Imp. K (EP): 8-Azaspiro[4,5]-decane-7,9-dione O (B) 100 mg

O New MM 0464.09 Imp. L (EP): 8-(4-Chlorobutyl)-8-azaspiro[4.5]- O (A) 50 mg decane-7,9-dione N Cl O New MM 0464.16 Imp. M (EP): 8-(4-Bromobutyl)-8-azaspiro[4.5]- O (A) 50 mg decane-7,9-dione N Br O Butalbital

H MM 0899.00 5,5-Diallybarbituric acid (Allobarbital) O N O (A) 100 mg [Controlled Substance] NH

O Butenafine Hydrochloride MM 1041.00 Butenafine Hydrochloride on request

N x HCl

Butetamate Citrate MM 0606.00 Butetamate Citrate O (A) 500 mg OH OH x O O N OH O OH O Butyl Parahydroxybenzoate MM 0496.00 Butyl Parahydroxybenzoate O (A) 500 mg O

HO MM 0045.01 Imp. A (EP): 4-Hydroxybenzoic Acid O (B) 100 mg OH

HO MM 0431.00 Imp. B (EP): Methyl 4-Hydroxybenzoate (Methyl O (A) 500 mg Parahydroxybenzoate) O

HO MM 0498.00 Imp. C (EP): Ethyl 4-Hydroxybenzoate (Ethyl Parahydroxybenzoate) O (A) 500 mg O

HO MM 0432.00 Imp. D (EP): Propyl 4-Hydroxybenzoate (Propyl O (A) 500 mg Parahydroxybenzoate) O HO MM 0496.05 Imp. E (Pharmeuropa): 2-Methylpropyl 4- O (A) 100 mg Hydroxybenzoate (Isobutyl Parahydroxybenzoate) O

40 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Butylhydroxytoluene MM 0679.00 Butylhydroxytoluene (A) 500 mg

Caffeine MM 0494.00 Caffeine O (A) 500 mg N N

O N N

O MM 0176.00 Imp. A (EP): Theophylline H (A) 500 mg N N

O N N

MM 0176.02 Imp. B (EP): N-(6-Amino-1,3-dimethyl-2,4-dioxo- O H (A) 100 mg N O 1,2,3,4-tetrahydropyrimidin- N

5-yl)formamide O N NH2

MM 0494.03 Imp. C (EP): 1,3,9-Trimethyl-3,9-dihydro- O (A) 50 mg 1H-purine-2,6-dione (Isocaffeine) N N O N N

MM 0577.00 Imp. D (EP): Theobromine O (A) 500 mg N HN

O N N

MM 0494.06 Imp. E (EP) as Nitrate: N,1-Dimethyl-4- O (A) 100 mg N (methylamino)-1H-imidazole-5-carbox- N x HNO3 amide Nitrate (Caffeidine Nitrate) H HN N

MM 0494.04 Imp. F (EP): 1,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione O (D) 50 mg N (Paraxanthine;1,7-Dimethylxanthine) N

O N N H Candesartan Cilexetil New MM 0776.01 Imp. A (Pharmeuropa): Ethyl 2-Ethoxy-1-[[2'- O (A) 100 mg O (1H-tetrazol-5-yl)-4-biphenylyl]methyl]-1H- N N benzimidazole-7-carboxylate N NH N

N O

New MM 0776.07 Trityl Candesartan Cilexetil (A) 100 mg O O O O O N N N N N

N O

New MM 0776.08 Trityl Candesartan O (A) 100 mg OH N N N N N N O

Capecitabine New MM 0992.02 2,3-O-Carbonyl-5-deoxy-5-fluoro- O (A) 100 mg N4-(pentyloxycarbonyl)cytidine HN O F N

O N O

O O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 41 Pharmaceutical impurities

Code Product Code Unit Captopril

OOH MM 0067.00 Captopril O (A) 500 mg

HS N

OOH MM 0067.01 Imp. A (EP): (2S,2'S)-1,1'-[Disulphanediyl-bis[(2S)- O (A) 100 mg NS 2-methyl-1-oxopropane-3,1-diyl]-bis[pyrrolidine- S N 2-carboxylic] Acid (Captopril-Disulphide) O HO O MM 0067.02 Imp. C (Pharmeuropa): (2RS)-2-Methyl-3-sulphanylpropanoic Acid O (A) 100 mg HS OH

MM 0067.06 Imp. D (Pharmeuropa): (2RS)-3-Bromo-2-methylpropanoic Acid O (A) 100 mg Br OH

O OH MM 0067.08 Imp. E (Pharmeuropa): (2S)-1-[2-Methylpropanoyl]- O (A) 100 mg pyrrolidine-2-carboxylic Acid N

OOH MM 0067.05 Imp. J (Pharmeuropa) as Hydrate: 1-[(2S)-3-(Acetylthio)- O O (A) 100 mg x H2O 2-methylpropanoyl]-L-proline Hydrate (S-Acetylcaptopril S N Hydrate) MM 0067.04 Imp. K (Pharmeuropa): (2S)-3-(Acetylthio)-2-methylpropanoic Acid O O (C) 100 mg S OH

MM 0067.15 Imp. N (Pharmeuropa): (2S,2'S)-3,3'-Disulphane- O (A) 50 mg HO S diylbis(2-methylpropanoic) Acid S OH O

OO MM 0067.03 Captopril Ethyl Ester O on request

HS N

Carbamazepine

MM 0076.00 Carbamazepine O (A) 250 mg

N NH2

MM 0076.04 Imp. A (EP): 10,11-Dihydro-5H-dibenzo[b,f]-azepine-5-carboxamide O (A) 100 mg (10,11-Dihydrocarbamazepine) N NH2

MM 0076.09 Imp. B (EP): 9-Methylacridine (A) 100 mg

MM 0076.12 Imp. C (EP): (5H-Dibenzo[b,f]azepin-5-yl-carbonyl)urea(N- O O (A) 100 mg Carbamoylcarbamazepine) N N NH2 H

MM 0076.08 Imp. D (EP): 5H-Dibenzo[b,f]azepine (Iminostilbene) (B) 100 mg

MM 0076.06 Imp. E (EP): 10,11-Dihydro-5H-dibenzo[b,f]-azepine (Iminodibenzyl) (B) 100 mg

MM 0076.01 Carbamazepine 10,11-Epoxide O (A) 100 mg

N NH2

42 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit

MM 0076.05 Imp. G (EP): 10-Bromo-5H-dibenzo[b,f]azepine- O (A) 100 mg 5-carboxamide (10-Bromocarbamazepine) N NH2

MM 0076.10 10-Hydroxy-10,11-dihydrocarbamazepine O (A) 100 mg

N NH2

MM 0076.17 Oxcarbazepine O (A) 100 mg

N NH2

O Carbasalate Calcium MM 0133.02 Imp. A (EP): 2-(Acetyloxy)benzoic Anhydride O (A) 100 mg (Acetylsalicylic Anhydride) OOO

O MM 0133.01 Imp. B (EP): 2-[[2-(Acetyloxy)benzoyl]oxy]benzoic Acid O (A) 100 mg (Acetylsalicylsalicylic Acid) OH O

O O

MM 0045.00 Imp. C (EP): Salicylic Acid O (A) 500 mg OH

OH MM 0133.03 Imp. D (EP): 2-[(2-Hydroxybenzoyl)oxy]- O (A) 100 mg benzoic Acid (Salicylsalicylic Acid) OH

O OH

Carbendazim

O MM 2500.00 Carbendazim H (A) 100 mg N O NH N

MM 2500.01 2,3-Diaminophenazine NNH2 (A) 100 mg

N NH2

MM 2500.02 2-Amino-3-hydroxyphenazine NNH2 (A) 100 mg

N OH Carbenicillin Sodium

O MM 0805.00 Carbenicillin Sodium ONa (A) 250 mg O O N

N S H H O ONa Carbocisteine MM 0236.00 Carbocisteine O (A) 500 mg HO SOH

O NH2 MM 0236.01 (S)-Carboxymethyl-L-cysteine O (A) 100 mg HO (R/S)-Sulphoxide SOH OONH2 MM 0236.02 Lactam of (S)-Carboxymethyl-L-cysteine O (A) 100 mg NH S OH

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 43 Pharmaceutical impurities

Code Product Code Unit MM 0236.03 L-Cysteinesulfinic Acid O (C) 100 mg HO SOH

O NH2 Carisoprodol

MM 0782.03 Imp. C (EP): 2-Methyl-2-propylpropane-1,3-diol HO OH (A) 100 mg

Carvedilol

OH MM 0291.00 Carvedilol H (A) 100 mg O N O O

MM 0291.02 Imp. B (EP): 1,1'-[[2-(2-Methoxyphenoxy) (A) 100 mg ethyl]nitrilo]bis[3-(9H-carbazol-4-yloxy) OH propan-2-ol] O NH OH O N O O

MM 0291.03 Imp. C (EP): (2RS)-1-[Benzyl[2-(2-methoxy- (A) 100 mg

phenoxy)ethyl]amino]-3-(9H-carbazol-4- OH yloxy)propan-2-ol O N O O

MM 0291.04 Imp. D (Pharmeuropa): Toluene (C) 100 mg

MM 0291.10 4-(2,3-Epoxypropoxy)carbazole O (A) 100 mg O

H2N MM 0291.11 2-(2-Methoxyphenoxy)ethylamine Hydrochloride O (A) 100 mg O x HCl

Cefaclor MM 0326.00 Cefaclor Monohydrate OOH (A) 100 mg O Cl NH2 N H x H2O N S H O

MM 0253.12 Imp. A (EP): (2R)-2-Amino-2-phenylacetic Acid NH2 (B) 100 mg (D-Phenylglycine) OH O MM 0253.08 Imp. F (EP): 3-Phenylpyrazin-2-ol NOH (A) 100 mg

Cefadroxil Monohydrate

MM 0232.09 Imp. A (EP): (2R)-2-Amino-2-(4-hydroxyphenyl)acetic Acid NH2 (B) 100 mg OH

O HO MM 0811.01 Imp. B (EP): (6R,7R)-7-Amino-3-methyl-8-oxo- O OH (A) 100 mg 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic O Acid (7-ADCA; 7-Aminodesacetoxycephalosporanic Acid) N S H2N H Cefalexin Monohydrate MM 0605.00 Cefalexin Monohydrate OOH (A) 500 mg O NH2 N H x H2O N S H O

44 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit

MM 0253.12 Imp. A (EP): (2R)-2-Amino-2-phenylacetic Acid NH2 (B) 100 mg (D-Phenylglycine) OH O MM 0811.01 Imp. B (EP): (6R,7R)-7-Amino-3-methyl-8-oxo-5-thia- O OH (A) 100 mg 1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid O (7-Aminodesacetoxycephalosporanic Acid; 7-ADCA) N S H2N H Cefazolin Sodium MM 0238.00 Cefazolin Sodium OONa (A) 100 mg O N S H N N S S N N H N O N N MM 0238.05 Imp. E (EP): 5-Methyl-1,3,4-thiadiazol-2-thiol (MMTD) SH (A) 100 mg S N N

OOH MM 0238.08 Imp. H (EP): (6R,7R)-3-[(Acetyloxy)methyl]-7-amino-8-oxo- O (A) 100 mg 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid (7-ACA) O N O

H2N S H Cefetamet MM 0811.01 7-Aminodesacetoxycephalosporanic Aicd O OH (A) 100 mg O N

S H2N H Cefoperazone Sodium MM 0853.03 Imp. C (EP): 1-Methyl-1H-tetrazole-5-thiol SH (A) 100 mg N N NN O OH MM 0238.08 Imp. E (EP): (6R,7R)-3-[(Acetyloxy)methyl]-7-amino-8-oxo- O (A) 100 mg 5-thia-1-azabicyclo- O [4.2.0]oct-2-ene-2-carboxylic Acid (7-ACA) N O S H2N H Cefradine MM 0811.01 Imp. A (EP): (6R,7R)-7-Amino-3-methyl-8-oxo- O OH (A) 100 mg 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic O Acid (7-Aminodeacetoxycephalosporanic Acid, N S 7-ADCA) H2N H Celecoxib

OO MM 0344.02 4-[5-[4-(Hydroxymethyl)phenyl]-3-(trifluoromethyl)-1H-pyrazol- S (D) 100 mg 1-yl]-benzenesulfonamide H2N N F N F F HO MM 0344.03 4-[1-[4-(Aminosulfonyl)phenyl]-3-(trifluoromethyl)-1H-pyrazol- OO (D) 100 mg S 5-yl]benzoic Acid H2N N F N F F HO

O Celiprolol Hydrochloride

O MM 0128.00 Celiprolol Hydrochloride OH (A) 100 mg H O N O x HCl N N H

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 45 Pharmaceutical impurities

Code Product Code Unit O MM 0128.01 Imp. A (EP): 1-[5-Amino-2-[(2RS)- OH (A) 100 mg H 3-[(1,1-dimethylethyl)amino]- O N 2-hydroxypropoxy]phenyl]ethanone

H2N O MM 0128.03 Imp. C (EP): 1-[3-Acetyl-4-[(2RS)- OH (A) 100 mg H 3-[(1,1-dimethylethyl)amino]- O N 2-hydroxypropoxy]phenyl]-3-(1,1-dimethylethyl)urea O N N H H O MM 0128.10 Imp. D (EP):3-[3-Acetyl-4-[(RS)-3-(diethylamino)- OH (D) 100 mg 2-hydroxypropoxy]phenyl]-1,1-diethylurea O N O

N N H

O O MM 0128.05 Imp. E (EP): 1,1'-[[(1,1-Dimethylethyl)- OH OH (D) 50 mg imino]bis[(2-hydroxypropane-1,3-diyl)- O N O oxy(3-acetyl- 1,4-phenylene)]]bis(3,3-diethylurea) HN NH

O N N O

MM 0128.07 Imp. F (EP): 3-(3-Acetyl-4-hydroxyphenyl)-1,1-diethylurea O (A) 100 mg OH O

N N H

MM 0128.06 Imp. G (EP): 3-[3-Acetyl-4-[[(RS)-oxiranyl]methoxy]phenyl]- O (A) 100 mg O 1,1-diethylurea O O

N N H

O MM 0128.04 Imp. H (EP): 3-[3-Acetyl-4-[(2RS)-3-bromo- OH (A) 100 mg 2-hydroxypropoxy]phenyl]-1,1-diethylurea (Bromhydrin O Br Compound) O N N H

MM 0128.11 3-Acetyl-4-hydroxyaniline Hydrochloride O (A) 100 mg

OH x HCl

H2N MM 0128.58 5-Acetamido-2-hydroxyacetophenone O (A) 100 mg OH O

N H Cethexonium Bromide

MM 0501.01 rac-trans-2-Dimethylaminocyclohexanol Hydrochloride N (A) 100 mg OH x HCl

and enantiomer Cetirizine Dihydrochloride MM 0380.00 Cetirizine Dihydrochloride O (A) 100 mg Cl O N OH N x 2 HCl

Cl MM 0380.01 Imp. A (EP): (RS)-1-[(4-Chlorophenyl)phenylmethyl]piperazine NH (A) 100 mg N

Cl OH MM 0380.02 Imp. B (EP) as Dihydrochloride: (RS)- N (A) 100 mg 2-[4-[(4-Chlorophenyl)phenylmethyl]- N O piperazin-1-yl]acetic Acid Dihydrochloride x 2 HCl

46 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0380.03 Imp. C (EP) as Dihydrochloride: (RS)-2-[2-[4-[(2-Chloro- O (A) 100 mg O phenyl)phenylmethyl]piperazin-1-yl]ethoxy]acetic Acid N OH Dihydrochloride N Cl x 2 HCl

MM 0380.04 Imp. D (EP): 1,4-Bis[(4-chlorophenyl)- (A) 100 mg phenylmethyl]piperazine

Cl N N Cl

Cl O OH MM 0380.05 Imp. E (EP) as Dihydrochloride: (RS)- N O (D) 100 mg 2-[2-[2-[4-[(4-Chlorophenyl)phenyl- N O methyl]piperazin-1-yl]ethoxy]ethoxy]- acetic Acid Dihydrochloride x 2 HCl (Ethoxycetirizine Dihydrochloride) MM 0380.06 Imp. F (EP) as Dihydrochloride: O (A) 100 mg O [2-[4-[Diphenylmethyl]piperazin-1-yl]ethoxy]acetic Acid N OH Dihydrochloride N x 2 HCl

Cl OH MM 0380.11 Imp. G (EP) as Dihydrochloride: 2-[4-[(RS)- N (A) 100 mg (4-Chlorophenyl)phenylmethyl]-piperazin-1-yl]ethanol N Dihydrochloride x 2 HCl

MM 0380.08 Isopropyl Ester of Cetirizine O (A) 100 mg Cl O N O N

MM 0380.09 4-Chlorobenzhydrol OH (B) 100 mg

Cl MM 0380.10 4-Chlorobenzophenone O (B) 100 mg

O MM 0380.13 Cetirizine N-Oxide O (A) 100 mg Cl O N OH N

MM 0380.15 Ethyl Ester of Cetirizine Dihydrochloride O (A) 100 mg Cl O N O N

x 2 HCl

New MM 0380.16 Methyl Ester of Cetirizine Dihydrochloride O (A) 100 mg Cl O N O N

x 2 HCl

New MM 0380.17 3-Chlorocetirizine Dihydrochloride ((RS)- O (A) 100 mg O 2-[2-[4-[(3-Chlorophenyl)phenyl-methyl]piperazin- N OH 1-yl]ethoxy]acetic AcidDihydrochloride) N Cl x 2 HCl

Chlorambucil MM 0821.00 Chlorambucil OH (A) 500 mg Cl O N

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 47 NEW

• Key references to • Metabolite standards FDA guidelines - labelled - unlabelled • Designed speciﬁcally for preclinical drug discovery • Enzyme inducers researchers • Enzyme transporter • Substrate and metabolites - substrates - inhibitors organised by metabolising enzyme • Model systems

Code Product Code Unit Chloramphenicol

OH NO2 MM 0516.00 Chloramphenicol O (A) 500 mg Cl N H Cl OH MM 0516.01 (D)-(-)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol OH NO2 (A) 100 mg

H2N OH Chlordiazepoxide Hydrochloride

H O MM 0028.02 Imp. A (EP): 7-Chloro-5-phenyl-1,3-dihydro- N (A) 100 mg 2H-1,4-benzodiazepin-2-one 4-Oxide (Demoxepam) Cl N O

N MM 0028.04 Imp. B (EP): 6-Chloro-2-(chloromethyl)-4-phenylquinazoline Cl (A) 100 mg 3-Oxide N Cl O

MM 0028.03 Imp. C (EP): (2-Amino-5-chlorophenyl)phenyl-methanone NH2 (B) 100 mg (Aminochlorobenzophenone) O Cl

Chlorhexidine Diacetate

Cl MM 0162.00 Chlorhexidine Diacetate NH NH (A) 500 mg H H H N N N N N N H H H NH NH Cl O x 2 OH

MM 0162.05 4-Chloroaniline NH2 (B) 100 mg

Cl H MM 0162.07 (4-Chlorophenyl)urea NNH2 (A) 100 mg

O Cl H MM 0162.08 (4-Chlorophenyl)guanidine Hydrochloride NNH2 (C) 50 mg x HCl NH Cl Chlorhexidine Dihydrochloride

H H H MM 0946.00 Chlorhexidine Dihydrochloride N N N (A) 500 mg

NH NH Cl x 2 HCl Cl NH NH

N N N H H H Chlormezanone MM 0017.00 Chlormezanone Cl (A) 250 mg OO S

O MM 0017.02 2-(4-Chlorophenyl)-3-methylperhydro-1,3-thiazin-4-one Cl on request S

O MM 0017.03 4-Chlorobenzaldehyde O (B) 100 mg Cl H Chlorobutanol Hemihydrate

OH MM 0535.00 Chlorobutanol Hemihydrate Cl (A) 500 mg x ½ H2O Cl Cl

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 49 Pharmaceutical impurities

Code Product Code Unit Chlorocresol MM 0459.00 Chlorocresol OH (A) 500 mg

Chlorphenamine Maleate MM 0090.00 Chlorphenamine Maleate Cl (A) 500 mg O

OH x N OH N O MM 0090.03 Imp. A (EP) as Dihydrochloride: 2-(4- Cl (D) 100 mg

Chlorophenyl)-4-(dimethylamino)-2- N [2-(dimethylamino)ethyl]butanenitrile x 2 HCl

Dihydrochloride N N

H MM 0090.04 Imp. B (EP): N-(Pyridin-2-yl)pyridin-2-amine N N (A) 100 mg (2,2'-Dipyridylamine) N MM 0090.13 Imp. C (EP) as Maleate: (3RS)-3-(4-Chloro- Cl (A) 100 mg phenyl)-N-methyl-3-(pyridin-2-yl)propan-1- O OH amine Maleate x OH N NH O

Cl MM 0090.05 Imp. D (EP) as Maleate: (2RS)-2-(4-Chloro- O (D) 100 mg phenyl)-4-(dimethylamino)-2-(pyridin-2- N OH yl)butanenitrile Maleate x N OH N O

MM 0090.11 Chlorphenamine N-Oxide Dihydrochloride Cl (A) 100 mg

x 2 HCl N N O

Chlorpromazine Hydrochloride MM 0420.00 Chlorpromazine Hydrochloride (A) 500 mg

N N x HCl S

Cl MM 0420.01 Imp. A (EP): 3-(2-Chloro-10H-phenothiazin-10-yl)-N,N- (A) 100 mg

dimethylpropan-1-amine S-Oxide (Chlorpromazine Sulphoxide) N N S O

Cl MM 0420.06 Imp. B (EP) as Dihydrochloride: N-[3-(2-Chloro-10H- (A) 100 mg

phenothiazin-10-yl)propyl]-N,N',N'-trimethylpropane- N N N 1,2-diamine Dihydrochloride S x 2 HCl

Cl MM 0290.00 Imp. C (EP) as Hydrochloride: Promazine Hydrochloride (A) 500 mg

N N x HCl S

MM 0420.07 Imp. D (EP) as Hydrochloride: 3-(2-Chloro-10H-phenothiazin- (A) 100 mg

10-yl)-N-methylpropan-1-amine Hydrochloride N NH x HCl (Desmethylchlorpromazine Hydrochloride) S

Cl MM 0420.04 Imp. E (EP): 2-Chloro-10H-phenothiazine (A) 100 mg

NH S

50 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit

MM 0420.02 Chlorpromazine Sulphoxide N-Oxide Maleate O (B) 10 mg

N N OH O x S OH O O Cl Chlorprothixene Hydrochloride New MM 1321.01 Imp. A (EP): (RS)-2-Chloro-9-[3-(dimethylamino)- (A) 100 mg OH propyl]-9H-thioxanthen-9-ol N S

Cl New MM 1321.05 Imp. E (EP): 2-Chloro-9H-thioxanthen-9-one (A) 100 mg O

Cl Chlorquinaldol MM 0390.00 Chlorquinaldol OH (A) 500 mg Cl N

Cl Chlortalidone

O MM 0297.00 Chlortalidone HN (A) 250 mg O O HO S H2N

Cl Chlortetracycline Hydrochloride

OH O OH O O MM 0607.00 Chlortetracycline Hydrochloride OH (A) 500 mg

NH2 H H x HCl OH Cl OH N

OH O OH O O MM 0636.00 Imp. B (EP) as Hydrochloride: Demeclocycline OH (A) 250 mg Hydrochloride NH2 H H x HCl OH Cl OH N

OH O OH O O MM 0452.00 Tetracycline Hydrochloride OH (A) 500 mg

NH2 H H x HCl OH HO N Cholecalciferol MM 0249.02 Imp. B (EP): Cholesta-5,7-dien-3i-ol (A) 100 mg (7,8-Didehydrocholesterol; Provitamin D3)

HO Ciclopirox Olamine

MM 0418.00 Ciclopirox Olamine OH (A) 250 mg NO x OH H2N

MM 0418.03 Imp. C (EP): 6-Cyclohexyl-4-methylpyridin-2(1H)-one (A) 50 mg H NO

Cimetidine Hydrochloride MM 0020.00 Cimetidine N (A) 500 mg

N N HN S N N H H

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 51 Pharmaceutical impurities

Code Product Code Unit MM 0020.08 Imp. A (EP): 3-Cyano-2-methyl-1-[2- N (A) 100 mg [[(5-methyl-1H-imidazol-4-yl)methyl]- N N sulphanyl]ethyl]isothiourea HN S N S H MM 0020.12 Imp. B (EP): 3-Cyano-2-methyl-1-[2-[[(5-methyl-1H-imidazol- N (A) 100 mg 4-yl)methyl]-sulphanyl]ethyl]isourea N N HN S N O H

MM 0020.03 Imp. C (EP) as Dihydrochloride: O NH2 (A) 100 mg

1-[(Methylamino)[[2-[[(5-methyl-1H-imidazol-4-yl)- N N x 2 HCl HN methyl]sulphanyl]ethyl]amino]- S N N methylene]urea Dihydrochloride (Cimetidine Amide H H Dihydrochloride) N NH MM 0020.06 Imp. D (EP) as Dihydrochloride:1-Methyl- HN (A) 100 mg S x 2 HCl 3-[2-[[(5-methyl-1H-imidazol- N N 4-yl)methyl]sulphanyl]ethyl]guanidine Dihydrochloride H H MM 0020.04 Imp. E (EP): 2-Cyano-1-methyl-3-[2-[[(5-methyl-1H-imidazol- N (A) 100 mg 4-yl)methyl]sulphinyl]ethyl]guanidine (Cimetidine Sulphoxide) N O N HN S N N H H MM 0020.15 Imp. G (EP): 2-Cyano-1,3-dimethylguanidine N (A) 100 mg

N N H H MM 0020.07 Imp. H (EP): 1,1'-(Disulphanediyldiethylene)bis N (A) 100 mg (2-cyano-3-methylguanidine) N H H S N N N N S H H N

N Imp. J (EP) as Dihydrobromide: 2-[[(5-Methyl-1H-imidazol- N MM 0020.50 HN (A) 100 mg 4-yl)methyl]-sulphanyl]ethanamine Dihydrobromide S x 2 HBr NH2

MM 0020.10 1,1-Dimethyl-3-cyanoguanidine H (A) 100 mg N N N NH

H MM 0056.01 Cyanoguanidine H2N N (B) 100 mg N NH Cinchocaine Hydrochloride

MM 0604.00 Cinchocaine Hydrochloride O (A) 500 mg O N N N H x HCl

MM 0604.02 Imp. B (EP): 2-Hydroxyquinoline-4-carboxylic Acid O (A) 100 mg HO OH N

MM 0604.05 Cinchocaine N-Oxide O (A) 100 mg O N N H O N

Cinnarizine

MM 1038.01 Imp. A (EP): 1-(Diphenylmethyl)piperazine NH (A) 100 mg N

52 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 1038.03 Imp. B (EP): (Z)-1-(Diphenylmethyl)-4-(3- (A) 100 mg phenylprop-2-enyl)piperazine

N N

MM 1038.04 Imp. C (EP): (4-(Diphenylmethyl)-1,1-bis[(E)- N+ (A) 100 mg 3-phenylprop-2-enyl]piperazinium Chloride N Cl-

MM 1038.06 Imp. E (EP): 1,4-Bis(diphenylmethyl)piperazine (A) 100 mg

N N

Ciprofloxacin Hydrochloride

MM 0018.06 Ciprofloxacin Hydrochloride Monohydrate HN (A) 500 mg N N x HCl x H2O OH F O O MM 0018.01 Imp. A (EP): 7-Chloro-1-cyclopropyl-6-fluoro-4-oxo- (A) 100 mg 1,4-dihydroquinoline-3-carboxylic Acid (Fluoroquinolonic Acid) Cl N

OH F O O

MM 0018.05 Imp. B (EP): 1-Cyclopropyl-4-oxo-7-(piperazin-1-yl)- HN (A) 100 mg 1,4-dihydroquinoline-3-carboxylic Acid (Desfluoro Compound) N N

O O MM 0018.04 Imp. C (EP): 7-(2-Aminoethylamino)-1-cyclopropyl-6-fluoro- (D) 50 mg H 4-oxo-1,4-dihydroquinoline-3-carboxylic Acid (Ethylenediamine N N H2N Compound) OH F O O MM 0018.02 Imp. D (EP): 7-Chloro-1-cyclopropyl-4-oxo-6-(piperazin-1-yl)- (D) 50 mg 1,4-dihydroquinoline-3-carboxylic Acid Cl N

OH N HN O O

MM 0018.03 Imp. E (EP): 1-Cyclopropyl-6-fluoro-7-(piperazin-1-yl)-quinolin-4(1H)- HN (A) 100 mg one (Decarboxylated Compound) N N

F O MM 0018.10 6-(2-Aminoethylamino)-7-chloro-1-cyclopropyl-4-oxo- (D) 100 mg

1,4-dihydroquinoline-3-carboxylic Acid Hydrochloride Cl N x HCl

H2N OH N H O O Citalopram Hydrobromide MM 0242.00 Citalopram Hydrobromide F (A) 250 mg

x HBr

N O

N MM 0242.14 Imp. A (EP): (1RS)-1-[3-(Dimethylamino)- F (A) 100 mg propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide (Citalopram- Amide) N O H2N

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 53 Pharmaceutical impurities

Code Product Code Unit MM 0242.17 Imp. C (EP): (3RS)-6-Cyano-3-[3-(dimethyl- F (A) 100 mg amino)propyl]-3-(4-fluorophenyl)isobenzofuran-1(3H)-one

N O

N O MM 0242.09 Imp. D (EP) as Hydrochloride: (1RS)-1-(4- F (A) 100 mg Fluorophenyl)-1-[3-(methylamino)propyl]-1,3- x HCl dihydroisobenzofuran-5-carbonitrile Hydro- chloride (Desmethylcitalopram Hydrochloride) N O H

N MM 0242.12 Imp. E (EP) as Oxalate: 3-[(1RS)-5-Chloro- F (A) 50 mg 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl]- HO O N,N-dimethylpropan-1-amine Oxalate x

N HO O O Cl Citric Acid Anhydrous MM 0988.00 Citric Acid Anhydrous O OH (A) 250 mg O HO O

HO OH Citric Acid Monohydrate MM 0575.00 Citric Acid Monohydrate O OH (A) 500 mg O O HO x H2O HO OH Clarithromycin MM 0057.00 Clarithromycin O on request

OH O N OH HO O O O

O O O

O OH

MM 0057.05 Imp. E (EP): 6,11-Di-O-methylerythromycin A O (D) 100 mg

OH O O OO

O N OH OO O OH O

Clindamycin Hydrochloride

New MM 0259.00 Clindamycin Hydrochloride N Cl (A) 100 mg H N

O HO O x HCl OH S OH Clioquinol MM 0312.00 Clioquinol OH (A) 500 mg I N

Cl MM 0312.01 Imp. A (EP): 5-Chloroquinolin-8-ol OH (B) 100 mg N

Cl MM 0312.02 Imp. B (EP): 5,7-Dichloroquinolin-8-ol OH (B) 100 mg Cl N

54 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0312.03 Imp. C (EP): 5,7-Diiodoquinolin-8-ol OH (B) 100 mg I N

I Clobenzorex Hydrochloride

MM 0649.00 Clobenzorex Hydrochloride H (A) 500 mg N x HCl Cl Clobetasol Propionate

Cl MM 0769.00 Clobetasol Propionate O O (A) 100 mg

HO O

F O Cl MM 0200.01 Imp. G (EP): 21-Chloro-9-fluoro-11i,17-dihydroxy-16i- O (A) 100 mg methylpregna-1,4-diene-3,20-dione (Clobetasol) HO OH

F O MM 0202.04 Imp. K (EP):9-Fluoro-11i,17-dihydroxy- O (A) 100 mg i O 16 -methyl-3,20-dioxopregna-1,4-dien- O 21-yl Propanoate (Betamethasone 21- Propionate) HO OH

F O Clobutinol Hydrochloride MM 0038.00 Clobutinol Hydrochloride on request N x HCl OH Cl MM 0038.01 1-Dimethylamino-2-methylbutan-3-one (A) 100 mg N

O Clomifene Citrate

MM 0650.00 Clomifene Citrate O (A) 250 mg O OH N OH x Cl O OH OH and Z-Isomer O

MM 0650.01 Clomifene N-Oxide Hydrochloride (A) 100 mg O N O Cl and Z-Isomer x HCl

MM 0650.03 Desethylclomifene Hydrochloride (A) 100 mg O N H Cl and Z-Isomer x HCl

Clomipramine Hydrochloride MM 0545.00 Clomipramine Hydrochloride Cl (A) 500 mg

N N x HCl

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 55 Pharmaceutical impurities

Code Product Code Unit MM 0545.01 Imp. A (EP) as Dihydrochloride: N-[3-(3- Cl on request Chloro-10,11-dihydro-5H-dibenzo[b,f]azepin- 5-yl)propyl]-N,N',N'-trimethylpropane-1,3- diamine Dihydrochloride N N N

x 2 HCl

MM 0077.00 Imp. B (EP) as Hydrochloride: Imipramine Hydrochloride (A) 500 mg

N N x HCl

MM 0545.03 Imp. C (EP) as Hydrochloride: 3-(3-Chloro-5H- Cl (C) 10 mg dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine Hydrochloride N N x HCl

MM 0545.04 Imp. D (EP) as Hydrochloride: 3-(3,7-Dichloro- Cl (A) 10 mg 10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N- dimethylpropan-1-amine Hydrochloride N N x HCl

Cl MM 0076.06 Imp. E (EP): 10,11-Dihydro-5H-dibenzo[b,f]-azepine (Iminodibenzyl) (B) 100 mg

MM 0545.06 Imp. F (EP): 3-Chloro-10,11-dihydro-5H-dibenzo[b,f]azepine Cl (A) 100 mg

MM 0545.07 Imp. G (EP): 3-Chloro-5-(prop-2-enyl)-10,11-dihydro-5H- Cl (C) 50 mg dibenzo[b,f]azepine

MM 0545.08 Desmethylclomipramine Hydrochloride Cl (A) 100 mg

N N x HCl H

MM 0545.09 Clomipramine N-Oxide Cl on request

N N O

MM 0545.13 3-Chloro-10-[3(dimethylamino)propyl]-9-acridanone Cl (A) 100 mg

N N

Clonazepam

New MM 0945.01 Imp. A (EP): (2-Amino-5-nitrophenyl)(2- NH2 (A) 100 mg chlorophenyl)methanone O O2N Cl

56 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit H New MM 0945.02 Imp. B (EP): 3-Amino-4-(2-chlorophenyl)-6-nitroquinolin-2(1H)-one N O (A) 50 mg

O2N NH2 Cl

New MM 0945.04 Methylclonazepam O (A) 50 mg N

O2N N

O New MM 0945.05 2-Bromo-2'-(2-chlorobenzoyl)-4'-nitroacetanilide Br (A) 50 mg NH

O O2N Cl

MM 0945.01 Imp. A (EP): (2-Amino-5-nitrophenyl)(2- NH2 (A) 100 mg chlorophenyl)methanone O O2N Cl

Clonidine Hydrochloride

Cl MM 0983.00 Clonidine Hydrochloride HN (A) 100 mg x HCl N N H Cl MM 0983.04 Imp. A (EP): 1-Acetylimidazolidin-2-one HN (A) 100 mg O N

O Cl New MM 0983.03 Imp. B (EP): 1-Acetyl-2-[(2,6-dichloro- N (A) 50 mg phenyl)amino]-4,5-dihydro-1H-imidazole N N H Cl O MM 0006.21 Imp. C (EP): 2,6-Dichloroaniline Cl (B) 100 mg NH2

Cl Cl MM 0983.02 1-(2,6-Dichlorophenyl)thiourea S (A) 100 mg

N NH2 H Cl Clopidogrel Hydrogen Sulphate MM 0455.10 Clopidogrel Hydrogen Sulphate OO (A) 100 mg x H SO N 2 4

S Cl MM 0455.09 Clopidogrel Alcohol OH (D) 100 mg

S Cl MM 0455.13 Imp. B (Pharmeuropa) as Racemate Hydrogen OO (A) 100 mg

Sulphate: Methyl (2RS)-(2-Chlorophenyl)[4,7- S x H2SO4 dihydrothieno[2,3-c]pyridin-6(5H)-yl]ethanoate N Hydrogen Sulphate Cl MM 0455.12 Imp. C (Pharmeuropa) as Hydrogen Sulphate: OO (A) 100 mg

Methyl (2R)-(2-Chlorophenyl)[6,7-dihydrothieno x H2SO4 [3,2-c]pyridin-5(4H)-yl]ethanoate Hydrogen N Sulphate ((R)-Clopidogrel Hydrogen Sulphate) S Cl Clotrimazole MM 0015.00 Clotrimazole Cl (A) 500 mg

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 57 Pharmaceutical impurities

Code Product Code Unit MM 0015.01 Imp. A (EP): (2-Chlorophenyl)diphenylmethanol (A) 100 mg

Cl OH

MM 0015.10 Imp. B (EP): 1-[(4-Chlorophenyl)diphenylmethyl]-1H-imidazole Cl (A) 100 mg

N MM 0015.03 Imp. C (EP): 1-Chloro-2-(chlorodiphenylmethyl)benzene (A) 100 mg

Cl Cl H MM 0015.02 Imp. D (EP): Imidazole N (B) 100 mg

N MM 0015.06 Imp. E (EP): (2-Chlorophenyl)phenylmethanone (A) 100 mg (2-Chlorobenzophenone)

Cl O MM 0015.11 Imp. F (EP): 1-(Triphenylmethyl)-1H-imidazole (A) 100 mg (Deschloroclotrimazole)

N MM 0015.04 (2-Chlorophenyl)diphenylmethane (A) 100 mg

MM 0015.05 (2-Chlorophenyl)diphenylmethyl Ethyl Ether (A) 100 mg

Cl O

MM 0015.07 (2-Chlorophenyl)phenyldichloromethane (A) 100 mg

Cl Cl Cl MM 0015.08 (2-Chlorophenyl)trichlormethane (A) 100 mg Cl

Cl Cl Cl MM 0015.09 1-[(2-Chlorophenyl)diphenylmethyl]-1H-pyrazole (C) 50 mg

Cl N N

Cloxacillin Sodium

MM 0682.00 Cloxacillin Sodium Monohydrate Cl O (A) 500 mg ONa O N N H x H2O O N S H O O MM 0026.04 Imp. C (EP): (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia- OH (B) 100 mg 1-azabicyclo[3.2.0]heptane-2-carboxylic Acid (6-Aminopenicillanic O Acid) N S H2N H MM 0682.04 Imp. D (EP): 3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylic Acid Cl (A) 100 mg N O OH

O Cloxiquine MM 0391.00 Cloxiquine OH (A) 500 mg N

58 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Clozapine

MM 0480.00 Clozapine Cl N (A) 100 mg N N

Cl MM 0480.01 Imp. A (EP): 8-Chloro-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin- H (A) 100 mg 11-one N O HN

MM 0480.03 Imp. C (EP): 8-Chloro-11-(piperazin-1-yl)-5H- Cl NH (A) 100 mg dibenzo[b,e][1,4]diazepine N N

Codeine

MM 0442.00 Codeine Phosphate Hemihydrate N (A) 100 mg [Controlled Substance] x H3PO4 x ½ H2O

O O OH

MM 0004.00 Codeine Monohydrate N (A) 100 mg [Controlled Substance] x H2O

O O OH h h MM 0004.03 Imp. A (EP): 7,8-Didehydro-4,5 -epoxy-3,6 -dimethoxy- N (A) 100 mg 17-methylmorphinan (O-Methylcodeine) [Controlled Substance]

O O O

MM 0037.00 Imp. B (EP) as Hydrochloride Trihydrate: Morphine N (A) 250 mg Hydrochloride Trihydrate

[Controlled Substance] x HCl x 3 H2O

HO O OH MM 0280.00 Imp. B (EP) as Hemisulphate Pentahemihydrate: (A) 250 mg N Morphine Hemisulphate Pentahemihydrate

[Controlled Substance] x H2SO4x 5 H2O

HO O OH 2 h h MM 0037.02 Imp. C (EP): 7,7',8,8'-Tetradehydro-4,5 :4',5' -diepoxy- N (A) 100 mg 3,3'-dimethoxy-17,17'-dimethyl-2,2'-bimorphinanyl-6h,6'h- HOO O diol (Codeine Dimer; Dimethyl Pseudomorphine)

O O OH N

MM 0004.01 Codeine N-Oxide O (A) 250 mg N [Controlled Substance]

O O OH

MM 0004.02 Codeinone N (A) 100 mg

O O O

MM 0004.04 Codeimethine N (C) 50 mg

O O OH MM 0004.05 Norcodeine HN (A) 100 mg [Controlled Substance]

O O OH

MM 0004.06 Acetylcodeine N (A) 100 mg [Controlled Substance]

O O O O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 59 Pharmaceutical impurities

Code Product Code Unit

MM 0004.08 Isocodeine N (A) 100 mg [Controlled Substance]

O O OH

MM 0037.01 Pseudomorphine N (A) 100 mg HOO OH

HO O OH N

Colchicine MM 1083.00 Colchicine O (A) 100 mg NH O O O O O MM 1083.04 Imp. D (EP): N-[(7S,12aS)-3-(i-D-Glucopyranosyloxy)- HO (A) 100 mg O 1,2,10-trimethoxy-9-oxo- O OH 5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide NH HO (Colchicoside) O OH O O O O Cortisone MM 0214.00 Cortisone O (A) 500 mg OH O OH

O Cortisone Acetate

O MM 0186.00 Cortisone Acetate O (A) 500 mg O O OH

O MM 0187.00 Imp. A (EP): Hydrocortisone Acetate O (A) 500 mg O HO OH

O Cyclizine Hydrochloride

New MM 1265.01 Imp. A (EP): 1-Methylpiperazine N (A) 100 mg HN MM 0490.02 Imp. B (EP): Diphenylmethanol (Benzhydrol) (B) 100 mg OH

Cyclobenzaprine Hydrochloride MM 0062.02 Cyclobenzaprine Hydrochloride (A) 100 mg

N x HCl

Cyclopentolate Hydrochloride

MM 0580.00 Cyclopentolate Hydrochloride O (A) 500 mg N O x HCl HO

MM 0580.01 Imp. A (EP): (2RS)-(1-Hydroxycyclopentyl)(phenyl)acetic Acid O (A) 100 mg

OH HO

60 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit

MM 0160.03 Imp. B (EP): Phenylacetic Acid [Drug Precursor] O (B) 100 mg

MM 0580.03 Imp. C (EP) as Hydrochloride: 2-(Dimethylamino)ethyl O (A) 100 mg x HCl N Phenylacetate Hydrochloride O Cynarine MM 0048.01 3,4-Dihydroxycinnamic Acid (Caffeic Acid) O (B) 100 mg HO OH

HO Cyproheptadine Hydrochloride

MM 0609.00 Cyproheptadine Hydrochloride Sesquihydrate N (A) 500 mg

1 x HCl x 1 /2 H2O

New MM 0609.01 Imp. A (EP): 5H-Dibenzo[a,d][7]annulene (A) 50 mg (Dibenzocycloheptene)

MM 0062.01 Imp. B (EP): 10,11-Dihydro-5H-dibenzo[a,d][7]- (B) 100 mg annulen-5-one (Dibenzosuberone) O

New MM 0609.07 Imp. C (EP) as Hydrochloride: 5-(1-Methyl- N (A) 50 mg piperidin-4-yl)-5H-dibenzo[a,d][7]annulen-5- OH ol Hydrochloride x HCl

MM 0609.02 5H-Dibenzo[a,d]cyclohepten-5-one (Dibenzosuberenone) (C) 100 mg O

MM 0609.04 Demethylcyproheptadine Hydrochloride NH (A) 100 mg

x HCl

MM 0609.05 Cyproheptadine -N-Oxide O (A) 100 mg N

MM 0609.06 Cyproheptadine !-N-Oxide O (A) 100 mg N

Cyproterone Acetate MM 0215.00 Cyproterone Acetate O (A) 250 mg O

O Cl Dacarbazine New N MM 1289.02 Imp. B (EP): 5-Amino-1H-imidazole-4-carboxamide HN (A) 100 mg NH2

H2N O H MM 0056.06 Imp. D (EP) as Hydrochloride: N-Methylmethanamine N x HCl (C) 100 mg Hydrochloride

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 61 Pharmaceutical impurities

Code Product Code Unit DDT MM 2513.01 2,2-Bis(4-chlorophenyl)-1-chloroethane Cl (A) 100 mg

Cl Cl MM 2513.02 1-Chloro-3-[1-(4-chlorophenyl)ethyl]benzene (A) 100 mg Cl

Cl MM 2513.05 1,1-Bis(4-chlorophenyl)ethane (A) 100 mg

Cl Cl Dembrexine Hydrochloride Monohydrate New MM 1200.03 Imp. C (EP): 3,5-Dibromo-2-hydroxybenzaldehyde O (A) 100 mg OH

Br Br MM 1200.04 Imp. D (EP): 2-Hydroxybenzaldehyde O (A) 100 mg (Salicylaldehyde) OH

New MM 1200.05 Imp. E (EP): 2,4,6-Tribromophenol Br (A) 100 mg OH

Br Br Demeclocycline Hydrochloride

OH O OH O O MM 0636.00 Demeclocycline Hydrochloride OH (A) 250 mg

NH2 H H x HCl OH Cl OH N Desipramine Hydrochloride MM 0589.00 Desipramine Hydrochloride (A) 250 mg

N N x HCl H

MM 0077.00 Imipramine Hydrochloride (A) 500 mg

N N x HCl

MM 0076.06 Iminodibenzyl (B) 100 mg

Dexamethasone MM 0213.00 Dexamethasone O (A) 250 mg OH HO OH

F O MM 0200.00 Imp. B (EP): Betamethasone O (A) 250 mg OH HO OH

F O MM 0213.01 Imp. C (EP): 9-h-Fluoro-11i,17h,21- O (D) 50 mg OH trihydroxy-16h-methylpregn-4-ene-3,20-dione HO OH

F O

62 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit O MM 0445.00 Imp. G (EP): Dexamethasone Acetate O (A) 250 mg O HO OH

F O Dexamethasone Acetate

O MM 0445.00 Dexamethasone Acetate O (A) 250 mg O HO OH

F O MM 0213.00 Imp. A (EP): 9-Fluoro-11i,17,21-trihydroxy- O (A) 250 mg OH 16h-methylpregna-1,4-diene-3,20-dione HO OH (Dexamethasone) F O O MM 0201.00 Imp. D (EP): 9-Fluoro-11i,17-dihydroxy-16i- O (A) 250 mg methyl-3,20-dioxopregna-1,4-dien-21-yl Acetate O HO (Betamethasone Acetate) OH

F O Dexamethasone Sodium Phosphate

O O MM 0210.00 Dexamethasone Sodium Phosphate ONa (A) 250 mg P HO O OH ONa

F O MM 0213.00 Imp. A (EP): Dexamethasone O (A) 250 mg OH HO OH

F O

O O MM 0303.00 Imp. B (EP): Betamethasone Sodium Phosphate ONa on request P HO O OH ONa

F O Dexchlorpheniramine Maleate MM 1114.00 Dexchlorpheniramine Maleate Cl (A) 100 mg O

OH x OH N N O

MM 0059.00 Imp. A (EP) as Maleate: (3RS)-N,N-Dimethyl-3- O (A) 100 mg

phenyl-3-(pyridin-2-yl)propan-1-amine Maleate OH x (Pheniramine Maleate) N OH N O Dextromethorphan Hydrobromide

MM 0033.00 Dextromethorphan Hydrobromide Monohydrate N (A) 500 mg

x HBr x H2O

O MM 0033.10 Imp. A (EP) as Hydrochloride: ent-3-Methoxymorphinan HN (A) 100 mg Hydrochloride x HCl

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 63 Pharmaceutical impurities

Code Product Code Unit

MM 0033.09 Imp. B (EP) as (L)-Tartrate: ent-17-Methylmorphinan- N (A) 100 mg 3-ol (L)-Tartrate OH O HO x OH O OH HO

MM 0033.02 Imp. C (EP): ent-3-Methoxy-17-methylmorphinan-10-one O N (D) 100 mg

O MM 0033.11 Dextromethorphan N-Oxide Hydrochloride N (A) 100 mg

x HCl

O Dextropropoxyphene Hydrochloride

MM 0098.01 Dextropropoxyphene Hydrochloride N (A) 50 mg

[Controlled Substance] O x HCl O

MM 0098.00 Dextropropoxyphene N (A) 50 mg

[Controlled Substance] O

MM 0098.06 Imp. A (EP): (2S,3R)-4-(Dimethylamino)-1,2-diphenyl-3-methylbutan- N (A) 100 mg 2-ol

MM 0098.07 Imp. B (EP) as Hydrochloride: (1S,2R)-1- N (A) 100 mg

Benzyl-3-(dimethylamino)-2-methyl-1- O phenylpropyl Acetate Hydrochloride x HCl (Acetoxyphene Hydrochloride) O

MM 0098.08 Imp. C: (EP) as Hydrochloride: (1S,2R)-1- N (A) 50 mg

Benzyl-3-(dimethylamino)-2-methyl-1-phenyl- O propyl Butanoate Hydrochloride (Butyroxy- x HCl phene Hydrochloride) O

MM 0291.04 Toluene (C) 100 mg

Diazepam

MM 0023.00 Diazepam O (A) 100 mg N [Controlled Substance] Cl N

H O MM 0023.02 Imp. A (EP): 7-Chloro-5-phenyl-1,3-dihydro-2H- N (A) 100 mg 1,4-benzodiazepin-2-one (Nordazepam) [Controlled Substance] Cl N

O MM 0023.04 Imp. B (EP): 2-Chloro-N-(4-chloro-2-benzoylphenyl)-N- Cl (A) 100 mg methylacetamide N

O Cl

64 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0023.03 Imp. C (EP): 3-Amino-6-chloro-1-methyl-4-phenylquinolin-2(1H)- (A) 100 mg N O one

Cl NH2

MM 0023.01 Imp. D (EP): [5-Chloro-2-(methylamino)phenyl]phenylmethanone (B) 100 mg NH (5-Chloro-2-(methylamino)benzophenone) O Cl

