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Opioid Analytical Standards

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Opioid Analytical Standards Cayman Chemical is dedicated to working with the forensic community to quickly make authentic reference standards available from our ISO/IEC 17025 and ISO 17034 laboratories. In response to the opioid epidemic, our catalog has expanded to now contain more than 600 opioid standards to help identify, confirm, and quantify these drugs of abuse. This includes a wide collection of fentanyls and other emerging synthetic opioids as well as plant-derived opiates and their metabolites and internal standards. A library of mass spectral data containing many of