O MM 0023.05 2'-Benzoyl-2,4'-dichloroacetanilide Cl (A) 100 mg NH

O Cl

Dibutyl Sebacate MM 0925.00 Dibutyl Sebacate O O (A) 500 mg

O O Dichlorobenzyl Alcohol

MM 0739.01 Bis-(2,4-dichlorobenzyl)Ether O (A) 100 mg

Cl Cl Cl Cl Diclofenac Sodium MM 0006.00 Diclofenac Sodium OONa (A) 500 mg

NH Cl Cl

MM 0006.01 Imp. A (EP): 1-(2,6-Dichlorophenyl)-1,3-dihydro-2H-indol-2-one (A) 100 mg O N Cl Cl

MM 0006.03 Imp. B (EP): 2-[(2,6-Dichlorophenyl)amino]benzaldehyde O (A) 100 mg

NH Cl Cl

MM 0006.04 Imp. C (EP): [2-[(2,6-Dichlorophenyl)amino]phenyl]methanol OH (A) 100 mg

NH Cl Cl

MM 0006.09 Imp. D (EP): 2-[2-[(2-Bromo-6-chlorophenyl)amino]phenyl]acetic Acid OH (D) 100 mg O NH Br Cl

MM 0006.05 Imp. D (EP) as Sodium Salt: Sodium 2-[2-[(2-Bromo- ONa (D) 100 mg 6-chlorophenyl)amino]phenyl]acetate O NH Br Cl

MM 0006.02 Imp. E (EP): 1,3-Dihydro-2H-indol-2-one (B) 100 mg O N H MM 0006.06 1-(2-Bromo-6-chlorophenyl)indolin-2-one (C) 10 mg O N Br Cl

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 65 Pharmaceutical impurities

Code Product Code Unit MM 0006.10 Methyl 2-[2-[(2,6-Dichlorophenyl)amino]phenyl]acetate O (A) 100 mg O (Methyl Ester of Diclofenac) NH Cl Cl

MM 0006.11 Ethyl [2-[(2,6-Dichlorophenyl)amino]phenyl]acetate O (A) 100 mg O (Ethyl Ester of Diclofenac) NH Cl Cl

MM 0181.06 Isopropyl 2-[2-[(2,6-Dichlorophenyl)amino]phenyl]acetate O (A) 100 mg O (Isopropyl Ester of Diclofenac) NH Cl Cl

MM 0006.12 2-(2,6-Dichlorophenylamino)benzoic Acid O (A) 100 mg OH

NH Cl Cl

MM 0006.15 2,6-Dichlorodiphenylamine (A) 100 mg

NH Cl Cl

MM 0006.16 2-Bromo-6-chlorodiphenylamine (A) 100 mg

NH Br Cl

MM 0006.17 1-(2,6-Dichlorophenyl)indolin-2,3-dione O (A) 100 mg O N Cl Cl

MM 0006.18 Diclofenac Potassium OK (A) 100 mg O NH Cl Cl

MM 0006.19 2-Chloro-N-(2,6-dichlorophenyl)-N-phenylacetamide Cl (A) 100 mg

N O Cl Cl

MM 0006.20 2-[2-[(2,6-Dichlorophenyl)amino]phenyl]acetic Acid (Diclofenac) OH (A) 100 mg O NH Cl Cl

MM 0006.21 2,6-Dichloroaniline NH2 (B) 100 mg Cl Cl

MM 0006.22 2-Bromo-6-chloroaniline NH2 on request Br Cl

MM 0006.27 N-Acetyl-N-phenyl-2,6-dichloroaniline O (A) 100 mg

N Cl Cl

MM 0006.28 Diethyl Phthalate O (C) 100 mg O O

O Dicloxacillin Sodium

MM 0229.00 Dicloxacillin Sodium Monohydrate O on request Cl ONa O N Cl N H x H O O N 2 S H O

66 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit

O MM 0026.04 Imp. C (EP): (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia- OH (B) 100 mg O 1-azabicyclo[3.2.0]-heptane-2-carboxylic Acid N

(6-Aminopenicillanic Acid) H N S 2 H Diflucortolone Valerate MM 0600.00 Diflucortolone Valerate O (A) 100 mg O O HO

F O F Digitoxin

MM 0336.01 Digitoxigenin O O (A) 50 mg

OH HO Digoxin

MM 0212.00 Digoxin O O (A) 250 mg OH

OH OO H

OO OH

OO OH HO OH Dihydrocodeine Hydrogen Tartrate New MM 0280.00 Imp. B (EP) as Hemisulphate Pentahemihydrate: N (A) 250 mg Morphine Hemisulphate Pentahemihydrate x H2SO4 [Controlled Substance] x 5 H2O

HO O OH 2

New MM 0037.00 Imp. B (EP) as Hydrochloride Trihydrate: N (A) 250 mg Morphine Hydrochloride Trihydrate x HCl [Controlled Substance] x 3 H2O

HO O OH

New MM 0004.00 Imp. A (EP) as Monohydrate: Codeine N (A) 100 mg Monohydrate [Controlled Substance] x H2O

O O OH

New MM 0442.00 Imp. A (EP) as Phosphate Hemihydrate: N (A) 100 mg

Codeine Phosphate Hemihydrate x H3PO4 [Controlled Substance] x 1/2 H2O

O O OH Diltiazem Hydrochloride MM 0068.00 Diltiazem Hydrochloride O (A) 500 mg

S O N O O

x HCl N

MM 0068.02 Imp. B (EP): (2S,3S)-2-(4-Methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro- O (A) 100 mg 1,5-benzothiazepin-3-yl Acetate S O N O H O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 67 Pharmaceutical impurities

Code Product Code Unit MM 0068.03 Imp. D (EP) as Hydrochloride: (2S,3S)-2-(4-Methoxyphenyl(- O (A) 100 mg 5-[2-(methylamino)ethyl]-4-oxo-2,3,4,5-tetrahydro- 1,5-benzothiazepin-3-yl Acetate Hydrochloride S (N-Desmethyldiltiazem Hydrochloride) O x HCl N O O

MM 0068.04 Imp. E (EP):(2S,3S)-3-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro- O (A) 100 mg 1,5-benzothiazepin-4(5H)-one S OH N H O MM 0068.05 Imp. F (EP):(2S,3S)-5-[2-(Dimethylamino)ethyl]-3-hydroxy- O (A) 100 mg 2-(4-methoxyphenyl)-2,3-dihydro-1,5- benzothiazepin-4(5H)-one S OH N O

MM 0068.07 Diltiazem Sulphoxide O (A) 100 mg O S O N O O

MM 0068.08 Diltiazem Maleate O (A) 100 mg

O S OH O x OH N O O O

Dimenhydrinate

MM 0599.00 Dimenhydrinate O (A) 500 mg H O N N N x Cl O N N

O MM 0176.00 Imp. A (EP): Theophylline H (A) 500 mg N N

O N N

O MM 0599.04 Imp. B (EP): 8-[(2-(Diphenylmethoxy)- H (A) 100 mg N ethyl)(methlyl)amino]-1,3-dimethyl-3,7-dihydro- N 1H-purine-2,6-dione N O N N O

MM 0494.00 Imp. C (EP): Caffeine O (A) 500 mg N N

O N N

MM 0490.03 Imp. F (EP) as Hydrochloride: (A) 100 mg 2-(Diphenylmethoxy)-N-methylethanamine H x HCl Hydrochloride (Diphenhydramine Imp. A N Hydrochloride; Nordiphenhydramine Hydrochloride) O

MM 0490.04 Imp. G (EP) as Hydrochloride: (A) 100 mg N,N-Dimethyl-2-[(4-methylphenyl)- (phenyl)methoxy]ethanamine Hydrochloride x HCl (4-Methyldiphenhydramine Hydrochloride) N O

MM 0640.00 Imp. H (EP) as Hydrochloride: 2-[(RS)-(4- (A) 100 mg Bromophenyl)(phenyl)methoxy]-N,N-dimethyl- x HCl ethanamine Hydrochloride (4-Bromodiphen- N hydramine Hydrochloride; Bromazine Hydro- O chloride) Br

68 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0490.02 Imp. I (EP): Diphenylmethanol (B) 100 mg (Benzhydrol)

MM 0630.01 Imp. J (EP): Diphenylmethanone (B) 100 mg (Benzophenone)

New MM 0599.14 Imp. K (EP): [Oxybis(methanetriyl)]tetrabenzene (A) 50 mg (Bis(diphenylmethyl) Ether)

MM 0490.00 Diphenhydramine Hydrochloride (A) 500 mg

x HCl N O

O MM 0155.02 8-Chlorotheophylline H (B) 100 mg N N Cl O N N

MM 0599.03 8-[N-(2-Diphenylmethoxyethyl)-N,N- O (A) 100 mg N- dimethylaminium]-1,3-dimethylxanthine N + inner salt N O N N O

Dimetindene Maleate MM 0595.01 Imp. A (EP): 2-Ethylpyridine N (B) 100 mg

Diphemanil Metilsulfate

MM 1163.00 Diphemanil Metilsulfate N+ (D) 100 mg

O O x S - O O

Diphenhydramine Hydrochloride MM 0490.00 Diphenhydramine Hydrochloride (A) 500 mg

x HCl N O

MM 0490.03 Imp. A (EP) as Hydrochloride: 2-(Diphenylmethoxy)-N- (A) 100 mg methylethanamine Hydrochloride H x HCl (Nordiphenhydramine Hydrochloride) N O

MM 0490.04 Imp. B (EP) as Hydrochloride: 2-[(RS)- (A) 100 mg (4-Methylphenyl)phenylmethoxy]-N,N- x HCl dimethylethanamine Hydrochloride N (4-Methyldiphenhydramine Hydrochloride O

MM 0640.00 Imp. C (EP) as Hydrochloride: 2-[(RS)- (A) 100 mg (4-Bromophenyl)phenylmethoxy]-N,N- x HCl dimethylethanamine Hydrochloride N (Bromazine Hydrochloride) O Br MM 0490.02 Imp. D (EP): Diphenylmethanol (Benzhydrol) (B) 100 mg

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 69 Pharmaceutical impurities

Code Product Code Unit MM 0630.01 Imp. E (EP): Diphenylmethanone (Benzophenone) (B) 100 mg

MM 0490.01 Diphenhydramine N-Oxide (A) 100 mg

O N O

Diphenylpyraline Hydrochloride MM 0557.00 Diphenylpyraline Hydrochloride (A) 500 mg O x HCl N

MM 0155.01 Diphenylpyraline (A) 100 mg O

MM 0490.02 Diphenylmethanol (Benzhydrol) (B) 100 mg OH

MM 0630.01 Diphenylmethanone (Benzophenone) (B) 100 mg O

MM 0557.04 Diphenylpyraline N-Oxide (A) 100 mg O

N O

MM 0468.04 N-Desmethyldiphenylpyraline Hydrochloride (A) 100 mg (4-(Diphenylmethoxy)piperidine Hydrochloride) NH x HCl O

Dipipanone Hydrochloride MM 0760.01 1,1-Diphenylbut-1-ene (A) 100 mg

MM 0760.02 1-(1-Methyl-3,3-diphenylpropyl)piperidine Hydrochloride (A) 100 mg

x HCl N

Dipotassium Clorazepate

MM 0028.03 Imp. A (EP): (2-Amino-5-chlorophenyl)phenylmethanone NH2 (B) 100 mg (Aminochlorobenzophenone) O Cl

H O MM 0023.02 Imp. B (EP): 7-Chloro-5-phenyl-1,3-dihydro-2H- N (A) 100 mg 1,4-benzodiazepin-2-one (Nordazepam) [Controlled Substance] Cl N

Diprafenon Hydrochloride MM 0428.01 2'-Hydroxy-3-phenylpropiophenone O (A) 100 mg

70 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Diprophylline

O MM 0176.01 Imp. A (Pharmeuropa): N-Methyl-5-(methylamino)-1H-imidazole- H (A) 100 mg N 4-carboxamide (Theophyllidine) N H HN N

O MM 0176.00 Imp. B (Pharmeuropa): 1,3-Dimethyl-3,7-dihydro-1H-purine-2,6-dione H (A) 500 mg N (Theophylline) N

O N N

MM 0603.00 Imp. C (Pharmeuropa): 7-(2-Hydroxyethyl)-1,3-dimethyl-3,7-dihydro- O (A) 500 mg OH N 1H-purine-2,6-dione (Etofylline) N

O N N

Dipyridamole

MM 0462.03 Imp. C (EP): 2,2'-[[6-Chloro-4,8-di(piperidin-1- OH (A) 100 mg

yl)pyrimido[5,4-d]pyrimidin-2-yl]nitrilo]diethanol N N N N OH N Cl N N

Disopyramide MM 0108.00 Disopyramide (A) 500 mg N

NH2

Dithranol MM 0137.00 Dithranol OH O OH (A) 500 mg

MM 0137.04 Imp. A (EP): Anthracen-9(10H)-one (Anthrone) O (A) 100 mg

MM 0137.01 Imp. B (EP): 1,8-Dihydroxyanthracene-9,10-dione (Danthron) OH O OH (A) 100 mg

O MM 0137.02 Imp. C (EP): 4,4',5,5'-Tetrahydroxy-9,9'-bianthracenyl-10,10'(9H,9'H)- OH O OH (A) 100 mg dione (Dithranol Dimer)

OH O OH Dobutamine Hydrochloride

MM 0384.00 Imp. A (EP) as Hydrochloride: Dopamine Hydrochloride HO NH2 (A) 500 mg x HCl HO MM 0675.02 Imp. B (EP): 4-(4-Hydroxyphenyl)butan-2-one OH (C) 100 mg O

Dodecylguanidinium Acetate MM 0451.03 Dodecylnitrile N (B) 100 mg

MM 0451.05 Dimethyldodecylamine (B) 100 mg N

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 71 Phytochemical reference standards from ChromaDex

More than 2500 reference substances for phytochemical analysis • Certified Reference Materials (CRM) • Botanical Reference Materials (BRM) • Extract Reference Materials (XRM) • Standards with various documentation grades • Reference standard kits • Analytical methods.

Reference standards for/from: • Artichoke • Belladonna • Bilbery • Black Cohosh • Carotenoids • Cat’s Claw • Devil’s Claw • Echinacea • Ephedra • Ginseng • Kava Kava • Reishi Mushroom • Rosemary • Soysaponins • St. John’s Wort • Tribulus Terrestris • Valerian • ... and many more.

www.lgcstandards.com Pharmaceutical impurities

Code Product Code Unit Domperidone

MM 0107.00 Domperidone O O (D) 100 mg

HN N N N NH

Cl MM 0107.06 Imp. A (EP): 5-Chloro-1-(piperidin-4-yl)-1,3-dihydro-2H-benzimidazol- O (A) 100 mg

2-one HN N NH

O MM 0107.05 Imp. B (EP): 4-(5-Chloro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)- O (A) 100 mg

1-formylpiperidine N N NH

MM 0107.03 Imp. F (EP): 1,3-Bis[3-[4-(5-chloro-2-oxo- O O O (A) 50 mg

2,3-dihydro-1H-benzimidazol-1-yl)piperidin- HN N N N N N N NH 1-yl]propyl]-1,3-dihydro-2H-benzimidazol- 2-one Cl Cl

H MM 0107.07 1,3-Dihydro-2H-benzimidazol-2-one N (B) 100 mg O N H Donepezil Hydrochloride MM 0677.00 Donepezil Hydrochloride (D) 100 mg N O x HCl O

O MM 0677.01 Donepezil (D) 100 mg N O O

O Dopamine Hydrochloride

MM 0384.00 Dopamine Hydrochloride HO NH2 (A) 500 mg x HCl HO

MM 0384.02 Imp. A (EP) as Hydrochloride: 5-(2-Aminoethyl)- HO NH2 (A) 100 mg x HCl 2-methoxyphenol Hydrochloride O (4-O-Methyldopamine Hydrochloride)

MM 0384.04 Imp. C (EP): 2-(3,4-Dimethoxyphenyl)ethanamine O NH2 (A) 100 mg

MM 0384.01 (R,S)--Methyldopamine Hydrobromide HO NH2 (A) 100 mg x HBr HO Dosulepin Hydrochloride

MM 0510.00 Dosulepin Hydrochloride N (A) 100 mg

x HCl

MM 0510.02 Imp. B (EP): Dibenzo[b,e]thiepin-11(6H)-one (A) 100 mg O

MM 0510.08 Nordosulepin Hydrochloride N (A) 50 mg H

x HCl

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 73 Pharmaceutical impurities

Code Product Code Unit Doxazosin Mesilate MM 0386.00 Doxazosin Mesilate O (A) 100 mg O N O N N O N O O O x S NH2 OH MM 0386.08 Doxazosin O (A) 100 mg O N O N N O N O

NH2 MM 0386.04 Imp. A (EP): (2RS)-2,3-Dihydro-1,4-benzodioxine-2-carboxylic Acid O (A) 100 mg HO O O

MM 0386.05 Imp. B (EP) as Hydrochloride: 1-[(2RS)-2,3-Dihydro- O (A) 100 mg 1,4-benzodioxin-2-ylcarbonyl]piperazine Hydrochloride N O x HCl HN O

MM 0386.06 Imp. C (EP): 1,4-Bis(2,3-dihydro-1,4-benzodioxin- O (A) 100 mg

2-ylcarbonyl)piperazine O N O O N O

H MM 0085.07 Imp. D (EP): 6,7-Dimethoxyquinazoline-2,4(1H,3H)-dione O N O (C) 100 mg

NH O O MM 0085.06 Imp. E (EP): 2,4-Dichloro-6,7-dimethoxyquinazoline O N Cl (A) 100 mg N O Cl MM 0386.01 Imp. F (EP): 2-Chloro-6,7-dimethoxyquinazolin-4-amine O N Cl (A) 100 mg N O

NH2 MM 0386.12 Imp. F (EP) as Mesilate: 2-Chloro-6,7-dimethoxy- O N Cl (A) 100 mg O O quinazolin-4-amine Mesilate N x S O OH

NH2

MM 0085.01 Imp. G (EP): 6,7-Dimethoxy-2-(piperazin-1-yl)quinazolin- NH (A) 100 mg 4-amine O N N

N O

NH2 MM 0085.03 Imp. H (EP): 2,2'-(Piperazine- NH2 (D) 100 mg O 1,4-diyl)bis(6,7-dimethoxyquinazolin-4-amine) N

N N O O N N

N O

NH2 Doxepin Hydrochloride

MM 0032.00 Doxepin Hydrochloride N (A) 500 mg

x HCl O

New MM 0032.03 Imp. A (EP): Dibenzo[b,e]oxepin-11(6H)-one (A) 100 mg (Doxepinone) O

74 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit New MM 0032.04 Imp. B (EP): (11RS)-11-[3-(Dimethylamino)- N (A) 50 mg propyl]-6,11-dihydrodibenzo[b,e]oxepin- OH 11-ol (Doxepinol)

Doxylamine Hydrogen Succinate MM 0101.00 Doxylamine Hydrogen Succinate O (A) 500 mg OH N N x O OH

O New MM 0101.02 Imp. B (EP) as Hydrochloride: (1RS)-1-Phenyl- (A) 50 mg 1-(pyridin-2-yl)ethanol Hydrochloride x HCl N OH

New MM 0101.03 Imp. C (EP) as Hydrogen Fumarate: N,N- O (A) 50 mg

Dimethyl-2-[(RS)-1-phenyl(pyridin-2-yl)- OH x methoxy]ethanamine Hydrogen Fumarate N N HO O O MM 0101.04 Imp. D (EP): Phenyl(pyridin-2-yl)methanone (A) 100 mg (2-Benzoylpyridine)

N O

MM 0101.05 Doxylamine N-Oxide Dihydrochloride (A) 100 mg

O x 2 HCl N N O

Drofenine Hydrochloride MM 0768.00 Drofenine Hydrochloride (A) 500 mg

x HCl O N O MM 0768.01 Drofenine N-Oxide Hydrochloride (A) 100 mg

x HCl O N O O Droperidol

MM 0138.01 Imp. A (EP): 1-(1,2,3,6-Tetrahydropyridin- HN (A) 50 mg

4-yl)-1,3-dihydro-2H-benzimidazol-2-one N

NH O MM 0138.04 Imp. D (EP) as Hydrochloride: (1RS)- F (A) 100 mg 1-[4-(4-Fluorophenyl)-4-oxobutyl]- O N 4-(2-oxo-2,3-dihydro-1H- x HCl O benzimidazol-1-yl)-1,2,3,6-tetrahydro- N pyridine 1-Oxide Hydrochloride NH O Dropropizine

MM 1017.00 Dropropizine N OH (A) 500 mg N OH

Duloxetine Hydrochloride New MM 0043.04 Imp. D (Pharmeuropa): Naphthalen-1-ol (1-Naphthol) (B) 100 mg

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 75 Pharmaceutical impurities

Code Product Code Unit Ebastine MM 0468.00 Ebastine (A) 100 mg

N O O

MM 0490.02 Imp. A (EP): Diphenylmethanol (Benzhydrol) (B) 100 mg

MM 0468.03 Imp. B (EP): 1-[4-(1,1-Dimethylethyl)phenyl]ethanone (A) 100 mg

O MM 0468.04 Imp. C (EP) as Hydrochloride: 4-(Diphenyl- (A) 100 mg

methoxy)piperidine Hydrochloride NH x HCl O

MM 0468.05 Imp. D (EP): 1-[4-(1,1-Dimethylethyl)phenyl]- (A) 100 mg 4-(4-hydroxypiperidin-1-yl)butan-1-one N O HO MM 0468.06 Imp. E (EP) as Hydrogen Fumarate: (A) 100 mg 1-[4-(1,1-Dimethylpropyl)phenyl]- 4-[4-(diphenylmethoxy)piperidin- N 1-yl]butan-1-one Hydrogen Fumarate O O

x O HO OH O Econazole Nitrate MM 0524.00 Econazole Nitrate Cl (A) 500 mg

Cl x HNO3 O N Cl N MM 0281.01 Imp. A (EP): (1RS)-1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol Cl (A) 100 mg

HO N

N MM 0524.02 Imp. B (EP) as Nitrate: (2RS)-2-[(4-Chlorobenzyl)oxy]- Cl (D) 100 mg 2-(2,4-dichlorophenyl) ethanamine Nitrate

Cl x HNO3 O

NH2 Cl MM 0524.03 Imp. C (EP) as Chloride: 1-(4-Chlorobenzyl)- Cl (A) 100 mg 3-[(2RS)-2-[(4-chlorobenzyl)oxy]- 2-(2,4-dichlorophenyl)ethyl] Cl imidazolium Chloride O Cl- N+ Cl N Cl

76 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Emedastine Difumarate New MM 1277.02 Imp. B (EP): 2-Chloro-1-(2-ethoxyethyl)-1H- O (A) 100 mg Benzimidazole N Cl

Enalapril Maleate

O MM 0010.00 Enalapril Maleate O OH O (A) 100 mg H N N OH x OH OO O

MM 0010.05 Imp. B (EP): (2S)-2-[[(1S)-1-(Ethoxycarbonyl)- O (A) 100 mg H N 3-phenylpropyl]amino]propanoic Acid OH

O MM 0010.01 Imp. C (EP): (2S)-1-[(2S)-2-[[(1S)-1-Carboxy- O OH (D) 100 mg H 3-phenylpropyl]amino]propanoyl]pyrrolidine-2- N N carboxylic Acid (Enalaprilat) HO O MM 0010.06 Imp. D (EP): Ethyl (2S)-2-[(3S,8aS)-3-Methyl-1,4-dioxo- H (A) 100 mg O octahydropyrrolo[1,2-h]pyrazin-2-yl]-4-phenylbutanoate N N (Enalapril diketopiperazine) O

H MM 0015.02 Imp. I (EP): 1H-Imidazole (Imidazole) N (B) 100 mg

MM 0010.15 (2S)-2[[(1S)-1-(Ethoxycarbonyl)- O (A) 100 mg H N 3-phenylpropyl]amino]propanoic Acid Ethyl Ester O Hydrochloride x HCl OO

Enilconazole MM 0281.01 Imp. E (EP): (1RS)-1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol Cl (A) 100 mg

HO N

N Enrofloxacin MM 0395.00 Enrofloxacin (A) 100 mg N N N

OH F O O MM 00018.01 Imp. A (EP): 7-Chloro-1-cyclo- (A) 100 mg

propyl-6-fluoro-4-oxo-1,4-dihydroquinoline- Cl N 3-carboxylic Acid OH F O O

MM 0018.06 Imp. B (EP) as Hydrochloride Monohydrate: HN (A) 500 mg Ciprofloxacin Hydrochloride Monohydrate N N x HCl x H2O OH F O O

MM 0395.01 Imp. C (EP) as Hydrochloride: N (A) 100 mg 1-Cyclopropyl-7-(4-ethylpiperazin-1-yl)-4- N N oxo-1,4-dihydroquinoline-3-carboxylic Acid x HCl Hydrochloride (Desfluoroenrofloxacin OH Hydrochloride) O O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 77 Pharmaceutical impurities

Code Product Code Unit MM 0018.04 Imp. G (EP): 7-[(2-Aminoethyl)amino]-1-cyclopropyl-6-fluoro- (D) 50 mg H2N 4-oxo-1,4-dihydroquinoline-3-carboxylic Acid HN N

OH F O O MM 0395.07 Enrofloxacin N-Oxide Hydrochloride O (A) 100 mg N N N x HCl OH F O O Entacapone New MM 1221.04 Imp. B (EP): Ethyl (2E)-2-Cyano-3-(3,4- O (A) 50 mg O2N dihydroxy-5-nitrophenyl)prop-2-enoate O

HO N OH New MM 1221.03 Imp. H (EP): (2E)-3-(3,4-Dihydroxy-5-nitro- O (A) 50 mg O2N phenyl)-2-(piperidin-1-ylcarbonyl)prop-2- N

ennitrile HO N OH MM 1221.09 Imp. I (EP): Propyl (2E)-2-Cyano-3-(3,4- O (A) 50 mg O2N dihydroxy-5-nitrophenyl)prop-2-enoate O

HO N OH

O2N MM 1221.01 Imp. C (Pharmeuropa): 3,4-Dihydroxy-5-nitro- O (A) 100 mg benzaldehyde HO OH New MM 1221.05 Imp. D (EP): (2E)-2-Cyano-3-(3-ethoxy-4- O (A) 50 mg O2N hydroxy-5-nitrophenyl)-N,N-diethylprop-2- N

enamide HO N O

New MM 1221.06 Imp. E (EP): 3,5-Dinitrobenzene-1,2-diol O2N NO2 (A) 50 mg

HO OH New MM 1221.07 Imp. F (EP): (2E)-2-Cyano-3-(3,4-dihydroxy- O (A) 50 mg O2N 5-nitrophenyl)prop-2-enoic Acid OH

HO N OH Ephedrine Hydrochloride

MM 0652.00 Ephedrine Hydrochloride OH H (A) 500 mg N [Drug Precursor] x HCl

Imp. B (EP) as Hydrochloride: Pseudoephedrine OH MM 2115.00 H (A) 500 mg N Hydrochloride x HCl [Drug Precursor] Ephedrine Sulphate

MM 1147.00 Ephedrine Sulphate OH (A) 250 mg H N [Drug Precursor] x H2SO4

2 Erdosteine

O MM 0544.00 Erdosteine S O O (A) 100 mg S N OH H

O MM 0544.01 2-Chloro-N-(2-oxotetrahydrothiophen-3-yl)acetamide S O (A) 100 mg Cl N H

78 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Erythromycin MM 0132.13 Imp. B (EP): N-Demethylerythromycin A O (D) 100 mg

OH HO HO OO

O NH OH OO O OH O

MM 0132.10 Imp. E (EP): Erythromycin A Enol Ether (A) 50 mg

O OH HO OO

O N OH OO O OH O

Esomeprazole Magnesium Trihydrate MM 0095.03 Imp. A (EP): 5-Methoxy-1H-benzimidazole-2-thiol (A) 100 mg O NH

N SH MM 0095.04 Imp. B (EP): 2-[(RS)-[(3,5-Dimethylpyridin- (A) 100 mg O NH 2-yl)methyl]sulphinyl]-5-methoxy-1H-benzimidazole N S O N MM 0095.06 Imp. C (EP): 5-Methoxy-2-[[(4-methoxy- (A) 100 mg O NH 3,5-dimethylpyridin-2-yl)methyl]- O sulphanyl]-1H-benzimidazole (Ufiprazole) N S N MM 0095.05 Imp. D (EP): 5-Methoxy-2-[[(4-methoxy- (A) 100 mg O NH 3,5-dimethylpyridin-2-yl)methyl] O -sulphonyl]-1H-benzimidazole (Omeprazole Sulphone) N S O O N MM 0095.07 Imp. E (EP): 4-Methoxy-2-[[(RS)-(5-methoxy-1H- (A) 100 mg O NH benzimidazol-2-yl) O -sulphinyl]methyl]-3,5-dimethylpyridine 1-Oxide N S O N (Omeprazole N-Oxide) O Estradiol Benzoate MM 0301.00 Estradiol Benzoate OH (A) 500 mg

MM 0300.00 Imp. A (EP) as Hemihydrate: Estradiol Hemihydrate OH (A) 500 mg

1 x /2 H2O

HO MM 0301.02 Imp. C (EP): Estra-1,3,5(10)-triene-3,17i-diyl O (A) 100 mg Dibenzoate (Estradiol 3,17-Dibenzoate) O

MM 0301.07 Imp. D (EP): 3-Hydroxyestra-1,3,5(10)-trien-17i-yl O (A) 100 mg Benzoate (Estradiol 17-Benzoate) O

HO MM 0301.03 Imp. E (EP): 17h-Hydroxyestra-1,3,5(10)-trien-3-yl Benzoate OH (C) 10 mg (17-epi-Estradiol Benzoate) O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 79 Pharmaceutical impurities

Code Product Code Unit MM 0301.08 Imp. G (EP): 17-Oxoestra-1,3,5(10)-trien-3-yl Benzoate O (A) 100 mg (Estrone Benzoate)

MM 0278.01 Benzoic Acid O (B) 100 mg OH

Estradiol Enanthate MM 0473.00 Estradiol Enanthate O (A) 100 mg O

HO Estradiol Hemihydrate MM 0300.00 Estradiol Hemihydrate OH (A) 500 mg

1 x /2 H2O

HO MM 0282.00 Imp. A (EP): 3-Hydroxyestra-1,3,5(10)-trien-17-one (Estrone) O (A) 500 mg

HO MM 0300.01 Imp. B (EP): Estra-1,3,5(10)-triene-3,17h-diol (17h-Estradiol; OH (A) 100 mg 17-epi-Estradiol)

HO MM 0300.06 Imp. C (EP): 4-Methylestra-1,3,5(10)-triene-3,17i-diol OH (A) 100 mg (4-Methylestradiol)

MM 0300.02 Imp. D (EP): Estra-1,3,5(10),9(11)-tetraene-3,17!-diol OH (D) 100 mg (9,11-Didehydroestradiol)

HO MM 0300.03 6i-Hydroxyestradiol OH (D) 50 mg

HO OH MM 0300.08 6-Ketoestradiol OH (A) 100 mg

HO O Estradiol Valerate MM 0209.00 Estradiol Valerate O (A) 500 mg O

HO MM 0300.00 Imp. A (EP) as Hemihydrate:Estradiol Hemihydrate OH (A) 500 mg

1 x /2 H2O

HO MM 0209.06 Imp. B (EP): 17i-Hydroxyestra-1,3,5(10)-trien-3-yl OH (A) 100 mg Pentanoate (Estradiol 3-Valerate) O

80 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0209.01 Imp. C (EP): 3-Hydroxyestra-1,3,5(10),9(11)-tetraen-17i-yl O (D) 100 mg Pentanoate (9,11-Didehydroestradiol Valerate) O

HO MM 0209.07 Imp. D (EP): 3-Hydroxy-4-methylestra-1,3,5(10)-trien- O (D) 100 mg 17i-yl Pentanoate O (4-Methylestradiol Valerate)

MM 0209.02 Imp. E (EP): Estra-1,3,5(10)-trien-3,17i-diyl O (A) 100 mg Dipentanoate (Estradiol 3,17-Divalerate) O

O MM 0209.04 Imp. F (EP): 3-Hydroxyestra-1,3,5(10)-trien-17i-yl Butanoate O (A) 100 mg (Estradiol Butyrate) O

HO MM 0209.03 17-epi-Estradiol Valerate (17h-Estradiol Valerate) O (D) 100 mg O

HO Estramustine Sodium Phosphate MM 0100.01 Estramustine OH (D) 100 mg

O Cl N O Cl MM 0100.02 17i-17'i-Bis3-{bis(2- NaO O O ONa (D) 50 mg P P chloroethyl)carbamo O O O yloxy}estra-1,3,5(10)- O O trienyl Cl Cl Pyrophosphate N O O N Disodium Salt Cl Cl Estriol MM 0130.00 Estriol OH (A) 100 mg OH

HO MM 0130.06 Imp. A (EP): Estra-1,3,5(10),9(11)-tetraene-3,16h,17i-triol OH (D) 100 mg (9,11-Didehydroestriol) OH

HO MM 0282.00 Imp. B (EP): 3-Hydroxyestra-1,3,5(10)-trien-17-one (Estrone) O (A) 500 mg

HO MM 0130.01 Imp. C (EP): 3-Methoxyestra-1,3,5(10)-triene-16h,17i-diol OH (D) 100 mg (Estriol 3-Methyl Ether) OH

O MM 0300.00 Imp. D (EP) as Hemihydrate: Estradiol OH (A) 500 mg Hemihydrate 1 x /2 H2O

HO MM 0130.05 Imp. E (EP): Estra-1,3,5(10)-triene-3,16h,17h-triol OH (D) 100 mg (17-epi-Estriol) OH

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 81 Pharmaceutical impurities

Code Product Code Unit MM 0130.04 Imp. F (EP): Estra-1,3,5(10)-triene-3,16i,17i-triol OH (D) 100 mg (16-epi-Estriol) OH

HO MM 0130.03 Imp. G (EP): Estra-1,3,5(10)-triene-3,16i,17h-triol OH (D) 100 mg (16,17-epi-Estriol) OH

HO MM 0130.22 Imp. I (EP): 3-Hydroxy-17-oxa-D-homoestra-1,3,5(10)-trien-17a- O on request one O

HO MM 0130.02 6h-Hydroxyestriol OH (D) 100 mg OH

HO OH MM 0130.14 Estriol 16,17-Diacetate O (D) 100 mg O

O O

HO MM 0130.15 Estriol Triacetate O (D) 100 mg O

O O O

O MM 0130.16 Estriol 3-Benzyl Ether OH (D) 100 mg OH

O MM 0130.17 16-Oxoestradiol OH (D) 100 mg O

HO MM 0130.18 6-Oxoestriol OH (D) 100 mg OH

HO O Estrogens conjugated New MM 0282.00 Estrone O (A) 500 mg

HO Estrone MM 0282.00 Estrone O (A) 500 mg

HO MM 0282.01 Estrone 3-Methyl Ether O (A) 100 mg

O Ethacridine Lactate Monohydrate

MM 0798.00 Ethacridine Lactate Monohydrate NH2 O (A) 250 mg O x x H O OH 2 OH H2N N Ethinylestradiol MM 0123.00 Ethinylestradiol OH (A) 500 mg

82 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0123.02 Imp. B (EP): 19-Nor-17h-pregna-1,3,5(10),9(11)-tetraen- OH (D) 50 mg 20-yne-3,17-diol (9,11-Didehydroethinylestradiol)

HO MM 0282.00 Imp. C (EP): 3-Hydroxyestra-1,3,5(10)-trien-17-one (Estrone) O (A) 500 mg

HO MM 0300.00 Imp. D (EP) as Hemihydrate: OH (A) 500 mg Estradiol Hemihydrate 1 x /2 H2O

HO MM 0123.07 Imp. E (EP): 19-Nor-17h-pregna- OH (D) 100 mg 1,3,5(10)-trien-20-yne-3,6h,17-triol (6h-Hydroxyethinylestradiol) HO OH MM 0123.06 Imp. F (EP): 19-Nor-17h-pregna- OH (D) 25 mg 1,3,5(10)-trien-20-yne-3,6i,17-triol (6i-Hydroxyethinylestradiol)

HO OH MM 0123.05 Imp. G (EP): 3,17-Dihydroxy-19- OH (D) 100 mg nor-17h-pregna-1,3,5(10)-trien-20-yn-6-one (6-Oxoethinylestradiol, 6-Ketoethinylestradiol) HO O MM 0123.08 Imp. I (EP): 19-Nor-17h-pregna- OH (D) 50 mg 1,3,5(10),6-tetraen-20-yne-3,17-diol (6,7-Didehydroethinylestradiol) HO MM 0300.01 Imp. L (EP): Estra-1,3,5(10)-triene- OH (A) 100 mg 3,17h-diol (17h-Estradiol; 17-epi-Estradiol)

HO Ethionamide MM 0845.00 Ethionamide S (A) 250 mg

NH2 N

O MM 0845.01 Ethionamide Sulphoxide S (D) 100 mg

NH2 N Ethosuximide MM 0750.00 Ethosuximide H (A) 500 mg O N O

Ethyl Parahydroxybenzoate MM 0498.00 Ethyl Parahydroxybenzoate O (A) 500 mg O

HO MM 0498.05 Sodium Ethyl Parahydroxybenzoate O (A) 500 mg O

NaO MM 0045.01 Imp. A (EP): 4-Hydroxybenzoic Acid O (B) 100 mg OH

HO MM 0431.00 Imp. B (EP): Methyl 4-Hydroxybenzoate (Methyl Parahydroxybenzoate) O (A) 500 mg O

HO MM 0432.00 Imp. C (EP): Propyl 4-Hydroxybenzoate O (A) 500 mg (Propyl Parahydroxybenzoate) O HO

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 83 Pharmaceutical impurities

Code Product Code Unit MM 0496.00 Imp. D (EP): Butyl 4-Hydroxybenzoate O (A) 500 mg (Butyl Parahydroxybenzoate) O HO Ethylmorphine Hydrochloride

MM 0037.00 Imp. B (EP) as Hydrochloride Trihydrate: N (A) 250 mg

Morphine Hydrochloride Trihydrate x HCl [Controlled Substance] x 3 H2O

HO O OH

MM 0280.00 Imp. B (EP) as Hemisulphate Pentahemihydrate: Morphine N (A) 250 mg Hemisulphate Pentahemihydrate x H2SO4 [Controlled Substance] x 5 H2O

HO O OH 2

MM 0004.00 Imp. C (EP) as Monohydrate: Codeine Monohydrate N (A) 100 mg [Controlled Substance] x H2O

O O OH

MM 0442.00 Imp. C (EP) as Phosphate Hemihydrate: Codeine N (A) 100 mg Phosphate Hemihydrate x H3PO4 [Controlled Substance] x 1/2 H2O

O O OH Etilefrine Hydrochloride

OH MM 0035.00 Etilefrine Hydrochloride H (A) 500 mg HO N x HCl

OH MM 0081.00 Imp. B (EP) as Hydrochloride: (1RS)- H (A) 500 mg HO N 1-(3-Hydroxyphenyl)-2-(methylamino)ethanol x HCl Hydrochloride (Phenylephrine Hydrochloride) MM 0973.00 Imp. C (EP) as Hydrochloride: (1RS)-2-Amino- OH (A) 500 mg HO NH 1-(3-hydroxyphenyl)ethanol Hydrochloride 2 x HCl (Norfenefrine Hydrochloride) MM 0035.05 Imp. E (EP): 1-(3-Hydroxyphenyl)ethanone (3-Hydroxyacetophenone) O (C) 100 mg HO

MM 0035.06 Imp. F (EP): N-Benzylethanamine (Benzylethylamine) (C) 100 mg

HN New MM 0035.08 Imp. D (EP) as Hydrochloride: 2-(Benzylethyl-amino)- (A) 100 mg

1-(3-hydroxyphenyl)ethanone Hydro-chloride O x HCl (Benzyletilefrone Hydrochloride) HO N

MM 0035.50 3-Benzoyloxyacetophenone O (A) 100 mg O

MM 0035.51 3-Benzoyloxy-h-bromoacetophenone O on request O Br

O Etodolac MM 0911.00 Etodolac O (A) 250 mg H N OH O

MM 0911.01 Imp. A (EP): 2-[(1RS)-1-Ethyl-1,3,4,9-tetrahydro- O (A) 100 mg pyrano[3,4-b]indol-1-yl]acetic Acid (8-Desethyl H N OH Etodolac) O

84 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0911.02 Imp. B (EP): 2-[(1RS)-1-Ethyl-8-methyl-1,3,4,9- O (A) 100 mg tetrahydropyrano[3,4-b]indol-1-yl]acetic Acid H N OH (8-Methyl Etodolac) O

MM 0911.03 Imp. C (EP): 2-[(1RS)-8-Ethyl-1-methyl-1,3,4,9- O (A) 100 mg tetrahydropyrano[3,4-b]indol-1-yl]acetic Acid H N OH (1-Methyl Etodolac) O

New MM 0911.04 Imp. D (EP): 2-[(1RS)-1-Ethyl-8-(1-methylethyl)- O (A) 50 mg 1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl]acetic H N OH Acid (8-Isopropyl Etodolac) O

MM 0911.06 Imp. F (EP): 2-[(1RS)-8-Ethyl-1-(1-methylethyl)- O (A) 100 mg 1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl]acetic H N OH Acid (1-Isopropyl Etodolac) O

MM 0911.07 Imp. G (EP): 2-[(1RS)-8-Ethyl-1-propyl-1,3,4,9- O (A) 100 mg tetrahydropyrano[3,4-b]indol-1-yl]acetic Acid H N OH (1-Propyl Etodolac) O

H MM 0911.08 Imp. H (EP): 2-(7-Ethylindol-3-yl)ethanol N (A) 100 mg OH

MM 0911.10 Imp. J (EP): (1RS)-1,8-Diethyl-1-methyl-1,3,4,9- (A) 100 mg H tetrahydropyrano[3,4-b]indole (Decarboxy N Etodolac O

MM 0911.11 Imp. K (EP): Methyl 2-[(1RS)-1,8-Diethyl-1,3,4,9- O (A) 100 mg tetrahydropyrano[3,4-b]indol-1-yl]acetate H N O (Etodolac Methyl Ester) O

Etofenamate MM 0410.00 Imp. A (EP): 2-[[3-(Trifluoromethyl)phenyl]-amino]benzoic Acid O (A) 500 mg (Flufenamic Acid) OH

F F MM 0105.02 Imp. B (EP): Butyl 2-[[3-(Trifluoromethyl)phenyl]-amino]benzoate O (A) 100 mg (Butyl Flufenamate) O

F F F MM 0105.03 Imp. C (EP): N-Phenyl-3-(trifluoromethyl)aniline (A) 100 mg

F F MM 0105.04 Imp. D (EP): 2,2'-Oxybis(ethylene) O O (A) 100 mg O Bis[2-[[3-(trifluoromethyl)phenyl] amino]benzoate] O O

NH HN

F F F F F F

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 85 Pharmaceutical impurities

Code Product Code Unit MM 0105.05 Imp. E (EP): 2-(2-Butoxyethoxy)ethyl 2-[[3- O (A) 100 mg O (Trifluoromethyl)phenyl]amino]benzoate O O

F F O MM 0105.06 Imp. F (EP): 2,2'-Oxydiethanol HO OH (A) 100 mg MM 0105.07 Imp. G (EP): 2-Hydroxyethyl O (A) 100 mg OH 2-[[3-(Trifluoromethyl)phenyl]amino]benzoate O

F F MM 0105.08 Etofenamate Myristate O O (A) 100 mg O O O

F F

MM 0105.09 Etofenamate Palmitate O O (A) 100 mg O O O

F F

MM 0105.10 Etofenamate Stearate O O (A) 100 mg O O O

F F

MM 0105.11 Triethylene Glycol Flufenamate O (A) 100 mg O OH O O

F F Etofylline MM 0603.00 Etofylline O (A) 500 mg OH N N

O N N

Famciclovir New MM 0620.01 9-[4-Acetoxy-3-(acetoxymethyl)butyl]-2-amino- Cl 100 mg O N 6-chloropurine N O N H2N N O

O Famotidine

NH2 MM 0029.00 Famotidine NH2 (A) 250 mg H2N N SNNH2 N S S OO

86 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit

NH MM 0029.06 Imp. A (EP) as Hydrochloride: 3-[[[2- NH2 (A) 100 mg H2N N SNHx HCl [(Diaminomethylene)amino]thiazol-4-yl]- N 2 methyl]sulphanyl]propanimidamide S Hydrochloride

OO MM 0029.05 Imp. B (EP) as Dimaleate: S (D) 50 mg N N 3,5-Bis[2-[[[2-[(diaminomethylene)amino]thi NH2 H2N H N NH 2 N S N S N 2 azol-4-yl]-methyl]sulphanyl]ethyl]-4H- N H N S S 1,2,4,6-thiatriazine 1,1-Dioxide Dimaleate O

OH x 2 OH

O OO MM 0029.01 Imp. C (EP) as Hydrochloride: NH2 (A) 100 mg S H2N N 3-[[[2-[(Diaminomethylene)amino]thiazol- SNNH2 N H 4-yl]methyl]sulphanyl]-N-sulphamoylpropanamide S Hydrochloride xHCl O MM 0029.02 Imp. D (EP): 3-[[[2-[(Diaminomethylene)amino]thiazol-4- NH2 (A) 100 mg H2N N yl]methyl]sulphanyl]propanamide SNH2 N S

MM 0029.07 Imp. E (EP): 2,2'-[Disulphanediylbis- NH2 H2N (A) 100 mg H N NH 2 N S S N 2 (methylenethiazole-4,2-diyl)]diguanidine N N S S

O MM 0029.03 Imp. F (EP): 3-[[[2-[(Diaminomethylene)amino]thiazol-4- NH2 (A) 100 mg H N N yl]methyl]sulphanyl]propanoic Acid 2 SOH N S

O MM 0029.09 Imp. G (EP) as Maleate: N-Cyano- NH (A) 100 mg NH2 N H N N OH 3-[[[2-(diaminomethylene)amino]thiazol- 2 SNx N H OH 4-yl]methyl]sulphanyl]propanimidamide Maleate S O

NH2 MM 0029.04 Famotidine Sulphoxide NH2 (A) 100 mg H2N N SNNH2 N S O S OO

O OO MM 0029.10 3-[[[2-[(Diaminomethylene)amino]thiazol- NH2 (D) 50 mg S H2N N 4-yl]methyl]sulphinyl]-N-sulphamoylpropanamide SNNH2 N H O S

N MM 0029.51 2-[(Diaminomethylene)amino]-4-(4-cyanobutyl)thiazole N on request Hydrochloride N x HCl H2N S NH2 Felodipine

H MM 0139.00 Felodipine N (A) 100 mg

O O

O O Cl

Cl MM 0139.01 Imp. A (EP): Ethyl Methyl 4-(2,3-Dichlorophenyl)- N (D) 50 mg 2,6-dimethylpyridine-3,5-dicarboxylate O O

O O Cl

Cl H MM 0139.02 Imp. B (EP): Dimethyl 4-(2,3-Dichlorophenyl)-2,6-dimethyl- N (A) 100 mg 1,4-dihydropyridine-3,5-dicarboxylate O O

O O Cl

Cl H MM 0139.03 Imp. C (EP): Diethyl 4-(2,3-Dichlorophenyl)-2,6-dimethyl- N (A) 100 mg 1,4-dihydropyridine-3,5-dicarboxylate O O

O O Cl

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 87 Pharmaceutical impurities

Code Product Code Unit Fenbendazole

O MM 2500.00 Imp. A (EP): Methyl (1H-Benzimidazol-2-yl)carbamate H (A) 100 mg N O (Carbendazim) NH N O MM 0518.01 Fenbendazole Sulphoxide (Oxfendazole) H (A) 100 mg N O NH S N O O MM 0518.02 Fenbendazole Sulphone H (A) 100 mg N O NH S N O O Fenbufen MM 0918.00 Fenbufen O (A) 500 mg OH

MM 0918.03 Imp. C (EP): Biphenyl (A) 100 mg

MM 0918.05 4-(4-Chlorophenyl)-4-oxobutanoic Acid O (A) 100 mg (3-(4-Chlorobenzoyl)propionic Acid) OH O Cl Fenfluramine Hydrochloride

H MM 0608.00 Fenfluramine Hydrochloride N (A) 500 mg x HCl

F F F MM 0608.01 Norfenfluramine Hydrochloride NH2 (A) 100 mg

x HCl F F F O MM 0608.02 N-Nitrosofenfluramine N (A) 100 mg N

F F F Fenofibrate MM 0505.00 Fenofibrate O (A) 500 mg Cl O O

O MM 0505.01 Imp. A (EP): (4-Chlorophenyl)(4-hydroxyphenyl)methanone Cl OH (C) 100 mg

O MM 0505.03 Imp. C (EP): (3RS)-3-[4-(4-Chlorobenzoyl)- O (A) 100 mg phenoxy]butan-2-one Cl O

O MM 0505.04 Imp. D (EP): Methyl 2-[4-(4-Chlorobenzoyl)- O (A) 100 mg Cl O phenoxy]-2-methylpropanoate O

O MM 0505.05 Imp. E (EP): Ethyl 2-[4-(4-Chlorobenzoyl)- O (A) 100 mg Cl O phenoxy]-2-methylpropanoate O

O MM 0505.06 Imp. F (EP): (4-Chlorophenyl)[4-(1-methyl- Cl O (A) 100 mg ethoxy)phenyl]methanone

88 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit New MM 0505.07 Imp. G (EP): 1-Methylethyl 2-[[2-[4- O (A) 50 mg Cl O O (4-Chlorobenzoyl)phenoxy]-2- O methylpropanoyl]oxy]-2- O

methylpropanoate O Fenoprofen Calcium MM 0790.00 Fenoprofen Calcium Dihydrate (A) 500 mg - O O Ca 2+ x 2 H2O O 2 Fentanyl MM 0528.00 Fentanyl (A) 100 mg

[Controlled Substance] O N

MM 0528.09 Imp. A (EP) as Hydrochloride: N-Phenyl-N- (A) 100 mg O [cis,trans-1-oxido-1-(2-phenylethyl)piperidin- O N 4-yl]propanamide Hydrochloride (Fentanyl x HCl N-Oxide Hydrochloride) N

MM 0528.08 Imp. B (EP): N-Phenyl-N-(piperidin-4-yl)propanamide O NH (A) 100 mg

MM 0528.03 Imp. C (EP): N-phenyl-N-[1-(2-phenylethyl)- (A) 100 mg piperidin-4-yl]acetamide O N

MM 0528.04 Imp. D (EP): N-phenyl-1-(2-phenylethyl)piperidin-4-amine (A) 100 mg

MM 0093.17 Imp. F (EP) as Hydrochloride: Aniline Hydrochloride NH2 (B) 100 mg x HCl (Phenylamine Hydrochloride) MM 0528.07 Imp. G (EP): N-Phenylpropanamide O (A) 100 mg NH

Fexofenadine Hydrochloride MM 0507.01 Imp. A (EP): 2-[4-[4-[4-(Hydroxydiphenyl- (A) 100 mg methyl)piperidin-1-yl]butanoyl]phenyl]- OH

2-methylpropanoic Acid O (Ketofexofenadine) N O

MM 0507.03 Imp. C (EP): (1RS)-4-[4-(Hydroxydiphenyl- (A) 100 mg methyl)piperidin-1-yl]-1-[4-(1-methylethyl)- OH

phenyl]butan-1-ol OH N

MM 0055.02 Imp. E (EP): Diphenyl(piperidin-4-yl)methanol (B) 100 mg OH

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 89 Pharmaceutical impurities

Code Product Code Unit Finasteride

O H MM 0415.00 Finasteride N (A) 100 mg

O N H O H MM 0415.01 Imp. A (EP): N-(1,1-Dimethylethyl)-3-oxo- N (A) 100 mg 4-aza-5-androstane-17!-carboxamide (Dihydrofinasteride)

O N H H O MM 0415.02 Imp. B (EP): Methyl 3-Oxo-4-aza-5h-androst- O (A) 100 mg 1-ene-17i-carboxylate (9-1-Aza Ester)

O N H H Flavoxate Hydrochloride MM 0156.00 Flavoxate Hydrochloride O (A) 100 mg

x HCl O N O O MM 0156.01 Imp. A (EP): 3-Methyl-4-oxo-2-phenyl-4H-1- O (A) 100 mg benzopyran-8-carboxylic Acid (3-Methyl- flavone-8-carboxylic Acid) O

O OH MM 0156.02 Imp. B (EP): Ethyl 3-Methyl-4-oxo-2-phenyl- O (A) 100 mg 4H-1-benzopyran-8-carboxylate (3-Methyl- flavone-8-carboxylic Acid Ethyl Ester) O

O O MM 0156.05 Imp. C (EP): 1-Methylethyl-3-Methyl-4-oxo- O (A) 50 mg 2-phenyl-4H-1-benzopyran-8-carboxylate (3-Methylflavone-8-carboxylic Acid Isopropyl O Ester) O O Flecainide Acetate MM 0488.04 Imp. D (EP): 2,5-Bis(2,2,2-trifluoroethoxy)benzoic Acid F F O (A) 100 mg O F OH F O F F

MM 0488.02 Imp. B (EP): (RS)-(Piperidin-2-yl)methanamine H2N (A) 100 mg HN Fluanisone MM 1247.02 1-(2-Methoxyphenyl)piperazine Dihydrochloride (A) 100 mg x 2 HCl N HN O Flubendazole

MM 0463.00 Flubendazole H O (A) 100 mg F N O NH N O

H MM 0463.02 Imp. B (EP): (2-Amino-1H-benzimidazol- F N (A) 100 mg 5-yl)(4-fluorophenyl)methanone NH2 N O

H MM 0463.03 Imp. C (EP): (4-Fluorophenyl)(2-hydroxy-1H-benzimidazol- F N (C) 50 mg 5-yl)methanone OH N O

H MM 0463.04 Imp. D (EP): (1H-Benzimidazol-5-yl)(4-fluorophenyl)methanone F N on request

N O

90 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit

MM 0463.05 Imp. E (EP): Methyl [5-(2-Fluorobenzoyl)-1H-benzimidazol- H O (C) 50 mg N O 2-yl]carbamate NH N F O MM 0463.06 Imp. F (EP): Methyl [5-(4-Fluorobenzoyl)-1-methyl-1H- O (C) 50 mg F N O benzimidazol-2-yl]carbamate NH N O

MM 0463.07 Imp. G (EP): Methyl [5-[4-(1-Methylethoxy)benzoyl]-1H- H O (D) 100 mg O N O benzimidazol-2-yl]carbamate NH N O Flucloxacillin Sodium

MM 0489.00 Flucloxacillin Sodium Hydrate O (A) 500 mg Cl ONa O N F N x H O H 2 O N S H O

MM 0489.01 Imp. A (EP) as Disodium Salt: (4S)-2-[Carboxy[[[3-(2-chloro- O (A) 100 mg Cl ONa 6-fluorophenyl)-5-methylisoxazol-4-yl]carbonyl]amino]methyl]- N F HN 5,5-dimethylthiazolidine-4-carboxylic Acid Disodium Salt H O N (Penicilloic Acids of Flucloxacillin Disodium Salt) S O OONa

MM 0489.02 Imp. B (EP): (2RS,4S)-2-[[[[3-(2-Chloro-6-fluorophenyl)- O (A) 50 mg Cl OH 5-methylisoxazol-4-yl]-carbonyl]amino]methyl]-5,5-dimethyl- N HN thiazolidine-4-carboxylic Acid (Penilloic Acids of Flucloxacillin) F O NH S O

O MM 0026.04 Imp. C (EP): (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia- OH (B) 100 mg O 1-azabicyclo[3.2.0]-heptane-2-carboxylic Acid (6-Aminopenicillanic N

Acid) H N S 2 H

MM 0489.03 Imp. D (EP): 3-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carboxylic Cl (C) 100 mg Acid N F O OH

O Fluconazole MM 0235.00 Fluconazole F (A) 100 mg

F N HO N N N N N MM 0235.11 Imp. A (EP): (2RS)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)- F (A) 100 mg

3-(4H-1,2,4-triazol-4-yl)propan-2-ol F N HO N N N

MM 0235.12 Imp. B (EP): 2-[2-Fluoro-4-(1H-1,2,4-triazol-1- N N (D) 100 mg yl)phenyl]-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol N

F N HO N N N N N

MM 0235.13 Imp. C (EP): 1,1'-(1,3-Phenylene)di-1H-1,2,4-triazole N N (A) 50 mg N

N N N MM 0235.14 Imp. D (EP): 2-(4-Fluorophenyl)-1,3-bis(1H- F (A) 100 mg 1,2,4-triazol-1-yl)propan-2-ol N HO N N N N N

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 91 Pharmaceutical impurities

Code Product Code Unit MM 0235.02 Imp. F (EP): (2RS)-2-(2,4-Difluorophenyl)-3-(1H-1,2,4-triazol- F (A) 50 mg

1-yl)propane-1,2-diol F N HO N N OH MM 0235.01 2-(2,4-Difluorophenyl)propane-1,2,3-triol F (A) 100 mg

F HO HO

OH H MM 0235.03 1H-1,2,4-Triazol N (B) 100 mg N N MM 0235.04 2-Chloro-2',4'-difluoroacetophenone F (C) 100 mg

O Cl MM 0235.06 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol F (A) 100 mg

HO N N N

MM 0235.09 4-Amino-1,2,4-triazole NH2 (C) 100 mg N N N Flucytosine MM 0593.00 Imp. A (Pharmeuropa): Fluorouracil O (A) 500 mg F HN

O N H Flufenamic Acid MM 0410.00 Flufenamic Acid O (A) 500 mg OH

F F Flumetasone Pivalate MM 0427.01 Imp. A (EP): 6h,9-Difluoro-11i,17,21-trihydroxy-16h- O (A) 100 mg OH methylpregna-1,4-diene-3,20-dione (Flumetasone) HO OH

F O F Flunarizine Dihydrochloride

F MM 0175.00 Flunarizine Dihydrochloride N (A) 500 mg N

x 2 HCl

F F MM 0175.04 Imp. A (EP): 1-[Bis(4-fluorophenyl)methyl]piperazine NH (A) 100 mg N

F F MM 0175.03 Imp. C (EP) as Dihydrochloride: N (A) 100 mg 1-[(RS)-(2-Fluorophenyl)(4-fluoro- N phenyl)methyl]-4-[(2E)-3-phenylprop- x 2 HCl F 2-enyl]piperazine Dihydrochloride

92 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0175.02 Chlorobis-(4-fluorophenyl)methane Cl (B) 100 mg

F F MM 0175.05 1-Bis(4-fluorophenyl)methyl-4-(ethoxycarbonyl)piperazine OO (B) 10 mg N

F F

O MM 0175.06 Flunarizine N-Oxide Dihydrochloride F (A) 100 mg N N

x 2 HCl

F Flunitrazepam

MM 0069.00 Flunitrazepam O on request N [Controlled Substance]

O2N N F

H O MM 0069.02 Imp. B (EP): 5-(2-Fluorophenyl)-7-nitro-1,3-dihydro-2H- N (A) 100 mg 1,4-benzodiazepin-2-one (Demethylflunitrazepam) O2N N F

Flunixin Meglumine MM 0915.00 Flunixin Meglumine F F (A) 100 mg F H N OH x HO N NH OH OH OH HO

O MM 0915.01 Imp. A (EP): 2-Chloropyridine-3-carboxylic Acid N Cl (A) 100 mg OH

O MM 0915.03 Imp. C (EP): Ethyl 2-Chloropyridine-3-carboxylate N Cl (A) 100 mg O

O Fluorescein Sodium MM 0294.01 Imp. A (EP): Resorcinol (B) 100 mg

HO OH MM 0133.04 Imp. C (EP): 2-(2,4-Dihydroxybenzoyl)benzoic Acid (A) 100 mg OH

O O

HO OH Fluorouracil MM 0593.00 Fluorouracil O (A) 500 mg F HN

O N H MM 0265.03 Imp. A (EP): Pyrimidine-2,4,6-(1H,3H,5H)- O (C) 100 mg trione (Barbituric Acid) HN

O N O H MM 0593.01 Imp. B (EP): Dihydropyrimidine-2,4,5(3H)- O (A) 100 mg O trione (Isobarbituric Acid or 5-Hydroxyuracil) HN

O N H

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 93 Pharmaceutical impurities

Code Product Code Unit MM 0593.03 Imp. C (EP): Pyrimidine-2,4(1H,3H)-dione (Uracil) O (C) 100 mg HN

O N H MM 0593.05 Imp. E (EP): 5-Chloropyrimidine-2,4(1H,3H)dione (5-Chlorouracil) O (A) 100 mg Cl HN

O N H MM 0593.06 Imp. F (EP): 2-Ethoxy-5-fluoropyrimidin- O (A) 100 mg F 4(1H)-one (2-Ethoxy-5-fluorouracil) N

O N H Fluoxetine Hydrochloride

H MM 0256.00 Fluoxetine Hydrochloride O N (A) 50 mg

F x HCl F F

H MM 0256.01 Imp. A (EP): (1RS)-3-(Methylamino)-1-phenylpropan-1-ol HO N (A) 100 mg

H MM 0256.02 Imp. B (EP) as Hydrochloride: N-Methyl-3- N (A) 100 mg phenylpropan-1-amine Hydrochloride x HCl (Methyl-3-phenylpropylamine Hydrochloride) [Controlled Substance] H MM 0256.03 Imp. C (EP) as Hydrochloride:(3RS)-N-Methyl-3-phenyl- O N (A) 100 mg

3-[3-(trifluoromethyl]phenoxy]propan-1-amine x HCl Hydrochloride F F F MM 0256.05 4-Hydroxybenzotrifluoride OH (B) 100 mg F

F F MM 0256.06 4-Chlorobenzotrifluoride Cl (B) 100 mg F

F F MM 0256.10 3-Dimethylamino-1-phenylpropan-1-ol OH (A) 100 mg N

MM 0256.16 N-Formylfluoxetine O (A) 100 mg ON

F F

F New MM 256.17 (3RS)-N-Methyl-3-phenyl-3-[2-(trifluoromethyl)- F (A) 100 mg F H phenoxy]propan-1-amine Hydrochloride O N (2-Trifluoromethylisomer of Fluoxetine Hydro-chloride) x HCl

Fluoxymesterone MM 0959.00 Fluoxymesterone OH (A) 100 mg HO

F O Flupentixol Decanoate

N MM 0182.00 Flupentixol Decanoate O on request N CF 3 O

S MM 0182.08 Imp. B (BP): 2-Trifluoromethylthioxanthone O (A) 100 mg CF3

HN MM 0182.05 1-(2-Hydroxyethyl)piperazine OH (B) 100 mg N

94 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0182.06 cis/trans-3-[2-(Trifluoromethyl)-9H-thioxanthen-9-ylidene]propene on request CF3

MM 0182.07 4-Chloro-3-nitrobenzotrifluoride O2N CF3 (B) 100 mg

MM 0182.09 4-Fluoro-3-nitrobenzotrifluoride O2N CF3 (B) 100 mg

F Flupentixol Dihydrochloride MM 0182.08 Imp. G (EP): 2-(Trifluoromethyl)-9H-thioxanthen-9-one O (A) 100 mg (2-Trifluoromethylthioxanthone) CF3 S

HN MM 0182.05 1-(2-Hydroxyethyl)piperazine OH (B) 100 mg N MM 0182.06 cis/trans-3-[2-(Trifluoromethyl)-9H-thioxanthen-9-ylidene]propene on request CF3

MM 0182.07 4-Chloro-3-nitrobenzotrifluoride O2N CF3 (B) 100 mg

Cl Fluphenazine Dihydrochloride MM 0114.00 Fluphenazine Dihydrochloride (A) 500 mg

N N S N x 2 HCl OH F

F F MM 0114.01 Imp. A (EP): 2-[4-[3-[5-Oxo-2-(trifluoromethyl)- (A) 100 mg 4- 10H-5 phenothiazin-10-yl]propyl]piperazin-1- N N yl]ethanol (Fluphenazine S-Oxide) S N O OH F

F F MM 0114.07 Imp. D (EP): 10,10'-[Piperazine-1,4-diylbis(propane- F F (A) 100 mg 3,1-diyl)] F

bis[2-(trifluoromethyl)-10H-phenothiazine] S N N N N S

F F MM0826.00 Imp. E (Pharmeuropa): 2-[4-[3-[2-Chloro-10H- (A) 100 mg

phenothiazin-10-yl]propyl]piperazin-1-yl]ethanol N N (Perphenazine) S N OH

Cl MM 0114.04 Fluphenazine N,N',S-Trioxide Dihydrochloride on request O N N S N x 2 HCl O OH O F

F F Flurazepam Monohydrochloride

H MM 0070.01 Imp. A (EP): [5-Chloro-2-[[2-(diethylamino)ethyl]amino]phenyl]- N on request N (2-fluorophenyl)methanone O Cl F

H O MM 0070.02 Imp. B (EP): 7-Chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4- N (A) 100 mg benzodiazepin-2-one Cl N

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 95 Pharmaceutical impurities

Code Product Code Unit

MM 0070.03 2-Chloro-10-(2-diethylaminoethyl)-9,10-dihydroacridin-9-one N (A) 100 mg

Cl O

MM 0070.06 Flurazepam N (A) 100 mg [Controlled Substance] O N

Cl N

Flurbiprofen MM 0727.01 (A) 50 mg Imp. A (EP): (2RS)-2-(Biphenyl-4-yl)propanoic OH Acid O

New MM 0727.03 Imp. C (EP): (2RS)-2-(2-Fluorobiphenyl-4-yl)- HO (A) 50 mg F OH 2-hydroxypropanoic Acid O

Flutamide

F F MM 0161.00 Flutamide H (A) 500 mg N F O NO2 MM 0161.03 Imp. A (EP): 4-Nitro-3-(trifluoromethyl)aniline F F (A) 100 mg H2N F

NO2 F F MM 0161.04 Imp. B (EP): N-[4-Nitro-3-(trifluoromethyl)phenyl]acetamide H (A) 100 mg N F O NO2 F F MM 0161.05 Imp. C (EP): N-[4-Nitro-3-(trifluoromethyl)phenyl]propanamide H (A) 100 mg N F O NO2 MM 0161.06 Imp. D (EP): 3-(Trifluoromethyl)aniline F F (B) 100 mg H2N F

F F MM 0161.07 Imp. E (EP): 2-Methyl-N-[3-(trifluoromethyl)phenyl]propanamide H (A) 100 mg N F O

F F MM 0161.08 Imp. F (EP): 2-Methyl-N-[2-nitro- H (D) 100 mg N 5-(trifluoromethyl)phenyl]propanamide F O O2N HO F F MM 0161.01 2-Hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)- H (A) 100 mg N phenyl]propanamide (2-Hydroxyflutamide) F O NO2 MM 0161.09 Trifluoromethylbenzene F F (B) 100 mg F

MM 0161.10 3-Nitrobenzotrifluoride F F (B) 100 mg O2N F

MM 0161.12 3-Trifluoromethyl-4-nitrophenol F F (A) 100 mg HO F

NO2 Fluticasone Propionate New O MM 1244.10 6alpha,9alpha-Difluoro-11beta,17alpha-dihydroxy-16alpha- OH (A) 100 mg methyl-3-oxoandrosta-1,4-diene-17beta-carboxylic Acid HO OH

F O F

96 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Fluvastatin Sodium MM 0676.00 Fluvastatin Sodium F (D) 100 mg

OH N OH O

ONa Folic Acid

OOH MM 0621.00 Folic Acid O (A) 500 mg

O N N H OH N N H O H2N N N H

OOH MM 0621.01 Imp. A (EP): (2S)-2-[(4-Aminobenzoyl)amino]pentanedioic Acid O (A) 100 mg

(N-(4-Aminobenzoyl)-L-glutamic Acid) N H OH H2N O MM 0621.02 Imp. B (EP) as Sulphate: 2,5,6-Triaminopyrimidin-4(1H)-one O (A) 100 mg NH N 2 Sulphate x H2SO4

H2N N NH2 H MM 0621.04 Imp. D (EP): 4-[[(2-Amino-4-oxo-1,4-dihydropteridin- O (D) 50 mg 6-yl)methyl]amino]benzoic Acid (Pteroic Acid) O OH N N N H

H2N N N H MM 0094.03 4-Aminobenzoic Acid O (B) 100 mg OH

H2N

MM 0169.00 L-Glutamine NH2 (A) 500 mg H2N OH O O Formoterol Fumarate Dihydrate

OH MM 0447.00 Formoterol Fumarate Dihydrate H (D) 50 mg N

HO O HN O and enantiomer 2 O xxHO 2 H O OH 2 O Furosemide MM 0014.00 Furosemide OOH (A) 500 mg H N O

H2N S O O Cl MM 0014.02 Imp. A (EP): 2-Chloro-4-[(furan-2-ylmethyl)amino]- OOH (A) 100 mg 5-sulphamoylbenzoic Acid Cl

H2N S O O HN O MM 0014.03 Imp. B (EP): 2,4-Dichloro-5-sulphamoylbenzoic Acid OOH (B) 100 mg Cl

H2N S O O Cl MM 0014.01 Imp. C (EP): 2-Amino-4-chloro-5-sulphamoylbenzoic Acid OOH (A) 100 mg

NH2

H2N S O O Cl

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 97 Pharmaceutical impurities

Code Product Code Unit MM 0014.04 Imp. D (EP): 2,4-Bis[(furan-2-ylmethyl)amino]- OOH (D) 100 mg H 5-sulphamoylbenzoic Acid N O

H2N S O O HN O MM 0014.05 Imp. E (EP): 2,4-Dichlorobenzoic Acid OOH (B) 100 mg Cl

Cl MM 0014.50 Ethyl 2,4-Dichloro-5-sulphamoylbenzoate OO (A) 100 mg Cl

H2N S O O Cl Gabapentin MM 0684.01 Imp. A (Pharmeuropa): 2-Azaspiro[4.5]decan- O (A) 100 mg HN 3-one (3,3-Pentamethylene-4-butyrolactam)

MM 0684.07 Imp. E (Pharmeuropa): 1-(Carboxymethyl)cyclo- O O (A) 100 mg HO hexanecarboxylic Acid OH

Ganciclovir MM 0061.02 Imp. F (EP): 2-Amino-1,9-dihydro-6H-purin-6-one (Guanine) O (B) 100 mg N HN

H N N N 2 H MM 0485.09 Imp. I (EP): 2-[(2-Amino-6-oxo-1,6-dihydro- O (A) 100 mg N 9H-purin-9-yl)methoxy]-propane-1,3-diyl HN

Dipropanoate (Ganciclovir Dipropionate) N H2N N O O O O

O MM 0485.10 Imp. J (EP): 2-[2-(Propanoylamino)-6-oxo- O (A) 100 mg N 1,6-dihydro-9H-purin-9-yl]methoxy] O HN propane-1,3-diyl dipropanoate N N N (Ganciclovir Tripropionate) H O O O O

O Gemcitabine Hydrochloride

MM 0749.05 Imp. A (EP): 4-Aminopyrimidin-2(1H)-one NH2 (A) 100 mg (Cytosine) N

O N H Gemfibrozil

MM 0641.00 Gemfibrozil OOH(A) 250 mg

MM 0641.08 Imp. A (EP): 2,5-Dimethylphenol (p-Xylenol) OH (A) 100 mg

MM 0641.07 Imp. E (EP): 5-[2,5-Dimethyl-4-(prop-1-enyl)- OOH(D) 100 mg phenoxy]-2,2-dimethylpentanoic Acid O

MM 0641.02 Imp. H (EP): 1,3-Bis(2,5-dimethylphenoxy)propane O O (A) 100 mg

MM 0641.01 3-(2,5-Dimethylphenoxy)propyl Chloride OCl (A) 100 mg (3-(2,5-Xylyloxy)propyl Chloride) MM 0641.03 Gemfibrozil Isobutyl Ester (A) 100 mg OO

98 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Gestodene MM 0124.06 Imp. L (EP): 13-Ethyl-17-hydroxy-18,19- OH (A) 100 mg dinor-17h-pregna-5,15-dien-20-yn-3-one (9$6)-Gestodene)

O Glibenclamide

MM 0008.00 Glibenclamide OOO (A) 500 mg S O N N Cl H H N H O

OO MM 0008.01 Imp. A (EP): 5-Chloro-2-methoxy-N- S (A) 100 mg (2-(4-sulfamoylphenyl)ethyl)benzamide O NH2 Cl N H O

MM 0008.02 Imp. B (EP): Methyl [[4-[2-[(5-Chloro- OOO (A) 100 mg S O N O 2-methoxybenzoyl)amino]ethyl]phenyl]- H Cl sulphonyl]carbamate N H O

New MM 0942.09 Imp. C (Pharmeuropa): 1-[[4-[2- O O O (A) 100 mg S [(Cyclohexylcarbamoyl)amino]ethyl] O N N phenyl]sulfonyl]-3-cyclohexylurea H H N N (N-(Cyclohexylcarbamoyl)-4-[2- H H [(cyclohexylcarbamoyl)amino]ethyl] benzene-Sulphonamide) MM 0008.03 5-Chloro-2-methoxybenzoic Acid O (B) 100 mg Cl OH

MM 0008.04 5-Chloro-N-(2-phenylethyl)-2-methoxybenzamide O (A) 100 mg Cl N H O Gliclazide

O MM 0325.00 Gliclazide OO (A) 500 mg S N N N H H

OO MM 0325.01 Imp. A (EP): 4-Methylbenzenesulphonamide S (C) 100 mg NH2

MM 0325.02 Imp. B (EP): 2-Nitroso-octahydrocyclopenta[c]pyrrole (A) 100 mg

N N O MM 0325.03 Imp. C (EP): Ethyl [(4-Methylphenyl)sulphonyl]- O O O (A) 100 mg S Carbamate N O H

MM 0325.06 Imp. F (EP): 1-(Hexahydrocyclopenta[c]pyrrol- (A) 100 mg O O O 2(1H)-yl)-3-[(2-methylphenyl)sulphonyl]urea S N N N H H

MM 0325.09 Methyl N-Methyl-p-tolylsulphoncarbamate O O O (A) 100 mg S N O

Glimepiride

MM 0647.00 Glimepiride O O O (D) 100 mg S N N H H O N

O N H

MM 0647.02 Imp. A (EP): 1-[[4-[2-[[(3-Ethyl-4-methyl-2-oxo- O O O (D) 100 mg 2,3-dihydro-1H-pyrrol-1-yl)carbonyl]- S N N amino]ethyl]phenyl]sulphonyl]-3-(cis- H H 4-methylcyclohexyl)urea (cis-Glimepiride) O N O N H

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 99 Pharmaceutical impurities

Code Product Code Unit MM 0647.01 Imp. B (EP): 3-Ethyl-4-methyl-2-oxo-N- O O (A) 100 mg S [2-(4-sulphamoylphenyl)ethyl]-2,3-dihydro-1H-pyrrole- O NH2

1-carboxamide (Glimepiride Sulphonamide) N N H O

MM 0647.03 Imp. C (EP): Methyl [[4-[2-[[(3-Ethyl-4-methyl-2-oxo- O O O (A) 100 mg S 2,3-dihydro-1H-pyrrol-1-yl) O N O carbonyl]amino]ethyl]phenyl]- H N N sulphonyl]carbamate (Glimepiride Carbamate) H O

MM 0647.04 Imp. D (EP): 1-[[3-[2-[[(3-Ethyl-4-methyl-2-oxo- O O O (D) 100 mg S 2,3-dihydro-1H-pyrrol-1-yl)carbonyl]amino]ethyl]- N N phenyl]sulphonyl]-3-(trans-4-methylcyclohexyl)- H H urea H N N

O O MM 0647.08 cis-4-Methylcyclohexylamine Hydrochloride (A) 100 mg x HCl

H2N Glipizide MM 0942.01 Imp. A (EP): 5-Methyl-N-[2-(4-sulphamoyl- O O (A) 100 mg S phenyl)ethyl]pyrazine-2-carboxamide O NH2 N N H N MM 0678.03 Imp. B (EP): Cyclohexanamine (C) 100 mg

H2N MM 0942.04 Imp. D (EP): 6-Methyl-N- O O (A) 100 mg S [2-(4-sulphamoylphenyl)ethyl]pyrazine-2-carboxamide O NH2 N N H N

MM 0942.05 Imp. E (EP): 1-Cyclohexyl-3-[[4-[2-[[(6-methyl- O O O (A) 100 mg S pyrazin-2-yl)carbonyl]amino]ethyl]phenyl]- O N N H H sulphonyl]urea N N H N MM 0942.06 Imp. F (EP): Ethyl [2-(4-Sulphamoylphenyl)- O O (A) 100 mg S ethyl]carbamate O NH2

O N H MM 0942.07 Imp. G (EP): Methyl [[4-[2-[[(5-Methylpyrazin- O O O (A) 100 mg S 2-yl)carbonyl]amino]ethyl]phenyl] O N O H sulphonyl]Carbamate N N H N MM 0942.08 Imp. H (EP): 4-[2-[(Cyclohexylcarbamoyl)amino]- O O (A) 100 mg S ethyl]benzenesulphonamide O NH2

N N H H

MM 0942.09 Imp. I (EP): N-(Cyclohexylcarbamoyl)- O O O (A) 100 mg S 4-[2-[(cyclohexylcarbamoyl)amino] O N N ethyl]benzenesulphonamide H H N N H H Glutamine

MM 0169.00 L-Glutamine NH2 (A) 500 mg H2N OH O O

MM 0169.01 N-Phenylacetyl-L-glutamine O (A) 100 mg (Phenylacetylglutamine) HN

H2N OH O O

MM 0169.02 Phenylacetamide NH2 (A) 100 mg O

MM 0169.03 D-Glutamine NH2 (A) 100 mg H2N OH O O

100 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Glycopyrronium Bromide

MM 0834.00 Glycopyrronium Bromide O (A) 100 mg N+ O Br- OH and enantiomer

MM 0834.05 Imp. B (Pharmeuropa): Oxophenylacetic Acid O (A) 100 mg

(Benzoylformic Acid) OH O

MM 0792.03 Imp. C (Pharmeuropa): (2RS)-Hydroxyphenyl- O (A) 100 mg

acetic Acid (Mandelic Acid) OH OH MM 0278.01 Imp. D (Pharmeuropa): Benzoic Acid (B) 100 mg OH

MM 0834.07 Imp. H (Pharmeuropa): Methyl Oxophenylacetate O (A) 100 mg

(Methyl Benzoylformate) O O

MM 0834.01 Imp. J (Pharmeuropa): 2-(RS)-Cyclopentylhydroxy- O (A) 100 mg h phenylacetic Acid -Cyclopentylmandelic Acid) OH OH

MM 0834.08 Imp. K (Pharmeuropa): 2-(RS)-Cyclopentylphenyl- O (A) 100 mg

acetic Acid OH

MM 0834.06 Imp. M (Pharmeuropa): Cyclopentylphenylmethanone (A) 100 mg O

Granisetron Hydrochloride MM 0398.00 Granisetron Hydrochloride H on request

N HN N N x HCl

O H

Griseofulvin

MM 0582.00 Griseofulvin Cl O (A) 500 mg O O O

O O Guaiacol MM 0354.04 Guaiacol OH (A) 500 mg

O MM 0814.04 Imp. A (EP): Benzene-1,2-diol (Pyrocatechol) OH (C) 100 mg

OH MM 0045.11 Imp. B (EP): Phenol OH (B) 100 mg

MM 0814.06 Imp. C (EP): 1,2-Dimethoxybenzene (Veratrole) O (C) 100 mg

O MM 0814.08 Imp. E (EP): Methyl Benzoate O (C) 100 mg O

MM 1131.00 Imp. G (EP): 4-Methoxyphenol (Mequinol) OH (A) 500 mg

O MM 0007.09 Imp. H (EP): 3-Methoxyphenol OH (B) 100 mg

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 101 From Atorvastatin to Zopiclone - 200 pharmaceutical impurities

LGC Standards offers 200 reference standards for pharmaceutical impurities to support the pharmaceutical industry worldwide.

• Acknowledged by regulation authorities worldwide • Impurities linked to the European Pharmacopoeia (EP) wherever possible • Customised pharmaceutical impurities created on request • Detailed certificates of analysis provided • Additional documentation on request • Assistance in finding the right material to suit your analyses

• Atorvastatin

• Bupropion • Clopidogrel

• Esomeprazol

• Ibuprofen

• Naproxen

• Omeprazole

• Risperidone

• Sildenafil

• Steroid hormones

• Venlafaxine

• Zopiclone

www.lgcstandards.com

Code Product Code Unit Guaifenesin MM 0354.00 Guaifenesin OH (A) 500 mg O OH

O MM 0354.04 Imp. A (EP): 2-Methoxyphenol (Guaiacol) OH (A) 500 mg

MM 0354.01 Imp. B (EP): 2-(2-Methoxyphenoxy)propane-1,3-diol HO OH (A) 100 mg (B-Isomer) O

O MM 0354.02 Imp. C (EP): 1,1'-Oxybis[3-(2-methoxyphenoxy) OH OH (A) 100 mg propan-2-ol](Bisether) O O O

O O MM 0354.03 Imp. D (EP): 1,3-Bis(2-methoxyphenoxy)propan-2-ol OH (A) 100 mg O O

O O Halofantrine Hydrochloride MM 0433.00 Halofantrine Hydrochloride Cl (A) 100 mg

F F Cl F x HCl

HO N

Haloperidol MM 1165.00 Haloperidol F (A) 250 mg Cl N O OH Haloperidol Decanoate MM 1276.12 Imp. L (EP): 1-(4-Fluorophenyl)ethanone F (A) 100 mg

O Harpagoside MM 0370.01 Methyl trans-Cinnamate O (B) 100 mg O

Heptaminol Hydrochloride

NH2 MM 0653.00 Heptaminol Hydrochloride x HCl on request HO Hexetidine

MM 0337.03 Imp. C (EP): 2,6-Bis(2-ethylhexyl)-7a- N (A) 100 mg methylhexahydro-1H-imidazo[1,5-c]imidazole N N (Hexedine) Hexylresorcinol MM 0111.00 Hexylresorcinol HO OH (A) 500 mg

MM 0045.11 Imp. A (EP): Phenol OH (B) 100 mg

MM 0294.01 Imp. B (EP): Resorcinol HO OH (B) 100 mg

Homatropine Methylbromide MM 0792.00 Homatropine Methylbromide H (A) 250 mg O H N+ Br- O OH H and enantiomer

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 103 Pharmaceutical impurities

Code Product Code Unit

MM 0792.03 Imp. C (EP): (2RS)-2-Hydroxy-2-phenylacetic Acid O (A) 100 mg

(Mandelic Acid) OH OH MM 0792.04 Imp. D (EP) as Bromide: (1R,2R,4S,5S,7s)-7-[[(2S)- H H (A) 100 mg O 3-Hydroxy-2-phenylpropanoyl]oxy]-9,9-dimethyl-3-oxa- H N+ O Br- 9-azoniatricyclo[3.3.1.02,4]nonane Bromide O

(Methylhyoscine Bromide) OH H H

MM 0792.06 Imp. F (EP): Methyl (2RS)-2-Hydroxy-2-phenylacetate (Methyl O (A) 100 mg

Mandelate) O OH Hydrochlorothiazide

OO OO MM 0011.00 Hydrochlorothiazide S S (A) 500 mg H2N NH Cl N H

OO OO MM 0011.03 Imp. A (EP): Chlorothiazide S S (A) 500 mg H2N NH Cl N

OO OO MM 0011.01 Imp. B (EP): 4-Amino-6-chlorobenzene-1,3-disulphonamide S S (B) 100 mg (Salamide) H2N NH2 Cl NH2 Hydrocodone Hydrogen Tartrate 2.5-Hydrate

MM 0037.00 Imp. A (EP) as Hydrochloride Trihydrate: Morphine N (A) 250 mg

Hydrochloride Trihydrate x HCl [Controlled Substance] x 3 H2O

HO O OH

MM 0280.00 Imp. A (EP) as Hemisulphate Pentahemihydrate: Morphine N (A) 250 mg Hemisulphate Pentahemihydrate x H2SO4 [Controlled Substance] x 5 H2O

HO O OH 2

MM 0004.00 Imp. C (EP) as Monohydrate: Codeine Monohydrate N (A) 100 mg [Controlled Substance] x H2O

O O OH

MM 0442.00 Imp. C (EP) as Phosphate Hemihydrate: Codeine N (A) 100 mg

Phosphate Hemihydrate x H3PO4 [Controlled Substance] x 1/2 H2O

O O OH MM 0672.00 Imp. D (EP) as Hydrochloride: 4,5h-Epoxy-14- N (A) 100 mg hydroxy-3-methoxy-17-methyl-morphinan-6- HO x HCl one Hydrochloride (Oxycodone Hydrochloride) [Controlled Substance] O O O MM 0004.02 Imp. E (EP): 7,8-Didehydro-4,5h-epoxy-3-methoxy- N (A) 100 mg 17-methylmorphinan-6-one (Codeinone)

O O O MM 0004.03 Imp. F (EP): 7,8-Didehydro-4,5h-epoxy-3,6h-dimethoxy- N (A) 100 mg 17-methylmorphinan (Methylcodeine; O-Methylcodeine) [Controlled Substance]

O O O MM 0630.01 Imp. H (EP): Diphenylmethanone (Benzophenone) O (B) 100 mg

Hydrocortisone MM 0185.00 Hydrocortisone O (A) 500 mg OH HO OH

104 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0193.00 Imp. A (EP): Prednisolone O (A) 500 mg OH HO OH

O MM 0214.00 Imp. B (EP): 17,21-Dihydroxypregn-4-ene- O (A) 500 mg OH 3,11,20-trione (Cortisone) O OH

O MM 0187.00 Imp. C (EP): Hydrocortisone Acetate O (A) 500 mg (Hydrocortisone 21-Acetate) O HO OH

O MM 0185.06 Imp. D (EP): 6i,11i,17,21-Tetrahydroxy-pregn-4-ene-3,20-dione O (A) 100 mg OH (6i-Hydroxyhydrocortisone) HO OH

O OH MM 0185.07 Imp. E (EP): 11i,17,21-Trihydroxypregna-4,6-diene-3,20-dione O (D) 100 mg OH (9%-Hydrocortisone) HO OH

O MM 0185.08 Imp. F (EP): 17,21-Dihydroxypregn-4-ene-3,20-dione O (A) 100 mg OH (Reichstein's Substance S) OH

O MM 0185.13 6-Hydroxyhydrocortisone O (D) 50 mg OH HO OH

O OH Hydrocortisone Acetate

O MM 0187.00 Hydrocortisone Acetate O (A) 500 mg O HO OH

O MM 0185.00 Imp. A (Pharmeuropa): 11i,17,21-Trihydroxy- O (A) 500 mg OH pregn-4-ene-3,20-dione (Hydrocortisone) HO OH

O MM 0187.06 Hydrocortisone 11,17,21-Triacetate O (B) 10 mg O O O O O

O MM 0187.09 11i,17,21-Trihydroxypregna-4,6-diene-3,20-dione 21-Acetate O (D) 100 mg O O HO OH

O MM 0194.00 Imp. C (Pharmeuropa): 11i,17-Dihydroxy-3,20- O (A) 500 mg dioxopregna-1,4-dien-21-yl Acetate O HO (Prednisolone Acetate) OH

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 105 Pharmaceutical impurities

Code Product Code Unit O MM 0186.00 Imp. D (Pharmeuropa): 17-Hydroxy-3,11,20-Trioxopregn- O (A) 500 mg 4-en-21-yl Acetate O O (Cortisone Acetate) OH

O Hydrocortisone 17-Butyrate

O MM 0188.00 Hydrocortisone 17-Butyrate OH (A) 500 mg HO O

O MM 0188.01 Hydrocortisone 21-Butyrate O (A) 100 mg O O HO OH

O Hydrocortisone Hydrogen Succinate MM 0185.00 Imp. A (EP): Hydrocortisone O (A) 500 mg OH HO OH

O MM 0187.00 Imp. B (EP): Hydrocortisone Acetate O (A) 500 mg O HO OH

O Hydromorphone Hydrochloride

MM 0037.00 Imp. C (EP) as Hydrochloride Trihydrate: N (A) 250 mg Morphine Hydrochloride Trihydrate x HCl [Controlled Substance] x 3 H2O

HO O OH

MM 0280.00 Imp. C (EP) as Hemisulphate Pentahemi- N (A) 250 mg hydrate: Morphine Hemisulphate Pentahemi- x H2SO4 hydrate x 5 H2O [Controlled Substance] HO O OH 2 Hydroxychloroquine Sulphate MM 0764.00 Hydroxychloroquine Sulphate Cl N (A) 500 mg x H2SO4

HN OH N

MM 0764.02 Desethylhydroxychloroquine Dihydrochloride Cl N (D) 100 mg x 2 HCl

HN OH N H MM 0764.04 O-Acetylhydroxychloroquine Cl N (A) 100 mg

HN O N O MM 0764.05 Hydroxychloroquine N-Oxide Dihydrochloride Cl N (B) 10 mg

x 2 HCl HN OH N O

Hydroxyethyl Salicylate MM 0112.00 Hydroxyethyl Salicylate O (A) 500 mg OH O

106 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0045.00 Imp. A (EP): Salicylic Acid O (A) 500 mg OH

OH Hydroxyzine Hydrochloride

Cl O MM 0852.00 Hydroxyzine Hydrochloride N OH (A) 250 mg N x 2 HCl

Cl MM 0380.01 Imp. A (EP): (RS)-1-[(4-Chlorophenyl)phenylmethyl]piperazine NH (A) 100 mg N

O MM 0852.02 Imp. B (EP) as Dihydrochloride: N OH (A) 50 mg 2-[2-[4-(Diphenylmethyl)piperazin-1-yl]ethoxy]- N ethanol Dihydrochloride (Decloxizine x 2 HCl Dihydrochloride)

Hymechromone MM 0294.00 Hymecromone HO O O (A) 500 mg

MM 0294.01 Imp. A (EP): 1,3-Dihydroxybenzene (Resorcinol) HO OH (B) 100 mg

MM 0294.02 Imp. B (EP): 7-Hydroxy-2-methyl-4H-1-benzopyran-4-one HO O (A) 100 mg

O MM 0294.03 2,4-Dihydroxyacetophenone HO OH (B) 100 mg O

MM 0294.04 Hymecromone Acetate O O O (A) 100 mg O

MM 0294.50 7-Acetoxy-3-acetyl-2-4H-1-benzopyran-4-one OO (A) 100 mg O

OO Hyoscine Butylbromide MM 0683.00 Hyoscine Butylbromide H (A) 500 mg O H + N O Br O

OH H

MM 0546.00 Imp. A (EP) as Hydrobromide Trihydrate: Hyoscine H H (A) 500 mg O H x HBr Hydrobromide Trihydrate N O O x 3 H2O H OH H

MM 0601.03 Imp. B (EP): (2RS)-3-Hydroxy-2-phenylpropanoic O (A) 100 mg

Acid (DL-Tropic Acid; Tropic Acid) OH

OH Hyoscine Hydrobromide MM 0546.00 Hyoscine Hydrobromide Trihydrate H H (A) 500 mg O H x HBr N O O x 3 H2O H OH H MM 0546.06 Imp. C (EP): (1R,2R,4S,5S,7s)-9-Methyl-3-oxa- H H (A) 100 mg 2,4 O 9-azatricyclo[3.3.1.0 ]non-7-yl 2-Phenylprop- H N O 2-enoate (Apohyoscine) O H H

MM 0601.03 Imp. D (EP): (2RS)-3-Hydroxy-2-phenylpropanoic O (A) 100 mg

Acid (DL-Tropic Acid; Tropic Acid) OH

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 107 Pharmaceutical impurities

Code Product Code Unit MM 0546.07 Hyoscine N-Oxide Hydrobromide H H (A) 100 mg O H N O x HBr O O H OH H Hyoscyamine Sulphate

MM 0601.03 Imp. A (EP): (2RS)-3-Hydroxy-2-phenylpropanoic Acid O (A) 100 mg

(DL-Tropic Acid; Tropic Acid) OH

OH MM 0546.00 Imp. D (EP) as Hydrobromide Trihydrate: Hyoscine H H (A) 500 mg O Hydrobromide Trihydrate H x HBr N O O x 3 H2O H OH H MM 0289.01 Imp. G (EP) as Hydrochloride: (1R,3r,5S)-8-Methyl- H (D) 100 mg O 8-azabicyclo[3.2.1]oct-3-yl 2-Phenylprop-2-enoate H N x HCl Hydrochloride (Apoatropine Hydrochloride) O H Ibuprofen MM 0002.00 Ibuprofen (A) 500 mg OH

MM 0002.13 Imp. A (EP): (2RS)-2-[3-(2-Methylpropyl)phenyl]propanoic Acid (A) 100 mg OH

MM 0002.01 Imp. B (EP):(2RS)-2-(4-Butylphenyl)propanoic Acid (A) 100 mg OH

MM 0002.10 Imp. C (EP): (2RS)-2-[4-(Methylpropyl)phenyl]propanamide (A) 100 mg NH2 O

MM 0002.11 Imp. D (EP): (2RS)-2-(4-Methylphenyl)propanoic Acid (A) 100 mg OH

MM 0002.04 Imp. E (EP): 1-[4-(2-Methylpropyl)phenyl]ethanone O (A) 100 mg

MM 0002.28 Imp. F (EP): 3-[4-(2-Methylpropyl)phenyl]propanoic Acid O (A) 100 mg OH

MM 0002.38 Imp. G (EP): (1RS,4RS)-7-(2-Methylpropyl)-1- OOH (D) 50 mg [4-(2-methylpropyl)phenyl]-1,2,3,4-tetrahydronaphthalene-1,4-dicarboxylic Acid

and enantiomer MM 0002.30 Imp. H (EP):(3RS)-1,3-Bis[4-(2-methylpropyl)phenyl]butan- O (D) 100 mg 1-one

MM 0002.31 Imp. I (EP): 1-(2-Methylpropyl)-4-[(3RS)-3- (A) 50 mg [4-(2-methylpropyl)phenyl]butyl]benzene

MM 0002.02 Imp. J (EP): (2RS)-2-[4-(2-Methylpropanoyl)phenyl]propanoic Acid (A) 100 mg OH

O MM 0002.26 Imp. K (EP): (2RS)-2-(4-Formylphenyl)propanoic Acid (A) 100 mg OH

O O

MM 0002.24 Imp. L (EP): 2-[4-(1-Hydroxy-2-methylpropyl)phenyl]propanoic Acid (A) 100 mg OH (1-Hydroxyibuprofen) O

OH MM 0002.34 Imp. M (EP): (2RS)-2-Hydroxy- OH (A) 100 mg OH 2-[4-(2-methylpropyl)phenyl]propanoic Acid O

108 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0002.35 Imp. N (EP): (2RS)-2-(4-Ethylphenyl)propanoic Acid (A) 100 mg OH

MM 0002.33 Imp. O (EP): 2-[4-(1-Methylpropyl)phenyl]propanoic Acid (A) 100 mg OH

MM 0002.19 Imp. P (EP):(2RS)-2-[4-(2-Methylpropyl)phenyl]propan-1-ol (A) 100 mg OH

MM 0002.36 Imp. Q (EP): 2-[4-(2-Methylpropyl)phenyl]ethanol OH (A) 100 mg

MM 0002.37 Imp. R (EP): 1,1'-(Ethane-1,1-diyl)-4,4'-(2- (A) 100 mg methylpropyl)dibenzene

MM 0002.03 4-Isobutylbenzoic Acid O (A) 100 mg OH

MM 0002.07 2-(4-Isobutyrylphenyl)propanamide (A) 100 mg NH2 O

O MM 0002.08 4-Acetylbenzoic Acid O (A) 100 mg OH

O MM 0002.09 4-Isobutyrylacetophenone O (A) 100 mg

O MM 0002.14 2-(4-Isobutyrylphenyl)propane (A) 100 mg

O MM 0002.15 2-Hydroxypropyl 2-(4-Isobutylphenyl)propanoate OH (A) 100 mg O

MM 0002.16 1-Hydroxyprop-2-yl 2-(4-Isobutylphenyl)propanoate on request O OH O

MM 0002.17 2,3-Dihydroxypropyl 2-(4-Isobutylphenyl)propanoate OH on request O OH

MM 0002.18 1,3-Dihydroxyprop-2-yl 2-(4-Isobutylphenyl)propanonate on request O OH O OH MM 0002.20 2-(4-n-Propylphenyl)propanoic Acid (A) 100 mg OH

MM 0002.21 2-(4-Isobutylphenyl)propionitrile (A) 100 mg

MM 0002.23 Isopropyl 2-(4-Isobutylphenyl)propanonate (A) 100 mg O

MM 0002.25 1-Ethyl-4-isobutylbenzene (A) 100 mg

MM 0002.29 (1RS,4SR)-7-(2-Methylpropyl)-1-[4-(2-methyl- OOH (D) 100 mg propyl)phenyl]-1,2,3,4-tetrahydronaphthalene- 1,4-dicarboxylic Acid

and enantiomer MM 0002.32 2-[4-(2-Hydroxy-2-methylpropyl)phenyl]propanoic Acid (A) 100 mg OH (2-Hydroxyibuprofen) O HO

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 109 Pharmaceutical impurities

Code Product Code Unit MM 0002.45 (2SR)-2-(4-Isobutylphenyl)-N-((SR)- (A) 100 mg H 1-phenylethyl)propanamide N

and enantiomer MM 0002.46 (2SR)-2-(4-Isobutylphenyl)-N-((RS)- (A) 100 mg H 1-phenylethyl)propanamide N

and enantiomer MM 0002.48 4-Isobutylstyrene (B) 10 mg

MM 0002.50 1-(4-Isobutylphenyl)ethanol (A) 100 mg OH

MM 0002.51 4-(1-Hydroxy-2-methylpropyl)acetophenone O (A) 100 mg

OH MM 0002.53 Ibuprofen Methyl Ester (A) 100 mg O

MM 0002.57 1-(4-Isopropylphenyl)ethanone O (A) 100 mg (4-Isopropylacetophenone)

MM 0002.59 2-(4-Isopropylphenyl)acrylic Acid (C) 50 mg OH

Idoxuridine MM 0791.00 Idoxuridine O (A) 500 mg I HN HO O N O

OH Imidocarb Dipropionate

MM 0742.00 Imidocarb Dipropionate O O (A) 100 mg H H N N x 2 N N OH H H N N Imipramine Hydrochloride MM 0077.00 Imipramine Hydrochloride (A) 500 mg

N N x HCl

MM 0589.00 Imp. A (EP) as Hydrochloride: 3-(10,11-Dihydro- (A) 250 mg 5H-dibenzo[b,f]azepin-5-yl)-N-methylpropan-1- N N x HCl amine Hydrochloride (Desipramine Hydrochloride) H

MM 0077.05 Imp. B (EP): 3-(5H-Dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan- (A) 100 mg 1-amine (Depramine; 10,11-Dehydroimipramine) N N

MM 0077.08 Imp. C (EP) as Hydrochloride: (A) 100 mg

10-[3-(Dimethylamino)propyl]acridin-9(10H)-one N N Hydrochloride x HCl O

MM 0077.03 N-[3-(10,11-Dihydro-5H-dibenzo-[b,f]azepin-5-yl)propyl]- (B) 10 mg N,N',N'-trimethylpropane-1,3-diamine Dihydrochloride N N N

x 2 HCl

110 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0077.04 10-Hydroxyimipramine BH Aduct (A) 100 mg 3-

N N x BH3

HO MM 0076.06 Iminodibenzyl (B) 100 mg

MM 0077.12 Imipramine N-Oxide (A) 100 mg

N N O

Indanazoline Hydrochloride MM 0588.02 4-Aminoindan Hydrochloride (A) 100 mg x HCl

NH2 Indapamide

MM 0477.00 Indapamide O O (A) 250 mg O S N N H N 2 H Cl MM 0477.01 Imp. A (EP): (2RS)-2-Methyl-1-nitroso- (A) 100 mg N 2,3-dihydro-1H-indole ON

MM 0477.02 Imp. B (EP): 4-Chloro-N-(2-methyl-1H- O O (A) 100 mg O S N indol-1-yl)-3-sulphamoylbenzamide N H N 2 H Cl

O O MM 0477.04 4-Chloro-3-sulfamoylbenzoic Acid O (C) 100 mg S OH H2N Cl

O O MM 0477.05 N-(4-Chloro-3-sulfamoylbenzoyl)-2-methylindoline O (D) 100 mg S N H2N Cl MM 0477.07 Triethylamine (C) 100 mg N MM 0477.08 2-Methylindoline (A) 100 mg HN

MM 0477.09 1-Amino-2-methylindoline Hydrochloride (D) 100 mg x HCl N H2N Indometacin MM 0584.00 Indometacin O (A) 500 mg OH N O Cl

O MM 0063.03 Imp. A (EP): 4-Chlorobenzoic Acid O (B) 100 mg OH

Cl New MM 0584.02 3,4-Dichloroindometacin ([1-(3,4-Dichlorobenzoyl)- O (A) 50 mg Cl OH 5-methoxy-2-methylindol-3-yl]acetic Acid) N O Cl

O Indoramin Hydrochloride

H MM 0802.02 Imp. A (BP): 3-(2-Bromoethyl)indole N (A) 100 mg

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 111 Pharmaceutical impurities

Code Product Code Unit Ipecacuanha

MM 0131.02 Emetine Dihydrochloride N (A) 100 mg x 2 HCl

H O O HN O O Ipratropium Bromide

New MM 0289.03 Atropic Acid O (A) 100 mg

New MM 0601.03 Imp. C (EP): (2RS)-3-Hydroxy-2-phenylpropanoic Acid O (A) 100 mg

(Tropic Acid) OH

OH Iprindole Hydrochloride

MM 0478.00 Iprindole Hydrochloride N (A) 100 mg N x HCl

Irbesartan MM 0862.01 Imp. A (EP): 1-(Pentanoylamino)-N-[[2'-(1H- O N N (A) 50 mg HN N tetrazol-5-yl)biphenyl-4-yl]methyl]cyclo- N H pentanecarboxamide NH O

Isoamyl Benzoate MM 1086.00 Isoamyl Benzoate O (A) 500 mg O

Isoconazol Nitrate MM 0541.00 Isoconazole Nitrate Cl (A) 100 mg

Cl Cl x HNO3 O N Cl N MM 0281.01 Imp. A (EP): (1RS)-1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl) ethanol (A) 100 mg N N

Cl Cl MM 0541.02 Imp. B (EP) as Nitrate: (2RS)-2-[(2,6-Dichlorobenzyl)oxy]- Cl (D) 100 mg 2-(2,4-dichlorophenyl)ethanamine Nitrate

Cl Cl x HNO3 O

NH2 Cl MM 0281.00 Imp. C (EP) as Nitrate: 1-[(2RS)- Cl (A) 500 mg 2-[(2,4-Dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethyl]- 1H-imidazole Nitrate (Miconazole Nitrate) Cl x HNO3 O N Cl Cl N Isoflurane MM 0500.02 Imp. B (EP): 2-(Difluoromethoxy)-1,1,1-trifluoroethane F (A) 100 mg F O F F F MM 0500.03 Imp. C (EP): (2RS)-2-Chloro-2-(chlorodifluoromethoxy)- Cl F F (A) 100 mg F 1,1,1-trifluoroethane O Cl F F

112 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0500.04 Imp. D (EP): 1,1-Dichloro-1-(difluoromethoxy)-2,2,2-trifluoroethane Cl Cl F (A) 100 mg F O F F F MM 0500.05 Imp. E (EP): 1,1-Dichloro-1-(chlorodifluoromethoxy)-2,2,2- Cl Cl F F (A) 100 mg F trifluoroethane O Cl F F MM 0500.06 Imp. F (EP): Acetone O (C) 100 mg

Isoproturon MM 2503.02 3-(2-Isopropylphenyl)-1,1-dimethylurea (A) 100 mg H NN

MM 2503.03 3-(3-Isopropylphenyl)-1,1-dimethylurea H (A) 100 mg NN

O Isosorbide Dinitrate

NO MM 0126.05 Imp. B (EP): Isosorbide 2-Nitrate H O 2 (A) 100 mg O

O HO H MM 0502.00 Imp. C (EP): Isosorbide Mononitrate (Isosorbide 5-Nitrate) H OH (A) 500 mg O

O O H O2N

MM 0126.01 2-Monomethyl Isosorbide H O on request O

O HO H

MM 0126.02 Dimethyl Isosorbide H O (B) 100 mg O

O O H

MM 0126.03 Isosorbide H OH (A) 500 mg O

O HO H NO MM 0126.04 Isomannit Dinitrate H O 2 on request O

O O H O2N Isosorbide Mononitrate

MM 0502.00 Isosorbide Mononitrate H OH (A) 500 mg O

O O H O2N NO MM 0126.05 Imp. C (EP): Isosorbide 2-Nitrate H O 2 (A) 100 mg O

O HO H

MM 0126.03 Isosorbide H OH (A) 500 mg O

O HO H Isoxsuprine Hydrochloride

MM 0576.00 Isoxsuprine Hydrochloride OH H (A) 500 mg N O x HCl

HO and enantiomere

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 113 Pharmaceutical impurities

Code Product Code Unit Itraconazole MM 0258.00 Itraconazole (A) 100 mg N N

N O

N and enantiomer

Cl Cl

O O N N N MM 0258.02 Imp. A (EP): 4-[4-[4-(4-Methoxyphenyl)piperazin- (A) 100 mg 1-yl]phenyl]-2-[(1RS)-1-methylpropyl]-2,4-dihydro- N N 3H-1,2,4-triazol-3-one N O

O MM 0258.04 Imp. C (EP): 4-[4-[4-[4-[[cis-2-(2,4-Dichlorophenyl)- (A) 100 mg 2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]- N N

methoxy]phenyl]piperazin-1-yl]phenyl]-2-propyl- N O 2,4-dihydro-3H-1,2,4-triazol-3-one

N and enantiomer

Cl Cl O

O O N N N MM 0258.05 Imp. D (EP): 4-[4-[4-[4-[[cis-2-(2,4-Dichlorophenyl)- (A) 100 mg 2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]- N N methoxy]phenyl]piperazin-1-yl]phenyl]-2-(1- N O methylethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

N and enantiomer

Cl Cl

O O N N N

114 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0258.07 Imp. F (EP): 2-Butyl-4-[4-[4-[4-[[cis-2-(2,4-dichloro- (A) 100 mg phenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan- N N 4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2,4- N O dihydro-3H-1,2,4-triazol-3-one

N and enantiomer

Cl Cl

O O N N N MM 0258.10 2,4-Dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol- N NH (A) 100 mg 3-one N O

O MM 0258.11 cis-2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)- and enantiomer (A) 100 mg 1,3-dioxolane-4-methanol Mesilate Cl Cl O

O S O N O O N N Ketamine Hydrochloride

O MM 0144.00 Ketamine Hydrochloride NH (A) 500 mg x HCl

MM 0144.01 Imp. A (EP): 1-[(2-Chlorophenyl)- N Cl (A) 100 mg HO (methylimino)methyl]cyclopentanol

O MM 0144.02 Imp. B (EP): (2RS)-2-(2-Chloro- OH Cl (A) 100 mg phenyl)-2-hydroxycyclohexanone

Ketoconazole MM 0145.00 Ketoconazole Cl (A) 500 mg Cl O

O O N N N N

O MM 0145.04 Imp. D (EP): 1-[4-[[(2RS,4SR)-2-(2,4-Dichlorophenyl)-2-(1H- Cl (A) 100 mg Cl imidazol-1-ylmethyl)-1,3-dioxolan- O 4-yl]methoxy]phenyl]piperazine O O N N N HN New MM 0145.05 O (A) 100 mg NOHN 1-Acetyl-4-(4-hydroxyphenyl)piperazine Ketoprofen MM 0001.00 Ketoprofen O (A) 500 mg OH

MM 0001.01 Imp. A (EP):1-(3-Benzoylphenyl)ethanone OO (A) 100 mg (3-Acetylbenzophenone)

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 115 Pharmaceutical impurities

Code Product Code Unit MM 0001.03 Imp. B (EP): (3-Benzoylphenyl)acetic Acid O (A) 100 mg OH

MM 0001.07 Imp. C (EP):3-[(1RS)-1-Carboxylethyl]benzoic Acid O (A) 100 mg OH HO O

MM 0001.12 Imp. D (EP): (2RS)-2-[3-(4-Methylbenzoyl)phenyl]propanoic Acid O (D) 100 mg OH

MM 0001.05 Imp. E (EP):(2RS)-2-(3-Benzoylphenyl)propanamide O (A) 100 mg NH2

MM 0001.04 Imp. F (EP): (2RS)-2-(3-Benzoylphenyl)propanenitrile O (A) 100 mg

MM 0001.20 Imp. G (EP): 3-[(1RS)-1-Cyanoethyl]benzoic Acid O (A) 100 mg HO N

MM 0001.22 Imp. H (EP): 3-(Cyanomethyl)benzoic Acid O (A) 100 mg HO N

MM 0001.14 Imp. I (EP): (3-Benzoylphenyl)ethanenitrile O (A) 100 mg

MM 0001.23 Imp. J (EP): (2RS)-2-[3-(2,4-Dimethylbenzoyl)- O (D) 50 mg phenyl]propanoic Acid OH O

MM 0001.02 3-Ethylbenzophenone O (A) 100 mg

MM 0001.11 3-(1-Hydroxyethyl)benzophenone OOH (A) 100 mg

MM 0001.13 3-Methylbenzophenone O (B) 100 mg

MM 0001.17 3-(1-Methoxyethyl)benzophenone OO (A) 100 mg

MM 0001.18 2-[3-(h-Hydroxybenzyl)phenyl]propanoic Acid OH (A) 100 mg OH

MM 0001.19 Ethyl 2-(3-Benzoylphenyl)propionate(Ketoprofen Ethyl Ester) O (A) 100 mg O

MM 0001.21 Isopropyl 2-(3-Benzoylphenyl)propionate O (A) 100 mg O

MM 0001.50 3-(1-Acetoxyethyl)benzophenone O O (A) 100 mg O

MM 0001.32 Methyl 2-(3-Benzoylphenyl)propionate (Ketoprofen Methyl O (A) 100 mg Ester) O O

MM 0001.33 2-Ethylhexyl 2-(3-Benzoylphenyl)propionate O (A) 100 mg (Ketoprofen 2-Ethylhexyl Ester) O

O Ketorolac Trometamol

O MM 0851.00 Ketorolac Trometamol OH (A) 250 mg OH x NH N 2 HO OH O MM 0851.03 Imp. I (EP): Phenyl(2,3-dihydro-1H-pyrrolizin- (A) 100 mg

5-yl)methanone N O

116 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Ketotifen Hydrogen Fumarate

MM 0180.00 Ketotifen Hydrogen Fumarate S N (A) 250 mg O HO O x OH O

MM 0180.04 Ketotifen S N (A) 100 mg

MM 0180.08 Imp. B (EP): (4RS)-10-Methoxy-4-(1-methyl- S N (A) 100 mg piperidin-4-yl)-4H-benzo[4,5]cyclohepta[1,2- b]thiophen-4-ol O OH

MM 0180.07 Imp. D (EP): 4-[(aRaS)-1-Methylpiperidin-4- O (A) 100 mg ylidene]-4,9-dihydro-10H-benzo[4,5]- S N cyclohepta[1,2-b]thiophen-10-one N-Oxide O (Ketotifen N-Oxide)

MM 0180.11 10-Methoxy-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one S (A) 100 mg O O

Labetalol Hydrochloride

MM 0438.00 Labetalol Hydrochloride OH (A) 500 mg H N x HCl HO

O NH2 Lacidipine

H MM 0407.00 Lacidipine N (A) 100 mg

O O O O O O

H MM 0407.01 Imp. A (BP): Ethyl Methyl (E)-4-{2-[2-(tert- N (A) 100 mg Butoxycarbonyl)vinyl]phenyl}-1,4-dihydro-2,6- dimethyl-pyridine-3,5-dicarboxylate O O O O O O

MM 0407.02 Imp. B (BP): Diethyl (E)-4-{2-[2-(tert-Butoxy- N (A) 100 mg carbonyl)vinyl]phenyl}-2,6-dimethylpyridine- O O 3,5-dicarboxylate O O O O

Lamivudine MM 0045.00 Imp. C (EP): Salicylic Acid O (A) 500 mg OH

MM 0749.05 Imp. E (EP): 4-Aminopyrimidin-2(1H)-one(Cytosine) NH2 (A) 100 mg N

O N H MM 0593.03 Imp. F (EP): Pyrimidine-2,4(1H,3H)-dione (Uracil) O (C) 100 mg HN

O N H

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 117 Pharmaceutical impurities

Code Product Code Unit Lamotrigine

N NH2 MM 0922.00 Lamotrigine N (A) 100 mg N

NH2 Cl Cl

N NH2 MM 0922.01 Imp. A (EP): 3-Amino-6-(2,3-dichlorophenyl)-1,2,4-triazin-5(4H)-one N (A) 100 mg NH

O Cl Cl

N NH2 MM 0922.03 Imp. C (EP): (2Z)-[2-(Diaminomethylidene)- N (A) 100 mg

diazanylidene](2,3-dichlorophenyl)acetonitrile NH2 N Cl Cl H New MM 0922.04 Imp. D (EP): 6-(2,3-Dichlorophenyl)-1,2,4- N O (A) 50 mg triazine-3,5(2H,4H)-dione N NH

O Cl Cl MM 0922.05 Imp. E (EP): 2,3-Dichlorobenzoic Acid O (A) 100 mg OH

Cl Cl

N NH2 New MM 0922.07 Imp. G (EP): 6-(2,4-Dichlorophenyl)-1,2,4- Cl N (A) 50 mg triazine-3,5-diamine N

NH2 Cl Lansoprazole MM 0474.00 Lansoprazole (A) 100 mg NH F F O N S F O N MM 0474.07 Imp. A (EP): 2-[(RS)-[[3-Methyl-1-oxido- (D) 100 mg NH 4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl]- F F O sulphinyl]-1H-benzimidazole (Lansoprazole N S F O N N-Oxide) O MM 0474.01 Imp. B (EP): 2-[[[3-Methyl-4-(2,2,2-trifluoro- (A) 100 mg NH ethoxy)pyridin-2-yl]methyl]sulphonyl]-1H- F F O benzimidazole (Lansoprazole Sulphone) N S F O O N MM 0474.06 Imp. C (EP): 2-[[[3-Methyl-4-(2,2,2-trifluoro- (A) 100 mg NH ethoxy)pyridin-2-yl]methyl]sulphanyl]-1H- F F O benzimidazole N S F N MM 0474.03 Imp. D (EP): 1H-Benzimidazol-2-ol (B) 100 mg NH

N OH MM 0474.05 Imp. E (EP): 1H-Benzimidazole-2-thiol (A) 100 mg NH

N SH MM 0474.02 Imp. F (EP): 2-[(RS)-[(4-Chloro-3-methylpyridin- (A) 100 mg NH 2-yl)methyl]sulphinyl]-1H-benzimidazole Cl N S O N

MM 0474.04 4-Ethoxyacetophenone O (C) 100 mg

O MM 0474.08 Lansoprazole Sulphone N-Oxide (A) 100 mg NH F F O N S F O O N O MM 0474.09 2-Chloromethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine F F (A) 100 mg O Hydrochloride Cl F x HCl N

118 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0474.13 1-Methyl-12-thioxopyrido[1',2':3,4]imidazo[1,2-a]benzimidazol- S (D) 100 mg O 2(12H)-one N N N Leflunomide

N MM 0859.00 Leflunomide H (D) 100 mg O N

O F

F F MM 0859.01 Imp. A (EP) as Hydrochloride: 4-(Trifluoro- H2N (A) 100 mg methyl)aniline Hydrochloride F x HCl

F F MM 0859.02 Imp. B (EP): (2Z)-2-Cyano-3-hydroxy-N-[4- N (A) 100 mg (trifluoromethyl)phenyl]but-2-enamide H (Teriflunomide) N OH O F

F F N MM 0859.03 Imp. C (EP): 5-Methyl-N-[3-(trifluoromethyl)- F F (A) 100 mg O H N phenyl]isoxazole-4-carboxamide F O MM 0859.04 Imp. D (EP): 5-Methylisoxazole-4-carboxylic Acid N (A) 100 mg O OH

O MM 0859.05 Imp. E (EP): 3-Methyl-N-[4-(trifluoromethyl)-phenyl]isoxazole- N (A) 50 mg O H 4-carboxamide N

O F

F F F MM 0859.06 Imp. F (EP): 5-Methyl-N-[2-(trifluoromethyl)- F (A) 100 mg N F phenyl]isoxazole-4-carboxamide O H N

O MM 0859.07 Imp. G (EP): 5-Methyl-N-(4-methylphenyl)- N (A) 100 mg O H isoxazole-4-carboxamide N O New MM 0859.08 Imp. H (EP): 2-Cyano-N-[4-(trifluoromethyl)- N (A) 50 mg phenyl]acetamide H N

O F

F F Levamisole Hydrochloride New N S MM 0706.00 Levamisole Hydrochloride x HCl (A) 100 mg N MM 0706.04 Imp. D (EP): 6-Phenyl-2,3-dihydro-imidazo[2,1-b]thiazole N S (A) 100 mg N Levocetirizine Dihydrochloride MM 1035.00 Levocetirizine Dihydrochloride O (D) 100 mg Cl O N OH N

x 2 HCl

Levodopa MM 0262.00 Levodopa O (A) 500 mg HO OH

NH2 HO MM 0634.00 Imp. B (EP): (2S)-2-Amino-3-(4-hydroxy- O (A) 100 mg phenyl)propanoic Acid (Tyrosine) OH

NH2 HO

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 119 Pharmaceutical impurities

Code Product Code Unit MM 0262.05 Imp. C (EP): (2RS)-2-Amino-3-(4-hydroxy- O (A) 100 mg 3-methoxyphenyl)propanoic Acid (3-Methoxy-DL-tyrosine; (DL)- OH

3-O-Methyldopa) NH2 HO O MM 0262.06 4-Hydroxy-3-methoxymandelic Acid OH (A) 100 mg OH

O HO O Levodropropizine

MM 1246.02 Imp. B (EP) as Hydrochloride: 1-Phenyl- NH (A) 100 mg piperazine Hydrochloride N x HCl

Levofloxacin

MM 0846.00 Levofloxacin N O (A) 100 mg N N

OH F O O Levomenthol MM 0388.00 Levomenthol OH (A) 500 mg

Levomepromazine Hydrochloride MM 0266.00 Levomepromazine Hydrochloride (A) 500 mg

N N x HCl S

O Levomepromazine Maleate

MM 0019.00 Levomepromazine Maleate O (A) 100 mg

N N OH x S OH

O O MM 0019.02 Imp. A (EP): 2-Methoxyphenothiazine (A) 100 mg

NH S

O MM 0019.01 Imp. B (EP): 10-[(2R)-3-(Dimethylamino)-2- (A) 100 mg

methylpropyl]-2-methoxy-10H-phenothiazine N N 5-Oxide (Levomepromazine S-Oxide) S O

O MM 0019.07 N-Demethyllevomepromazine Hydrochloride (D) 100 mg

N N H x HCl S

O MM 0019.09 Levomepromazine Sulphone Hydrochloride (A) 100 mg

N N x HCl O S O O Levonorgestrel

MM 0121.00 Levonorgestrel OH (A) 250 mg

120 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0121.08 Imp. G (Pharmeuropa): 13-Ethyl-6h17- OH (D) 50 mg dihydroxy-18,19-dinor-17h-pregn-4-en- 20-yn-3-one (6h-Hydroxylevonorgestrel) O OH MM 0121.01 Imp. H (Pharmeuropa): 13-Ethyl-6i17- OH (D) 100 mg dihydroxy-18,19-dinor-17h-pregn-4-en- 20-yn-3-one (6i-Hydroxylevonorgestrel) O OH

MM 0121.02 Imp. J (Pharmeuropa): 13-Ethyl-17-hydroxy- OH (D) 100 mg 18,19-dinor-17h-pregn-4-en-20-yn-3,6-dione (6-Oxolevonorgestrel, 6-Ketolevonorgestrel) O O MM 0121.12 Imp. L (Pharmeuropa): 13-Ethylgon-4-ene-3,17- O (D) 100 mg dione (Levodione, 18-Methyl-19-norandrost-4- ene-3,17-dione)

O MM 0121.11 Imp. M (Pharmeuropa): 13-Ethyl-17-hydroxy- OH (D) 100 mg 18,19-dinor-17h-pregna-4,6-dien-20-yn-3-one (96-Levonorgestrel, 6,7-Didehydrolevonorgestrel)

O Lidocaine Hydrochloride

MM 0102.04 Lidocaine Hydrochloride Monohydrate H (A) 500 mg N x HCl N x H O O 2

MM 0102.00 Lidocaine H (A) 500 mg N N O

MM 0102.02 Imp. A (EP): 2,6-Dimethylaniline (B) 100 mg NH2

H MM 0102.08 Imp. C (EP): N-(2,6-Dimethylphenyl)acetamide N (A) 100 mg

MM 0102.01 Imp. B (EP): 2-(Diethylazinoyl)-N-(2,6- H O (A) 100 mg N dimethylphenyl)acetamide (Lidocaine N2- N O Oxide)

MM 0102.05 Imp. D (EP) as Hydrochloride: N-(2,6- H (A) 100 mg N Dimethylphenyl)-2-(ethylamino)acetamide N x HCl H Hydrochloride (Monoethylglycinexylidide O Hydrochloride) MM 0102.09 Imp. E (EP) as Hydrochloride: 2,2'- H H (A) 100 mg N N N x HCl (Azanediyl)bis[N-(2,6-dimethylphenyl)- H acetamide] Hydrochloride O O

MM 0102.10 Imp. F (EP) as Hydrochloride: 2-(Diethyl- H (A) 100 mg N amino)-N-(2,3-dimethylphenyl)acetamide N x HCl Hydrochloride O

MM 0102.11 Imp. G (EP) as Hydrochloride: N-(2,6- H (A) 100 mg N N x HCl Dimethylphenyl)-2-[(1-methylethyl)amino]- H acetamide Hydrochloride O

MM 0102.03 Imp. H (EP): 2-Chloro-N-(2,6-dimethylphenyl)acetamide H (B) 100 mg N Cl O

H New MM 0102.12 Imp. I (EP) as Hydrochloride: 2-(Diethylamino)- N (A) 100 mg N-(2,4-dimethylphenyl)acetamide Hydrochloride N x HCl O

MM 0102.14 Imp. K (EP) as Hydrochloride: N-(2,6-Dimethyl- H (A) 100 mg N phenyl)-2-(ethylmethylamino)acetamide Hydro- N x HCl chloride O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 121 High purity solvents

• Range of over 80 solvents • Picograde® solvents for residue analysis • Optigrade® solvents for HPLC • LC MS solvents, additives and mixtures • New UHPLC solvents for Ultra High Performance Liquid Chromatography (UHPLC) • Headspace solvents • Compatible with FLORISIL® adsorbents, also available

LGC Standards Promochem® brand solvents for high accuracy measurement

• Packed to suit customer needs • Glass bottles from 1L to 4L • Cyclotainers

• Reservation of specific batches to maintain analytical consistency • Stock available for immediate delivery • Expert local customer service and technical support • Free samples available

www.lgcstandards.com

No part of this publication may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, recording or any retrieval system, without the written permission of the copyright holder. © LGC Standards, 2011. All rights reserved. 2787/SR/0111 Pharmaceutical impurities

Code Product Code Unit Liothyronine Sodium MM 0626.00 Liothyronine Sodium I (A) 50 mg O NH2 ONa HO I I O MM 0626.01 Liothyronine I (A) 100 mg O NH2 OH HO I I O Lisinopril Dihydrate

O MM 0598.00 Lisinopril Dihydrate O OH (A) 100 mg H N N x 2 H2O HO O

H2N MM 0598.01 Imp. A (EP): (2RS)-2-Amino-4-phenylbutanoic Acid (A) 100 mg

NH2

HO O MM 0598.02 Imp. B (EP) as Hydrate: 4-Methylbenzenesulphonic Acid Hydrate OO (C) 100 mg S OH x H2O

Lomustine

MM 0923.02 Imp. B (EP): 1-(2-Chloroethyl)-3-cyclohexylurea O (A) 100 mg Cl N N H H

MM 0923.03 Imp. C (EP): 1,3-Dicyclohexylurea O (A) 100 mg

N N H H Loperamide Hydrochloride MM 0025.00 Loperamide Hydrochloride Cl (A) 500 mg OH

N x HCl

MM 0025.15 Imp. B (EP) as Bromide: 4-(4-Chlorophenyl)- on request N O 1,1-bis[4-(dimethylamino)-4-oxo- 3,3-diphenylbutyl]-4-hydroxypiperidinium Bromide OH

N+ Br- Cl

MM 0025.04 Imp. C (EP): 4-(4-Chlorophenyl)piperidin-4-ol Cl (B) 100 mg OH

N H MM 0025.05 Imp. D (EP): 4-(4-Hydroxy-4-phenylpiperidin-1-yl)-N,N-dimethyl- (A) 100 mg 2,2-diphenylbutanamide OH

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 123 Pharmaceutical impurities

Code Product Code Unit MM 0025.09 Imp. F (EP): Loperamide Oxide Cl (A) 100 mg OH

N O

MM 0025.11 Imp. H (EP): 4-[4-(4-Chlorophenyl)-3,6- Cl (A) 100 mg dihydropyridin-1(2H)-yl]-N,N-dimethyl-2,2- diphenylbutanamide

MM 0025.07 Ethyl Diphenylacetate (A) 100 mg

MM 0025.08 h,h-Diphenyl-t-butyrolactone O (A) 100 mg

MM 0025.10 Dimethyl-(tetrahydro-3,3-diphenyl-2-furilidine)ammonium Bromide O (A) 100 mg

Br- N+

Loratadine

O MM 0257.00 Loratadine Cl (A) 100 mg N O

O MM 0257.03 Imp. A (EP): Ethyl 4-[(11RS)-8-Chloro-11- Cl (A) 100 mg hydroxy-6,11-dihydro-5H-benzo[5,6]cyclo- N O hepta[1,2-b]pyridin-11-yl]piperidine-1- OH carboxylate N

MM 0257.02 Imp. B (EP): 8-Chloro-5,6-dihydro-11H- Cl (A) 100 mg benzo[5.6]cyclohepta[1,2-b]pyridin-11-one O

O MM 0257.08 Imp. C (EP): Ethyl 4-(4,8-Dichloro-5,6-dihydro- Cl (D) 100 mg 11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11- N O ylidene)piperidine-1-carboxylate

Cl MM 0257.01 Imp. D (EP): 8-Chloro-11-(piperidin-4-ylidene)-6,11-dihydro-5H- Cl (A) 50 mg benzo[5,6]cyclohepta[1,2-b]pyridine NH (Descarboethoxyloratadine;Desloratadine)

MM 0257.05 Imp. G (EP): 8-Chloro-11-(1-methylpiperidin-4- Cl (A) 100 mg ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta- N [1,2-b]pyridine

124 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0257.07 Imp. H (EP): Ethyl 4-Oxopiperidine-1-carboxylate O (A) 100 mg N O

O MM 0257.06 (11RS)-8-Chloro-11-hydroxy-11-(1-methylpiperidin-4-yl)- Cl (A) 100 mg N 6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine OH

Lorazepam

H O MM 0071.00 Lorazepam N (A) 100 mg [Controlled Substance] OH Cl N

MM 0071.01 Imp. A (EP): (2-Amino-5-chlorophenyl)(2-chlorophenyl)methanone NH2 (B) 100 mg O (2-Amino-2',5-dichlorobenzophenone) Cl Cl

H O MM 0071.07 Imp. B (EP): (3RS)-7-Chloro-5-(2-chlorophenyl)- N (A) 100 mg 2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl O Acetate (Lorazepam Acetate) Cl N [Controlled Substance] O Cl

H O MM 0071.06 Imp. C (EP): 7-Chloro-5-(2-chlorophenyl)- N (A) 100 mg 1,3-dihydro-2H-1,4-benzodiazepin-2-one 4-Oxide Cl N O Cl

H O MM 0071.03 Imp. D (EP): (5RS)-7-Chloro-5-(2-chlorophenyl)- N (A) 100 mg 4,5-dihydro-1H-1,4-benzodiazepine-2,3-dione O Cl NH

MM 0071.02 Imp. E (EP): 6-Chloro-4-(2-chlorophenyl)- O (A) 100 mg quinazoline-2-carbaldehyde N N Cl Cl

MM 0071.04 6-Chloro-4-(2-chlorophenyl)-2-quinazolinecarboxylic Acid O (A) 100 mg N OH N Cl Cl

MM 0071.08 6-Chloro-4-(2-chlorophenyl)-2-quinazolinemethanol OH (A) 100 mg N

N Cl Cl

H MM 0071.09 6-Chloro-4-(2-chlorophenyl)-2(1H)-quinazolinone N O (A) 100 mg

N Cl Cl

Losartan Potassium

OH MM 0168.00 Losartan N N on request N NH N Cl N

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 125 Pharmaceutical impurities

Code Product Code Unit MM 0168.14 Imp. B (Pharmeuropa) : [2'-(1H-Tetrazol-5-yl)biphenyl- N N (A) 50 mg HN N 4-yl]methanol HO

MM 0168.04 Imp. C (Pharmeuropa) : [2-Butyl-5-chloro-1-[[2'-(1H- Cl N N (D) 50 mg HN N tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-imidazol- N

4-yl]methanol HO N

MM 0168.08 Imp. D (EP) : 2-Butyl-4-chloro-1H-imidazole-5-carbaldehyde O (A) 100 mg

NH Cl N

MM 0168.05 Imp. E (EP): 5-(4'-Methylbiphenyl-2-yl)-1H-tetrazole N N (A) 50 mg HN N

MM 0168.15 Imp. F (EP): 5-[4'[[2-Butyl-4-chloro-5-[[(1- O (A) 100 mg N N methylethyl)oxy]methyl]-1H-imidazol-1-yl]- HN N N methyl]biphenyl-2-yl]-1H-tetrazole (Losartan Cl Isopropyl Ether) N

MM 0173.04 Imp. G (EP) : Triphenylmethanol (A) 100 mg OH

MM 0168.16 Imp. H (EP) : [2-Butyl-4-chloro-1-[[2'-[2- (A) 100 mg (triphenylmethyl)-2H-tetrazol-5-yl]biphenyl- 4-yl]methyl]-1H-imidazol-5-yl]methanol OH N N N N N Cl N

MM 0168.18 Imp. J (EP) : [2-Butyl-4-chloro-1-[[2'-(1H- O (A) 100 mg tetrazol-5-yl)biphenyl-4-yl]methyl]-1H- O N N imidazol-5-yl]methyl Acetate HN N N Cl N

O MM 0168.12 Losartan Methyl Ether N N (A) 100 mg HN N N Cl N

Lovastatin MM 0050.00 Lovastatin O (A) 100 mg O

OH H OO

MM 0377.00 Imp. A (EP): (1S,7S,8S,8aR)-8-[2-[(2R,4R)-4-Hydroxy- O (A) 100 mg 6-oxotetrahydro-2H-pyran-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a- O hexahydronaphthalen-1-yl (2S)-2-Methylbutanoate (Mevastatin) OH OO

126 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0050.01 Imp. B (EP) as Sodium Salt: (3R,5R)-7-[(1S,2S,6R,8S,8aR)- O (A) 100 mg 2,6-Dimethyl-8-[[(2S)-2-methylbutanoyl]oxy]-1,2,6,7,8,8a- OH ONa OH hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic Acid Sodium H Salt (Lovastatin Hydroxy Acid Sodium Salt) OO

MM 0050.03 Imp. C (EP): (1S,3R,7S,8S,8aR)-3,7-Dimethyl-8-[2-[(2R)-6-oxo- O (A) 100 mg 3,6-dihydro-2H-pyran-2-yl]ethyl]-1,2,3,7,8,8a-hexahydronaphthalen- O

1-yl (2S)-2-Methylbutanoate (Dehydrolovastatin) H OO

Malic Acid New MM 1332.01 Imp. A (EP): (E)-Butenedioic Acid (Fumaric Acid) O (B) 100 mg HO OH O Maprotiline Hydrochloride MM 0820.00 Maprotiline Hydrochloride (A) 250 mg

N H x HCl

MM 0820.01 Imp. A (EP): 3-(9,10-Ethanoanthracen-9(10H)-yl)prop-2-enal (A) 50 mg

MM 0820.02 Imp. B (EP) as Hydrochloride: (C) 10 mg

3-(9,10-Ethanoanthracen-9(10H)-yl)-N- N [3-(9,10-ethanoanthracen-9(10H)-yl)propyl]-N- x HCl methylpropan-1-amine Hydrochloride

MM 0820.03 Imp. C (EP) as Hydrochloride: 3-(9,10-Ethanoanthracen- (C) 10 mg

9(10H)-yl)propan-1-amine Hydrochloride NH 2 x HCl

MM 0820.04 Imp. D (EP) as Hydrochloride: 3-(9,10-Ethanoanthracen- (A) 50 mg

9(10H)-yl)-N-methylprop-2-en-1-amine Hydrochloride N (Dehydromaprotiline Hydrochloride) H x HCl

MM 0820.05 Imp. E (EP) as Hydrochloride: 3-(9,10-Ethanoanthracen- (A) 100 mg

9(10H)-yl)-N,N-dimethylpropan-1-amine Hydrochloride N x HCl

Mebendazole

O MM 0882.06 Imp. F (EP): Methyl [5-(4-Methylbenzoyl)-1H- H (A) 50 mg N O benzimidazol-2-yl]carbamate NH N O O MM 0882.05 Imp. E (EP): Ethyl (5-Benzoyl-1H-benzimidazol- H (A) 50 mg N O 2-yl)carbamate NH N O H MM 0882.02 Imp. B (EP): (2-Hydroxy-1H-benzimidazol-5- N (A) 50 mg yl)phenylmethanone OH N

O MM 0882.04 Imp. D (EP): Methyl (5-Benzoyl-1-methyl-1H- O (A) 50 mg N O benzimidazol-2-yl)carbamate NH N O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 127 Pharmaceutical impurities

Code Product Code Unit Mebeverine Hydrochloride

MM 0319.00 Mebeverine Hydrochloride O (A) 100 mg N O

O O O x HCl MM 0319.02 Imp. A (Pharmeuropa): 4-Methoxyphenylacetone O (B) 100 mg

O MM 0319.03 Imp. B (Pharmeuropa) as Hydrochloride: N-[(1RS)- (A) 100 mg NH 1-[(4-Methoxyphenyl)methyl]ethyl]ethanamine x HCl Hydrochloride O MM 0319.01 Imp. D (Pharmeuropa): 3,4-Dimethoxybenzoic Acid (Veratric Acid) O (B) 100 mg HO

O O Mechlorethamine Hydrochloride

MM 0823.00 Mechlorethamine Hydrochloride N x HCl (A) 500 mg Cl Cl Meclofenoxate Hydrochloride MM 0044.00 Meclofenoxate Hydrochloride O (A) 500 mg O N O x HCl

Cl MM 0044.02 (4-Chlorophenoxy)acetic Acid O (B) 100 mg O OH

Cl Meclozine Hydrochloride

Cl MM 0586.00 Meclozine Dihydrochloride N (A) 500 mg N

x 2 HCl

MM 0380.09 Imp. B (Pharmeuropa): (RS)-(4-Chlorophenyl)(phenyl)methanol Cl (B) 100 mg (4-Chlorobenzhydrol) OH

MM 0380.10 Imp. C (Pharmeuropa): (4-Chlorophenyl)- Cl (B) 100 mg (phenyl)methanone (4-Chlorobenzophenone) O

MM 0380.04 Imp. F (Pharmeuropa): 1,4-Bis[(4-chlorophenyl)- (A) 100 mg phenylmethyl]piperazine

Cl N N Cl

Cl MM 0380.01 Imp. H (Pharmeuropa): 1-[(RS)-(4-Chlorophenyl)- NH (A) 100 mg phenylmethyl]piperazine ((RS)-1-[(4-Chlorophenyl)- N phenylmethyl]piperazine)

O MM 0586.05 Meclozine N-Oxide Cl (B) 10 mg N N

N MM 0586.07 N-(3-Methylbenzyl)piperazine Dihydrochloride x 2 HCl (A) 100 mg HN

128 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0586.08 Imp. D (Pharmeuropa): 1,1'-(Benzene- (A) 50 mg 1,3-diyldimethanediyl) bis[4-[(4-chlorophenyl)- phenylmethyl]piperazine] N N Cl

N N Cl

MM 0586.09 Imp. E (Pharmeuropa): 1-(Diphenylmethyl)- N (A) 50 mg 4-(3-methylbenzyl)piperazine N

Medroxyprogesterone MM 0635.00 Medroxyprogesterone O (A) 100 mg OH

Medroxyprogesterone Acetate MM 0532.00 Medroxyprogesterone Acetate O (A) 100 mg O

MM 0532.01 Imp. A (EP): 6i-Hydroxy-6-methyl-3,20-dioxopregn-4-en-17-yl O (D) 100 mg O Acetate (6i-Hydroxymedroxyprogesterone Acetate) O

O OH MM 0635.00 Imp. B (EP):17-Hydroxy-6h-methylpregn-4-ene-3,20-dione O (A) 100 mg OH (Medroxyprogesterone)

MM 0532.05 Imp. E (EP): 6-Methylidene-3,20-dioxopregn-4-en-17-yl O (A) 100 mg Acetate (6-Methylenehydroxyprogesterone Acetate) O O

MM 0532.06 Imp. F (EP): 6h-Methyl-3,20-dioxo-5i-pregnan-17-yl Acetate O (D) 50 mg O (4,5i-Dihydromedroxyprogesterone Acetate) O

O H MM 0532.07 Imp. G (EP): 6-Methyl-3,20-dioxopregna-4,6-dien-17-yl O (A) 250 mg Acetate (Megestrol Acetate) O O

MM 0532.09 Imp. H (EP): 3,20-Dioxopregn-4-en-17-yl Acetate O (A) 100 mg

(Hydroxyprogesterone Acetate) O

O Mefenamic Acid MM 0327.00 Mefenamic Acid O (A) 500 mg OH

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 129 Pharmaceutical impurities

Code Product Code Unit

MM 0327.01 Imp. A (EP): 2,3-Dimethylaniline NH2 (B) 100 mg

MM 0327.02 Imp. B (EP): N-(2,3-Dimethylphenyl)- (A) 100 mg 2-[(2,3-dimethylphenyl)amino]benzamide O

N H NH

MM 0217.14 Imp. C (EP): 2-Chlorobenzoic Acid O (A) 100 mg OH

Cl MM 0278.01 Imp. D (EP): Benzoic Acid O (B) 100 mg OH

Mefloquine Hydrochloride

F MM 1198.01 2,8-Bis-(trifluoromethyl)-4-quinolinol F (A) 100 mg F F F N F

OH Megestrol Acetate MM 0532.07 Megestrol Acetate O (A) 250 mg

MM 0532.00 Imp. A (EP): 6h-Methyl-3,20-dioxopregn-4-en-17-yl O (A) 100 mg Acetate (Medroxyprogesterone Acetate) O

New MM 0532.09 Imp. K (Pharmeuropa): 3,20-Dioxopregn-4-en-17-yl O (A) 100 mg

Acetate O

O Meloxicam

OO MM 0246.00 Meloxicam S (A) 500 mg N H N N

OH O S

OO MM 0084.03 Imp. A (EP): Ethyl 4-Hydroxy-2-methyl- S (A) 100 mg 2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide N O

OH O

H N MM 0246.01 Imp. B (EP): 5-Methylthiazol-2-amine 2 N (A) 100 mg S

MM 0246.16 Imp. C (EP): N-[(2Z)-3,5-Dimethylthiazol-2(3H)- O O (A) 50 mg S ylidene]-4-hydroxy-2-methyl-2H-1,2-benzothiazine- N 3-carboxamide 1,1-Dioxide N N OH O S

MM 0246.17 Imp. D (EP): N-[(2Z)-3-Ethyl-5-methylthiazol-2(3H)-ylidene]- O O (A) 50 mg S 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide N 1,1-Dioxide N N OH O S

130 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit

OO MM 0084.02 Imp. E (EP): Methyl 4-Hydroxy-2-methyl- S (A) 100 mg 2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide N O

OH O MM 0084.12 Imp. F (EP): Isopropyl 4-Hydroxy-2-methyl-2H- O O (A) 100 mg S 1,2-benzothiazine-3-carboxylate 1,1-Dioxide N (1-Methylethyl 4-Hydroxy-2-methyl-2H-1,2- O

benzothiazine-3-carboxylate 1,1-Dioxide) OH O Melperone

MM 0321.00 Melperone O (A) 100 mg N

F Memantine Hydrochloride MM 1045.01 1-Hydroxy-3,5-dimethyladamantane OH (A) 100 mg

MM 1045.04 1-Chloro-3,5-dimethyladamantane Cl (A) 100 mg

Mephenesin MM 0810.00 Mephenesin OH (A) 500 mg O OH

Mephentermine Hemisulphate

H MM 0740.00 Mephentermine Hemisulfate N (A) 500 mg x ½ H2SO4

Mepivacaine Hydrochloride MM 0368.00 Mepivacaine Hydrochloride (A) 500 mg H N x HCl N O MM 0102.02 Imp. A (EP): 2,6-Dimethylaniline (B) 100 mg NH2

MM 0368.02 Imp. B (EP) as Hydrochloride: (RS)-N-(2,6- (A) 50 mg H N x HCl Dimethylphenyl)piperidine-2-carboxamide N H Hydrochloride O MM 0368.03 Imp. C (EP): N-(2,6-Dimethylphenyl)pyridine-2-carboxamide (A) 100 mg H N N O MM 0368.06 Mepivacaine N-Oxide (A) 100 mg H N N O O Mepyramine Maleate

MM 0559.00 Mepyramine Maleate O (A) 500 mg N N OH x ON OH O

MM 0559.02 Imp. A (EP): N-(4-Methoxybenzyl)pyridin-2-amine NH (A) 100 mg

MM 0164.03 Imp. B (EP): 4-Methoxybenzaldehyde (Anisaldehyde) O (C) 100 mg

O MM 0084.01 Imp. C (EP): Pyridin-2-amine NH2 (B) 100 mg N

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 131 Pharmaceutical impurities

Code Product Code Unit

MM 0559.05 Mepyramine N-Oxide Dihydrochloride O (A) 100 mg N N x 2 HCl ON

Mequinol MM 1131.00 Mequinol O (A) 500 mg

HO Mesalazine MM 0217.00 Mesalazine O (A) 500 mg H2N OH

OH MM 0042.01 Imp. A (EP): 4-Aminophenol H2N (B) 100 mg

OH MM 0042.07 Imp. B (EP): 3-Aminophenol (B) 100 mg

H2N OH MM 0217.06 Imp. C (EP): 2-Aminophenol (A) 100 mg

NH2 MM 0217.07 Imp. D (EP): 3-Aminobenzoic Acid O (A) 100 mg OH

NH2 MM 0217.09 Imp. F (EP): 3-Amino-2-hydroxybenzoic O (A) 100 mg Acid (3-Aminosalicylic Acid) OH

NH2 MM 0217.10 Imp. G (EP): 2,5-Dihydroxybenzoic Acid O (A) 100 mg HO OH

OH MM 0045.00 Imp. H (EP): 2-Hydroxybenzoic Acid O (A) 500 mg (Salicylic Acid) OH

MM 0217.12 Imp. I (EP): 2-Hydroxy-5-(phenyldiazenyl)benzoic Acid O (A) 50 mg N (Phenylazosalicylic Acid) N OH

OH MM 0093.17 Imp. K (EP) as Hydrochloride: Aniline Hydrochloride H2N (B) 100 mg x HCl

MM 0217.14 Imp. L (EP): 2-Chlorobenzoic Acid O (A) 100 mg OH

Cl MM 0217.15 Imp. M (EP): 2-Chloro-5-nitrobenzoic Acid O (A) 100 mg O2N OH

Cl MM 0217.16 Imp. N (EP): 2-Hydroxy-5-nitrobenzoic Acid O (A) 100 mg O2N (5-Nitrosalicylic Acid) OH

OH MM 0227.04 Imp. O (Pharmeuropa): 4-Aminobenzene- H2N (A) 100 mg sulphonic Acid (Sulphanilic Acid) OH S O O MM 0217.02 5-Acetaminosalicylic Acid OOH (A) 100 mg OH O

N H Metamizole Sodium

O MM 0052.00 Metamizole Sodium Monohydrate O O (A) 500 mg NS ONa N x H2O N

132 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit

MM 0052.02 O H (A) 100 mg Imp. A (EP): 4-Formylamino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H- N O pyrazol-3-one (4-Formylaminophenazone) N N

MM 0052.04 Imp. B (EP): 4-Amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol- O (A) 100 mg NH2 3-one (Ampyrone) N N

O H MM 0052.10 Imp. C (EP) as Hydrochloride: 4-Methylamino-1,5-dimethyl- N (A) 100 mg 2-phenyl-1,2-dihydro-3H-pyrazol-3-one Hydrochloride N x HCl (4-Methylaminophenazone Hydrochloride) N

MM 0052.05 Imp. D (EP): 4-Dimethylamino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H- O (A) 100 mg N pyrazol-3-one (4,4-Dimethylaminophenazone) N N

MM 0052.01 4-Acetylaminophenazone O H (A) 100 mg NO N N

MM 0052.50 4-Benzylideneaminoantipyrine O (A) 100 mg N N N

Metformin Hydrochloride MM 0056.00 Metformin Hydrochloride NH NH (A) 500 mg x HCl H2NNN H

NH MM 0056.01 Imp. A (EP): Cyanoguanidine N (B) 100 mg

H2NN H MM 0056.07 Imp. B (EP) as Nitrate: (4,6-Diamino-1,3,5- NH2 (A) 100 mg

triazin-2-yl)guanidine Nitrate NNNH x HNO3

H2NNN NH2 H MM 0056.03 Imp. C (EP): N,N-Dimethyl-1,3,5-triazine-2,4,6-triamine (A) 100 mg H2NNN NN

NH2

MM 0056.04 Imp. D (EP): 1,3,5-Triazine-2,4,6-triamine (Melamine) H2NNHN 2 (B) 100 mg NN

NH2 MM 0056.05 Imp. E (EP) as Hydrochloride:1-Methylbiguanide Hydrochloride NH NH (A) 100 mg x HCl H2NNN H H

H MM 0056.06 Imp. F (EP) as Hydrochloride: N-Methylmethanamine Hydrochloride N x HCl (C) 100 mg Methadone Hydrochloride MM 0531.06 Imp. E (EP): Diphenylacetonitrile (A) 100 mg N

Methamphetamine Hydrochloride

H MM 0964.00 Methamphetamine Hydrochloride N (A) 100 mg [Controlled Substance] x HCl

Methotrexate

OOH MM 0040.00 Methotrexate O (A) 500 mg

NH2 N H N OH N N O H2N N N

MM 0040.08 Imp. A (EP) as Hydrochloride: (2,4-Diaminopteridin- NH2 (A) 100 mg N 6-yl)methanol Hydrochloride N OH x HCl

H2N N N

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 133 Pharmaceutical impurities

Code Product Code Unit Methoxsalen

MM 0555.00 Methoxsalen O (A) 500 mg O O O

MM 0555.01 5-Methoxypsoralen (Bergapten) O O O (A) 100 mg

O Methoxyphenamine Hydrochloride

H MM 0655.00 Methoxyphenamine Hydrochloride N (A) 500 mg x HCl O

Methyl Nicotinate MM 0549.00 Methyl Nicotinate O (A) 500 mg NO

MM 0553.00 Imp. A (EP): Nicotinic Acid O (A) 500 mg NOH

Methyl Parahydroxybenzoate MM 0431.00 Methyl Parahydroxybenzoate O (A) 500 mg O

HO MM 0045.01 Imp. A (EP): 4-Hydroxybenzoic Acid O (B) 100 mg OH

HO MM 0498.00 Imp. B (EP): Ethyl 4-Hydroxybenzoate O (A) 500 mg (Ethyl Parahydroxybenzoate) O HO MM 0432.00 Imp. C (EP): Propyl 4-Hydroxybenzoate O (A) 500 mg (Propyl Parahydroxybenzoate) O HO MM 0496.00 Imp. D (EP): Butyl 4-Hydroxybenzoate O (A) 500 mg (Butyl Parahydroxybenzoate) O HO MM 0431.01 Sodium Methyl Parahydroxybenzoate O (A) 500 mg O

NaO Methylphenidate Hydrochloride MM 1031.04 Ritalinic Acid O OH (A) 100 mg H N

Methylprednisolone

O MM 0190.00 Methylprednisolone OH (A) 100 mg HO OH

O MM 0190.01 Imp. A (EP): 17,21-Dihydroxy-6h-methylpregna-1,4-diene- OH (D) 50 mg OH 3,11,20-trione O

Methylprednisolone Acetate MM 0191.00 Methylprednisolone Acetate O (D) 100 mg O O HO OH

134 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit

O MM 0190.00 Imp. B (EP): Methylprednisolone OH (A) 100 mg HO OH

MM 0194.00 Imp. E (EP): Prednisolone Acetate O (A) 500 mg O O HO OH

O Methylprednisolone Hydrogen Succinate MM 0192.00 Methylprednisolone Hydrogen Succinate Sodium Salt O on request O ONa O HO OH O

O MM 0190.00 Imp. A (EP): Methylprednisolone OH (A) 100 mg HO OH

MM 0191.00 Imp. C (EP): Methylprednisolone Acetate O (D) 100 mg O O HO OH

Methyltestosterone MM 0558.00 Methyltestosterone OH (A) 250 mg

O MM 0323.00 Testosterone OH (A) 500 mg

O Metixene Hydrochloride MM 0125.01 Imp. A (EP): 9H-Thioxanthene (A) 100 mg

MM 0125.02 Imp. B (EP): 9H-Thioxanthen-9-one (B) 100 mg (Thioxanthone) O

MM 0125.03 3-Chloromethyl-1-methylpiperidine Cl on request

Metoclopramide

MM 0073.00 Metoclopramide Hydrochloride Monohydrate O (A) 500 mg Cl N N x HCl H x H2O H2N O

MM 0073.03 Imp. A (EP): 4-(Acetylamino)-5-chloro-N- O (A) 100 mg Cl N [2-(diethylamino)ethyl]-2-methoxybenzamide O N H N O H MM 0073.04 Imp. B (EP): Methyl 4-(Acetylamino)-5-chloro-2-methoxybenzoate O (A) 100 mg Cl OO

N O H MM 0073.02 Imp. C (EP): 4-Amino-5-chloro-2-methoxybenzoic Acid O (B) 100 mg Cl OH

H2N O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 135 Pharmaceutical impurities

Code Product Code Unit MM 0073.05 Imp. D (EP): Methyl 4-(Acetylamino)-2-methoxybenzoate O (A) 100 mg OO

N O H MM 0073.01 Imp. E (EP): N,N-Diethylethane-1,2-diamine (B) 100 mg N H2N

MM 0073.06 Imp. F (EP): 4-Amino-5-chloro-N-[2-(diethylamino)ethyl]- O (A) 100 mg Cl N 2-hydroxybenzamide N H H2N OH

MM 0073.07 Imp. G (EP): N'-(4-Amino-5-chloro-2-methoxybenzoyl)-N,N- O (A) 100 mg Cl N diethylethane-1,2-diamine N-Oxide (Metoclopramide N-Oxide) N H O H2N O MM 0073.08 Imp. H (EP): 4-(Acetylamino)-2-hydroxybenzoic Acid O (A) 100 mg OOH

N OH H MM 0073.09 Methyl 4-Amino-2-hydroxybenzoate O (A) 100 mg O

H2N OH MM 0073.10 Methyl 4-(Acetylamino)-2-hydroxybenzoate O (A) 100 mg OO

N OH H Metoprolol Succinate

OH MM 0279.00 Metoprolol Succinate H (A) 100 mg O N

O 2 O x HO OH O

OH MM 0027.04 Imp. A (EP): (2RS)-1-(Ethylamino)-3-[4-(2-methoxyethyl)- H (A) 100 mg phenoxy]propan-2-ol O N O MM 0027.01 Imp. B (EP): 4-(2-Methoxyethyl)phenol OH (A) 100 mg

MM 0027.24 Imp. C (EP) as Hydrochloride: 4-[(2RS)-2- OH H (A) 100 mg O N Hydroxy-3-[(1-methylethyl)amino]propoxy]- x HCl benzaldehyde Hydrochloride O MM 0027.06 Imp. D (EP): (2RS)-3-[4-(2-Methoxyethyl)phenoxy]propane- OH (A) 100 mg 1,2-diol O OH O

OH MM 0027.07 Imp. E (EP): (2RS)-1-[2-(2-Methoxyethyl)phenoxy]- H (A) 100 mg 3-[(1-methylethyl)amino]propan-2-ol O N O

OH MM 0027.08 Imp. F (EP): (2RS)-1-[(1-Methylethyl)amino]-3-phenoxypropan-2-ol H (A) 100 mg O N

MM 0027.09 Imp. G (EP): 2-(4-Hydroxyphenyl)ethanol OH (A) 100 mg

OH MM 0027.10 Imp. H (EP): (2RS)-1-[4-(2-Hydroxyethyl)phenoxy]- H (A) 100 mg 3-[(1-methylethyl)amino]propan-2-ol O N HO

OH MM 0027.11 (2RS)-1-(4-Ethenylphenoxy)-3-[(1-methylethyl)amino]- H (A) 100 mg propan-2-ol O N

OH OH MM 0027.12 Imp. J (EP): 1-[2-Hydroxy- H (A) 50 mg 3-[(1-methylethyl)amino]propoxy]- O O N 3-[4-(2-methoxyethyl)phenoxy]propan-2-ol O

OH MM 0027.13 (2RS)-1-[4-[(EZ)-2-Methoxyethenyl]phenoxy]- H (A) 100 mg O N 3-[(1methylethyl)amino]propan-2-ol O

OH MM 0027.28 Imp. M (EP) as Dihydrochloride: H H (A) 100 mg 1,3-Bis[(1-methylethyl)amino]propan-2-ol Dihydrochloride N N x 2 HCl

136 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit

OH MM 0027.16 Imp. N (EP): (2RS)-3-[(1-Methylethyl)amino]propane-1,2-diol H (A) 100 mg HO N

MM 0027.03 Imp. O (EP): 1,1'-[(1-Methylethyl)imino]bis- OH OH (A) 100 mg [3-[4-(2-methoxyethyl)phenoxy] O N O

propan-2-ol] O O Metoprolol Tartrate

OH MM 0027.00 Metoprolol Tartrate H (A) 500 mg O N

O 2 OH O x HO OH O OH

OH MM 0027.04 Imp. A (EP): (2RS)-1-(Ethylamino)- H (A) 100 mg 3-[4-(2-methoxyethyl)phenoxy]propan-2-ol O N O MM 0027.01 Imp. B (EP): 4-(2-Methoxyethyl)phenol OH (A) 100 mg

OH MM 0027.07 Imp. E (EP): (2RS)-1-[2-(2-Methoxyethyl)- H (A) 100 mg phenoxy]-3-[(1-methylethyl)amino]propan-2-ol O N O

OH MM 0027.08 Imp. F (EP): (2RS)-1-[(1-Methylethyl)amino]- H (A) 100 mg 3-phenoxypropan-2-ol O N

MM 0027.09 Imp. G (EP): 2-(4-Hydroxyphenyl)ethanol OH (A) 100 mg

OH MM 0027.10 Imp. H (EP): (2RS)-1-[4-(2-Hydroxyethyl)- H (A) 100 mg phenoxy]-3-[(1-methylethyl)amino]propan-2-ol O N HO

OH MM 0027.11 (2RS)-1-(4-Ethenylphenoxy)-3-[(1-methylethyl)amino]propan- H (A) 100 mg 2-ol O N

OH OH MM 0027.12 Imp. J (EP): 1-[2-Hydroxy- H (A) 50 mg 3-[(1-methylethyl)amino]propoxy]-3-[4- O O N (2-methoxyethyl)phenoxy]propan-2-ol O

OH MM 0027.13 (2RS)-1-[4-[(EZ)-2-Methoxyethenyl]phenoxy]- H (A) 100 mg O N 3-[(1methylethyl)amino]propan-2-ol O

OH MM 0027.28 Imp. M (EP) as Dihydrochloride: H H (A) 100 mg 1,3-Bis[(1-methylethyl)amino]propan-2-ol Dihydrochloride N N x 2 HCl

OH MM 0027.16 Imp. N (EP): (2RS)-3-[(1-Methylethyl)amino]propane-1,2-diol H (A) 100 mg HO N

MM 0027.03 Imp. O (EP): 1,1'-[(1-Methylethyl) OH OH (A) 100 mg imino]bis-[3-[4-(2-methoxyethyl) O N O

phenoxy]propan-2-ol] O O

O MM 0027.02 1-[4-(2-Methoxyethyl)phenoxy]-2,3-epoxypropane O (A) 100 mg

O MM 0027.17 1-Chloro-3-[4-(2-methoxyethyl)phenoxy]propan-2-ol OH (A) 100 mg OCl

O MM 0027.18 4,4'-(2-Hydroxy-1,3-propandiyldioxy)- OH (A) 100 mg bis[(2-methoxyethyl)benzene)] OO O O MM 0027.22 3-Chloropropane-1,2-diol OH (B) 100 mg Cl OH

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 137 Pharmaceutical impurities

Code Product Code Unit

MM 0027.26 1-[2-(2-Methoxyethyl)phenyoxy]-2,3-epoxypropane O O (C) 50 mg O

Metronidazole

O2N MM 0012.00 Metronidazole OH (A) 500 mg N N MM 0012.02 Imp. A (EP): 2-Methyl-4-nitroimidazole NH (B) 100 mg O2N N

MM 0012.05 Imp. B (EP): 4-Nitroimidazole NH (C) 100 mg O2N N

OH MM 0012.06 Imp. C (EP): 2-(4-Nitro-1H-imidazol-1-yl)ethanol N (A) 100 mg O2N N MM 0012.07 Imp. D (EP): 2-(5-Nitro-1H-imidazol-1-yl)ethanol O2N (A) 100 mg OH N

OH MM 0012.01 Imp. E (EP): 2-(2-Methyl-4-nitro-1H-imidazol-1-yl)ethanol N (A) 100 mg O2N N

MM 0012.09 Imp. G (EP): 2-(2-Methyl-5-nitro-1H- O2N (A) 100 mg OH imidazol-1-yl)acetic Acid N O N

O2N MM 0012.04 1-(2-Hydroxyethyl)-2-hydroxymethyl-5-nitroimidazole OH (A) 100 mg (Hydroxymetronidazole) N N OH Metronidazole Benzoate

MM 0278.00 Metronidazole Benzoate O2N (A) 100 mg O N O N

MM 0012.00 Imp. A (EP): Metronidazole O2N (A) 500 mg OH N

MM 0012.02 Imp. B (EP): 2-Methyl-5-nitroimidazole O2N (B) 100 mg (2-Methyl-4-nitroimidazole) NH N MM 0278.01 Imp. C (EP): Benzoic Acid O (B) 100 mg OH

MM 0278.04 2-(2-Methyl-4-nitro-1H-imidazol-1-yl)ethyl Benzoate (A) 100 mg O N O2N O N Mevastatin MM 0377.00 Mevastatin O (A) 100 mg O

OH OO

Mexiletine Hydrochloride

MM 0146.00 Mexiletine Hydrochloride NH2 (A) 500 mg O x HCl

MM 0146.01 Imp. A (EP): 2,6-Dimethylphenol (A) 100 mg OH

MM 0146.02 Imp. B (EP): 1-(2,6-Dimethylphenoxy)propan-2-one O (A) 100 mg O

138 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Mianserin Hydrochloride

MM 0147.00 Mianserin Hydrochloride N (A) 100 mg

N x HCl

MM 0147.01 Imp. A (EP): [2-[(2RS)-4-Methyl-2-phenylpiperazin-1-yl] N (A) 100 mg phenyl]methanol N

MM 0147.04 Imp. C (EP): (2-Aminophenyl)methanol H2N (B) 100 mg

OH MM 0147.06 Mianserin N-Oxide O (D) 100 mg N

Miconazole Nitrate MM 0281.00 Miconazole Nitrate Cl (A) 500 mg

Cl x HNO3 O N Cl Cl N MM 0074.00 Miconazole Cl (A) 250 mg

O N Cl Cl N MM 0281.01 Imp. A (EP): (1RS)-1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol Cl (A) 100 mg

HO N

N MM 0524.00 Imp. B (EP) as Nitrate: 1-[(2RS)-2-[(4-Chlorobenzyl)oxy]- Cl (A) 500 mg 2-(2,4-dichlorophenyl)ethyl]-1H-imidazole Nitrate (Econazole Nitrate) Cl x HNO3 O N Cl N MM 0281.03 Imp. C (EP) as Nitrate: (2RS)-2-[(2,4-Dichlorobenzyl)oxy]- Cl (D) 100 mg 2-(2,4-dichlorophenyl)ethanamine Nitrate

Cl x HNO3 O

NH2 Cl Cl MM 0541.00 Imp. D (EP) as Nitrate: 1-[(2RS)-2-[(2,6-Dichlorobenzyl)oxy]- Cl (A) 100 mg 2-(2,4-dichlorophenyl)- ethyl]-1H-imidazole Nitrate (Isoconazole Nitrate) Cl Cl x HNO3 O N Cl N

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 139 Pharmaceutical impurities

Code Product Code Unit MM 0281.06 Imp. F (EP) as Nitrate: 1-[(2RS)- Cl (A) 100 mg 2-[(3,4-Dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethyl]- 1H-imidazole Nitrate Cl x HNO3 O N Cl Cl N MM 0281.07 Imp. G (EP) as Nitrate: 1-[(2RS)- Cl (A) 100 mg 2-[(2,5-Dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethyl]- 1H-imidazole Nitrate Cl x HNO3 Cl O N Cl N MM 0281.08 Imp. H (EP) as Nitrate: 1-[(2RS)-2-Benzyloxy- Cl (A) 100 mg 2-(2,4-dichlorophenyl)ethyl]-1H-imidazole Nitrate

Cl x HNO3 O N

N MM 0281.09 Imp. I (EP) as Nitrate: 1-[(2RS)-2-[(2-Chlorobenzyl)- Cl (A) 100 mg oxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole Nitrate

Cl x HNO3 O N Cl N MM 0281.10 1-(2,4-Dichlorobenzoylmethyl)imidazole Cl (A) 100 mg

O N

N Midazolam

H O MM 0070.02 Imp. F (EP): 7-Chloro-5-(2-fluorophenyl)-1,3- N (A) 100 mg dihydro-2H-1,4-benzodiazepin-2-one (1-Des[(diethylamino)ethyl]flurazepam) Cl N

Minoxidil MM 0521.00 Minoxidil (A) 500 mg

NNHN 2

N O

NH2

MM 0521.01 Imp. A (EP): 6-Chloropyrimidine-2,4-diamine 3-Oxide ClN NH2 (A) 100 mg N O

NH2

MM 0521.02 Imp. B (EP): 6-Chloropyrimidine-2,4-diamine ClN NH2 (C) 100 mg N

NH2 MM 0521.05 Imp. E (EP): 6-(Piperidin-1-yl)pyrimidine-2,4-diamine (A) 100 mg (Desoxyminoxidil) NNHN 2 N

NH2 Mirtazapine MM 1005.01 Imp. E (EP): (2RS)-4-Methyl-1-(3-methyl- (A) 100 mg pyridin-2-yl)-2-phenylpiperazine N N

140 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 1005.02 Imp. A (EP): (14bRS)-2-Methyl-1,2,3,4,10- (A) 100 mg 14b-hexahydropyrazino[2,1-a]pyrido[2,3- O c][2]benzazepine 2-Oxide N N

MM 1005.03 Imp. B (EP): [2-[(2RS)-4-Methyl-2-phenyl- (A) 100 mg piperazin-1-yl]pyridin-3-yl]methanol N HO N

MM 1005.07 1-Methyl-3-phenylpiperazine (A) 100 mg

N HN Moclobemide

MM 0250.00 Moclobemide O O (A) 100 mg N N H Cl Modafinil New MM 0599.14 Imp. K (EP): [Oxybis(methanetriyl)]tetrabenzene (A) 50 mg (Bis(diphenylmethyl) Ether)

Molsidomine MM 0267.00 Molsidomine O (A) 250 mg O O N - N N+ N O

O MM 0267.02 Imp. A (EP) as Hydrochloride: 3-(Morpholin-4-yl)sydnonimine N - (A) 100 mg HN + Hydrochloride N x HCl N (Linsidomine Hydrochloride) O MM 0267.03 Imp. B (EP): 4-Nitrosomorpholine O (A) 100 mg N N O

N MM 0267.01 Imp. C (EP): (2E)-(Morpholin-4-ylimino)acetonitrile N (A) 100 mg N O

MM 0267.06 Imp. E (EP): Morpholine HN (A) 100 mg O Montelukast Sodium

MM 0698.00 Montelukast Sodium O on request Cl N S ONa

Morphine Hydrochloride

MM 0037.00 Morphine Hydrochloride Trihydrate N (A) 250 mg [Controlled Substance] x HCl x 3 H2O

HO O OH

MM 0442.00 Imp. A (EP) as Phosphate Hemihydrate: N (A) 100 mg Codeine Phosphate Hemihydrate x H3PO4 [Controlled Substance] x ½ H2O

O O OH

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 141 Pharmaceutical impurities

Code Product Code Unit h h MM 0037.01 Imp. B (EP): 7,7',8,8'-Tetradehydro-4,5 :4',5' -diepoxy- N (A) 100 mg 17,17'-dimethyl-2,2'-bimorphinanyl-3,3',6h,6'h-tetrol HOO OH (Pseudomorphine; 2,2'-Bimorphine)

HO O OH N

MM 0037.03 Imp. F (EP): (17S)-7,8-Didehydro-4,5h-epoxy-17-methylmorphinan- (A) 100 mg O N 3,6h-diol 17-Oxide (Morphine N-Oxide) [Controlled Substance] HO O OH

MM 0037.02 7,7',8,8'-Tetradehydro-4,5a:4',5'a-diepoxy-3,3'-dimethoxy- N (A) 100 mg 17,17'-dimethyl-2,2'-bimorphinanyl-6a,6'a-diol(Codeine HOO O Dimer; Dimethyl Pseudomorphine)

O O OH N

Morphine Sulphate

MM 0280.00 Morphine Hemisulphate Pentahemihydrate N (A) 250 mg [Controlled Substance] x H2SO4 x 5 H2O

HO O OH 2

MM 0442.00 Imp. A (EP) as Phosphate Hemihydrate: N (A) 100 mg Codeine Phosphate Hemihydrate x H3PO4 [Controlled Substance] x ½ H2O

O O OH h h MM 0037.01 Imp. B (EP): 7,7',8,8'-Tetradehydro-4,5 :4',5' -diepoxy- N (A) 100 mg 17,17'-dimethyl-2,2'-bimorphinanyl-3,3',6h,6'h-tetrol HOO OH (Pseudomorphine;2,2'-Bimorphine)

HO O OH N

MM 0037.03 h (A) 100 mg Imp. F (EP): (17S)-7,8-Didehydro-4,5 -epoxy- O N 17-methylmorphinan-3,6h-diol 17-Oxide (Morphine N-Oxide) [Controlled Substance]

HO O OH Moxifloxacin Hydrochloride MM 0885.00 Moxifloxacine Hydrochloride H (D) 100 mg O HN N N H x HCl OH F O O Moxonidine MM 1278.02 Imp. B (EP): N-(Imidazolidin-2-ylidene)-4,6- (A) 100 mg N O dimethoxy-2-methylpyrimidin-5-amine HN N (4-Methoxymoxonidine) N N H O Mycophenolate Mofetil

MM 1001.00 Mycophenolate Mofetil O OH (D) 100 mg O N O O O O

MM 1001.05 Imp. E (EP): Methyl (4E)-6-(4-Hydroxy-6- O OH (A) 100 mg methoxy-7-methyl-3-oxo-1,3-dihydroiso- O O benzofuran-5-yl)-4-methylhex-4-enoate O O

MM 1001.06 Imp. F (EP): (4E)-6-(4-Hydroxy-6-methoxy-7- O OH (A) 100 mg methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)- OH O 4-methylhex-4-enoic Acid (Mycophenolic Acid) O O

OH MM 1001.07 Imp. G (EP): 2-(Morpholin-4-yl)ethyl O O (A) 100 mg O (4E)-6-(4-Hydroxy-6-methoxy-7-methyl- N O 3-oxo-1,3-dihydroisobenzofuran-5-yl)- O O O 4-methylhex-4-enoate N-Oxide

142 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit

MM 1001.08 Imp. H (EP): 7-Hydroxy-5-methoxy-4-methyl- O OH (A) 100 mg 6-[2-[(2RS)-2-methyl-5-oxotetrahydrofuran-2- O O yl]ethyl]isobenzofuran-1(3H)-one O O

Nabumetone MM 0153.00 Nabumetone O (A) 500 mg

O MM 0153.02 Imp. A (EP): 3-(6-Methoxynaphthalen-2-yl)- O (A) 100 mg 5-methylcyclohexanone

O MM 0153.03 Imp. B (EP): (5RS)-5-(6-Methoxynaphthalen-2-yl)- O (A) 100 mg 3-methylcyclohex-2-enone

O MM 0153.04 Imp. C (EP): (2RS)-4-(6-Methoxynaphthalen-2-yl)-butan-2-ol OH (A) 100 mg

O MM 0153.05 Imp. D (EP): (E)-4-(6-Methoxynaphthalen-2-yl)-but-3-en-2-one O (A) 100 mg

O New MM 0153.06 Imp. E (EP): 1,5-Bis(6-methoxynaphthalen- O (A) 50 mg 2-yl)pentan-3-one

O O MM 0153.07 Imp. F (EP): 6,6'-Dimethoxy-2,2'-binaphthalenyl O (A) 100 mg

O MM 0152.01 (6-Methoxy-2-naphthyl)acetic Acid ((6-Methoxynaphthalen- OH (A) 100 mg 2-yl)acetic O O Acid, h-Demethylnaproxen) Nadolol MM 0439.00 Nadolol OH on request HO OH H O N

and enantiomers

MM 0439.06 Imp. F (EP) as Hydrochloride: (2RS)-1-[(1,1- OH (A) 50 mg H Dimethylethyl)amino]-3-(naphthalen-1-yloxy)- O N x HCl propan-2-ol Hydrochloride

MM 0439.07 Imp. G (EP) as Hydrochloride: (2RS)-1-[(1,1- OH (A) 50 mg H Dimethylethyl)amino]-3-[(5,6,7,8-tetrahydro- O N x HCl naphtalen-1-yl)oxy]-propan-2-ol Hydrochloride Nafcillin Sodium

O MM 0392.00 Nafcillin Sodium ONa on request O N O S NH H

HO MM 0392.02 Penilloic Acids of Nafcillin O (D) 100 mg O HN H N S

O MM 0026.04 6-Aminopenicillanic Acid OH (B) 100 mg O N

H N S 2 H MM 0392.04 2-Ethoxynaphthoic Acid O OH (B) 100 mg O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 143 Pharmaceutical impurities

Code Product Code Unit Naftidrofuryl Hydrogen Oxalate

MM 0373.00 Naftidrofuryl Hydrogen Oxalate O (A) 500 mg N OOH O x O OH O Naloxone Hydrochloride Dihydrate MM 0272.00 Naloxone Hydrochloride Dihydrate (A) 250 mg N OH x HCl x 2 H2O

HO O O Naltrexone

MM 0233.00 Naltrexone Hydrochloride N (A) 100 mg

HO x HCl

HO O O Nandrolone MM 0660.00 Nandrolone OH (A) 250 mg H

O MM 0660.01 19-Norandrost-4-ene-3,17-dione (Estr-4-ene-3,17-dione) O (A) 100 mg

O Nandrolone Decanoate MM 0982.00 Nandrolone Decanoate O (A) 100 mg O

O MM 0660.00 Imp. D (EP): 17!-Hydroxyestr-4-en-3-one (Nandrolone) OH (A) 250 mg

O Naphazoline Hydrochloride

MM 0075.00 Naphazoline Hydrochloride HN (A) 500 mg N x HCl

MM 0075.06 Imp. A (EP) as Hydrochloride: N-(2-Aminoethyl)- O (A) 100 mg NH 2-(naphthalen-1-yl)acetamide Hydrochloride N 2 H x HCl (Naphthylacetylethylenediamine Hydrochloride)

MM 0075.02 Imp. B (EP): (Naphthalen-1-yl)acetic Acid O (B) 100 mg (1-Naphthylacetic Acid) OH

MM 0075.04 Imp. C (EP): (Naphthalen-1-yl)acetonitrile N (B) 100 mg (1-Naphthylacetonitrile)

MM 0075.05 Ethyl (1-Naphthyl)acetate O (A) 100 mg O

144 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0075.07 (Naphthalen-1-y)lacetamide (1-Naphthylacetamide) O (A) 100 mg

NH2

Naphazoline Nitrate

MM 0286.00 Naphazoline Nitrate HN (A) 500 mg N x HNO3

MM 0075.06 Imp. A (EP) as Hydrochloride: O (A) 100 mg NH2 N-(2-Aminoethyl)-2-(naphthalen-1-yl)acetamide N Hydrochloride (Naphthylacetylethylenediamine H x HCl Hydrochloride)

MM 0075.02 Imp. B (EP): (Naphthalen-1-yl)acetic Acid O (B) 100 mg (1-Naphthylacetic Acid) OH

MM 0075.04 Imp. C (EP): (Naphthalen-1-yl)acetonitrile (1-Naphthylacetonitrile) N (B) 100 mg

MM 0075.05 Ethyl (1-Naphthyl)acetate O (A) 100 mg O

MM 0075.07 (Naphthalen-1-yl)acetamide O (A) 100 mg

(1-Naphthylacetamide) NH2

Naproxen MM 0152.00 Naproxen (A) 500 mg OH

O O MM 0152.06 Imp. A (EP): (2S)-2-(6-Hydroxynaphthalen-2-yl)- (A) 100 mg OH propanoic Acid (O-Demethylnaproxen) O HO MM 0152.09 Imp. B (EP): (2S)-2-(5-Chloro-6-methoxy- (A) 100 mg OH naphthalen-2-yl)propanoic Acid O (5-Chloronaproxen) O Cl MM 0152.10 Imp. C (EP): (2S)-2-(5-Bromo-6-methoxy- (A) 100 mg OH naphthalen-2-yl)propanoic Acid O (5-Bromonaproxen) O Br MM 0152.11 Imp. D (EP): (2S)-2-(5-Iodo-6-methoxy- (A) 100 mg OH naphthalen-2-yl)propanoic Acid O (5-Iodonaproxen) O I MM 0152.02 Imp. E (EP): Methyl (2S)-2-(6-Methoxy- (A) 100 mg O naphthalen-2-yl)propanoate O (Naproxen Methyl Ester) O MM 0152.12 Imp. F (EP): Ethyl (2S)-2-(6-Methoxy- (A) 100 mg O naphthalen-2-yl)propanoate O (Naproxen Ethyl Ester) O MM 0152.14 Imp. H (EP): 6-Methoxynaphthalen-2-ol (Hydroxynerolin) OH (A) 100 mg

O MM 0152.01 Imp. I (EP):(6-Methoxynaphthalen-2-yl)acetic Acid OH (A) 100 mg O (h-Demethylnaproxen) O MM 0152.18 Imp. J (EP): 2-Ethyl-6-methoxynaphthalene (Ethylnerolin) (A) 100 mg

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 145 Pharmaceutical impurities

Code Product Code Unit MM 0152.16 Imp. K (EP): (1RS)-1-(6-Methoxynaphthalen-2-yl)ethanol OH (A) 100 mg

O MM 0152.07 Imp. L (EP): 1-(6-Methoxynaphthalen-2-yl)ethanone (Acetylnerolin) O (B) 100 mg

O MM 0152.08 Imp. M (EP): 2-Methoxynaphthalene (Nerolin) (B) 100 mg

O MM 0152.17 Imp. N (EP): 2-Bromo-6-methoxynaphthalene Br (C) 100 mg

O MM 0152.04 Naproxen Sodium (A) 500 mg ONa

O O MM 0152.15 2-Carboxy-6-methoxynaphthalene O (A) 100 mg OH

O Nateglinide

O OH MM 0847.00 Nateglinide O on request

N H

New MM 0314.03 Imp. C (EP): Phenylalanine O (B) 100 mg H2N OH

Nevirapine Anhydrous MM 1146.01 Imp. A (EP): 11-Ethyl-4-methyl-5,11-dihydro- (A) 100 mg 6H-dipyrido [3,2-b:2',3'-e][1,4]diazepin-6-one N N N

NH O H MM 1146.02 Imp. B (EP): 4-Methyl-5,11-dihydro-6H- N N N (A) 100 mg dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one NH O MM 1146.03 Imp. C (EP): 4-Methyl-11-propyl-5,11-dihydro- (D) 100 mg 6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one N N N

NH O MM 1146.04 3-Amino-2-chloro-4-methylpyridine Cl N (A) 100 mg

H2N

Nicardipine Hydrochloride

H MM 0465.00 Nicardipine Hydrochloride N (A) 250 mg

O O N x HCl O O

NO2 MM 0465.01 3-Methyl 5-[Methyl(phenylmethyl)amino]- N on request ethyl 2,6-Dimethyl-4-(3-nitrophenyl)pyridine- O O N x 2 HCl 3,5-dicarboxylate Dihydrochloride O O

NO2 Nicergoline

Br MM 0115.00 Nicergoline H (A) 100 mg N N O N O O

146 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Cl MM 0115.02 Imp. A (EP): [(6aR,9R,10aS)-10a-Methoxy- H (D) 50 mg 4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydro- N N indolo[4,3-fg]quinolin-9-yl]methyl 5-Chloro- O N O pyridine-3-carboxylate O

MM 0115.04 Imp. C (EP): [(6aR,9R,10aS)-10a-Methoxy-4,7-dimethyl- H (D) 100 mg N 4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin- N 9-yl]methanol (Methylmethoxylumilysergol) OH O

MM 0115.06 Imp. D (EP): 5-Bromopyridine-3-carboxylic Acid Br (B) 100 mg

HO N

MM 0115.03 5-Debromonicergoline H on request N N O N O O Nicorandil MM 0924.00 Nicorandil O (A) 100 mg O N NO2 H N Nicotinamide MM 0552.00 Nicotinamide O (A) 500 mg

NNH2

MM 0552.01 Isonicotinamide O (A) 100 mg

NH2 N Nicotine MM 0517.00 Nicotine (A) 500 mg N N

MM 0517.03 Imp. C (EP): (5S)-1-Methyl-5-(pyridin-3-yl)pyrrolidin-2-one (Cotinine) (A) 100 mg N N O

MM 0517.01 Imp. G (EP): 3-[(2S)-Piperidin-2-yl]pyridine (Anabasine) (A) 100 mg

NN H

Nicotinic Acid MM 0553.00 Nicotinic Acid O (A) 500 mg NOH

MM 0553.03 Imp. E (Pharmeuropa): Pyridine-4-carboxylic Acid O (A) 100 mg (Isonicotinic Acid) OH N MM 0549.00 Methyl Nicotinate O (A) 500 mg NO

MM 0104.00 Benzyl Nicotinate O (A) 500 mg NO

Nifedipine

H MM 0003.00 Nifedipine N (A) 500 mg

O O

O O NO2

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 147 Reference materials for physical properties

LGC Standards, Europe’s most comprehensive single Thermal properties source of reference materials, offers over 750 reference materials for physical properties. For manufacturers, the determination of the physical properties of their product Optical properties can be one of the most important steps in quality assurance. Surface properties Our range covers many physical properties including thermal, surface properties, particle shape and size, ion Particle shape and size activity, viscosity, electrical, and polymeric properties. Of particular interest are the products for determination of optical properties such as molecular absorption, Ion activity luminescence, colour measurement and refractive index. Viscosity

• Materials and standards from commercial sources Electrical properties and international bodies • Fast delivery of high quality materials Polymeric properties • Expert local customer service and technical support

To receive a copy of our catalogue 'Reference materials for physical properties' please contact your local office or visit our website.

www.lgcstandards.com Pharmaceutical impurities

Code Product Code Unit MM 0003.02 Imp. A (EP): Dimethyl 2,6-Dimethyl-4-(2-nitrophenylpyridine- N (A) 100 mg 3,5-dicarboxylate (Nitrophenylpyridine Analogue of Nifedipine) O O

O O NO2

MM 0003.01 Imp. B (EP): Dimethyl 2,6-Dimethyl-4-(2-nitrosophenylpyridine- N (A) 100 mg 3,5-dicarboxylate (Nitrosophenylpyridine Analogue of Nifedipine) O O

O O NO

MM 0003.07 Imp. C (EP) as E/Z-Mixture: Methyl (E/Z)-2-(2-Nitrobenzylidene)- O (A) 100 mg 3-oxobutanoate O

O NO2

MM 0003.08 Imp. D (EP): Methyl 3-Aminobut-2-enoate H2N (C) 100 mg O

O MM 0003.03 2-Nitrobenzaldehyde O (B) 100 mg

NO2

Niflumic Acid MM 0850.00 Niflumic Acid O (A) 250 mg OH

N NH

F F MM 0915.01 Imp. A (EP): 2-Chloropyridine-3-carboxylic N Cl (A) 100 mg Acid (2-Chloronicotinic Acid) OH

O N OH MM 0850.05 Imp. B (EP): 2-Hydroxy-N-[3-(trifluoro- F F (A) 100 mg H methyl)phenyl]pyridine-3-carboxamide N F O MM 0161.06 Imp. C (EP): 3-(Trifluoromethyl)aniline F F (B) 100 mg F

NH2 MM 0850.01 Imp. F (EP): Methyl 2-[[3-(Trifluoromethyl)- F F (A) 100 mg phenyl]amino]pyridine-3-carboxylate F (Niflumic Acid Methyl Ester)

N NH

O Nifuroxazide MM 0574.00 Nifuroxazide OH (A) 500 mg H O N O2N N O MM 0574.01 Imp. A (EP): 4-Hydroxybenzohydrazide OH (C) 100 mg H (p-Hydroxybenzohydrazide) N H2N O MM 0431.00 Imp. B (EP): Methyl 4-Hydroxybenzoate OH (A) 500 mg (Methyl Parahydroxybenzoate) O

O MM 0943.02 Imp. C (EP): (5-Nitrofuran-2-yl)methylidene O (A) 100 mg Diacetate ((5-Nitrofuran-2-yl)methylene Diacetate) O O N O 2 O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 149 Pharmaceutical impurities

Code Product Code Unit Nifursol

OH O MM 0444.00 Nifursol NO (A) 100 mg O N N 2 2 N O H

NO2

MM 0444.01 5-Nitro-2-furfural O (C) 100 mg O NO2

MM 0444.02 5-Nitrofurfural Hydrazone N (A) 100 mg H2N O NO2 MM 0444.03 3,5-Dinitrosalicylic Acid Hydrazide OH O (A) 100 mg O N NH 2 N 2 H

NO2 Nikethamide MM 0627.00 Nikethamide O on request NN

Nimesulide

H MM 0378.00 Nimesulide N (A) 250 mg S O O O2N O

MM 0378.01 Imp. A (EP): N-(2,4-Dinitro-6-phenoxyphenyl)methanesulphonamide NO2 H (A) 100 mg N S O O O2N O

H MM 0378.02 Imp. B (EP): N-(2-Phenoxyphenyl)methanesulphonamide N (A) 100 mg S O O O

MM 0378.03 Imp. C (EP): 2-Phenoxyaniline NH2 (A) 100 mg

MM 0378.04 Imp. D (EP): 4-Nitro-2-phenoxyaniline NH2 (A) 100 mg

O2N O

MM 0378.05 Imp. E (EP): N,N-Bis(methylsulphonyl)-2- O (A) 100 mg O S phenoxyaniline N S O O O

MM 0378.06 Imp. F (EP): N,N-Bis(methylsulphonyl)-4- O (A) 100 mg O S nitro-2-phenoxyaniline N S O O O2N O

MM 0378.07 Imp. G (EP): 4-Nitro-2-phenoxyphenol OH (A) 50 mg

O2N O

150 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Nimodipine

H MM 0416.00 Nimodipine N (A) 100 mg

O O O O O

NO2 MM 0416.01 Imp. A (EP): 2-Methoxyethyl 1-Methylethyl 2,6-Dimethyl- N (A) 100 mg O O 4-(3-nitrophenyl)pyridine-3,5-dicarboxylate O O O

NO2

H MM 0416.02 Imp. B (EP): Bis(1-methylethyl) 2,6-Dimethyl-4-(3-nitrophenyl)- N (A) 100 mg 1,4-dihydropyridine-3,5-dicarboxylate O O

O O

NO2

H MM 0416.03 Imp. C (EP): Bis(2-methoxyethyl) 2,6-Dimethyl- N (A) 100 mg 4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate O O O O O O

NO2 Nitrazepam

H O MM 0078.00 Nitrazepam N (A) 100 mg [Controlled Substance] O2N N

H MM 0078.02 Imp. A (EP): 3-Amino-6-nitro-4-phenylquinolin-2(1H)-one N O (A) 100 mg

O2N NH2

MM 0078.01 Imp. B (EP): (2-Amino-5-nitrophenyl)phenylmethanone NH2 (B) 100 mg (2-Amino-5-nitrobenzophenone) O O2N

O MM 0078.03 Imp. C (EP): 2-Bromo-N-[4-nitro-2-(phenyl- Br (A) 50 mg carbonyl)phenyl]acetamide NH

O O2N

MM 0078.05 Imp. D (EP): 2-(1,3-Dioxo-1,3-dihydro-2H- O (A) 50 mg O isoindol-2-yl)-N-[4-nitro-2-(phenylcarbonyl)- N NH phenyl]acetamide O O O2N

H O MM 0078.07 7-Aminonitrazepam N (A) 100 mg

H2N N

Nitrendipine

H MM 0092.00 Nitrendipine N (A) 500 mg

O O

NO2 MM 0092.03 Imp. A (EP): Ethyl Methyl 2,6-Dimethyl-4-(3-nitrophenyl)pyridine- N (A) 100 mg 3,5-dicarboxylate (Photolysis Product) O O O O

NO2

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 151 Pharmaceutical impurities

Code Product Code Unit

H MM 0092.01 Imp. B (EP): Dimethyl 2,6-Dimethyl-4-(3-nitrophenyl)- N (A) 100 mg

1,4-dihydropyridine-3,5-dicarboxylate O O

O O

NO2

H MM 0092.02 Imp. C (EP): Diethyl 2,6-Dimethyl-4-(3-nitrophenyl)- N (A) 100 mg

1,4-dihydropyridine-3,5-dicarboxylate O O

O O

NO2

H MM 0092.04 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic N (A) 50 mg

Acid Methyl Ester O OH

O O

NO2

H MM 0092.05 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic N (A) 50 mg

Acid Ethyl Ester O OH

O O

NO2 Nitrofural

H MM 0943.00 Nitrofural O2N O N NH2 (A) 500 mg N O MM 0943.02 Imp. B (EP): (5-Nitrofuran-2-yl)methylene Diacetate O (A) 100 mg O

O2N O O

O Nitrofurantoin

H MM 0506.00 Nitrofurantoin O N (A) 500 mg O O O N N 2 N

Nizatidine MM 0220.00 Nizatidine (A) 500 mg N NO2 N S S N N H H MM 0220.01 Imp. A (EP): N,N‘-Dimethyl-2-nitroethene-1,1-diamine NO2 (A) 100 mg

N N H H MM 0220.09 Imp. B (EP): (EZ)-N-Methyl-1-methylsulphanyl)-2-nitroethen-1-amine NO2 (A) 100 mg

S N H MM 0220.02 Imp. C (EP): (EZ)-N-[2-[[[2-[(Dimethylamino)methyl]thiazol- (C) 50 mg N NO2 4-yl]methyl]sulphinyl]ethyl]-N‘-methyl-2-nitroethene- N O S 1,1-diamine S N N H H

MM 0220.04 Imp. D (EP) as Dioxalate: 2-[[[2-[(Dimethyl- N HO O (A) 50 mg amino)methyl]thiazol-4-yl]methyl]sulphanyl]- N x 2 S ethanamine Dioxalate S HO O NH2

MM 0220.10 Imp. G (EP): N,N'-Bis[2-[[[2-[(dimethylamino)- N N (A) 50 mg methyl]thiazol-4-yl]methyl]sulphanyl]ethyl]-2- NO2 nitroethene-1,1-diamine N N S S S S N N H H S MM 0220.11 Imp. H (EP) as Hydrochloride: 2-(Dimethylamino)thioacetamide x HCl (A) 100 mg N Hydrochloride NH2

S N MM 0086.07 Imp. K (EP): 3-(Methylamino)-5,6-dihydro-2H-1,4-thiazin-2-one Oxime OH (A) 100 mg

N N H

152 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Nonivamide MM 1033.00 Nonivamide O (A) 500 mg O N H HO O MM 1033.01 4-(Aminomethyl)-2-methoxyphenol Hydrochloride NH2 (A) 100 mg (Vanillylamine Hydrochloride) x HCl HO MM 1033.02 N-[(4-Hydroxy-3-methoxyphenyl)methyl]octanamide O (A) 100 mg O (N-Vanillyloctanamide) N H HO MM 1033.03 N-[(4-Hydroxy-3-methoxyphenyl)methyl]- O (A) 100 mg O decanamide (N-Vanillyldecanamide) N H HO MM 1033.04 N,O-Dinonanoylvanillylamine O (A) 100 mg O N H O

O Noradrenaline Tartrate

OH MM 0614.02 Imp. A (EP): Adrenaline (L-Adrenaline) H (A) 500 mg HO N

HO MM 0384.00 Imp. C (EP) as Hydrochloride: Dopamine Hydrochloride HO NH2 (A) 500 mg x HCl HO Norethisterone MM 0218.00 Norethisterone OH (A) 250 mg

O MM 0218.04 Imp. A (EP): 17-Hydroxy-19-nor-17h-pregna-4,6-dien-20-yn-3-one OH (D) 100 mg (6,7-Didehydronorethisterone)

O MM 0660.01 Imp. B (EP): Estr-4-ene-3,17-dione (Norandrostenedione) O (A) 100 mg

O MM 0218.01 Imp. H (EP): 6i,17-Dihydroxy-19-nor-17h-pregn-4-en-20-yn-3-one OH (D) 100 mg (6!-Hydroxynorethisterone)

O OH MM 0218.02 6h-Hydroxynorethisterone OH (D) 50 mg

O OH MM 0218.03 6-Ketonorethisterone OH (D) 100 mg

O O Norethisterone Acetate MM 0219.00 Norethisterone Acetate O (A) 100 mg O

O MM 0218.00 Imp. A (EP): Norethisterone OH (A) 250 mg

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 153 Pharmaceutical impurities

Code Product Code Unit MM 0219.10 Imp. B (EP): 3-Oxo-19-nor-17h-pregn-5(10)-en-20-yn-17-yl O on request Acetate O

O MM 0219.01 Imp. F (EP): 6i-Hydroxy-3-oxo-19-nor-17h-pregn-4-en-20-yn-17-yl O (D) 100 mg Acetate (6i-Hydroxynorethisterone Acetate) O

O OH MM 0219.03 Imp. G (EP): 3,6-Dioxo-19-nor-17h-pregn-4-en-20-yn-17-yl O (D) 100 mg Acetate (6-Ketonorethisterone Acetate) O

O O MM 0219.02 6h-Hydroxynorethisterone Acetate O (D) 50 mg O

O OH MM 0219.04 6,7-Didehydronorethisterone Acetate O (D) 100 mg O

O Norfenefrine Hydrochloride MM 0973.00 Norfenefrine Hydrochloride OH (A) 500 mg HO NH 2 x HCl

Norfloxacin

MM 0350.00 Norfloxacin HN (A) 250 mg NN

OH F O O MM 0350.01 Imp. A (EP): 7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline- (A) 100 mg 3-carboxylic Acid Cl N

OH F O O

MM 0350.03 Imp. D (EP): 1-Ethyl-6-fluoro-7-(piperazin-1-yl)quinolin-4(1H)-one HN (D) 100 mg N N

F O

MM 0350.04 Imp. G (EP): 1-Ethyl-6-fluoro-7-(4-formyl-piperazin-1-yl)- O N (D) 100 mg 4-oxo-1,4-dihydroquinoline-3-carboxylic Acid N N OH F O O Nortriptyline Hydrochloride MM 0079.00 Nortriptyline Hydrochloride (A) 500 mg

x HCl

N H MM 0062.01 Imp. A (EP): 10,11-Dihydro-5H-dibenzo[a,d][7]annulen-5-one (B) 100 mg (Dibenzosuberone) O MM 0079.01 Imp. B (EP) as Hydrochloride: 3-(5H-Dibenzo- (A) 50 mg [a,d][7]annulen-5-ylidene)-N-methylpropan-1- N amine Hydrochloride (Norcyclobenzaprine H x HCl Hydrochloride)

154 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit

MM 0062.03 Imp. D (EP): 5-[3-(Dimethyl- N (A) 100 mg amino)propyl]-10,11-dihydro-5H-dibenzo- [a,d][7]annulen-5-ol OH

MM 0062.02 Imp. E (EP) as Hydrochloride: 3-(5H- (A) 100 mg Dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethylpropan-1-amine Hydrochloride (Cyclobenzaprine N x HCl Hydrochloride)

MM 0062.00 Imp. F (EP) as Hydrochloride: (A) 500 mg Amitriptyline Hydrochloride N x HCl

MM 0062.12 Imp. J (EP) as Hydrochloride: [3-(10,11- (B) 10 mg Dihydro-5H-dibenzo[a,d][7]annulen- O 5-ylidene)propyl]-dimethylamine Oxide Hydrochloride N x HCl (Amitriptyline N-Oxide Hydrochloride)

Nucleosides

New MM 1316.01 Cytidine NH2 (A) 100 mg N

HO O N O

OH OH New MM 1316.02 2'-Deoxycytidine NH2 (A) 100 mg N

HO O N O

OH Ofloxacin

MM 0228.00 Ofloxacin N O (A) 500 mg N N

OH F O O

MM 0228.04 Imp. A (EP): (RS)-9,10-Difluoro-3-methyl-7-oxo-2,3-dihydro-7H- O (A) 100 mg pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid (FPA) F N

OH F O O

MM 0228.05 Imp. B (EP): (RS)-9-Fluoro-3-methyl-10-(4- N O (A) 100 mg methylpiperazin-1-yl)-2,3-dihydro-7H-pyrido- N N [1,2,3-de]-1,4-benzoxazin-7-one F O

MM 0228.08 Imp. E (EP): (RS)-9-Fluoro-3-methyl-7-oxo-10-(piperazin- HN O (A) 100 mg 1-yl)-2,3-dihydro-7H-pyrido[1,2,3-de]-1,4-benzoxazine- N N

6-carboxylic Acid OH F O O

MM 0228.10 Imp. F (EP) as Hydrochloride: 4-[(RS)-6-Carboxy- N O (A) 100 mg O 9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H- N N x HCl pyrido[1,2,3-de]-1,4-benzoxazine-10-yl]- OH 1-methylpiperazine 1-Oxide Hydrochloride (Ofloxacin F N-Oxide Hydrochloride) O O Olanzapine MM 0329.07 Imp. C (Pharmeuropa): 1-(Chloromethyl)-1- Cl (A) 100 mg N+ methyl-4-(2-methyl-10H-thieno[2,3-b][1,5]- N N benzodiazepin-4-yl)piperazin-1-ium Chloride Cl- (Olanzapine-N-Chloromethyl Chloride) HN S

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 155 Pharmaceutical impurities

Code Product Code Unit MM 0329.08 Imp. A (Pharmeuropa): 5-Methyl-2-[(2-nitro- N (A) 50 mg phenyl)amino]thiophene-3-carbonitrile HN O2N S

H MM 0329.02 Imp. B (Pharmeuropa): 2-Methyl-5,10-dihydro- N O (A) 50 mg 4H-thieno[2,3-b][1,5]benzodiazepin-4-one (Olanzapine Lactame) HN S Omeprazole MM 0095.00 Omeprazole O (A) 500 mg H N S N O N O

H MM 0095.03 Imp. A (EP): 5-Methoxy-1H-benzimidazole-2-thiol N (A) 100 mg SH O N MM 0095.04 Imp. B (EP): 2-[(RS)-[(3,5-Dimethylpyridin-2-yl) (A) 100 mg H methyl]sulphinyl]-5-methoxy-1H-benzimidazole N S N O N O MM 0095.06 Imp. C (EP): 5-Methoxy-2-[[(4-methoxy-3,5-dimethylpyridin- O (A) 100 mg H 2-yl)methyl]sulphanyl]-1H-benzimidazole (Ufiprazole) N S N O N MM 0095.05 Imp. D (EP): 5-Methoxy-2-[[(4-methoxy-3,5-dimethylpyridin- O (A) 100 mg H 2-yl) methyl]sulphonyl]-1H-benzimidazole (Omeprazole N S N Sulphone) O O N O MM 0095.07 Imp. E (EP): 4-Methoxy-2-[[(RS)-(5-methoxy-1H- (A) 100 mg O NH benzimidazol-2-yl)sulphinyl]methyl]-3,5-dimethylpyridine O 1-Oxide (Omeprazole N-Oxide) N S O N O MM 0095.01 Imp. F (EP): 8-Methoxy-1,3-dimethyl- S (D) 50 mg 12-thioxopyrido[1',2':3,4]imidazo[1,2-a]-benzimidazol-2(12H)- N O O one N N

MM 0095.02 Imp. G (EP): 9-Methoxy-1,3-dimethyl- O S (D) 50 mg 12-thioxopyrido[1',2':3,4]imidazo[1,2-a]-benzimidazol-2(12H)- N O one N N

MM 0095.15 Imp. H (EP): 2-[(RS)-[(4-Chloro-3,5-dimethylpyridin- (D) 100 mg O NH 2-yl)methyl]sulfinyl]-5-methoxy-1H-benzimidazole Cl N S O N MM 0095.16 Imp. I (EP): 4-Methoxy-2-[[(5-methoxy-1H-benzimidazol- (A) 100 mg O NH 2-yl)sulphonyl]methyl]-3,5-dimethylpyridine 1-Oxide O (Omeprazole Sulphone N-Oxide) N S O O N O MM 0095.08 5-Methoxy-2-[[(3,5-dimethylpyridin-2-yl)methyl]sulphanyl]- (A) 100 mg O NH 1H-benzimidazole N S N MM 0095.19 5-Methoxy-2-[[(4-chloro-3,5-dimethylpyridin-2-yl) (D) 100 mg O NH methyl]sulphanyl]-1H-benzimidazole Cl N S N MM 0095.20 5-Methoxy-1,3-dihydrobenzimidazol-2-one (A) 100 mg O NH

N O H MM 0095.23 2-[[(4-Methoxy-3,5-dimethylpyridin-2-yl)methyl]sulphinyl]-1H- (A) 100 mg NH benzimidazole O N S O N MM 0095.24 5-Methoxy-2-(4-methoxy-3,5-dimethylpyridin-2-yl)-1H- (A) 100 mg O NH benzimidazole O N N

156 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Ondansetron Hydrochloride Dihydrate MM 0252.00 Ondansetron Hydrochloride Dihydrate on request N N x HCl N x 2 H2O

O MM 0252.09 Ondansetron on request N N N

O MM 0252.03 Imp. A (EP): (3RS)-3-(Dimethylamino)methyl-9-methyl- (A) 100 mg N 1,2,3,9-tetrahydro-4H-carbazol-4-one N

O MM 0252.02 (D) 50 mg Imp. B (EP): 6,6'-Methylene bis[(3RS)- NN 9-methyl-3-[(2-methyl-1H-imidazol- 1-yl)methyl]-1,2,3,9-tetrahydro-4H-carbazol- 4-one] N N N O O N

MM 0252.01 Imp. C (EP): 9-Methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one (A) 100 mg N

O MM 0252.04 Imp. D (EP): 9-Methyl-3-methylene-1,2,3,9-tetrahydro-4H-carbazol- (A) 100 mg N 4-one

O MM 0015.02 Imp. E (EP): 1H-Imidazole (Imidazole) N (B) 100 mg N H MM 0252.06 Imp. F (EP): 2-Methyl-1H-imidazole N (B) 100 mg N H MM 0252.07 Imp. G (EP): (3RS)-3-[(1H-Imidazol-1-yl)methyl]-9-methyl- (A) 100 mg N 1,2,3,9-tetrahydro-4H-carbazol-4-one N N (C-Demethylondansetron) O MM 0252.08 Imp. H (EP): (3RS)-3-[(2-Methyl-1H-imidazol-1-yl)methyl]- H (A) 100 mg N N 1,2,3,9-tetrahydro-4H-carbazol-4-one N (N-Demethylondansetron) O Opipramol Dihydrochloride MM 0422.01 5-(3-Piperazin-1-yl-propyl)-5H-dibenzo[b,f]azepine (A) 100 mg Dihydrochloride N x 2 HCl

N NH Ornidazole

MM 0948.00 Ornidazole O2N (A) 500 mg N Cl OH N

MM 0012.02 2-Methyl-4-nitroimidazole O2N (B) 100 mg NH

MM 0948.02 3-(2-Methyl-5-nitro-1H-imidazol-1-yl)propane-1,2-diol O2N (A) 100 mg N OH OH N

MM 0948.03 3-(2-Methyl-5-nitro-1H-imidazol-1-yl)-1,2-epoxypropane O2N (A) 100 mg N O N

MM 0948.04 1-(3-Chloro-2-hydroxypropyl)-2-methyl-4-nitroimidazole N Cl (A) 100 mg O2N OH N Orphenadrine Hydrochloride MM 0801.00 Orphenadrine Hydrochloride (A) 500 mg

x HCl N O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 157 Pharmaceutical impurities

Code Product Code Unit MM 0801.01 Imp. A (EP): (RS)-(2-Methylphenyl)phenylmethanol (A) 100 mg (2-Methylbenzhydrol)

MM 0801.02 Imp. B (EP): (2-Methylphenyl)phenylmethanone (2-Methylbenzophenone) (A) 100 mg

MM 0801.03 Imp. C (EP) as Hydrochloride: (RS)-2-[(2-Methyl- (A) 50 mg phenyl)phenylmethoxy]ethanamine Hydrochloride x HCl NH2 O

MM 0490.00 Imp. D (EP) as Hydrochloride: Diphenhydramine (A) 500 mg Hydrochloride x HCl N O

MM 0801.05 Imp. E (EP) as Hydrochloride: (RS)-N,N-Dimethyl- (A) 100 mg 2-[(3-methylphenyl)phenylmethoxy]ethanamine

Hydrochloride (meta-Methylbenzyl Isomer Hydrochloride) N x HCl O

MM 0490.04 Imp. F (EP) as Hydrochloride: (RS)-N,N- (A) 100 mg Dimethyl-2-[(4-methylphenyl)phenylmethoxy] x HCl ethanamine Hydrochloride (para-Methylbenzyl N Isomer Hydrochloride; O 4-Methyldiphenhydramine Hydrochloride) MM 0801.07 N-Desmethylorphenadrine Hydrochloride (A) 100 mg

H x HCl N O

Oxacillin Sodium

O MM 0686.00 Oxacillin Sodium Monohydrate ONa (A) 250 mg O O N x H2O N N S H H O

O MM 0026.04 Imp. A (EP): (2S,5R,6R)-6-Amino-3,3-dimethyl- OH (B) 100 mg 7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2- O carboxylic Acid (6-Aminopenicillanic Acid) N S H2N H

MM 0682.00 Imp. E (EP) as Sodium Salt Monohydrate: Cl O (A) 500 mg ONa Cloxacillin Sodium Monohydrate O N N H x H2O O N S H O Oxalic Acid Dihydrate MM 0928.00 Oxalic Acid Dihydrate O OH (A) 500 mg x 2 H2O O OH MM 0928.01 Oxalic Acid O OH (A) 500 mg

O OH Oxaliplatin MM 0928.00 Imp. A (EP) as Dihydrate: Ethanedioic Acid O OH (A) 500 mg x 2 H O Dihydrate (Oxalic Acid Dihydrate) 2 O OH

158 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Oxazepam

H O MM 0080.00 Oxazepam N (D) 100 mg [Controlled Substance] OH Cl N

MM 0028.03 Imp. D (EP): (2-Amino-5-chlorophenyl)phenylmethanone NH2 (B) 100 mg O (2-Amino-5-chlorobenzophenone) Cl

H O MM 0028.02 Imp. E (EP): 7-Chloro-5-phenyl-1,3-dihydro- N (A) 100 mg 2H-1,4-benzodiazepin-2-one 4-Oxide (Demoxepam) Cl N O

MM 0080.03 6-Chloro-4-phenyl-3,4-dihydroquinazoline-2-carboxylic Acid O (A) 100 mg N OH NH Cl

Oxcarbazepine MM 0076.17 Oxcarbazepine O (A) 100 mg

ONH2 MM 0076.10 10-Hydroxy-10,11-dihydrocarbamazepine HO (A) 100 mg

ONH2 Oxeladin Hydrogen Citrate MM 0547.00 Oxeladin Hydrogen Citrate O (A) 500 mg OH O O O O N x OH OH OH O O MM 0547.02 Imp. A (EP): 2-[2-(Diethylamino)ethoxy]ethanol HO N (A) 100 mg

MM 0547.01 Oxeladin N-Oxide O (B) 10 mg O O N O

Oxfendazole

O MM 0518.02 Imp. B (EP): Methyl [5-(Phenylsulphonyl)- H (A) 100 mg N O 1H-benzimidazol-2-yl]carbamate (Fenbendazole Sulphone) NH S N O O Oxolinic Acid MM 0898.00 Oxolinic Acid (A) 250 mg O N

OH O O O Oxomemazine MM 0957.00 Oxomemazine (A) 100 mg N

S O O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 159 Pharmaceutical impurities

Code Product Code Unit MM 0958.00 Trimeprazine Tartrate (A) 500 mg N OH O x HO N OH O OH S 2 MM 0958.02 Trimeprazine Sulphoxide Hydrochloride (A) 100 mg N

N x HCl

S O

MM 0958.04 Oxomemazine N-Oxide Hydrochloride (Trimeprazine Sulphone O (A) 100 mg N N-Oxide Hydrochloride) N x HCl

S O O Oxprenolol Hydrochloride

MM 0129.00 Oxprenolol Hydrochloride OH H (A) 500 mg O N x HCl

OH New MM 0129.01 1-(2-Hydroxyphenoxy)-3-(isopropylamino)-2-propanol H (A) 50 mg O N Hydrochloride x HCl

OH Oxybuprocaine Hydrochloride

MM 0543.00 Oxybuprocaine Hydrochloride O (A) 500 mg N O x HCl H2N O MM 0094.03 Imp. A (EP): 4-Aminobenzoic Acid O (B) 100 mg OH

H2N MM 0543.02 Imp. B (EP): 4-Amino-3-butoxybenzoic Acid O (A) 100 mg OH

H2N O MM 0543.03 Imp. C (EP): 4-Amino-3-hydroxybenzoic Acid O (A) 100 mg OH

H2N OH

MM 0543.05 Oxybuprocaine N-Oxide Dihydrochloride O (A) 100 mg N O O x 2 HCl H2N O Oxybutynin Hydrochloride MM 0047.00 Oxybutynin Hydrochloride (A) 250 mg HO N O x HCl

MM 0047.06 Imp. B (EP): 4-(Diethylamino)but-2-ynyl (A) 100 mg HO 2-Hydroxy-2,2-diphenylacetate N (Diphenyl analogue of Oxybutynin) O O

MM 0047.04 Imp. C (EP) as Hydrochloride: 4-(Ethylmethylamino)but- (D) 100 mg HO 2-ynyl (RS)-2-Cyclohexyl-2-hydroxy-2-phenylacetate N O x HCl Hydrochloride (Methylethyl analogue of Oxybutynin Hydrochloride) O MM 0047.01 Imp. D (EP): (RS)-2-Cyclohexyl-2-hydroxy-2-phenylacetic Acid (A) 100 mg (Phenylcyclohexylglycolic Acid) HO OH

160 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0047.07 Imp. E (EP): 4-(Ethylpropylamino)but-2-ynyl (RS)- (A) 100 mg HO 2-Cyclohexyl-2-hydroxy-2-phenylacetate (Ethylpropyl N analogue of Oxybutynin) O O

MM 0047.02 Methyl (RS)-2-Cyclohexyl-2-hydroxy-2- O (A) 100 mg

phenylacetate (Phenylcyclohexylglycolic O Acid Methyl Ester) OH

MM 0047.03 4-Diethylaminobut-2-yn-1-ol N (A) 100 mg HO

MM 0047.11 Desethyloxybutynin Hydrochloride (D) 100 mg HO N x HCl O H O

MM 0047.50 Propargyl (RS)-2-Cyclohexyl-2-hydroxy-2-phenylacetate (B) 10 mg (Phenylcyclohexylglycolic Acid Propargyl Ester) HO O

O Oxycodone Hydrochloride

MM 0672.00 Oxycodone Hydrochloride N (A) 100 mg [Controlled Substance] HO x HCl

O O O H MM 0672.03 Imp. C (EP) as Hydrochloride: 4,5h-Epoxy-14-hydroxy- N (D) 50 mg 3-methoxymorphinan-6-one Hydrochloride (Noroxycodone HO Hydrochloride) x HCl

O O O MM 0672.05 4,5h-Epoxy-3-methoxy-17-methylmorphinan-6i,14-diol N on request Hydrochloride(6i-Oxycodol Hydrochloride) HO x HCl [Controlled Substance]

O O OH O MM 0672.06 Oxycodone N-Oxide N (D) 50 mg

O O O Oxymetazoline Hydrochloride MM 0177.00 Oxymetazoline Hydrochloride (A) 250 mg HO N x HCl HN

MM 0177.01 Imp. A (EP) as Hydrochloride: N-(2-Aminoethyl)- H (A) 100 mg HO N 2-[4-(1,1-dimethylethyl)-3-hydroxy- NH2 x HCl O 2,6-dimethylphenyl)]acetamide Hydrochloride

MM 0089.00 Imp. B (EP) as Hydrochloride: Xylometazoline (A) 500 mg N Hydrochloride x HCl N H MM 0177.07 Imp. C (EP): 2-[4-(1,1-Dimethylethyl)-3- OH (A) 100 mg hydroxy-2,6-dimethylphenyl]acetamide O

NH2

MM 0177.04 Imp. D (EP): [4-(1,1-Dimethylethyl)-3-hydroxy- OH (A) 100 mg 2,6-dimethylphenyl]acetic Acid O

MM 0177.05 Imp. E (EP): [4-(1,1-Dimethylethyl)-3-hydroxy- OH (D) 100 mg 2,6-dimethylphenyl]acetonitrile N

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 161 Pharmaceutical impurities

Code Product Code Unit Oxyphenbutazone MM 0933.00 Oxyphenbutazone Monohydrate OH (A) 250 mg O

N x H2O N

Oxytetracycline Hydrochloride

OH O OH O O MM 0554.00 Oxytetracycline Hydrochloride OH (A) 500 mg

NH2 H H x HCl OH HO OH N

OH O OH O O MM 0452.00 Imp. B (EP) as Hydrochloride: Tetracycline Hydrochloride OH (A) 500 mg

NH2 H H x HCl OH HO N Pantoprazole Sodium Sesquihydrate MM 0099.00 Pantoprazole Sodium (D) 100 mg O NNa O F O F N S O N MM 0099.01 Pantoprazole (D) 100 mg O NH O F O F N S O N MM 0099.02 Imp. A (EP): 5-(Difluoromethoxy)- (A) 100 mg O NH 2-[[(3,4-dimethoxypyridin-2-yl) F O methyl]sulphonyl]-1H-benzimidazole (Pantoprazole F N S O O Sulphone) O N MM 0099.03 Imp. B (EP): 5-(Difluoromethoxy)-2-[[(3,4- (A) 100 mg O NH O dimethoxypyridin-2-yl)methyl]sulphanyl]- F O 1H-benzimidazole F N S N MM 0099.04 Imp. C (EP): 5-(Difluoromethoxy)-1H-benzimidazole-2-thiol (A) 100 mg O NH F F N SH MM 0099.11 Mixture of Imp. D and F (EP): 5- and 6-(Di- (D) 100 mg O N O fluoromethoxy)-2-[(RS)-[(3,4-dimethoxypyridin- F O 2-yl)methyl]sulphinyl]-1-methyl-1H-benzimidazole F N S O N F + O F N O O N S O N

MM 0099.05 2-Chloromethyl-3,4-dimethoxypyridine Hydrochloride O O (A) 100 mg Cl x HCl N MM 0099.06 Pantoprazole N-Oxide (D) 100 mg O NH O F O F N S O N O MM 0099.07 Pantoprazole Sulphone N-Oxide (A) 100 mg O NH O F O F N S O O N O Paracetamol

H MM 0042.00 Paracetamol N (A) 500 mg

O HO

MM 0042.08 Imp. A (EP): N-(2-Hydroxyphenyl)acetamide OH H (B) 100 mg (2-Acetamidophenol) N O

162 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit

H MM 0042.05 Imp. B (EP): N-(4-Hydroxyphenyl)propanamide N (A) 100 mg

(N-Propionyl-4-aminophenol) O HO

H MM 0042.09 Imp. C (EP): N-(3-Chloro-4-hydroxyphenyl)acetamide Cl N (A) 100 mg (3-Chloro-4-hydroxyacetanilide) O HO

H MM 0042.10 Imp. D (EP): N-Phenylacetamide (Acetanilide) N (B) 100 mg

MM 0042.11 Imp. E (EP): 1-(4-Hydroxyphenyl)ethanone O (B) 100 mg (4-Hydroxyacetophenone) HO

MM 0042.03 Imp. F (EP): 4-Nitrophenol NO2 (B) 100 mg

HO MM 0042.12 Imp. G (EP): 1-(4-Hydroxyphenyl)ethanone Oxime N (A) 100 mg (4-Hydroxyacetophenone Oxime)

H MM 0042.04 Imp. H (EP): 4-(Acetylamino)phenyl Acetate N (A) 100 mg O (N,O-Diacetyl-4-aminophenol) O O MM 0042.13 Imp. I (EP): 1-(2-Hydroxyphenyl)ethanone O (B) 100 mg (2-Hydroxyacetophenone) OH

H MM 0042.02 Imp. J (EP): N-(4-Chlorophenyl)acetamide N (B) 100 mg

(4-Chloroacetanilide) O Cl

MM 0042.01 Imp. K (EP): 4-Aminophenol NH2 (B) 100 mg

MM 0042.07 3-Aminophenol HO NH2 (B) 100 mg

Paroxetine Hydrochloride Anhydrous

MM 1032.02 Imp. B (EP): 1,3-Benzodioxol-5-ol (Sesamol) O OH (A) 100 mg

O MM 1032.07 Imp. G (EP) as Hydrochloride: 4-(4-Fluorophenyl)- F (A) 100 mg 1-methyl-1,2,3,6-tetrahydropyridine Hydrochloride x HCl

N MM 1032.12 [(3S,4R)-4-(4-Fluorophenyl)-1-methylpiperidin-3-yl]methanol F (A) 100 mg

HO N Pentetrazol

MM 0692.00 Pentetrazol N (A) 500 mg N N N Pentoxifylline MM 0761.00 Pentoxifylline O O (A) 500 mg N N

O N N

MM 0577.00 Imp. A (EP): Theobromine O (A) 500 mg N HN

O N N

O MM 0176.03 Imp. B (EP): 3-Methyl-3,7-dihydro-1H-purine- H (A) 100 mg N 2,6-dione (3-Methylxanthine) HN

O N N

O MM 0176.00 Imp. C (EP): Theophylline H (A) 500 mg N N

O N N

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 163 Pharmaceutical impurities

Code Product Code Unit MM 0494.00 Imp. F (EP): Caffeine O (A) 500 mg N N

O N N

Pentoxyverine Hydrogen Citrate

MM 1268.01 Imp. A (EP): 1-Phenylcyclopentanecarboxylic Acid O (A) 100 mg

Peppermint Oil MM 0388.00 (-)-Menthol (Levomenthol) (A) 500 mg

MM 0163.12 (+)-(R)-Pulegone (A) 100 mg

Perazine Dimaleate

MM 0815.00 Perazine Dimaleate N O (A) 100 mg N HO x 2 N HO

O S Perazine Dimalonate

MM 0157.00 Perazine Dimalonate N on request N O OH N x 2 O S HO

MM 0157.01 Perazine Sulphoxide N (A) 100 mg N

S O

H MM 0157.02 Phenothiazine N (B) 100 mg

MM 0157.03 1-(3-Chloropropyl)-4-methylpiperazine N on request Cl N Perphenazine MM 0826.00 Perphenazine (A) 100 mg

N N S N OH

Cl MM 0826.01 Imp. A (EP): 2-[4-[3-(2-Chloro-5-oxido-10H- (A) 100 mg

phenothiazin-10-yl)propyl]piperazin-1-yl]- N N ethanol (Perphenazine Sulphoxide) S N O OH

Cl New MM 0826.02 Imp. B (EP): 2-[4-[3-(10H-Phenothiazin-10- (A) 50 mg

yl)propyl]piperazin-1-yl]ethanol N N S N OH

Phenacetin

H MM 0551.00 Phenacetin N (A) 100 mg

O O

H MM 0042.00 Paracetamol N (A) 500 mg

O HO

164 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit

MM 0042.01 4-Aminophenol NH2 (B) 100 mg

HO Phenethyl Alcohol MM 0953.00 Phenylethyl Alcohol OH (A) 500 mg

Pheniramine Maleate

MM 0059.00 Pheniramine Maleate N O (A) 100 mg N OH x OH

MM 0059.02 Imp. A (EP): 2-Benzylpyridine N (C) 100 mg

MM 0059.03 Imp. B (EP): 4-Benzylpyridine N (C) 100 mg

MM 0059.09 Imp. C (EP) as Sesquifumarate: (3RS)- N O (A) 100 mg N N,N-Dimethyl-3-phenyl-3-(pyridin-4-yl) OH x 1,5 propan-1-amine Sesquifumarate HO

MM 0059.08 Imp. D (EP) as Dihydrochloride: N,N,N',N'-Tetramethyl- N (D) 100 mg 3-phenyl-3-(pyridin-2-yl)pentane-1,5-diamine Dihydrochloride N x 2 HCl N

MM 0059.01 Pheniramine N (A) 100 mg N

MM 0059.05 Pheniramine N-Oxide Dihydrochloride N (A) 100 mg O N x 2 HCl

MM 0059.06 Norpheniramine Maleate N O (A) 100 mg H N OH x OH

O Phentolamine Mesilate MM 0171.04 Imp. B (Pharmeuropa) as Hydrochloride: 2-(Chloro- N 100 mg x HCl methyl)-4,5-dihydro-1H-imidazole Hydrochloride N H Cl Phenobarbital

H MM 0265.07 Imp. B (Pharmeuropa): 6-Amino-5-ethyl- O N O (A) 50 mg 5-phenylpyrimidine-2,4(3H,5H)-dione NH

H MM 0265.08 Imp. C (Pharmeuropa): 5-Methyl-5-phenylpyrimidine-2,4,6(1H,3H,5H)- O NO (A) 50 mg trione NH

MM 0265.01 Phenylethylacetylurea O O (A) 100 mg

N NH2 (2-Phenylbutyrylurea) H

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 165 Pharmaceutical impurities

Code Product Code Unit MM 0265.02 N-Benzoyl-N'-(2-phenyl)butanoylurea O OO (A) 100 mg N N H H

H MM 0265.03 Barbituric Acid O N O (C) 100 mg

O Phenoxyethanol

O MM 0952.00 Phenoxyethanol OH (A) 500 mg

Phenoxymethylpenicillin Potassium

O MM 0026.00 Phenoxymethylpenicillin Potassium OK (A) 250 mg O N H N O S H O O MM 0160.00 Imp. A (EP) as Potassium Salt: Benzylpenicillin OK (A) 250 mg Potassium O N H N S H O MM 0026.03 Imp. B (EP): Phenoxyacetic Acid (B) 100 mg OH O O O MM 0026.04 Imp. C (EP): (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia- OH (B) 100 mg 1-azabicyclo[3.2.0]-heptane-2-carboxylic Acid O (6-Aminopenicillanic Acid) N S H2N H O MM 0026.02 Imp. D (EP): (2S,5R,6R)-3,3-Dimethyl-7-oxo- OH (A) 100 mg 6-[[2-(4-hydroxyphenoxy)acetyl]amino]-4-thia- HO O N 1-azabicyclo[3.2.0]heptane-2-carboxylic Acid H N O S (4-Hydroxyphenoxymethylpenicillin) H O O MM 0026.01 Imp. E (EP): (4S)-2-[Carboxy[(phenoxyacetyl) OH (A) 100 mg amino]methyl]-5,5-dimethylthiazolidine-4- HN carboxylic Acid (Penicilloic Acids of H N Phenoxymethylpenicillin) O S O OOH

O MM 0026.05 Imp. F (EP): (2RS,4S)-5,5-Dimethyl-2- OH (A) 100 mg

[[(phenoxyacetyl)amino]methyl]thiazolidine- HN 4-carboxylic Acid S (Penilloic Acids of Phenoxymethylpenicillin) NH O O Phenylbutazone

MM 0548.00 Phenylbutazone O (A) 500 mg N N O

MM 0548.01 Imp. A (EP): (2RS)-2-[(1,2-Diphenyldiazanyl)- O (D) 100 mg carbonyl]hexanoic Acid N NH O OH

MM 0548.02 Imp. B (EP): 4-Butyl-4-hydroxy-1,2-diphenylpyrazolidine-3,5-dione O (A) 50 mg N N OH O

MM 0548.03 Imp. C (EP): 1,2-Diphenyldiazane H (A) 100 mg N (1,2-Diphenylhydrazine) N H

166 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0548.04 Imp. D (EP): 1,2-Diphenyldiazene (C) 100 mg N N

MM 0548.05 Imp. E (EP) as Dihydrochloride: Biphenyl-4,4'-diamine (A) 100 mg H2NNH2 x 2 HCl Dihydrochloride (Benzidine Dihydrochloride) Phenylephrine Hydrochloride

OH MM 0081.00 Phenylephrine Hydrochloride H (A) 500 mg HO N x HCl

O MM 0081.03 Imp. C (EP) as Hydrochloride: 1-(3-Hydroxy-phenyl)- H (D) 100 mg HO N 2-(methylamino)ethanone Hydrochloride (Phenylephrone x HCl Hydrochloride)

MM 0081.08 Imp. E (EP) as Hydrochloride: 2-(Benzyl- O (D) 100 mg methylamino)-1-(3-hydroxyphenyl)ethanone HO N x HCl Hydrochloride (Benzylphenylephrone Hydrochloride)

MM 0081.05 1,2,3,4-Tetrahydro-4,6-dihydroxy-2-methylisoquinoline OH (A) 100 mg HO Hydrochloride x HCl N

MM 0081.06 1,2,3,4-Tetrahydro-4,8-dihydroxy-2-methylisoquinoline OH (A) 50 mg

Hydrochloride x HCl N

OH Phenylpropanolamine Hydrochloride MM 0656.00 Phenylpropanolamine Hydrochloride OH (A) 500 mg NH [Drug Precursor] 2 x HCl

and enatiomere Phenyltoloxamine Citrate MM 0770.00 Phenyltoloxamine Citrate O (A) 500 mg OH N O OH x O OH OH O Phenytoin MM 0630.00 Phenytoin (A) 500 mg H N O

NH O

MM 0630.01 Imp. A (EP): Diphenylmethanone (Benzophenone) (B) 100 mg

MM 0630.02 Imp. B (EP): Diphenylethanedione (Benzil) O (B) 100 mg

MM 0630.04 Imp. C (EP): Amino(diphenyl)acetic Acid (2,2-Diphenylglycine) (A) 100 mg

NH2 OH

O MM 0630.08 Imp. F (EP): 5-(4-Methylphenyl)-5-phenylimidazolidine-2,4-dione (A) 100 mg H N O

MM 0630.07 1-Methyl-5,5-diphenylimidazolidine-2,4-dione (D) 100 mg N O

H MM 0630.03 5-(4-Methylphenyl)hydantoin N O (A) 100 mg

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 167 Pharmaceutical impurities

Code Product Code Unit

MM 0630.06 Imp. E (EP): (Carbamoylamino)(diphenyl)acetic Acid O (A) 50 mg HN

NH2 OH O Phenytoin Sodium

MM 0622.00 Phenytoin Sodium H (A) 500 mg N ONa N O

MM 0630.01 Imp. A (EP): Diphenylmethanone (Benzophenone) (B) 100 mg

MM 0630.02 Imp. B (EP): Diphenylethanedione (Benzil) O (B) 100 mg

O MM 0630.04 Imp. C (EP): Amino(diphenyl)acetic (A) 100 mg Acid (2,2-Diphenylglycine) NH2 OH

O MM 0630.08 Imp. F (EP): 5-(4-Methylphenyl)-5- (A) 100 mg H phenylimidazolidine-2,4-dione N O NH

MM 0630.07 1-Methyl-5,5-diphenylimidazolidine- (D) 100 mg 2,4-dione N O NH

H MM 0630.03 5-(4-Methylphenyl)hydantoin N O (A) 100 mg

O Pholcodine

MM 0037.00 Imp. A (EP) as Hydrochloride Trihydrate: N (A) 250 mg Morphine Hydrochloride Trihydrate x HCl [Controlled Substance] x 3 H2O

HO O OH

MM 0280.00 Imp. A (EP) as Hemisulphate Pentahemihydrate: Morphine N (A) 250 mg Hemisulphate Pentahemihydrate x H2SO4 [Controlled Substance] x 5 H2O

HO O OH 2

MM 0422.00 Imp. B (EP) as Phosphate Hemihydrate: N (A) 100 mg Codeine Phosphate Hemihydrate x H3PO4 [Controlled Substance] x 1/2 H2O

O O OH

MM 0004.00 Imp. B (EP) as Monohydrate: Codeine Monohydrate N (A) 100 mg [Controlled Substance] x H2O

O O OH Pilocarpine Hydrochloride

O MM 0338.00 Pilocarpine Hydrochloride N O (A) 500 mg x HCl N

O MM 0338.01 Imp. A (EP) as Hydrochloride: (3R,4R)-3-Ethyl-4- N O (A) 100 mg [(1-methyl-1H-imidazol-5-yl)methyl]dihydrofuran- x HCl N 2(3H)-one Hydrochloride (Isopilocarpine Hydrochloride)

168 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit OH MM 0338.02 Imp. B (EP) as Sodium Salt: (2S,3R)-2-Ethyl-3- N O (A) 100 mg (hydroxymethyl)-4-(1-methyl-1H-imidazol-5- N yl)butanoic Acid Sodium Salt (Pilocarpic Acid ONa Sodium Salt) OH MM 0338.03 Imp. C (EP) as Sodium Salt: (2R,3R)-2-Ethyl-3- N O (A) 100 mg (hydroxymethyl)-4-(1-methyl-1H-imidazol-5- N yl)butanoic Acid Sodium Salt (Isopilocarpic ONa Acid Sodium Salt) Pindolol MM 0082.00 Pindolol (A) 250 mg ON H OH

N H

OH OH MM 0082.08 Imp. B (EP): 1-[4-[2-Hydroxy-3-[(1-methyl- H H (D) 100 mg ethyl)amino]propoxy]-1H-indol-1-yl]-3-[(1- N N O N methylethyl)amino]propan-2-ol

MM 0082.06 Imp. C (EP): 1,1'-[(1-Methylethyl)imino]bis[3- OH OH (A) 100 mg (1H-indol-4-yloxy)propan-2-ol] HN ONO NH

MM 0082.02 Imp. D (EP): (2RS)-3-(1H-Indol-4-yloxy)propane- OH (A) 100 mg HN 1,2-diol OOH

MM 0082.01 Imp. E (EP): 1H-Indol-4-ol OH (A) 100 mg

N H Pipazetate Hydrochloride MM 0486.06 Bis-(2-piperidinoethyl)ether Dihydrochloride (BPEE (A) 100 mg x 2 HCl N N Dihydrochloride) O MM 0486.02 1,2-Dipiperidinoethane (DPE) (A) 100 mg N N

MM 0486.05 2-(2-Piperidinoethoxy)ethanol Hydrochloride x HCl (A) 100 mg HO N O Pipemidic Acid Trihydrate

MM 0401.00 Pipemidic Acid Trihydrate HN (A) 250 mg N NN x 3 H2O N OH

O O Pipenzolate Bromide MM 0783.00 Pipenzolate Bromide (A) 500 mg N+ O Br- O OH

MM 0630.01 Diphenylmethanone (Benzophenone) (B) 100 mg O

MM 0783.09 Benzilic Acid O (B) 100 mg

HO OH

Piperacillin

MM 0295.00 Piperacillin N (A) 100 mg O N O OH O O O NH N H N S H O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 169 Pharmaceutical impurities

Code Product Code Unit Piperacillin Sodium

MM 0296.00 Piperacillin Sodium N (A) 100 mg NaO N O O O O O NH N H N S H O

NaO MM 0253.00 Imp. A (EP) as Sodium Salt: Ampicillin Sodium O (A) 500 mg O NH2 N H N S H O

MM 0296.05 Imp. E (EP): 1-Ethylpiperazine-2,3-dione N (A) 100 mg NH O O

MM 0296.07 Imp. G (EP): (2R)-2-[[(4-Ethyl-2,3-dioxopiperazin-1-yl)- N (A) 100 mg N O carbonyl]amino]-2-phenylacetic Acid O O NH OH

O MM 0026.04 Imp. H (EP): (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia- OH (B) 100 mg O 1-azabicyclo[3.2.0]-heptane-2-carboxylic Acid (6-Aminopenicillanic N

Acid) H N S 2 H Piprinhydrinate

MM 0155.00 Piprinhydrinate O on request O H N N Cl N O N N

MM 0155.01 Diphenylpyraline (A) 100 mg O

O MM 0155.02 8-Chlorotheophylline H (B) 100 mg N N Cl O N N

MM 0490.02 Diphenylmethanol (Benzhydrol) (B) 100 mg OH

Piracetam MM 0083.00 Piracetam O (A) 500 mg N NH2 O MM 0083.05 Imp. A (EP): Pyrrolidin-2-one (2-Pyrrolidone) (B) 100 mg NH O

MM 0083.04 Imp. B (EP): Methyl (2-Oxopyrrolidin-1-yl)acetate O (A) 100 mg N O O

MM 0083.02 Imp. C (EP): Ethyl (2-Oxopyrrolidin-1-yl)acetate O (A) 100 mg N O O

MM 0083.01 Imp. D (EP): (2-Oxopyrrolidin-1-yl)acetic Acid O (A) 100 mg N OH O MM 0083.03 N-Vinyl-2-pyrrolidone (A) 100 mg N O MM 0083.06 2-Chloroacetamide O (C) 100 mg Cl NH2

170 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Piroxicam

OO MM 0084.00 Piroxicam S (A) 500 mg N H NN

OH O

MM 0084.01 Imp. A (EP): Pyridin-2-amine (2-Pyridylamine) N NH2 (B) 100 mg

MM 0084.08 OO (A) 100 mg Imp. B (EP): 4-Hydroxy-N-(pyridin-2-yl)-2H-1,2-benzothiazine- S NH 3-carboxamide 1,1-Dioxide H NN

OH O

OO MM 0084.09 Imp. C (EP): 4-Hydroxy-2-methyl-2H-1,2-benzothiazine- S (A) 100 mg 3-carboxamide1,1-Dioxide N NH2 OH O

O MM 0084.07 Imp. D (EP): Methyl (1,1-Dioxido-3-oxo-1,2-benzisothiazol-2(3H)- O (A) 100 mg S yl)acetate N O O O

O MM 0084.05 Imp. E (EP): Ethyl (1,1-Dioxido-3-oxo-1,2-benzisothiazol-2(3H)- O (A) 100 mg S yl)acetate N O O O

O MM 0084.10 Imp. F (EP): 1-Methylethyl (1,1-Dioxido-3-oxo-1,2-benzisothiazol- O (A) 100 mg S 2(3H)-yl)acetate N O O O

OO MM 0084.04 Imp. G (EP): Methyl 4-Hydroxy- 2H-1,2-benzothiazine-3-carboxylate S (A) 100 mg 1,1-Dioxide NH O

OH O

OO MM 0084.06 Imp. H (EP): Ethyl 4-Hydroxy- 2H-1,2-benzothiazine-3-carboxylate S (A) 100 mg 1,1-Dioxide NH O

OH O

OO MM 0084.11 Imp. I (EP): 1-Methylethyl 4-Hydroxy-2H-1,2-benzothiazine- S (A) 100 mg 3-carboxylate 1,1-Dioxide NH O

OH O

OO MM 0084.02 Imp. J (EP): Methyl 4-Hydroxy-2-methyl-2H-1,2-benzothiazine- S (A) 100 mg 3-carboxylate 1,1-Dioxide N O

OH O

OO MM 0084.03 Imp. K (EP): Ethyl 4-Hydroxy-2-methyl-2H-1,2-benzothiazine- S (A) 100 mg 3-carboxylate 1,1-Dioxide N O

OH O

OO MM 0084.12 Imp. L (EP): 1-Methylethyl 4-Hydroxy-2-methyl-2H- S (A) 100 mg 1,2-benzothiazine-3-carboxylate 1,1-Dioxide N O

OH O

O MM 0084.13 N-Methylsaccharin O (A) 100 mg S N

4-Isopropoxy-2-methyl-N-(2-pyridinyl)-2H- OO MM 0084.15 S (A) 100 mg N 1,2-benzothiazine-3-carboxamide 1,1-Dioxide H NN

MM 0084.16 O (C) 50 mg N,N'-Di-(2-pyridinyl)oxamide H N N N N H O

O MM 0084.17 N-(2-Pyridinyl)oxamic Acid Hydrochloride H (A) 100 mg N N OH x HCl O

O MM 0084.20 2-(1,1-Dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)acetamide O (A) 100 mg S N NH2 O O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 171 Pharmaceutical impurities

Code Product Code Unit

OO MM 0084.21 N-(6-Methyl-2-pyridyl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine- S (B) 10 mg 3-carboxamide-1,1-Dioxide N H NN

OH O

OO MM 0084.22 4-Methoxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine- S (C) 10 mg 3-carboxamide-1,1-Dioxide N H NN

OO MM 0084.23 2-Methyl-N-2-(1-methylpyridinium)-2H-1,2-benzothiazine- S (B) 10 mg 3-carboxamide-4-olate 1,1-Dioxide N H NN

OO MM 0084.24 4-Hydroxy-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide S (B) 10 mg NH

NH2

OH O Potassium Sorbate MM 0955.00 Potassium Sorbate O (A) 500 mg OK Povidone MM 0083.03 Imp. A (EP): 1-Ethenylpyrrolidin-2-one (A) 100 mg (1-Vinylpyrrolidin-2-one, N-Vinyl-2-pyrrolidone) N O

MM 0083.05 Imp. B (EP): Pyrrolidin-2-one (2-Pyrrolidone) H (B) 100 mg N O

MM 0537.01 Vinyl Acetate O (B) 100 mg O Pralidoxime Methyl Sulphate MM 0689.00 Pralidoxime Methyl Sulphate (A) 100 mg N OH O N O S O O

MM 0689.01 2-Carboxy-N-methylpyridinium Iodide O (A) 100 mg N OH I-

MM 0689.02 2-Carbamoyl-N-methylpyridinium Methanesulfonate O (A) 100 mg N O O NH2 S O

Prasterone MM 0651.00 Prasterone O (A) 500 mg

MM 0651.02 16-Dehydropregnenolone Acetate Oxime N (A) 100 mg OH

O Pravastatin Sodium MM 0503.00 Pravastatin Sodium O (A) 100 mg OH ONa

OH H OO

OH MM 0503.04 Imp. D (EP): (1S,3S,7S,8S,8aR)-3-Hydroxy-8-[2-[(2R,4R)- O (D) 100 mg 4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl]-7-methyl- O 1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-Methylbutanoate OH (Pravastatin Lactone) H OO

172 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Prazepam

H O MM 0023.02 Imp. A (EP): 7-Chloro-5-phenyl-1,3-dihydro- N (A) 100 mg 2H-1,4-benzodiazepin-2-one (Nordazepam) [Controlled Substance] Cl N

MM 0028.03 Imp. C (EP): (2-Amino-5-chlorophenyl)phenyl- NH2 (B) 100 mg methanone O Cl

Praziquantel MM 0615.00 Praziquantel O (A) 250 mg O N N H

MM 0615.02 Imp. B (EP): 2-(Cyclohexylcarbonyl)- O on request O 2,3,6,7-tetrahydro-4H-pyrazino[2,1-a]- N isoquinolin-4-one N

Prazosin Hydrochloride MM 0085.00 Prazosin Hydrochloride O (A) 100 mg N O N N O x HCl N O

NH2 MM 0085.04 Imp. A (EP): 2-Chloro-6,7-dimethoxyquinazoline-4-amine O N Cl (A) 100 mg N O

NH2 MM 0085.05 Imp. B (EP): 1,4-Bis(furan-2-ylcarbonyl)piperazine O (A) 100 mg O N N O

MM 0085.01 Imp. C (EP): 6,7-Dimethoxy-2-(piperazin-1-yl)quinazolin-4-amine NH (A) 100 mg O N N

N O

NH2 MM 0085.02 Imp. D (EP): 1-(Furan-2-ylcarbonyl)piperazine O (A) 100 mg N HN O

MM 0085.03 Imp. E (EP): 2,2'-(Piperazin-1,4-diyl)bis- NH2 (D) 100 mg O (6,7-dimethoxyquinazolin-4-amine) N

N N O O N N

N O

NH2 MM 0085.06 2,4-Dichloro-6,7-dimethoxyquinazoline O N Cl (A) 100 mg N O Cl H MM 0085.07 6,7-Dimethoxyquinazoline-2,4(1H,3H)-dione O N O (C) 100 mg

NH O O Prednisolone MM 0193.00 Prednisolone O (A) 500 mg OH HO OH

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 173 Pharmaceutical impurities

Code Product Code Unit MM 0185.00 Imp. A (EP): Hydrocortisone O (A) 500 mg OH HO OH

O MM 0482.00 Imp. B (Pharmeuropa): 17,21-Dihydroxypregna-1,4-diene- O (A) 250 mg OH 3,11,20-trione (Prednisone) O OH

O O MM 0194.00 Imp. C (Pharmeuropa): 11i,17-Dihydroxy- O (A) 500 mg 3,20-dioxopregna-1,4-dien-21-yl Acetate O HO (Prednisolone Acetate) OH

O MM 0193.01 (20R)-Hydroxyprednisolone HO (C) 10 mg OH HO OH

O MM 0193.02 (20S)-Hydroxyprednisolone HO (D) 50 mg OH HO OH

O Prednisolone Acetate MM 0194.00 Prednisolone Acetate O (A) 500 mg O O HO OH

O MM 0187.00 Imp. A (EP): Hydrocortisone Acetate O (A) 500 mg O O HO OH

O MM 0193.00 Imp. B (EP): Prednisolone O (A) 500 mg OH HO OH

O MM 0194.04 Prednisolone 17-Acetate O (C) 50 mg OH HO O

O O MM 0194.07 Prednienic Acid OH (A) 100 mg HO OH

O Prednisolone Pivalate

O MM 0304.00 Prednisolone Pivalate O (D) 250 mg O HO OH

O Prednisolone Sodium Phosphate

O O ONa MM 0305.00 Prednisolone Sodium Phosphate P (A) 100 mg O ONa HO OH

174 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Prednisolone Sodium Sulfobenzoate

MM 0484.01 Sodium 3-Sulfobenzoate O OO (C) 100 mg S HO ONa

Prednisone

O MM 0482.00 Prednisone OH (A) 250 mg O OH

O Prednisone Acetate MM 0196.00 Prednisone Acetate O (A) 250 mg O O O OH

O Prilocaine Hydrochloride

MM 0563.00 Prilocaine Hydrochloride H (A) 500 mg N N x HCl O H

MM 0563.01 H (A) 100 mg Imp. A (EP): (RS)-2-Chloro-N-(2-methylphenyl)- N Propanamide Cl O

MM 0563.02 Imp. B (EP): 2-Methylbenzenamine NH2 (A) 100 mg (o-Toluidine)

MM 0563.03 H (A) 50 mg Imp. C (EP) as Hydrochloride: (RS)-2-Ethylamino- N N x HCl N-(2-methylphenyl)propanamide Hydrochloride H O

MM 0563.04 Imp. D (EP) as Hydrochloride: (RS)-N-(3-Methyl- H (A) 50 mg N N phenyl)-2-(propylamino)propanamide Hydrochloride H x HCl O

MM 0563.05 H (A) 50 mg Imp. E (EP) as Hydrochloride: (RS)-N-(4-Methylphenyl)- N N x HCl 2-(propylamino) H propanamide Hydrochloride O Primidone

MM 1030.01 Imp. A (EP) as Hydrate: 2-Ethyl-2-phenylpropane- O NH2 (A) 100 mg

diamide Hydrate (Ethylphenylmalonamide Hydrate) NH2 x H2O O

MM 1030.03 Imp. C (EP): (2RS)-2-Phenylbutanamide (A) 100 mg

NH2

O MM 1030.05 Imp. E (EP): (2RS)-2-Phenylbutanoic Acid (A) 100 mg OH

O Probenecid MM 0657.00 Probenecid O (A) 500 mg OH N S O O Procainamide Hydrochloride

MM 0550.00 Procainamide Hydrochloride O (A) 500 mg N N x HCl H H2N

MM 0550.02 Procainamide N-Oxide Dihydrochloride O (A) 100 mg O N N x 2 HCl H

H2N

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 175 Pharmacopoeias of the world

LGC Standards has over 30 years of experience with providing the pharmaceutical industry with

• Reference substances • Reference spectra • System suitability standards • Peak identification standards • Controlled substances • Publications and Subscriptions from

• United States Pharmacopeia • European Pharmacopeia • British Pharmacopoeia • World Health Organization • Swiss Pharmacopeia • Japanese Pharmacopoeia

www.lgcstandards.com

No part of this publication may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, recording or any retrieval system, without the written permission of the copyright holder. © LGC Standards, 2011. All rights reserved. 2888/SR/0211 Pharmaceutical impurities

Code Product Code Unit Procaine Hydrochloride

MM 0596.00 Procaine Hydrochloride O (A) 500 mg N O x HCl

H2N MM 0094.03 4-Aminobenzoic Acid O (B) 100 mg OH

H2N Progesterone MM 0222.00 Progesterone O (A) 500 mg

O MM 0222.03 Imp. C (EP): (20R)-20-Hydroxypregn-4-en-3-one HO (A) 100 mg

O MM 0222.01 Imp. E (EP): (20R)-3-Oxopregn-4-en-20-yl Acetate O (D) 100 mg O

O MM 0222.08 11-Hydroxyprogesterone O (A) 100 mg HO

O MM 0222.12 11-Ketoprogesterone O (A) 100 mg O

O MM 0222.14 Pregnanediol (5!-Pregnane-3,20(S)-diol) HO (A) 100 mg

HO H MM 0222.15 Pregnanetriol (5!-Pregnane-3,17,20(S)-triol) HO on request

HO H Proguanil Hydrochloride MM 0162.05 Imp. B (EP): 4-Chloroaniline Cl (B) 100 mg

NH2 Prolintane Hydrochloride MM 0663.00 Prolintane Hydrochloride (A) 100 mg N x HCl

Promazine Hydrochloride MM 0290.00 Promazine Hydrochloride (A) 500 mg N

N x HCl

S MM 0290.01 Imp. A (EP): 3-(10H-Phenothiazin-10-yl)-N,N-dimethylpropan-1-amine (A) 100 mg N S-Oxide (Promazine Sulphoxide) N

S O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 177 Pharmaceutical impurities

Code Product Code Unit MM 0290.02 N,N-Dimethyl-3-chloropropylamine Hydrochloride (B) 100 mg Cl N x HCl

H MM 0157.02 Phenothiazine N (B) 100 mg

S Promethazine Hydrochloride MM 0412.00 Promethazine Hydrochloride (A) 500 mg N N x HCl S

MM 0157.02 Imp. A (EP): Phenothiazine (B) 100 mg

NH S

MM 0412.02 Imp. B (EP) as Hydrochloride: (2RS)-N,N- (A) 100 mg N Dimethyl-2-(10H-phenothiazin-10-yl)propan- N x HCl 1-amine Hydrochloride (Isopromethazine S Hydrochloride)

New MM 0412.03 Imp. C (EP) as Hydrochloride: (2RS)-N-Methyl- (A) 50 mg H N 1-(10H-phenothiazin-10-yl)propan-2-amine N x HCl Hydrochloride (Norpromethazine Hydrochloride) S

MM 0412.04 Imp. D (EP): (2RS)-N,N-Dimethyl-1-(10H-phenothiazin-10-yl)propan- (A) 100 mg N 2-amine S-Oxide (Promethazine Sulphoxide) N S O

MM 0412.05 Promethazine Sulphoxide N-Oxide Hydrochloride (A) 100 mg O N N x HCl S O

MM 0412.06 (2RS)-N-Methyl-2-(10H-phenothiazin-10-yl)propan-1-amine (A) 100 mg H N Hydrochloride (Norisopromethazine Hydrochloride) N x HCl S

Propafenone Hydrochloride

MM 0405.00 Propafenone Hydrochloride O O N (A) 500 mg H OH x HCl

MM 0405.02 Imp. A (EP): 1-(2-Hydroxyphenyl)-3-phenylpropan-1-one O OH (A) 100 mg

MM 0405.03 Imp. B (EP) as Hydrochloride: (2E)-1-[2-[(2RS)- O O N (A) 50 mg H 2-Hydroxy-3-(propylamino)propoxy]phenyl]- OH x HCl 3-phenylprop-2-en-1-one Hydrochloride

MM 0405.04 Imp. C (EP): 1-[2-[[(2RS)-Oxiranyl]methoxy]-phenyl]- O O (A) 50 mg O 3-phenylpropan-1-one

New MM 0405.05 Imp. D (EP): 1-[2-[(2RS)-2,3-Dihydroxy-propoxy]phenyl]- O O OH (A) 50 mg 3-phenylpropan-1-one OH

MM 0405.06 Imp. E (EP): 1-[2-[(2RS)-3-Chloro-2-hydroxy- O O Cl (A) 50 mg propoxy]phenyl]-3-phenylpropan-1-one OH

MM 0405.07 Imp. F (EP): 1,1'-[2-Hydroxypropane- O O O O (A) 50 mg 1,3-diylbis(oxy- OH 2,1-phenylene)]bis(3-phenylpropan-1-one)

178 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0405.09 Imp. H (EP): (2RS)-2-Phenyl-2,3-dihydro-4H-1-benzopyran-4-one (A) 100 mg

MM 0405.01 5-Hydroxypropafenone Hydrochloride O O N (A) 100 mg OH H x HCl

OH Propentofylline

MM 0875.01 3-Methyl-7-propylxanthine O (A) 100 mg N HN

O N N

MM 0875.02 1-(3-Hydroxypropyl)-3-methyl-7-propylxanthine O (A) 100 mg N HO N

O N N

MM 0875.03 1,7-Bis-(5-oxohexyl)-3-methylxanthine O (A) 100 mg

O O N N

O N N

Propofol MM 0461.00 Propofol OH (A) 250 mg

MM 0461.03 Imp. A (EP): 2,4-Bis(1-methylethyl)phenol OH (A) 100 mg

MM 0461.04 Imp. C (EP): 2-(1-Methylethyl)phenol OH (C) 100 mg

MM 0461.02 Imp. E (EP): 3,3',5,5'-Tetrakis (A) 100 mg (1-Methylethyl)bisphenyl-4,4'-diol HO OH

MM 0461.05 Imp. F (EP): 3-(1-Methylethyl)phenol (C) 100 mg HO

MM 0461.08 Imp. G (EP): 2-(1-Methylethoxy)-1,3-bis(1-methylethyl)benzene (A) 100 mg O

MM 0461.06 Imp. H (EP): 4-(1-Methylethyl)phenol HO (C) 100 mg

MM 0461.07 Imp. I (EP): Oxydibenzene O (B) 100 mg

MM 0461.13 Imp. J (EP): 2,6-Bis(1-methylethyl)benzene-1,4-dione O (A) 50 mg

O MM 0461.11 Imp. K (EP): 1-(1-Methylethoxy)-2-(1-methylethyl)benzene (A) 100 mg O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 179 Pharmaceutical impurities

Code Product Code Unit MM 0461.15 Imp. M (Pharmeuropa): 2,6-Diisopropylbenzoic Acid O OH (A) 50 mg

Propranolol Hydrochloride

MM 0043.00 Propranolol Hydrochloride OH H (A) 500 mg O N x HCl

MM 0043.01 Imp. A (EP): (2RS)-3-(Naphthalen-1- OH (A) 100 mg yloxy)propane-1,2-diol (Diol Derivative) O OH

MM 0043.03 Imp. B (EP) as Hydrochloride: 1,1'-[(1- OH OH (A) 100 mg Methylethyl)imino]bis[3-(naphthalen-1- O N O

yloxy)propan-2-ol] Hydrochloride x HCl (Tertiary Amine Derivative Hydrochloride) MM 0043.04 1-Naphthol (B) 100 mg

MM 0043.05 1-(1-Naphtyloxy)-2,3-epoxypropane O (A) 100 mg O

Propyl Gallate MM 1037.00 Propyl Gallate O (A) 500 mg HO O

HO OH Propyl Parahydroxybenzoate MM 0432.00 Propyl Parahydroxybenzoate O (A) 500 mg O

HO MM 0045.01 Imp. A (EP): 4-Hydroxybenzoic Acid O (B) 100 mg OH

HO MM 0431.00 Imp. B (EP): Methyl 4-Hydroxybenzoate O (A) 500 mg (Methyl Parahydroxybenzoate) O HO MM 0498.00 Imp. C (EP): Ethyl 4-Hydroxybenzoate (Ethyl Parahydroxybenzoate) O (A) 500 mg O

HO MM 0496.00 Imp. D (EP): Butyl 4-Hydroxybenzoate (Butyl O (A) 500 mg Parahydroxybenzoate) O HO MM 0432.01 Sodium Propyl Parahydroxybenzoate O (B) 100 mg O

NaO Propylhexidrine Hydrochloride

MM 0664.00 Propylhexidrine Hydrochloride x HCl (A) 100 mg NH Propyphenazone

MM 0036.00 Propyphenazone O (A) 500 mg

N N

MM 0036.05 Imp. A (EP): Phenazone O (A) 100 mg

N N

MM 0036.04 Imp. C (EP): 4-[(1RS)-1,3-Dimethylbutyl]- O (A) 50 mg

1,5-dimethyl-2-phenyl-1,2-dihydro-3H- N pyrazol-3-one N

180 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Proxymetacaine Hydrochloride

MM 0404.00 Proxymetacaine Hydrochloride O (A) 500 mg

H2N N O x HCl

O MM 0404.01 3-Amino-4-propoxybenzoic Acid Hydrochloride O (A) 100 mg H2N OH x HCl

MM 0404.02 Proxymetacaine N-Oxide Dihydrochloride O (C) 50 mg H2N N x 2 HCl O O O Proxyphylline MM 1284.00 Proxyphylline OH (A) 250 mg O N N

O N N

Pseudoephedrine Hydrochloride MM 2115.01 Methcathinone Hydrochloride O (A) 100 mg NH (2-Methylamino-1-phenylpropan-1-one Hydrochloride) x HCl [Controlled Substance] MM 2115.04 (1S,2S)-N-Acetylpseudoephedrine OH (A) 100 mg N

O MM 2115.05 (1S,2S)-N,O-Diacetylpseudoephedrine O (A) 100 mg O N

New MM 0652.00 Ephedrine Hydrochloride OH H (A) 500 mg N [Drug Precursor] x HCl

New MM 1147.00 Ephedrine Sulphate OH (A) 250 mg H N [Drug Precursor] x H2SO4

2 Pyrazinamide MM 0385.00 Pyrazinamide O on request N NH2

N MM 0385.01 Imp. A (EP): Pyrazine-2-carboxylic Acid O (A) 100 mg N OH

N Pyridostigmine Bromide MM 0429.02 Imp. B (EP) as Iodide: 3-Hydroxy-1-methyl- (A) 100 mg I- N+ pyridinium Iodide HO Pyridoxine Hydrochloride MM 0021.00 Pyridoxine Hydrochloride N (A) 500 mg OH HO x HCl

OH MM 0021.01 Imp. A (EP) as Hydrochloride: 6-Methyl- N (D) 100 mg 1,3-dihydrofuro[3,4-c]pyridin-7-ol x HCl HO Hydrochloride O MM 0021.02 Imp. B (EP) as Hydrochloride: 5-(Hydroxymethyl)- N (A) 100 mg 2,4-dimethylpyridin-3-ol Hydrochloride OH x HCl HO

MM 0021.03 Pyridoxine Diacetate N (A) 100 mg O HO O O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 181 Pharmaceutical impurities

Code Product Code Unit MM 0021.05 Pyridoxal Hydrochloride N (A) 100 mg OH HO x HCl

O MM 0021.06 Pyridoxamine Dihydrochloride N (A) 100 mg OH HO x 2 HCl

NH2 MM 0021.07 4-Pyridoxic Acid N (D) 50 mg OH HO

O OH Quetiapine Fumarate

H MM 1130.09 Imp. G (Pharmeuropa): Dibenzo[b,f][1,4]thiazepin- N O (A) 100 mg 11(10H)-one S

MM 1130.01 Imp. B (Pharmeuropa) as Dihydrochloride: NH (A) 100 mg 11-(Piperazin-1-yl)dibenzo[b,f][1,4]thiazepine N N Dihydrochloride x 2 HCl S

Quinapril Hydrochloride MM 0011.01 4-Amino-6-chlorobenzene-1,3-disulphonamide (Salamide) OO OO (B) 100 mg S S H2N NH2

Cl NH2

MM 0010.05 Imp. B (Pharmeuropa): (2S)-2-[[(1S)-1- O (A) 100 mg H N (Ethoxycarbonyl)-3-phenylpropyl]amino]- OH propanoic Acid OO

Quinine Dihydrochloride MM 0458.00 Quinine Dihydrochloride H (A) 500 mg

HO N H x 2 HCl O

N Quinuclidinyl Benzilate MM 0783.09 Benzilic Acid O (B) 100 mg OH HO

MM 0825.02 3-Quinuclidinol N (A) 100 mg

OH Rabeprazole Sodium MM 0618.01 Rabeprazole Sodium O on request

Na N S N N O MM 0618.00 Rabeprazole O on request

H N S N N O MM 0618.02 2-[[[4-(3-Methoxypropoxy)-3-methyl- O (A) 100 mg 2-pyridinyl]methyl]thio]-1H-benzimidazole H N O S N N

182 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0618.03 Rabeprazole Sulphone O (A) 100 mg H O O N O S N N MM 0618.04 Rabeprazole N-Oxide O (D) 100 mg H N O O S N N O MM 0618.05 Rabeprazole Sulphone N-Oxide O (A) 100 mg H O O N O S N N O MM 0618.07 2-Chloromethyl-3-methyl-4-(3-methoxy-propoxy)pyridine O (A) 100 mg

Hydrochloride O x HCl Cl

N Raloxifene Hydrochloride

MM 0738.00 Raloxifene Hydrochloride HO S (A) 100 mg OH

x HCl

O N O Ramipril MM 0448.05 Imp. D (EP): Ethyl (2S)-2-[(3S,5aS,8aS,9aS)-3- H (A) 100 mg Methyl-1,4-dioxodecahydro-2H-cyclopenta[4,5]- H O pyrrolo[1,2-a]pyrazin-2-yl]-4-phenylbutanoate N H N (Ramipril Diketopiperazine) O

O O

MM 0010.05 Imp. F (EP): (2S)-2-[[(1S)-1-(Ethoxycarbonyl)- O (A) 100 mg H N 3-phenylpropyl]amino]propanoic Acid OH

O O

MM 0291.04 Imp. G (EP): Methylbenzene (Toluene) (C) 100 mg

O OH MM 0448.04 Imp. M (EP): (2R,3R)-2,3-Bis(benzoyloxy)- O (A) 100 mg butanedioic Acid (Dibenzoyltartric Acid) O O O HO O Ranitidine Hydrochloride

H H MM 0086.00 Ranitidine Hydrochloride O N N (A) 500 mg N S x HCl

NO2

H H MM 0086.02 Imp. A (EP): N,N'- O N N O (A) 100 mg Bis[2-[[[5-[(dimethylamino)methyl]furan-2-yl]- N S SN methyl]sulphanyl]ethyl]-2-nitroethene- NO2 1,1-diamine

O NH MM 0086.01 Imp. B (EP): 2-[[[5-[(Dimethylamino)methyl]- N S 2 (A) 100 mg furan-2-yl]methyl]sulphanyl]ethanamine H H MM 0086.03 Imp. C (EP): N-[2-[[[5-[(Dimethylamino)- O N N (A) 100 mg methyl]furan-2-yl]methyl]sulphinyl]ethyl]-N'- N S methyl-2-nitroethene-1,1-diamine O NO (Ranitidine Sulphoxide) 2 H MM 0086.06 Imp. D (EP) as Sodium Salt: N-[2-[[[5- O N ONa (A) 100 mg [(Dimethylamino)methyl]furan-2-yl]- N S methyl]sulphanyl]ethyl]-2-nitroacetamide NO Sodium Salt 2

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 183 Pharmaceutical impurities

Code Product Code Unit O H H MM 0086.05 Imp. E (EP): N-[2-[[[5-[(Dimethyloxidoamino) O N N (D) 100 mg methyl]furan-2-yl]methyl]sulphanyl] N S ethyl]-N'-methyl-2-nitroethene-1,1-diamine NO (Ranitidine N-Oxide) 2 O MM 0086.17 Imp. F (EP) as Hydrochloride: [5-[(Dimethyl- N OH x HCl (A) 100 mg amino)methyl]furan-2-yl]methanol Hydrochloride

MM 0086.08 Imp. H (EP): N-Methyl-2-nitroacetamide NO2 (A) 100 mg

O N H H H MM 0086.10 Imp. I (EP): 2,2'-Methylenebis[N-[2-[[[5-[(dimethyl- O N N (A) 100 mg amino)methyl]furan-2-yl]methyl]sulphanyl]ethyl]-N'- N S NO2 methyl-2-nitroethene-1,1-diamine] NO2 N S O N N H H MM 0220.09 Imp. K (EP): N-Methyl-1-methylthio-2- NO2 (A) 100 mg nitroethenamine ((EZ)-N-Methyl-1-(methylsulphanyl)-2-nitroethen-1-amine) S N H

S N MM 0086.07 Imp. G (EP): 3-(Methylamino)-5,6-dihydro-2H-1,4-thiazin-2-one Oxime OH (A) 100 mg

N N H Ranolazine Dihydrochloride New MM 1320.01 2-[(2-Methoxyphenoxy)methyl]oxirane O (A) 100 mg O

O Reagents MM 0334.01 Diethylhexylphthalate (Bis-(2-ethylhexyl) Phthalate) O (C) 500 mg O O

OH MM 0334.02 3-(N-Morpholino)propane Sulfonic Acid (MOPS) NS (C) 500 mg O O O MM 0334.03 3-(N-Morpholino)ethane Sulfonic Acid (MES) O O (C) 500 mg S N OH O MM 0334.08 Salicylaldehyde Azine HO (A) 100 mg

N N

OH Repaglinide

New MM 0944.00 Repaglinide O (A) 100 mg

N O OH

N O H

New MM 0944.01 Imp. C (EP) as N-Acetyl-L-glutamate: (1S)- O O (A) 100 mg

3-Methyl-1-[2-(piperidin-1-yl)phenyl] N HO OH x butan-1-amine N-Acetyl-L-glutamate HN NH2 O New MM 0944.02 Imp. B (EP): [3-Ethoxy-4-(ethoxycarbonyl)- O (A) 100 mg phenyl]acetic Acid O O

HO O Ribavirin MM 0542.00 Ribavirin O (A) 250 mg

H2N N HO N N O

OH OH MM 0542.01 Imp. A (EP): 1-i-D-Ribofuranosyl-1H-1,2,4- O (D) 100 mg triazole-3-carboxylic Acid HO N HO N N O

OH OH

184 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0542.03 Imp. C (EP): 1H-1,2,4-Triazole-3-carboxylic Acid O (D) 100 mg HO N N N H MM 0542.04 Imp. D (EP): 1H-1,2,4-Triazole-3-carboxamide O (D) 100 mg

H2N N N N H MM 0542.05 Imp. E (EP): 1-(5-O-Benzoyl-i-D-ribofuranosyl)-1H-1,2,4-triazole- O (D) 100 mg 3-carboxamide (5'-O-Benzoylribavirin) H2N N O N N O O

OH OH MM 0542.06 Imp. F (EP): 1-(5-O-Acetyl-i-D-ribofuranosyl)-1H-1,2,4-triazole- O (D) 100 mg 3-carboxamide (5'-O-Acetylribavirin) H2N N O N N O O

OH OH Riboflavin MM 0030.00 Riboflavin OH (A) 500 mg HO OH

OH N N O

NH N O Rifampicin MM 0514.02 3-Formylrifamycin Isonicotinylhydrazone O on request N OH O H N O N O HN O OH OH O O OH O

Risedronate Sodium 2.5 Hydrate New OH MM 0777.00 Risedronate Sodium 2.5 Hydrate O OH (A) 100 mg HO P x 2,5 H O N OH 2 P ONa O Risperidone MM 0491.00 Risperidone N (A) 100 mg N F N O

NO MM 0491.01 Imp. A (EP): 3-[2-[4-[(E)-(2,4-Difluorophenyl)- N (D) 100 mg (hydroxyimino)methyl]piperidin-1-yl]ethyl]-2- N F methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]- N O pyrimidin-4-one N F HO MM 0491.02 Imp. B (EP): 3-[2-[4-[(Z)-(2,4-Difluorophenyl)- N (A) 100 mg (hydroxyimino)methyl]piperidin-1-yl]ethyl]-2- N F methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]- N O pyrimidin-4-one N F OH N MM 0491.04 Imp. D (EP): 3-[2-[4-(5-Fluoro-1,2-benzisoxazol- F (D) 100 mg 3-yl)piperidin-1-yl]ethyl]-2-methyl-6,7,8,9- N tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one N O

NO MM 0491.05 Imp. E (EP): (6RS)-3-[2-[4-(6-Fluoro-1,2- N (D) 50 mg benzisoxazol-3-yl)piperidin-1-yl]ethyl]-2,6- N F dimethyl-6,7,8,9-tetrahydro-4H-pyrido- N O [1,2-a]pyrimidin-4-one NO

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 185 Pharmaceutical impurities

Code Product Code Unit N MM 0491.08 Imp. F (EP): 2-[2-Methyl-4-oxo-6,7,8,9-tetrahydro- O (A) 100 mg 4H-pyrido[1,2-a] N F pyrimidin-3-yl]ethyl 4-(6-Fluoro-1,2-benzisoxazol- ON O 3-yl) piperidin-1-carboxylate NO MM 0491.10 Imp. H (EP): 3-[2-[4-(2,4-Difluorobenzoyl)piperidin- N (A) 100 mg 1-yl]ethyl]-2-methyl-6,7,8,9-tetrahydro-4H-pyrido- N F [1,2-a]pyrimidin-4-one N O

O F MM 0491.03 Imp. C (EP): (9RS)-3-[2-[4-(6-Fluoro- OH (D) 100 mg 1,2-benzisoxazol-3-yl)piperidin-1-yl]ethyl]-9-hydroxy- N N F 2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin- N 4-one (9-Hydroxyrisperidone) O

NO MM 0491.09 3-[2-[4-(4-Fluoro-2-hydroxybenzoyl)piperidin- N (A) 100 mg 1-yl]ethyl]-2-methyl-6,7,8,9-tetrahydro-4H-pyrido- N F [1,2-a]pyrimidin-4-one N O

O OH MM 0491.13 Imp. L (Pharmeuropa) as Hydrochloride: 3-(2- N (A) 100 mg Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H- N x HCl pyrido[1,2-a]pyrimidin-4-one Hydrochloride Cl O (Risperidone Piperidopyrimidinone Intermediate Hydrochloride) New MM 0491.18 3-[2-[4-[2-Fluoro-4-[4-(6-fluoro- F (D) 50 mg 1,2-benzisoxazol-3-yl)piperidin- 1-yl]benzoyl]piperidin-1-yl]ethyl]-2-methyl- O 6,7,8,9-tetrahydro-4H-pyrido-[1,2-a]- N pyrimidin-4-one N N N N O

O F Ritodrine Hydrochloride

MM 0063.06 Imp. A (BP): Tyramine NH2 (B) 100 mg

HO Ronidazole MM 1026.01 (1-Methyl-5-nitroimidazol-2-yl)methanol (A) 100 mg O N N 2 OH N Rosiglitazone Maleate

O MM 0522.01 Rosiglitazone Maleate S (D) 100 mg O OH N x O N O H OH N O Rosuvastatin Calcium New MM 0936.02 4-(4-Fluorophenyl)-6-isopropyl- O O (A) 100 mg S 2-[methyl(methylsulfonyl)amino]pyrimidine-5-methanol N

HO F Rutoside Trihydrate MM 0109.03 Imp. C (EP) as Dihydrate: 2-(3,4-Dihydroxyphenyl)- HO OH (A) 100 mg 3,5,7-trihydroxy-4H-1-benzopyran-4-one Dihydrate O (Quercetin Dihydrate) O HO x 2 H2O

OH OH

186 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Saccharin Sodium

MM 0818.00 Saccharin Sodium O O (A) 500 mg S NNa

O Salbutamol Sulphate

OH MM 0381.00 Salbutamol Sulphate H (A) 500 mg N

x H2SO4 HO

OH 2

OH MM 0381.02 Imp. B (EP): (1RS)-2-[(1,1-Dimethylethyl)- H (A) 50 mg amino]-1-(4-hydroxyphenyl)ethanol N

MM 0381.03 Imp. C (EP): (1RS)-2-[(1,1-Dimethylethyl)amino]-1-(4-hydroxy- OH H (A) 50 mg 3-methylphenyl)ethanol N HO

MM 0381.05 Imp. E (EP): (1RS)-2-[Benzyl(1,1-dimethyl- (A) 100 mg

ethyl)amino]-1-[4-hydroxy-3-(hydroxymethyl)- OH phenyl]ethanol N

H MM 0381.08 Imp. H (EP): 4-[2-[1,1-Dimethylethyl)amino]ethyl]-2-methylphenol N (A) 100 mg

MM 0381.07 Imp. G (EP) as Hydrochloride: (D) 50 mg

2-[Benzyl(1,1-dimethylethyl)amino]-1-[4-hydroxy- O

3-(hydroxy-methyl)phenyl]ethanone Hydrochloride N x HCl

OH O MM 0381.10 Imp. J (EP) as Hydrochloride: 2-[(1,1-Dimethyl- H (D) 50 mg ethyl)amino]-1-[4-hydroxy-3-(hydroxymethyl)- N phenyl]ethanone Hydrochloride (Salbutamone x HCl HO Hydrochloride) OH OH MM 0381.17 4-[(1RS)-2-(tert-Butylamino)-1-hydroxyethyl]-2- H (A) 50 mg ethylphenol Hydrobromide N x HBr HO

Salicylic Acid MM 0045.00 Salicylic Acid O (A) 500 mg OH

OH MM 0045.01 Imp. A (EP): 4-Hydroxybenzoic Acid O (B) 100 mg HO

OH MM 0045.02 Imp. B (EP): 4-Hydroxyisophthalic Acid O O (A) 100 mg HO OH

OH MM 0045.11 Imp. C (EP): Phenol (B) 100 mg

O MM 0045.12 Imidazole Salicylate H (A) 100 mg O N

OH N H MM 0045.13 Choline Salicylate O on request OH O N OH

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 187 Pharmaceutical impurities

Code Product Code Unit MM 0045.14 N,N-Diethylsalicylamide O (A) 100 mg N

OH Salmeterol Xinafoate

OH New MM 0536.07 Imp. F (EP): (1RS)-1-(4-Hydroxy-3-methylphenyl)- H (A) 50 mg 2-[[6-(4-phenylbutoxy)hexyl]amino]ethanol N

HO O

OH New MM 0536.03 Imp. B (EP): (1RS)-1-[4-Hydroxy-3-(hydroxy- H (A) 100 mg methyl)phenyl]-2-[[6-(2-phenylethoxy)hexyl]- N amino]ethanol HO O

OH Secnidazole MM 0119.00 Secnidazole OH (A) 100 mg

N O2N N

MM 0012.02 2-Methyl-4-nitroimidazole NH (B) 100 mg O2N N Selegiline Hydrochloride MM 0656.00 Imp. C (EP) as Hydrochloride: (1RS, 2SR)-2- OH (A) 500 mg NH Amino-1-phenylpropan-1-ol Hydrochloride 2 x HCl (Phenylpropanolamine Hydrochloride) and enatiomer Sertraline Hydrochloride

MM 0317.01 Sertraline Hydrochloride HN (A) 100 mg

x HCl

Cl Cl

MM 0317.00 Sertraline HN (A) 100 mg

Cl Cl

MM 0317.05 Imp. B (EP) as Hydrochloride: (1RS,4RS)-N- HN (A) 100 mg Methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen- 1-amine Hydrochloride x HCl

and enantiomer

MM 0317.06 Imp. C (EP) as Hydrochloride: (1RS,4RS)-4- HN (D) 100 mg 4-Chlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine Hydrochloride

x HCl

Cl and enantiomer

MM 0792.03 Imp. E (EP) as Racemate: Hydroxyphenylacetic Acid (Mandelic Acid) O (A) 100 mg

OH OH MM 0317.09 Imp. F (EP) as Racemate: 4-(3,4-Dichlorophenyl)- O (A) 100 mg 3,4-dihydronaphthalen-1(2H)-one (Sertraline Tetralone Derivative)

Cl Cl

188 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit

MM 0317.10 Imp. E (EP): (2R)-Hydroxyphenylacetic Acid O (A) 100 mg

((R)-Mandelic Acid) OH OH Sibutramine Hydrochloride

Cl MM 0991.02 Imp. D (Pharmeuropa) as Hydrochloride: (1RS)- HN (A) 100 mg 1-[1-(4-Chlorophenyl)cyclobutyl]- x HCl N,3-dimethylbutan-1-amine Hydrochloride (N-Monodesmethylsibutramine Hydrochloride) Cl MM 0991.03 Imp. G (Pharmeuropa) as Hydrochloride: (1RS)- NH2 (A) 100 mg 1-[1-(4-Chlorophenyl)cyclobutyl]-3-methylbutan- x HCl 1-amine Hydrochloride (N,N-Didesmethyl- sibutramine Hydrochloride) New MM 0991.05 Imp. B (Pharmeuropa) as Hydrochloride: (1RS)- (A) 50 mg 1-[1-(3-Chlorophenyl)cyclobutyl]-N,N,3-trimethyl- Cl x HCl butan-1-amine Hydrochloride N New MM 0991.06 Imp. C (Pharmeuropa) as Hydrochloride: (1RS)- (A) 50 mg 1-[1-(4-Chlorophenyl)cyclobutyl]-N,N-dimethyl- x HCl pentan-1-amine Hydrochloride N Cl New MM 0991.07 Imp. E (Pharmeuropa): (4-Chlorophenyl)acetonitrile (A) 50 mg N Cl MM 0991.09 Imp. H (Pharmeuropa): 2-(4-Chlorophenyl)-2-(prop- 50 mg 2-en-1-yl)pent-4-enenitrile N Cl MM 0991.10 Imp. I (Pharmeuropa): (1RS)-1-[1-(4-Chlorophenyl)- (A) 50 mg cyclobutyl]-3-methylbutan-1-ol OH Cl New MM 0991.11 Imp. J (Pharmeuropa): 1-[1-(4-Chlorophenyl)cyclo- (A) 50 mg butyl]-3-methylbutan-1-one O Cl Sildenafil Citrate

MM 0254.00 Sildenafil Citrate O O (D) 100 mg

N HO O O O HN N x S HO N N HO OH N O O MM 0254.09 Sildenafil O (D) 100 mg HN N O O N S N N N O MM 0254.01 4-[[2-Ethoxy-5-[(4-methyl-1-piperazinyl)- O on request N sulfonyl]benzoyl]amino]-1-methyl-3-propyl-1H- O H2N O O N pyrazole-5-carboxamide S N N H N O

MM 0254.02 2-Ethoxy-5-[(4-methyl-1-piperazinyl)sulfonyl]benzoic Acid O O O (A) 100 mg S N OH N O MM 0254.04 Sildenafil N-Oxide O (A) 100 mg HN N O O N S N N O N O MM 0254.05 4-Amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide O (A) 100 mg N H2N N

H2N

MM 0254.06 3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H- O on request pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxy-benzenesulfonic Acid HN N O O N S HO N

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 189 Pharmaceutical impurities

Code Product Code Unit MM 0254.08 1-[[3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H- O (D) 100 mg pyrazolo[4,3-d]pyrimidin-5-yl)- HN N O O N 4-ethoxyphenyl]sulfonyl]piperazine S N N (Desmethylsildenafil) HN O MM 0254.11 3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H- O on request N pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxy-N- HN OO N [2-(methylamino)ethyl]- S N N benzenesulfonamide H NH O

MM 0254.21 2-Ethoxy-5-(4-methylpiperazine-1-sulfonyl)benzaldehyde O O O (A) 100 mg S (1-[(4-Ethoxy-3-formylphenyl)sulfonyl]-4-methylpiperazine) N N O MM 0254.22 Desethylsildenafil (5-[2-Hydroxy- O (D) 100 mg 5-(4-methylpiperazinylsulfonyl)phenyl]-1-methyl-3-n- HN N O O N propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one S N N N OH New MM 0254.29 5-(2-Ethoxyphenyl)-1-methyl-3n-propyl-1,6-dihydro-7H- O (A) 100 mg N pyrazolo[4,3-d]pyrimidin-7-one HN N N

O Silybin

O MM 0472.00 Silybin OH on request HO O O O

OH OH OH O Simvastatin MM 0158.00 Simvastatin O (A) 100 mg O

OH H OO

MM 0158.01 Imp. A (EP) as Sodium Salt: (3R,5R)-7- O (A) 100 mg [(1S,2S,6R,8S,8aR)-8-[(2,2-Dimethylbutanoyl) OH ONa oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen- OH 1-yl]-3,5-dihydroxyheptanoic Acid Sodium Salt (Tenivastatin H OO Sodium Salt; Simvastatin Hydroxy Acid Sodium Salt)

MM 0158.02 Imp. B (EP): (1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-(Acetyloxy)- O (A) 100 mg 6-oxotetrahydro-2H-pyran-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a- O O O hexahydronaphthalen-1-yl 2,2-Dimethylbutanoate (Simvastatin H Acetate Ester) OO

MM 0158.03 Imp. C (EP): (1S,3R,7S,8S,8aR)-3,7-Dimethyl-8-[2-[(2R)-6-oxo- O (A) 100 mg 3,6-dihydro-2H-pyran-2-yl]ethyl]-1,2,3,7,8,8a-hexahydronaphthalen- O

1-yl 2,2-Dimethylbutanoate (Anhydrosimvastatin) H OO

MM 0050.00 Imp. E (EP): Lovastatin O (A) 100 mg O

OH H OO

Sodium Benzoate MM 0730.00 Sodium Benzoate O (A) 500 mg ONa

190 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Sodium Cromoglicate MM 0039.00 Sodium Cromoglicate O O (A) 500 mg OO NaO ONa

OH O OOO

MM 0039.01 Succinophenone; Diphenacyl O (A) 100 mg

MM 0039.02 1,3-Bis(2-acetyl-3-hydroxyphenoxy)-2-propanol HO OH (A) 100 mg

OH O OOO

MM 0039.03 2',6'-Dihydroxyacetophenone OH O (B) 100 mg

OH MM 0039.04 Ethyl Cromoglicate O O (A) 100 mg OO O O

OH O OOO Sodium Cyclamate

H MM 0678.05 Cyclamic Acid N OH (A) 100 mg S O O

MM 0093.17 Imp. B (EP) as Hydrochloride: Aniline Hydrochloride NH2 (B) 100 mg x HCl (Phenylamine Hydrochloride)

MM 0678.03 Imp. C (EP): Cyclohexanamine NH2 (C) 100 mg

H MM 0678.04 Imp. D (EP): N-Cyclohexylcyclohexanamine N (C) 100 mg

Sodium Fluoride

MM 0734.00 Sodium Fluoride NaF (A) 500 mg Sodium Picosulfate

NaO OOONa MM 0054.00 Sodium Picosulfate S S (A) 500 mg O O O O

HO O ONa MM 0054.01 Imp. A (EP): 4-[(RS)-(4-Hydroxyphenyl)- S (A) 100 mg (pyridin-2-yl)methyl]phenyl Sodium Sulphate O O (4-[(Pyridin-2-yl)(4-hydroxyphenyl)methyl]- phenyl Sodium Sulphate) N

MM 0031.01 Imp. B (EP): 4,4'-[(Pyridin-2-yl)methylene]- HO OH (A) 100 mg diphenol (4,4'-(Pyridin-2-ylmethylene)di-

phenol) N

O ONa MM 0054.02 Imp. C (EP): 2-[(RS)-(Pyridin-2-yl)[4-(sulphonato- S (D) 50 mg oxy)phenyl]methyl]phenyl Disodium Sulphate O O (2,4'-[(Pyridin-2-yl)-methylene]bisphenyl Bis- NaO O (Sodium Sulphate)) S N O O

MM 0031.04 2,4'-[(Pyridin-2-yl)methylene]bisphenol(2-[(RS)- HO (A) 50 mg (4-Hydroxyphenyl)(pyridin-2-yl)methyl]phenol) OH N

Sodium Thiophene-2-carboxylate MM 1081.00 Sodium Thiophene-2-carboxylate O (A) 250 mg S ONa

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 191 Pharmaceutical impurities

Code Product Code Unit Sorbic Acid MM 0954.00 Sorbic Acid O (A) 500 mg OH Sotalol Hydrochloride

OH MM 0046.00 Sotalol Hydrochloride H (A) 100 mg N OO x HCl S N H

H MM 0046.01 Imp. A (EP) as Hydrochloride: N-[4-[2- N (A) 100 mg O O x HCl [(1-Methylethyl)amino]ethyl]phenyl]- S N methanesulphonamide Hydrochloride H

O MM 0046.02 Imp. B (EP) as Hydrochloride: N-[4-[[(1- H (A) 100 mg N Methylethyl)amino]acetyl]phenyl]- OO x HCl methanesulphonamide Hydrochloride S N H MM 0046.03 Imp. C (EP):N-(4-Formylphenyl)methanesulphonamide O (A) 100 mg OO S N H Spironolactone MM 0197.00 Spironolactone O (A) 500 mg O

O New MM 0197.01 Imp. F (EP): (2'R)-3',4'-Dihydro-5'H-spiro[androst- O (A) 100 mg 4,6-diene-17,2'-furan]-3,5'-dione (Canrenone) O

O Stavudine MM 0534.01 Imp. A (EP): 5-Methylpyrimidine-2,4(1H,3H)-dione (Thymine) O (A) 100 mg HN

O N H MM 0534.03 Imp. C (EP): 1-(2-Deoxy-i-D-erythro-pentofuranosyl)- O (A) 100 mg 5-methylpyrimidine-2,4(1H,3H)-dione (Thymidine) HN HO O N O

OH Strychnine Nitrate MM 0658.00 Strychnine Nitrate (A) 500 mg H N

H x HNO3 N H OO MM 0658.02 Strychnine N-Oxide Hydrochloride O on request H N

H x HCl N H OO Sulfacetamide

MM 0579.00 Sulfacetamide O O O (A) 500 mg S N H H2N Sulfacetamide Sodium MM 1087.00 Sulfacetamide Sodium Monohydrate O O O (A) 500 mg S N x H2O Na

H2N

192 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0227.05 Imp. A (EP): Sulfanilamide O O (A) 100 mg S NH2

H2N Sulfadiazine

MM 0623.00 Sulfadiazine O O N (A) 500 mg S N N H H2N

MM 0623.03 Imp. A (Pharmeuropa): Pyrimidin-2-amine N (A) 100 mg

H2NN MM 0227.04 Imp. B (Pharmeuropa): 4-Aminobenzenesulfonic Acid (Sulphanilic O O (A) 100 mg S Acid) OH

H2N MM 0227.05 Imp. D (Pharmeuropa): 4-Aminobenzenesulfonamide O O (A) 100 mg S (Sulfanilamide) NH2

H2N

MM 0623.02 N4-Acetylsulfadiazine O O N (A) 50 mg S O N N H N H Sulfadimidine

MM 623.00 Imp. B (Pharmeuropa): 4-Amino-N-pyrimidin-2- O O N (A) 500 mg S ylbenzenesulphonamide (Sulfadiazine) N N H

H2N MM 0227.04 Imp. F (Pharmeuropa): 4-Aminobenzenesulphonic O O (A) 100 mg S Acid (Sulphanilic Acid) OH

H2N MM 0227.05 Imp. D (Pharmeuropa): 4-Aminobenzenesulphonamide O O (A) 100 mg S (Sulfanilamide) NH2

H2N MM 0579.00 Imp. E (Pharmeuropa): N-[(4-Aminophenyl)sulfonyl]- O O O (A) 500 mg S acetamide (Sulfacetamide) N H

H2N MM 0581.00 Imp. A (Pharmeuropa): 4-Amino-N-(4-methyl-2- (A) 500 mg pyrimidyl)benzenesulphonamide (Sulfamerazine) O O N S N N H

H2N MM 0883.00 Imp. C (Pharmeuropa): (4-Aminophenylsulphonyl)- O O NH (A) 100 mg S guanidine (Sulfaguanidine) N NH2 H

H2N Sulfadimethoxine Sodium

MM 1020.00 Sulfadimethoxine Sodium O (A) 500 mg

O O N N S N O Na

H2N Sulfafurazole

N MM 0583.00 Sulfafurazole O O O (A) 500 mg S N H H2N Sulfaguanidine MM 0883.00 Sulfaguanidine O O NH (A) 100 mg S N NH2 H

H2N MM 0227.05 Imp. A (EP): 4-Aminobenzenesulphonamide (Sulphanilamide) O O (A) 100 mg S NH2

H2N

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 193 Pharmaceutical impurities

Code Product Code Unit MM 0883.02 Imp. B (EP): N-[(4-Aminophenyl)sulphonyl]- O O O (A) 50 mg S urea (Sulphacarbamide) N NH2 H

H2N Sulfamerazine MM 0581.00 Sulfamerazine (A) 500 mg O O N S N N H H2N MM 0227.05 Sulphanilamide O O (A) 100 mg S NH2

H2N Sulfamethoxazole MM 0227.00 Sulfamethoxazole (A) 500 mg OO O S N N H

H2N MM 0227.01 Imp. A (EP): N-[4-[(5-Methylisoxazol-3-yl)- (A) 100 mg OO sulphamoyl]phenyl]acetamide O S O N N H N H MM 0227.03 Imp. B (EP): 4-[[(4-Aminophenyl)sulphonyl]amino]-N- (A) 100 mg O O (5-methylisoxazol-3-yl)benzenesulphonamide O S O O N N H S N H

H2N MM 0227.02 Imp. C (EP): 5-Methylisoxazol-3-amine (B) 100 mg O

H2N N OO MM 0227.04 Imp. D (EP): 4-Aminobenzenesulphonic Acid S (A) 100 mg (Sulphanilic Acid) OH

H2N OO MM 0227.05 Imp. E (EP): 4-Aminobenzenesulphonamide (Sulphanilamide) S (A) 100 mg NH2

H2N Sulfamethylphenazole MM 1108.00 Sulfamethylphenazole (A) 100 mg O O N S N N H

H2N

Sulfaquinoxaline Sodium

MM 0702.00 Sulfaquinoxaline Sodium NH2 on request Na N N S O O N Sulfasalazine MM 0045.00 Imp. H (EP): Salicylic Acid (A) 500 mg

O OH Sulfathiazole

MM 0578.00 Sulfathiazole O O N (A) 500 mg S N S H H2N

194 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Sulindac MM 0624.00 Sulindac (A) 500 mg OH

O S O F Sulpiride

MM 0051.00 Sulpiride O O (A) 500 mg O S N N H2N H O MM 0051.01 Imp. A (EP): [(2RS)-1-Ethylpyrrolidin-2-yl]methanamine (A) 100 mg N H2N

O O MM 0051.02 Imp. B (EP): Methyl 2-Methoxy-5-sulphamoylbenzoate H2N (A) 100 mg S O O O

O O MM 0051.03 Imp. C (EP): Ethyl 2-Methoxy-5-sulphamoylbenzoate H2N (A) 100 mg S O O O

O O MM 0051.04 Imp. D (EP): 2-Methoxy-5-sulphamoylbenzoic Acid H2N (A) 100 mg S OH O O

O O MM 0051.05 Imp. E (EP): 2-Methoxy-5-sulphamoylbenzamide H2N (A) 100 mg S NH O 2 O

MM 0051.06 Imp. F (EP): 1-Ethyl-2-[[(2-methoxy-5- NH O (A) 100 mg O 2 O sulphamoylbenzoyl)amino]methyl]pyrrolidine 1 S N N -Oxide (Sulpiride N-Oxide) O H O

MM 0051.07 Imp. G (EP): (RS)-N-[(1-Ethylpyrrolidin-2-yl)methyl]- O O (A) 100 mg O 2-hydroxy-5-sulphamoylbenzamide S N N H2N H OH

O O MM 0051.08 5-Sulphamoylsalicylic Acid H2N (A) 100 mg S OH O OH

O O MM 0051.09 5-Sulphosalicylic Acid Dihydrate HO (C) 100 mg S OH x 2 H O O 2 OH Sumatriptan Succinate

H New MM 0310.04 Imp. D (EP) as Maleate: N,N-Dimethyl- N O (A) 100 mg 2-[5-[(methylsulfamoyl)methyl]-1H-indol- O O S OH N x 3-yl]-ethanamine N-Oxide Maleate H OH N O O H New MM 0310.05 Imp. E (EP): [3-(2-Aminoethyl)-1H-indol-5-yl]- N (A) 100 mg O O N-methylmethanesulfonamide S N H

NH2 Suplatast Tosilate

O O MM 0722.01 Methyl Toluene-4-sulphonate S (B) 100 mg O

Tamoxifen Citrate

MM 0053.00 Tamoxifen Citrate O (A) 100 mg O N HO OH x HO HO O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 195 Pharmaceutical impurities

Code Product Code Unit MM 0053.02 Imp. B (EP): 1-[4-(2-Dimethylaminoethoxy)phenyl]- (A) 100 mg O 1,2-diphenylbutan-1-ol N

MM 0053.14 Imp. C (EP) Z-Isomer: 2-[4-[(Z)-1,2-Diphenyl- on request O ethenyl]phenoxy]-N,N-dimethylethanamine N

O MM 0053.15 Imp. C (EP) E-Isomer: 2-[4-[(E)- N (A) 50 mg 1,2-Diphenylethenyl]phenoxy]-N,N-dimethylethanamine

MM 0053.16 Imp. D (EP) Z-Isomer: 2-[4-[(Z)-1,2-Diphenylprop- (A) 50 mg O 1-enyl]phenoxy]-N,N-dimethylethanamine N

O MM 0053.17 Imp. D (EP) E-Isomer: 2-[4-[(E)-1,2-Diphenylprop- N on request 1-enyl]phenoxy]-N,N-dimethylethanamine

MM 0053.05 Imp. E (EP):2-[2-[(EZ)-1,2-Diphenylbut-1-enyl)phenoxy]-N,N- (A) 100 mg dimethylethanamine

O N

MM 0053.12 Imp. F (EP) as Hydrochloride: 2-[4-[(Z)-1,2-Diphenylbut- (A) 100 mg O 1-enyl]phenoxy]-N-methylethanamine Hydrochloride N H

x HCl

MM 0053.07 Imp. G (EP): (2RS)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]- (A) 100 mg O 2-phenylbutan-1-one N

O MM 0053.08 1,2-Diphenylbutan-1-one (A) 100 mg

O MM 0053.09 1-(4-Methoxyphenyl)-1,2-diphenylbutan-1-ol (A) 100 mg O

MM 0053.10 (EZ)-1-(4-Hydroxyphenyl)-1,2-diphenylbut-1-ene (C) 50 mg OH

MM 0053.18 Tamoxifen N-Oxide (A) 100 mg O N O

196 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Tamsulosin Hydrochloride

MM 0938.00 Tamsulosin Hydrochloride O O (D) 100 mg H N S x HCl O NH2 O O MM 0938.02 Imp. A (EP) as Hydrochloride: 5-[(2R)-2- O (A) 100 mg [Bis[2-(2-ethoxyphenoxy)ethyl]amino]- propyl]-2-methoxybenzenesulfonamide O x HCl Hydrochloride O O N S O NH2 O O MM 0938.03 Imp. B (EP): 5-[(2R)-2-Aminopropyl]- O O (A) 100 mg H2N S 2-methoxybenzenesulfonamide NH2

MM 0938.04 Imp. C (EP) as Hydrochloride: 2-Methoxy-5-[(2R)- O O (A) 100 mg H 2-[(2-phenoxyethyl)amino] N S x HCl O NH2 propyl]benzenesulfonamide Hydrochloride O

MM 0938.05 Imp. D (EP) as Hydrochloride: O O (A) 100 mg H 2-Methoxy-5-[(2R)-2-[[2- N S x HCl O NH2 (2-methoxyphenoxy)ethyl]amino]propyl] O benzenesulfonamide Hydrochloride O MM 0938.06 Imp. E (EP): 5-Formyl-2-methoxybenzene- O O (A) 50 mg S Sulfonamide O NH2

O MM 0938.07 Imp. F (EP) as Hydrochloride: 2-(2-Ethoxy- (A) 100 mg NH2 x HCl phenoxy)ethanamine Hydrochloride O O MM 0938.01 Imp. H (EP) as Racemate Hydrochloride: (A) 100 mg H N x HCl (2RS)-N-[2-(2-Ethoxyphenoxy)ethyl]-1- O (4-methoxyphenyl)propan-2-amine O Hydrochloride O MM 0938.09 Imp. I (EP): 1-(2-Bromoethoxy)-2-ethoxybenzene (A) 100 mg Br O O Telmisartan New MM 0939.01 Imp. A (EP): 4-Methyl-6-(1-methyl-1H-benz- (A) 100 mg

imidazol-2-yl)-2-propyl-1H-benzimidazole N N

O O New MM 0939.10 Methyl 4'-(Bromomethyl)biphenyl-2-carboxylate Br (A) 100 mg

Temazepam

MM 0087.00 Temazepam O on request N [Controlled Substance] OH Cl N

MM 0023.01 Imp. A (EP): [5-Chloro-2-(methylamino)- (B) 100 mg NH phenyl]phenylmethanone O (5-Chloro-2-(methylamino)benzophenone) Cl

H O MM 0080.00 Imp. B (EP): Oxazepam N (D) 100 mg [Controlled Substance] OH Cl N

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 197 Pharmaceutical impurities

Code Product Code Unit Tenoxicam

MM 0084.01 Imp. A (EP): Pyridin-2-amine H2N (B) 100 mg N MM 0247.01 Imp. B (EP): Methyl 4-Hydroxy-2-methyl-2H-thieno[2,3-e]1,2-thiazine- O O (A) 100 mg S 3-carboxylate 1,1-Dioxide N O S OH O

MM 0247.04 Imp. C (EP): N-Methylthiophene-2-carboxamide H (A) 100 mg N S O

MM 0247.06 Imp. E (EP): 2-Methylthieno[2,3-d]isothiazol-3(2H)-one 1,1-Dioxide O O (A) 100 mg S N S O New MM 0247.10 2-(Methoxycarbonyl)-3-thiophenesulfonyl Chloride O O (A) 100 mg S Cl O S O Terazosin Hydrochloride Dihydrate MM 0843.00 Terazosin Hydrochloride Dihydrate O (A) 100 mg N O N N O x HCl x 2 H2O N O

NH2 MM 0085.04 Imp. A (EP): 2-Chloro-6,7- O N Cl (A) 100 mg dimethoxyquinazolin-4-amine N O

NH2 MM 0843.02 Imp. B (EP): 1-(4-Hydroxy- O (A) 100 mg 6,7-dimethoxyquinazolin-2-yl)-4-[[(2RS)- N tetrahydrofuran-2-yl]carbonyl]piperazine O N N O

N O OH

MM 0085.01 Imp. C (EP): 6,7-Dimethoxy- NH (A) 100 mg 2-(piperazin-1-yl)quinazolin-4-amine O N N

N O

NH2 MM 0843.04 Imp. D (EP) as Hydrochloride: 1-(4-Amino-6,7- O (A) 100 mg dimethoxyquinazolin-2-yl)-4-formylpiperazine N Hydrochloride O N N x HCl

N O

NH2

MM 0085.03 Imp. E (EP): 2,2'-(Piperazine-1,4-diyl)bis(6,7- NH2 (D) 100 mg O dimethoxyquinazolin-4-amine) N

N N O O N N

N O

NH2 MM 0085.00 Imp. K (EP) as Hydrochloride: O (A) 100 mg Prazosin Hydrochloride N O N N O x HCl N O

NH2 MM 0085.02 Imp. L (EP): 1-(Furan-2-ylcarbonyl)piperazine O (A) 100 mg N HN O MM 0085.05 Imp. M (EP): 1,4-Bis(furan-2- O (A) 100 mg ylcarbonyl)piperazine O N N O

198 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0843.15 Imp. N (EP): 1-[[(2RS)-Tetrahydrofuran-2-yl]carbonyl]piperazine O (A) 100 mg N HN O MM 0843.16 Imp. O (EP): 1,4-Bis[(tetrahydrofuran-2-yl)carbonyl]piperazine O (A) 100 mg O N N O

O Terbinafine Hydrochloride MM 0696.00 Terbinafine Hydrochloride (A) 100 mg

N x HCl

MM 0696.02 Imp. A (EP) as Hydrochloride: N-Methyl-C-(naphthalen- (A) 100 mg x HCl 1-yl)methanamine Hydrochloride (Secundary Amine NH Hydrochloride)

MM 0696.03 Imp. B (EP) as Hydrochloride: (2Z)-N,6,6-Trimethyl- (D) 100 mg N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine x HCl Hydrochloride (cis-Terbinafine Hydrochloride) N

MM 0696.04 Imp. C (EP) as Hydrochloride: (2E)- N (D) 100 mg x HCl N,6,6-Trimethyl-N-(naphthalen-2-ylmethyl)hept- 2-en-4-yn-1-amine Hydrochloride (trans-iso- Terbinafine Hydrochloride) MM 0696.05 Imp. D (EP) as Hydrochloride: (2E)-N,6,6-Trimethyl- (D) 100 mg

N-[(4-methylnaphthalen-1-yl)methyl]-hept-2-en-4-yn- N x HCl 1-amine Hydrochloride (4-Methylterbinafine Hydrochloride MM 0696.07 N-Demethylterbinafine Hydrochloride (D) 50 mg

N x HCl H

New MM 0696.10 Imp. F (EP) as Hydrochloride: (2Z)- (D) 50 mg N,6,6-Trimethyl-N-(naphthalen-2-ylmethyl)hept- x HCl 2-en-4-yn-1-amine Hydrochloride (cis-Iso- N terbinafine Hydrochloride) Terbutaline Sulphate MM 0708.01 Imp. A (EP): 3,5-Dihydroxybenzoic Acid (h-Resorcylic Acid) O (B) 100 mg HO OH

OH MM 0708.03 Imp. B (EP) as Hemisulphate: (4RS)- OH (D) 100 mg 2-(1,1-Dimethylethyl)-1,2,3,4-tetrahydroisoquinoline- HO x 1/2 H2SO4 4,6,8-triol Hemisulphate N

OH Terfenadine MM 0055.00 Terfenadine (A) 500 mg

N OH

MM 0055.04 Imp. A (EP): 1-[4-(1,1-Dimethylethyl)phenyl]- (A) 100 mg 4-[4-(hydroxydiphenylmethyl) piperidin-1-yl]butan- 1-one (Terfenadone) N O

MM 0055.07 Imp. B (EP): (1RS)-1-[4-(1,1-Dimethylethyl)phenyl]- (A) 100 mg 4-[4- (diphenylmethyl)piperidin-1-yl]butan-1-ol N OH

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 199 Pharmaceutical impurities

Code Product Code Unit MM 0055.12 Imp. E (EP) as Hydrochloride: 1-[(4RS)- (A) 100 mg 4-[4-(1,1-Dimethylethyl)phenyl]- 4-hydroxybutyl]piperidine-4-carboxylic Acid N Hydrochloride HO OH

O x HCl MM 0055.09 Imp. G (EP): [1-[4-[4-(1,1-Dimethylethyl)- (A) 100 mg phenyl]but-3-enyl]piperidin-4- yl]diphenylmethanol N

MM 0055.10 Imp. H (EP): (A) 100 mg [1-[4-[4-(1,1-Dimethylethyl)phenyl]butyl]piperidin- 4-yl]diphenylmethanol N

MM 0055.02 Imp. I (EP): Diphenyl(piperidin-4-yl)methanol (Azacyclonol) NH (B) 100 mg

MM 0055.03 Imp. J (EP): Ethyl 1-[(4RS)- (A) 100 mg 4-[4-(1,1-Dimethylethyl)phenyl]-4-hydroxybutyl]- piperidine-4-carboxylate N O OH

O Testosterone MM 0323.00 Testosterone OH (A) 500 mg

O MM 0323.01 Imp. A (EP): Androst-4-ene-3,17-dione (Androstenedione) O (A) 100 mg

O MM 0323.02 Imp. B (EP): 3-Ethoxyandrosta-3,5-dien-17-one (Androstenedione O (A) 100 mg Ethylenolether)

O MM 0323.03 Imp. C (EP): 17h-Hydroxyandrost-4-en-3-one (Epitestosterone) OH (A) 100 mg

O MM 0323.04 Imp. D (EP): Androst-4-ene-3i,17i-diol OH (A) 100 mg (94-Androstenediol)

HO MM 0323.05 Imp. E (EP): 3-Oxoandrost-4-en-17i-yl Acetate O (A) 100 mg (Testosterone Acetate) O

O MM 0565.00 Imp. F (EP): 17i-Hydroxy-5h-androstan-3-one OH (A) 250 mg (Androstanolone, Stanolone)

O H MM 0323.07 Imp. G (EP): Androsta-1,4-diene-3,17-dione (Androstadienedione) O (A) 100 mg

200 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0864.00 Imp. H (EP): 17i-Hydroxyandrosta-1,4-dien-3-one (Boldenone) OH (A) 100 mg

O MM 0323.12 Imp. I (EP): 17i-Hydroxyandrosta-4,6-dien-3-one OH (A) 100 mg (96-testosterone)

O MM 0323.13 Imp. J (EP): 3-Methoxyandrosta-3,5-dien- O (A) 100 mg 17-one (Androstenedione Methylenolether)

O Testosterone Benzoate MM 0493.00 Testosterone Benzoate O (D) 250 mg O

O MM 0323.00 Testosterone OH (A) 500 mg

O MM 0278.01 Benzoic Acid O (B) 100 mg OH

Testosterone Enantate MM 1119.00 Testosterone Enantate O (A) 100 mg O

O MM 0863.08 Imp. B (EP): 3-Oxoandrost-4-en-17i-yl Hexanoate O (A) 100 mg (Testosterone Caproate) O

O MM 0323.00 Imp. D (EP): 17i-Hydroxyandrost-4-en-3-one (Testosterone) OH (A) 500 mg

O Testosterone Isocaproate MM 0863.00 Testosterone Isocaproate O (A) 100 mg O

O MM 0323.00 Imp. A (EP): Testosterone OH (A) 500 mg

O MM 0323.05 Imp. B (EP): 3-Oxoandrost-4-en-17i-yl Acetate O (A) 100 mg (Testosterone Acetate) O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 201 Pharmaceutical impurities

Code Product Code Unit MM 0897.00 Imp. C (EP): Testosterone Propionate O (A) 100 mg O

O MM 0863.07 Imp. D (EP): 3-Oxoandrost-4-en-17i-yl 2-Methylpropanoate O (A) 100 mg (Testosterone Isobutyrate) O

O MM 0863.08 Imp. E (EP): 3-Oxoandrost-4-en-17i-yl O (A) 100 mg Hexanoate (Testosterone Caproate) O

O MM 1119.00 Imp. F (EP): Testosterone Enantate O (A) 100 mg O

O MM 0863.09 Imp. G (EP): 3-Oxoandrost-4-en-17h-yl O (A) 100 mg 4-Methylpentanoate O (Epitestosterone Isocaproate)

O Testosterone Propionate MM 0897.00 Testosterone Propionate O (A) 100 mg O

O MM 0323.05 Imp. A (EP): 3-Oxoandrost-4-en-17i-yl Acetate O (A) 100 mg (Testosterone Acetate) O

O MM 0863.07 Imp. B (EP): 3-Oxoandrost-4-en-17i-yl 2-Methyl- O (A) 100 mg propanoate (Testosterone Isobutyrate) O

O MM 0323.00 Imp. C (EP): Testosterone OH (A) 500 mg

O MM 0897.04 Imp. D (EP): 3-Oxoandrosta-1,4-dien-17i-yl Propanoate O (C) 50 mg O

O MM 0897.05 Imp. E (EP): 3-Oxoandrosta-4,6-dien-17i-yl O (A) 100 mg Propanoate O

202 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Tetracaine Hydrochloride MM 0504.00 Tetracaine Hydrochloride O (A) 500 mg N O x HCl N H MM 0094.03 Imp. A (EP): 4-Aminobenzoic Acid O (B) 100 mg OH

H2N MM 0504.01 Imp. B (EP): 4-(Butylamino)benzoic Acid O (A) 100 mg OH

N H MM 0504.04 Imp. C (EP): Methyl 4-(Butylamino)benzoate O (A) 100 mg O

N H O MM 0504.02 Tetracaine N-Oxide O (A) 100 mg N O

N H Tetracycline Hydrochloride

OH O OH O O MM 0452.00 Tetracycline Hydrochloride OH (A) 500 mg

NH2 H H x HCl OH HO N Tetramisole Hydrochloride MM 0703.00 Tetramisole Hydrochloride N S (A) 500 mg x HCl N Tetrazepam

MM 0091.00 Tetrazepam O (A) 100 mg N [Controlled Substance] Cl N

H O MM 0091.06 Imp. B (EP): 7-Chloro-5-cyclohexyl-1,3-dihydro-2H- N (A) 100 mg 1,4-benzodiazepin-2-one Cl N

H O MM 0091.03 Imp. E (EP): 7-Chloro-5-(cyclohex-1-enyl)-1,3- N (A) 100 mg dihydro-2H-1,4-benzodiazepin-2-one (Nortetrazepam) Cl N

MM 0091.07 Imp. C (EP): 7-Chloro-5-cyclohexyl-1-methyl- O (A) 100 mg N 1,3-dihydro-2H-1,4-benzodiazepin-2-one

Cl N

MM 0091.04 6-Chloro-2-methyl-4-oxo-4H-3,1-benzoxazine N (A) 100 mg O Cl O

O MM 0091.52 2-Bromo-4'-chloro-2'-(cyclohexylcarbonyl)acetanilide Br on request NH

O Cl

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 203 Pharmaceutical impurities

Code Product Code Unit Tetryzoline Hydrochloride MM 0088.00 Tetryzoline Hydrochloride (A) 100 mg HN N x HCl

MM 0088.03 Imp. A (EP): (1RS)-1,2,3,4-Tetrahydronaphthalene-1-carbonitrile N (A) 100 mg (h-Cyanotetraline)

MM 0088.02 1,2,3,4-Tetrahydro-1-naphthalenecarboxylic Acid OOH (A) 100 mg

MM 0088.04 Methyl 1,2,3,4-Tetrahydro-1-naphthalenecarboxylate OO (A) 100 mg

H MM 0088.05 N-(2-Aminoethyl)-1,2,3,4-tetrahydro- O N (A) 100 mg naphthalene-1-yl-carboxamide Hydrochloride NH2 x HCl ((1,2,3,4-Tetrahydro-1-naphthyl)formyl- ethylenediamine Hydrochloride)

MM 0088.06 2-(1,2,3,4-Tetrahydro-1-naphthalenyl)-1H-imidazole Hydrochloride HN N (A) 100 mg

x HCl

Thalidomide MM 0940.00 Thalidomide O (A) 100 mg

N O NH O O Theobromine MM 0577.00 Theobromine O (A) 500 mg HN N

O N N

Theophylline

O MM 0176.00 Theophylline H (A) 500 mg N N

O N N

MM 0494.00 Imp. A (EP): Caffeine O (A) 500 mg N N

O N N

MM 0176.03 O (A) 100 mg Imp. B (EP): 3-Methyl-3,7-dihydro-1H-purine-2,6-dione H (3-Methylxanthine) HN N

O N N

O MM 0176.02 Imp. C (EP): N-(6-Amino-1,3-dimethyl-2,4- H (A) 100 mg N dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)formamide N O O N NH2

MM 0176.01 Imp. D (EP): N-Methyl-5-(methylamino)-1H-imidazole- O (A) 100 mg N N 4-carboxamide (Theophyllidine) H HN N H

OH MM 0603.00 Imp. F (EP): Etofylline O (A) 500 mg N N

O N N

MM 0176.04 1-Methylxanthine O on request N N

O N N H H

204 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0176.05 7-Methylxanthine O (A) 100 mg HN N

O N N H Theophylline-Ethylenediamine MM 0494.00 Imp. A (EP): Caffeine O (A) 500 mg N N

O N N

MM 0176.03 Imp. B (EP): 3-Methyl-3,7-dihydro-1H-purine-2,6-dione O (A) 100 mg H (3-Methylxanthine) HN N

O N N

O MM 0176.02 Imp. C (EP): N-(6-Amino-1,3-dimethyl-2,4- H (A) 100 mg N dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)form- N amide O O N NH2

MM 0176.01 Imp. D (EP): N-Methyl-5-(methylamino)-1H- O (A) 100 mg imidazole-4-carboxamide (Theophyllidine) N N H HN N H

OH MM 0603.00 Imp. F (EP): Etofylline O (A) 500 mg

N N

O N N

MM 0577.00 Imp. G (EP): Theobromine O (A) 500 mg N HN

O N N

Thiamazole MM 0889.00 Thiamazole S (A) 500 mg N NH

MM 0889.02 Imp. B (EP): 1-Methyl-1H-imidazole N (B) 100 mg N MM 0889.03 Imp. C (EP): 1-Methyl-2-(methylsulphanyl)-1H-imidazole S (A) 100 mg N N

MM 0889.04 Imp. C (EP) as Hydrochloride: 1-Methyl-2-(methylsulphanyl)-1H- S (A) 100 mg N x HCl imidazole Hydrochloride N Thiamine Hydrochloride

N MM 0049.00 Thiamine Hydrochloride (Vitamin B1) S (A) 500 mg N+ N x HCl HO - Cl NH2

MM 0049.05 Imp. E (EP): 3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]- S S N (A) 100 mg 5-(2-hydroxyethyl)-4-methylthiazol-2(3H)-thione N N HO (Thioxothiamine) NH2

MM 0049.02 5-(2-Hydroxyethyl)-4-methylthiazole N (A) 100 mg

S OH

MM 0049.04 4-Amino-5-hydroxymethyl-2-methylpyrimidine Hydrochloride N OH (A) 100 mg x HCl

NNH2 Thiamphenicol MM 0737.00 Thiamphenicol O O (A) 500 mg OH S O Cl N H Cl OH Thioctic Acid MM 0127.00 Thioctic Acid O (A) 500 mg OH SS

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 205 Pharmaceutical impurities

Code Product Code Unit Thioridazine Hydrochloride MM 0116.05 2-Methylthiophenothiazine (A) 100 mg

NH S

S Tiabendazole MM 0602.00 Tiabendazole H (A) 500 mg N S N N

MM 0602.01 Imp. A (EP): Benzene-1,2-diamine NH2 (C) 100 mg

NH2 Tiamulin Hydrogen Fumarate

MM 0394.00 Tiamulin Hydrogen Fumarate O (A) 100 mg N O O S OH x O H HO

O HO MM 0460.10 Fumaric Acid O (B) 100 mg HO OH O MM 0394.04 Imp. A (EP): (3aS,4R,5S,6S,8R,9R,9aR,10R)- (A) 100 mg HO O 6-Ethenyl-5,8-dihydroxy-4,6,9,10-tetramethyl- octahydro-3a,9-propano-3aH-cyclopentacyclo- H octen-1(4H)-one (Mutilin) HO New MM 0394.06 Imp. C (EP) as Dihydrochloride: 2,2'-(Disulfane- (A) 50 mg N S 1,2-diyl)bis(N,N-diethylethanamine) S N Dihydrochloride x 2 HCl MM 0394.18 Imp. P (EP): (3aS,4R,5S,6S,8R,9R,9aR,10R)-6- O O (A) 50 mg S O O Ethenyl-5-hydroxy-4,6,9,10-tetramethyl-1-oxo- O decahydro-3a,9-propano-3aH-cyclopentacyclo- O H octen-8-yl [(Phenylsulphonyl)oxy]acetate HO Tiapride Hydrochloride New MM 0073.01 Imp. C (EP): N,N-Diethylethane-1,2-diamine (B) 100 mg N H2N Ticlopidine Hydrochloride MM 0150.00 Ticlopidine Hydrochloride S (A) 500 mg N x HCl

Cl MM 0150.12 Imp. A (EP): Thieno[3,2-c]pyridine S (A) 100 mg N

MM 0150.06 Imp. B (EP): 6,7-Dihydrothieno[3,2-c]pyridin-4(5H)-one S (A) 100 mg HN

O MM 0150.01 Imp. C (EP) as Hydrochloride: (2-Chloro- (A) 100 mg phenyl)methanamine Hydrochloride NH2 x HCl

Cl MM 0150.07 S (A) 100 mg Imp. D (EP) as Hydrochloride: 5-Benzyl- x HCl 4,5,6,7-tetrahydrothieno[3,2-c]pyridine Hydrochloride N MM 0150.13 Imp. E (EP) as Chloride: 5-(2-Chlorobenzyl)- S (A) 50 mg thieno[3,2-c]pyridinium Chloride N+ Cl- Cl New MM 0150.14 Imp. F (EP) as Hydrochloride: 6-(2-Chloro- (A) 50 mg N x HCl benzyl)-4,5,6,7-tetrahydrothieno[2,3-c]- S pyridine Hydrochloride Cl MM 0150.08 Imp. G (EP) as Hydrochloride: 5-(3-Chlorobenzyl)- S (A) 100 mg x HCl N 4,5,6,7-tetrahydrothieno[3,2-c]pyridine Hydrochloride Cl

MM 0150.09 Imp. H (EP) as Hydrochloride: 5-(4-Chlorobenzyl)- Cl S (C) 50 mg x HCl 4,5,6,7-tetrahydrothieno[3,2-c]pyridine Hydrochloride N

206 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0150.11 Imp. I (EP) as Hydrochloride: N-(2-Chlorobenzyl)- S (A) 100 mg 2-(thiophen-2-yl)ethanamine Hydrochloride NH x HCl

MM 0150.10 Imp. J (EP) as Dihydrochloride: N,N'- N (A) 100 mg H NH x 2 HCl Bis(2-chlorobenzyl)ethane-1,2-diamine Dihydrochloride Cl Cl MM 0150.15 Imp. L (EP): 5-(2-Chlorobenzyl)-6,7-dihydrothieno[3,2-c]pyridin- S (A) 50 mg 4(5H)-one N Cl O MM 0150.04 5-(2-Chlorobenzoyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine S (A) 100 mg N

Cl O Tilidine Hydrochloride Hemihydrate

MM 0134.00 Tilidine Hydrochloride Hemihydrate N (A) 100 mg [Controlled Substance] x HCl x 1/2 H2O

O O and enantiomer

MM 0134.01 Imp. A (EP): Ethyl (1RS,2RS)-2-(Dimethylamino)-1-phenylcyclohex- N (D) 100 mg 3-enecarboxylate (cis-Tilidine) [Controlled Substance]

O O and enantiomer MM 0134.03 Imp. D (EP) as Hydrochloride: Ethyl (2RS)-3-Dimethylamino- (A) 100 mg N 2-phenylpropanoate Hydrochloride x HCl O

MM 0134.05 Tilidine N (A) 100 mg [Controlled Substance]

O O and enantiomer Timolol Maleate

OH O MM 0440.00 Timolol Maleate H (A) 250 mg N O N OH S x OH N N O O MM 0440.04 Imp. D (Pharmeuropa): 4-Morpholin-4-yl- N OH (A) 100 mg 1,2,5-thiadiazol-3-ol S N N O MM 0440.03 N-Benzyl-tert-butylamine (B) 100 mg

MM 0440.05 3-Hydroxy-4-morpholino-1,2,5-thiadiazole 1-Oxide N OH (A) 100 mg O S N N O MM 0440.02 (S)-Isotimolol (A) 100 mg HO N H N O S N N O Tinidazole

MM 0012.02 Imp. A (EP): 2-Methyl-5-nitro-1H-imidazole O2N (B) 100 mg (2-Methyl-4-nitroimidazole) NH N

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 207 Custom synthesis of impurities

This catalogue features approx. 2500 reference substances for impurities and APIs from which they derive. If you are not able to find the substance of your interest, you might want to consider a custom synthesis of complex chemical molecules in multigram quantities. As such, the main features of our company are:

• Strong organisation of a flexibility and multi-skilled workforce • Excellently equipped operations for synthesis and measurement • A highly experienced research group with knowledge of a diverse range of chemistries for synthetic design, and a strong expertise in pharmaceutical science for consultancy and molecular prediction • In-depth skills in practical synthetic chemistry that includes a well developed background in the production of natural products and molecules with multiple chiral centres

For further information or to receive any one of our catalogues please contact your local office or visit our website.

www.lgcstandards.com Pharmaceutical impurities

Code Product Code Unit Tioconazole MM 0281.01 Imp. D (EP): (1RS)-1-(2,4-Dichlorophenyl)-2- Cl (A) 100 mg (1H-imidazol-1-yl)ethanol

HO N

N Tiotropium Bromide Monohydrate New MM 1293.05 Imp. E (EP): Methyl 2-Hydroxy-2,2-dithiophen-2-ylacetate S O (A) 100 mg O S OH

MM 1293.06 Imp. F (EP): Dithiophen-2-ylmethanone S (A) 100 mg O

Tizanidine Hydrochloride New MM 0887.04 N-Acetyltizanidine N (A) 50 mg S Cl N N NH

O New MM 0887.05 1-Acetylimidazolidine-2-thione O (A) 50 mg

N S N H Tolazoline Hydrochloride MM 0585.00 Tolazoline Hydrochloride N (A) 500 mg x HCl HN Tolbutamide MM 0325.01 Imp. A (Pharmeuropa): (4-Methylphenyl)- O O (C) 100 mg S sulphonamide (Toluenesulphonamide; 4-Methyl- NH2 benzenesulphonamide) Tolnaftate MM 0731.01 Imp. A (EP): Naphthalen-2-ol (i-Naphthol) (A) 100 mg

New MM 0731.03 S (A) 50 mg

O-Naphthalen-2-yl Chlorothioformate Cl O MM 0731.04 Imp. D (EP): N,3-Dimethylaniline (N-Methyl-m-toluidine) (A) 100 mg

Tolmetin Sodium Dihydrate MM 0571.00 Tolmetin Sodium Dihydrate O on request N ONa

x 2 H2O O Torasemide, Anhydrous New MM 1283.03 Imp. C (EP): 1-Ethyl-3-[[4-[(3-methylphenyl)amino]- O O O (A) 50 mg S N N N pyridin-3-yl]sulfonyl]urea H H NH

New MM 1283.04 Imp. D (EP): 1-Butyl-3-[[4-[(3-methylphenyl)amino]- O O O (A) 50 mg S N N N pyridin-3-yl]sulfonyl]urea H H NH

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 209 Pharmaceutical impurities

Code Product Code Unit Tramadol Hydrochloride

MM 0007.00 Tramadol Hydrochloride O (A) 500 mg OH x HCl N

and enantiomer

MM 0007.01 Imp. A (EP) as Hydrochloride: (1RS,2SR)- O (A) 100 mg OH 2-[(Dimethylamino)methyl]-1-(3-methoxyphenyl)- x HCl cyclohexanol Hydrochloride N

and enantiomer MM 0007.03 Imp. B (EP) as Hydrochloride: O (A) 100 mg [2-(3-Methoxyphenyl)cyclohex-1-enyl]-N,N- x HCl dimethylmethanamine Hydrochloride N

MM 0007.04 Imp. C (EP) as Hydrochloride: (1RS)-[2-(3-Methoxy- O (A) 100 mg phenyl)-cyclohex-2-enyl]-N,N-dimethylmethanamine x HCl Hydrochloride N

MM 0007.06 Imp. D (EP) as Hydrochloride: (1RS,2RS)-2- HO (A) 100 mg OH [(Dimethylamino)methyl]-1-(3-hydroxyphenyl)- x HCl cyclohexanol Hydrochloride N

and enantiomer MM 0007.02 Imp. E (EP) as Hydrochloride: (2RS)- O (A) 100 mg 2-[(Dimethylamino)methyl]- N x HCl cyclohexanone Hydrochloride MM 0007.05 3-Bromoanisole OBr (B) 100 mg

MM 0007.07 N-Desmethyltramadol Hydrochloride O (A) 100 mg OH x HCl

and enantiomer

MM 0007.08 N,O-Didesmethyltramadol Hydrochloride HO (A) 100 mg OH x HCl N H

and enantiomer MM 0007.09 3-Methoxyphenol OOH (B) 100 mg

MM 0007.11 Tramadol N-Oxide O (A) 100 mg OH

N O

and enantiomer MM 0007.50 [2-(3-Hydroxyphenyl)cyclohex-1-enyl]-N,N-dimethylmethanamine HO (A) 100 mg Hydrochloride x HCl N

Tranexamic Acid MM 0330.00 Tranexamic Acid O (A) 500 mg OH

H2N

MM 0330.04 Imp. D (EP): 4-Aminomethylbenzoic Acid O (B) 100 mg OH

H2N Trazodone Hydrochloride MM 0421.00 Trazodone Hydrochloride (A) 100 mg

N N Cl N x HCl N N

210 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0421.13 Imp. A (BP) as Hydrochloride: (A) 50 mg

4-(3-Chloro-phenyl)-1-[3-(3-oxo-2,3- N N Cl N x HCl dihydro-1,2,4-triazolo[4,3-a] N N pyridin-2-yl)propyl]piperazine O O N1-oxide Hydrochloride (Trazodone N-Oxide Hydrochloride) New MM 0421.02 Imp. B (BP): 2-[3-(4-Phenylpiperazin-1-yl) (A) 50 mg

propyl]-1,2,4-triazolo[4,3-a]pyridin-3 N N N (2H)-one N N

O MM 0421.03 Imp. C (BP) as Dihydrochloride: Cl on request 2-[3-[4-(4-Chlorophenyl)piperazin-1-yl]propyl]- N N x 2 HCl 1,2,4-triazolo[4,3-a]pyridin-3(2H)-one N Dihydrochloride N N O New MM 0421.04 Imp. D (BP) as Hydrochloride: 2-3- (A) 50 mg [4-(3-Bromo-phenyl)piperazin-1-yl] N N Br x HCl N propyl-1,2,4-triazolo[4,3-a]-pyridin- N N 3(2H)-one Hydrochloride O MM 0421.06 Imp. F (BP) as Hydrochloride: 1-(3-Chlorophenyl)- (A) 100 mg 4-(3-chloropropyl)piperazine Hydrochloride N Cl x HCl Cl N

New MM 0421.07 Imp. G (BP) as Hydrochloride: 3-[4-(3- (D) 50 mg x HCl Chloro-phenyl)piperazin-1-yl]propyl N Cl Isobutyl Ether Hydrochloride O N MM 0421.08 Imp. H (BP) as Dihydrochloride: 1,3-Bis-[4-(3-chloro- (A) 100 mg phenyl)piperazin-1-yl]propane Dihydrochloride Cl N N Cl N N x 2 HCl MM 0421.10 3-[4-(3-Chlorophenyl)piperazin-1-yl]propanol (A) 100 mg

N Cl HO N MM 0421.11 1,2,4-Triazolo-[4,3-a]pyridine-3(2H)-one (A) 100 mg N N NH

O MM 0421.12 1,4-Bis-3-chlorophenylpiperazine on request

N Cl Cl N

Triacetin MM 0966.00 Triacetin O (A) 500 mg O O O

O O Triamcinolone

OH MM 0198.01 Triamcinolone O (A) 250 mg

HO OH OH

F O MM 0198.02 Imp. A (EP): 9-Fluoro-11i,17-dihydroxy-3,20-dioxopregna- O (A) 100 mg O 1,4-diene-16h,21-diyl Diacetate (Triamcinolone O 16,21-Diacetate) HO OH O

F O O OH MM 0508.03 Imp. C (EP): 9-Fluoro-11i,16h,17,21-tetrahydroxypregn- O on request 4-ene-3,20-dione (Pretriamcinolone) HO OH OH

F O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 211 Pharmaceutical impurities

Code Product Code Unit Triamcinolone Acetonide

OH MM 0198.00 Triamcinolone Acetonide O (A) 250 mg

HO O O

F O OH MM 0198.01 Imp. A (EP): Triamcinolone O (A) 250 mg

HO OH OH

F O MM 0198.02 Triamcinolone 16,21-Diacetate O (A) 100 mg O O

HO OH O O F O OH MM 0198.05 Triamcinolone Acetonide 21-Aldehyde Hydrate O (A) 100 mg

OH HO O O

F O Triamcinolone Hexacetonide MM 0306.00 Triamcinolone Hexacetonide O (A) 100 mg O O

HO O O

F O OH MM 0198.00 Imp. A (EP): Triamcinolone Acetonide O (A) 250 mg

HO O O

F O OH MM 0198.01 Triamcinolone O (A) 250 mg

HO OH OH

F O Triamterene

MM 0269.00 Triamterene H2N N N NH2 (A) 500 mg N N

NH2

MM 0269.02 Imp. A (EP): 5-Nitrosopyrimidine-2,4,6-triamine NH2 (B) 100 mg NO (Nitrosotriaminopyrimidine) N

H2N N NH2

MM 0269.01 Sodium Hydroxytriamterene Sulphate H2N N N NH2 (B) 10 mg N O O N S NH NaO O 2 Tributyl Acetylcitrate

O O MM 0499.00 Tributyl Acetylcitrate O on request O O O O O O O MM 0499.01 Imp. A (EP): Tributyl 2-Hydroxypropane- O (C) 100 mg 1,2,3-tricarboxylate (Tributyl Citrate) HO O

O O

212 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit O O MM 0499.02 Imp. B (EP) (E-Isomer): Tributyl (E)-Propene- O (A) 100 mg 1,2,3-tricarboxylate (Tributyl (E)-Aconitate) O

O O Triclabendazole

Cl MM 0313.00 Triclabendazole H (D) 100 mg Cl O N S Cl N Triclosan MM 0610.00 Triclosan Cl OH (A) 500 mg O

Cl Cl Trihexyphenidyl Hydrochloride MM 0237.00 Trihexyphenidyl Hydrochloride (A) 500 mg OH x HCl N

MM 0237.03 Imp. A (EP) as Hydrochloride: 1-Phenyl-3- O (A) 100 mg (piperidin-1-yl)propan-1-one Hydrochloride N x HCl

MM 0237.01 Acetophenone O (B) 100 mg

MM 0237.04 Trihexyphenidyl N-Oxide (C) 50 mg

OH O N

Trimebutine MM 0417.00 Trimebutine O (A) 500 mg O O N O O

MM 0417.05 Trimebutine Maleate O O (A) 500 mg O O OH N x OH O

O O

MM 0417.01 Imp. A (Pharmeuropa) as Hydrochloride: (2RS)- OH (A) 100 mg 2-(Dimethylamino)-2-phenylbutanol Hydrochloride N x HCl

MM 0093.13 Imp. B (Pharmeuropa): 3,4,5-Trimethoxybenzoic Acid O (B) 100 mg O

OH O O MM 0093.11 Imp. C (Pharmeuropa): Methyl 3,4,5-Trimethoxybenzoate O (A) 100 mg O O

O O

O MM 0417.07 Imp. E (Pharmeuropa) as Hydrochloride: H (A) 50 mg O N (2RS)-2-(Methylamino)-2-phenylbutyl- O x HCl 3,4,5-Trimethoxybenzoate Hydrochloride O (N-Desmethyltrimebutine Hydrochloride) O

HO MM 0417.10 1-Dimethylaminomethyl-1-phenyl-1-propanol Hydrochloride (alpha- N (A) 100 mg [(Dimethylamino)methyl]-alpha-ethyl-benzenemethanol x HCl Hydrochloride)

MM 0417.11 Imp. D (Pharmeuropa): (1RS)-1-[(Dimethylamino)-methyl]- N (A) 50 mg 1-phenylpropyl 3,4,5-Trimethoxybenzoate O O O

O O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 213 Pharmaceutical impurities

Code Product Code Unit Trimeprazine Tartrate MM 0958.00 Trimeprazine Tartrate (A) 500 mg N OH O x HO N OH O OH S 2 MM 0957.00 Trimeprazine Sulphone (Oxomemazine) (A) 100 mg N

S O O MM 0958.02 Trimeprazine Sulphoxide Hydrochloride (A) 100 mg N

N x HCl

S O

MM 0958.04 Trimeprazine Sulphone N-Oxide Hydrochloride O (A) 100 mg N (Oxomemazine N-Oxide Hydrochloride) N x HCl

S O O Trimetazidine Dihydrochloride

MM 0539.00 Trimetazidine Dihydrochloride O (A) 100 mg O N x 2 HCl HN O MM 0539.01 Imp. A (EP) as Dihydrochloride: 1-(3,4,5- (A) 100 mg O Trimethoxybenzyl)piperazine Dihydrochloride N x 2 HCl HN O O

MM 0539.02 Imp. B (EP): 1,4-Bis(2,3,4-trimethoxy- O (A) 100 mg O O benzyl)piperazine N N O O O

MM 0539.03 Imp. C (EP): 2,3,4-Trimethoxybenzaldehyde O (B) 100 mg O O

MM 0539.04 Imp. D (EP): (2,3,4-Trimethoxyphenyl)methanol O (A) 100 mg O HO

MM 0539.05 Imp. E (EP) as Dihydrochloride: 1-(2,4,5- O (A) 100 mg

Trimethoxybenzyl)piperazine Dihydrochloride N x 2 HCl HN O O

MM 0539.06 Imp. F (EP) as Dihydrochloride: 1-(2,4,6-Tri- O (A) 100 mg methoxybenzyl)piperazine Dihydrochloride N x 2 HCl HN O O

MM 0539.07 Imp. G (EP) as Hexahydrate: Piperazine Hexahydrate NH (B) 100 mg x 6 H2O HN

MM 0539.09 Imp. H (EP): Ethyl 4-(2,3,4-Trimethoxybenzyl)- O (A) 100 mg O piperazine-1-carboxylate N O N O O

MM 0539.10 Imp. I (EP) as Dihydrochloride: 1-Methyl-4- O (A) 100 mg O x 2 HCl (2,3,4-trimethoxybenzyl)piperazine N Dihydrochloride (N-Methyltrimetazidine N Dihydrochloride) O

MM 0539.08 1-Formyl-4-(2,3,4-trimethoxybenzyl)piperazine O (A) 100 mg O Hydrochloride N x HCl O N O

214 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Trimethoprim

MM 0093.00 Trimethoprim O (A) 500 mg O NNH2 N O

NH2 2- MM 0093.06 Imp. A (EP): N Methyl-5-(3,4,5-trimethoxybenzyl)pyrimidine- O (A) 100 mg 2,4-diamine O NNH N O

NH2

MM 0093.01 Imp. B (EP): (2,4-Diaminopyrimidin-5-yl)-(3,4,5-trimethoxy- O (A) 100 mg phenyl)methanone O NNH2 N O

O NH2

MM 0093.08 Imp. C (EP): (RS)-(2,4-Diaminopyrimidin-5-yl)(3,4,5-trimethoxy- O (A) 100 mg phenyl)methanol O NNH2 N O

OH NH2

MM 0093.04 Imp. D (EP): 2-Amino-5-(3,4,5-trimethoxybenzyl)pyrimidin-4-ol O (A) 100 mg O NNH2 N O OH

MM 0093.03 Imp. E (EP): 4-Amino-5-(3,4,5-trimethoxybenzyl)pyrimidin-2-ol O (A) 100 mg O NOH

N O

NH2

MM 0093.09 Imp. F (EP): 5-(3-Bromo-4,5-dimethoxybenzyl)pyrimidine- O (A) 100 mg 2,4-diamine O NNH2 N Br

NH2

MM 0093.10 Imp. G (EP): 5-(4-Ethoxy-3,5-dimethoxybenzyl)pyrimidine- O (A) 100 mg 2,4-diamine O NNH2 N O

NH2

MM 0093.11 Imp. H (EP): Methyl 3,4,5-Trimethoxybenzoate O (A) 100 mg O

O O O

MM 0093.12 Imp. I (EP): 3-(Phenylamino)-2-(3,4,5-trimethoxy- O (A) 100 mg H benzyl)prop-2-enenitrile (E/Z-mixture) O N

O N

MM 0093.13 Imp. J (EP): 3,4,5-Trimethoxybenzoic Acid O (B) 100 mg O

OH O O

MM 0093.17 Imp. K (EP) as Hydrochloride: Aniline NH2 (B) 100 mg x HCl Hydrochloride

MM 0093.02 5-(3,4,5-Trimethoxybenzyl)pyrimidin-2,4-diol O (B) 10 mg O NOH

N O OH

MM 0093.05 2-Amino-5-(4-hydroxy-3,5-dimethoxybenzyl)pyrimidin-4-ol O (A) 100 mg HO NNH2 N O OH 4- MM 0093.07 N Methyl-5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine O (C) 50 mg O NNH2 N O NH Trimipramine Maleate

MM 0240.00 Trimipramine Maleate O (A) 500 mg

OH N N x OH

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 215 Pharmaceutical impurities

Code Product Code Unit MM 0240.01 Trimipramine (A) 100 mg

N N

MM 0240.04 Imp. A (EP): (2RS)-3-(10,11-Dihydro-5H-dibenzo- (A) 100 mg [b,f]azepin-5-yl)-N,N,2-trimethylpropan-1-amine N N N-oxide (Trimipramine N-Oxide) O

MM 0240.02 Imp. B (EP) as Hydrochloride: (2RS)-3-(10,11- (A) 100 mg Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,2-di- N N methylpropan-1-amine Hydrochloride H x HCl (Desmethyltrimipramine Hydrochloride)

MM 0077.00 Imp. D (EP) as Hydrochloride: Imipramine (A) 500 mg Hydrochloride N N x HCl

MM 0076.06 Imp. F (EP): 10,11-Dihydro-5H-dibenzo[b,f]azepine (Iminodibenzyl) (B) 100 mg

MM 0240.05 Imp. C (EP) as Hydrochloride: (2RS)-3-(5H- (A) 50 mg Dibenzo[b,f]azepin-5-yl)-N,N,2-trimethylpropan- N N 1-amine Hydrochloride x HCl

Tropicamide

MM 0601.00 Tropicamide O (A) 250 mg

N N OH

MM 0601.01 Imp. A (EP): N-(Pyridin-4-ylmethyl)ethanamine HN (A) 100 mg N

MM 0601.03 Imp. C (EP): (2RS)-3-Hydroxy-2-phenylpropanoic Acid O (A) 100 mg

(Tropic Acid) OH

MM 0160.03 Imp. D (Pharmeuropa): Phenylacetic Acid [Drug Precursor] O (B) 100 mg

OH Tropisetron Hydrochloride MM 0763.01 Imp. A (EP): (1R,3r,5S)-8-Methyl-8- H (A) 100 mg azabicyclo[3.2.1]oct-3-ol (Tropine) H N HO

H MM 0763.02 Imp. B (EP): 1H-Indole-3-carboxylic Acid O (A) 100 mg OH HN

Trospium Chloride

MM 0783.09 Imp. A (EP): Hydroxydiphenylacetic Acid O (B) 100 mg

(Benzilic Acid) OH OH

Tryptophan

H MM 0172.00 L-Tryptophan N (A) 500 mg NH2 OH

216 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0172.09 Imp. A (EP): 3,3'-[Ethylidenebis(1H-indole- (D) 100 mg 1,3-diyl)]bis[(2S)-2-aminopropanoic] Acid (1,1'-Ethylidenebistryptophan) N N NH2 HO OH NH2 O O H MM 0172.03 Imp. D (EP): (S)-2-Amino-3-(5-hydroxy-1H-indol-3-yl)propanoic N (A) 100 mg NH Acid (5-Hydroxytryptophan) 2 OH

O HO O MM 0172.13 N-Acetyltryptophan H (A) 100 mg N HN OH

O Tyrosine

HO MM 0634.00 Tyrosine NH2 (A) 100 mg OH

O Valaciclovir Hydrochloride MM 0061.02 Imp. A (Pharmeuropa): 2-Amino-1,9-dihydro-6H-purin-6-one (Guanine) O (B) 100 mg N HN

H N N N 2 H MM 0061.00 Imp. B (Pharmeuropa): 2-Amino-9-[(2-hydroxy- O (A) 500 mg N ethoxy)methyl]-1,9-dihydro-6H-purin-6-one (Aciclovir) HN

N OH H2N N O

MM 0619.07 Imp. G (Pharmeuropa): N,N-Dimethylpyridin-4-amine N (A) 100 mg

N MM 0061.01 Imp. I (Pharmeuropa): 2-[(2-Amino-6-oxo-1,6- O (A) 100 mg N dihydro-9H-purin-9-yl)methoxy]ethyl Acetate HN

N O H2N N O O Valproic Acid MM 0751.00 Valproic Acid O (A) 500 mg OH

MM 0751.11 Sodium Valproate O (A) 500 mg ONa

MM 0751.01 Imp. A (EP): Pentanoic Acid (Valeric Acid) O (C) 100 mg OH MM 0751.02 Imp. B (EP): (2RS)-2-Ethylpentanoic Acid O (A) 100 mg OH

MM 0751.03 Imp. C (EP): (2RS)-2-(1-Methylethyl)pentanoic Acid O (A) 100 mg OH

MM 0751.04 Imp. D (EP): 2,2-Dipropylpentanoic Acid O (A) 100 mg OH

MM 0751.05 Imp. E (EP): Pentanamide (Valeramide) O (A) 100 mg

NH2 MM 0751.06 Imp. F (EP): 2-Propylpentanamide O (A) 100 mg

NH2

MM 0751.07 Imp. G (EP): 2,2-Dipropylpentanamide O (A) 100 mg

NH2

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 217 Pharmaceutical impurities

Code Product Code Unit MM 0751.08 Imp. H (EP): Pentanenitrile (Valeronitrile) N (C) 100 mg MM 0751.09 Imp. I (EP): 2-Propylpentanenitrile N (A) 100 mg

MM 0751.10 Imp. J (EP): 2,2-Dipropylpentanenitrile N (A) 100 mg

Vancomycin Hydrochloride

NH2 MM 0239.00 Vancomycin Hydrochloride HO (A) 100 mg OH NH H O O Cl N HO O OH O HN O O O O HO NH O O NH2 Cl x HCl HN O

O NH HO O OH OH OH O N H

OH Venlafaxine Hydrochloride MM 0393.00 Venlafaxine Hydrochloride on request OH x HCl N

O MM 0393.02 Imp. A (EP) as Hydrochloride: 2-(4- (A) 100 mg N Methoxyphenyl)-N,N-dimethylethanamine x HCl

Hydrochloride O MM 0393.07 Imp. B (EP) as Hydrochloride: Ethyl (2RS)-3- (A) 100 mg (Dimethylamino)-2-(4-methoxyphenyl)propanoate O O x HCl Hydrochloride N

O MM 0393.08 Imp. C (EP) as Hydrochloride: 1-[(1RS)-2-Amino- (A) 100 mg OH 1-(4-methoxyphenyl)ethyl]cyclohexanol Hydrochloride x HCl NH2

O MM 0393.04 Imp. D (EP) as Hydrochloride: 1-[(1RS)-1-(4- (A) 100 mg OH Methoxyphenyl)-2-(methylamino)ethyl]cyclo- H x HCl hexanol Hydrochloride N

O MM 0393.09 Imp. E (EP) as Hydrochloride: (5RS)-5-(4- (A) 100 mg O Methoxyphenyl)-3-methyl-1-oxa-3-azaspiro- x HCl [5.5]undecane Hydrochloride N

O MM 0393.10 Imp. F (EP) as Hydrochloride: (2RS)-2- (A) 100 mg (Cyclohex-1-enyl)-2-(4-methoxyphenyl)- x HCl N,N-dimethylethanamine Hydrochloride N

O MM 0393.11 Imp. H (EP): 1-[(1RS)-1-(4-Methoxyphenyl)- (A) 50 mg OH 2-[[2-(4-methoxyphenyl)ethyl]amino]ethyl]- H Cyclohexanol N

O O MM 0393.03 Imp. G (EP) as Hydrochloride: (2RS)-2- (A) 100 mg Cyclohexyl-2-(4-methoxyphenyl)-N,N- x HCl dimethylethanamine Hydrochloride N

218 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0393.01 O-Desmethylvenlafaxine (A) 100 mg OH

HO Verapamil Hydrochloride

MM 0022.00 Verapamil Hydrochloride O (A) 500 mg O O

xHCl N MM 0022.07 Imp. A (EP) as Dihydrochloride: N,N'- O x 2 HCl O (A) 100 mg Bis[2-(3,4-dimethoxyphenyl) ethyl]-N,N'-dimethylpropane-1,3-diamine ONNO Dihydrochloride MM 0022.08 Imp. B (EP) as Hydrochloride: 2-(3,4-Dimethoxyphenyl)-N- O (A) 100 mg methylethanamine Hydrochloride x HCl ONH

MM 0022.09 Imp. C (EP) as Hydrochloride: 2-(3,4- O (A) 100 mg Dimethoxyphenyl)-N,N-dimethylethan- x HCl amine Hydrochloride ON MM 0022.02 Imp. D (EP): 3-Chloro-N-[2-(3,4-dimethoxyphenyl)ethyl]-N- O (A) 100 mg methylpropan-1-amine ONCl

MM 0022.05 Imp. E (EP): (3,4-Dimethoxyphenyl)methanol O (B) 100 mg OH O

MM 0022.10 Imp. F (EP) as Hydrochloride: (2RS)-2- O (A) 100 mg (3,4-Dimethoxyphenyl)-5-(methylamino)- O 2-(1-methylethyl)pentanenitrile x HCl Hydrochloride HN

MM 0022.04 Imp. G (EP): 3,4-Dimethoxybenzaldehyde O (B) 100 mg O

MM 0022.11 Imp. H (EP) as Hydrochloride: (2RS)- O (A) 100 mg 2-(3,4-Dimethoxyphenyl)- O x HCl O 5-[[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino]- 2-ethylpentanenitrile Hydrochloride ON

N MM 0022.12 Imp. I (EP) as Hydrochloride: (2RS)- O N (A) 50 mg

2-(3,4-Dimethoxyphenyl)-2-[2-[[2-(3,4-dimethoxy- O phenyl)ethyl](methyl)amino]ethyl]-3-methyl- O N butanenitrile Hydrochloride x HCl O MM 0022.21 Imp. J (EP) as Maleate: (2RS)- O (A) 100 mg OH 2-(3,4-Dimethoxyphenyl)- x 5-[[2-(3,4-dimethoxyphenyl)ethyl]amino]- OH O 2-(1-methylethyl)pentanenitrile Maleate O (N-Norverapamil Maleate) O O

ON H

MM 0022.03 Imp. K (EP): (2RS)-2-(3,4-Dimethoxyphenyl)-3-methylbutylnitrile O (A) 100 mg O

MM 0022.13 Imp. L (EP): 1-(3,4-Dimethoxyphenyl)-2- O (A) 100 mg methylpropan-1-one O

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 219 Pharmaceutical impurities

Code Product Code Unit

MM 0022.15 Imp. N (EP) as Hydrochloride: 5,5'- O O (A) 50 mg (Methylimino)bis[2-(3,4-dimethoxy- O x HCl O phenyl)-2-(1-methylethyl) pentanenitrile]Hydrochloride N N N

MM 0022.16 Imp. O (EP) as Hydrochloride: (2RS)- O (A) 100 mg 2-(3,4-Dimethoxyphenyl)- O x HCl O 5-[2-[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino]- ON

2-propylpentanenitrile Hydrochloride N

MM 0022.06 Diisopropylhomoveratylcyanide O (D) 100 mg O N

MM 0022.18 3,4-Dimethoxyphenylacetonitrile O (A) 100 mg O

MM 0022.19 Verapamil N-Oxide Hydrochloride O (C) 50 mg O O O ON

x HCl N Vincamine MM 0519.00 Vincamine (A) 100 mg H N N HO O O Vinpocetine MM 0406.00 Vinpocetine O (D) 100 mg O N N H

MM 0406.02 Imp. A (EP): Ethyl (12RS,13aSR,13bSR)-13a- O (D) 100 mg O Ethyl-12-hydroxy-2,3,5,6,12,13,13a,13b-octa- HO hydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]- N N naphthyridine-12-carboxylate (Ethyl Vincaminate) H

and enantiomer MM 0406.01 Imp. B (EP): Methyl (13aS,13bS)-13a-Ethyl- O (D) 100 mg 2,3,5,6,13a,13b-hexahydro-1H-indolo[3,2,1- O de]pyrido[3,2,1-ij][1,5]naphthyridine-12- N N carboxylate (Apovincamine) H

Voriconazole New MM 1094.04 Imp. A (Pharmeuropa): 1-(2,4-Difluorophenyl)- F (A) 100 mg 2-(1H-1,2,4-triazol-1-yl)ethanone

O N N N Warfarin Sodium MM 0732.01 Imp. A (EP): (5RS)-3-(2-Hydroxyphenyl)-5-phenylcyclohex- OH (A) 100 mg 2-enone

220 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit MM 0732.02 Imp. B (EP): 4-Hydroxy-2H-1-benzopyran- O O (A) 100 mg 2-one (4-Hydroxycoumarin)

OH MM 0732.03 Imp. C (EP): (3E)-4-Phenylbut-3-en-2-one (A) 100 mg (Benzalacetone)

O Xylazine Hydrochloride

MM 0515.00 Xylazine Hydrochloride H (A) 500 mg S N x HCl N

MM 0102.02 Imp. A (EP): 2,6-Dimethylaniline (2,6-Xylidine) (B) 100 mg H2N

Xylometazoline Hydrochloride MM 0089.00 Xylometazoline Hydrochloride (A) 500 mg N x HCl N H

MM 0089.07 Imp. A (EP) as Hydrochloride: N-(2- (A) 100 mg O Aminoethyl)-2-[4-(1,1-dimethylethyl)- x HCl NH2 2,6-dimethylphenyl]acetamide N Hydrochloride H MM 0089.04 Imp. B (EP): 2-(Chloromethyl)-5-(1,1-dimethylethyl)- (A) 100 mg 1,3-dimethylbenzene Cl

MM 0089.03 Imp. C (EP): [4-(1,1-Dimethylethyl)-2,6-dimethylphenyl]acetonitrile (A) 100 mg

MM 0089.05 Imp. D (EP): 1-(1,1-Dimethylethyl)-3,5-dimethylbenzene (C) 100 mg

MM 0089.02 Imp. F (EP): [4-(1,1-Dimethylethyl)-2,6-dimethylphenyl]acetic Acid (A) 100 mg O

Zaleplon New MM 1322.02 N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]phenyl]-N-ethylacetamide (A) 100 mg N

Zidovudine MM 0534.00 Imp. A (EP): 1-[(2R,5S)-5-(Hydroxymethyl)-2,5-dihydrofuran-2-yl)- O (A) 100 mg 5-methylpyrimidine-2,4(1H,3H)-dione (Stavudine) HN HO O N O

MM 0173.02 Imp. B (EP): 1-(3-Chloro-2,3-dideoxy-i-D- O (A) 100 mg erythro-pentofuranosyl)-5-methylpyrimidine- HN HO 2,4(1H,3H)-dione O N O

Cl MM 0534.01 Imp. C (EP): 5-Methylpyrimidine-2,4(1H,3H)dione (Thymine) O (A) 100 mg HN

O N H

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 221 Pharmaceutical impurities

Code Product Code Unit MM 0173.04 Imp. D (EP): Triphenylmethanol (A) 100 mg OH

New MM 0534.03 Thymidine O (A) 100 mg HN HO O N O

OH Zileuton MM 1297.03 1-Benzo-[b]thien-2-ylethanone O (A) 100 mg

S Zolpidem Tartrate MM 0333.01 Imp. A (EP): N,N-Dimethyl-2-[7-methyl- (D) 100 mg 2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide N O N N

MM 0333.02 2-[6-Methyl-2-(4-methylphenyl)imidazo-[1,2-a]pyridin-3-yl]acetamide (A) 100 mg N O N

NH2

MM 0333.03 2-[6-Methyl-2-(4-methylphenyl)imidazo-[1,2-a]pyridin-3-yl]acetic (A) 100 mg Acid N O N OH

MM 0333.04 Methyl 2-[6-Methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin- (D) 50 mg 3-yl]acetate N O N O

MM 0333.05 6-Methyl-2-(4-methylphenyl)imidazo-[1,2-a]pyridine-3-acetonitrile (A) 100 mg N

N N

MM 0333.06 Oxozolpidem (N,N,6-Trimethyl-2-(4-methylphenyl)-h-oxo- (D) 100 mg imidazo [1,2-a]pyridine-3-acetamide) N O N N O MM 0333.07 Zolpaldehyde (6-Methyl-2-(4-methylphenyl)-imidazo[1,2-a]pyridine- (A) 100 mg 3-carboxaldehyde) N

N O

MM 0333.08 Zolpyridine (4-Methyl-N-(5-methyl-2-pyridinyl)-benzamide) (A) 100 mg H N

N O

MM 0333.09 6-Methyl-2-(4-methylphenyl)-h-oxo-imidazo[1,2- (A) 100 mg a]pyridine-3-acetamide N O N

NH2 O MM 0333.10 Methyl h-Hydroxy-6-methyl-2-(4-methylphenyl)- (A) 100 mg imidazo[1,2-a]pyridine-3-acetate N O N O HO

222 All your needs for pharmaceutical analysis - email [email protected] Edition 2011 Pharmaceutical impurities

Code Product Code Unit Zopiclone MM 0149.00 Zopiclone O (D) 100 mg Cl N O N N N N

O N MM 0149.01 Imp. A (EP): (5RS)-6-(5-Chloropyridin-2-yl)-7-oxo- O (D) 100 mg Cl 6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-Methylpiperazine- N O O N 1-carboxylate 4-Oxide (Zopiclone Oxide) N N N

O N Cl MM 0149.02 Imp. B (EP): (7RS)-6-(5-Chloropyridin-2-yl)-7-hydroxy-6,7-dihydro- HO (D) 100 mg 5H-pyrrolo[3,4-b]pyrazin-5-one N N N

O N MM 0149.04 2-Amino-5-chloropyridine Cl (A) 250 mg

H2N N Cl MM 0149.05 3-(5-Chloropyridine-2-carbamoyl)-2-pyrazinecarboxylic Acid O on request N N N H OH N O Cl MM 0149.06 6-(5-Chloropyridin-2-yl)- 6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin- O (A) 100 mg 5,7-dione N N N

O N Cl MM 0149.07 5-(Chloropyridine-2-yl-carbamoyl)pyrazine O (A) 100 mg N N N H N Cl MM 0149.50 2-Acetylamino-5-chloropyridine O (A) 100 mg

N N H

Edition 2011 Looking for the latest impurities? See www.lgcstandards.com/newimpurities 223

NEW!

Microbiology catalogue

Microbiology catalogue available from LGC Standards.

A comprehensive directory of ATCC® organisms available for pharmaceutical, food and water analysis including useful technical resource.

Contact your local LGC Standards ofﬁce for your copy www.lgcstandards-atcc.org or download the catalogue www.lgcstandards.com/media/484509382.pdf. Catalogues from LGC Standards

LGC Standards provides products and services to improve measurement and quality control within your laboratory.

Our extensive range of catalogues: • Analytical reference materials and standards for food, industrial and environmental applications • ATCC cell biology catalogue • ATCC microbiology catalogue • ChromaDex phytochemical reference standards • Clinical, forensic and sports drugs reference materials • High purity solvents and acids • Higher order reference materials • Metals and related products - reference materials • Pharmaceutical reference substances and impurities • Proﬁ ciency testing schemes catalogue • Reference materials for physical properties • Tools for ADME/Tox: reagents, standards and model systems.

To download a PDF copy of any of our catalogues, please visit www.lgcstandards.com

To receive a printed copy of any of our catalogues for your laboratory or ofﬁ ce, please contact your local ofﬁ ce www.lgcstandards.com/contact.aspx

www.lgcstandards.com

Brazil • Bulgaria • China • Czech Republic • Finland • France • Germany • Hungary • Ireland • India • Italy Netherlands • Poland • Romania • Russia • Spain • Sweden • Turkey • UAE • United Kingdom • USA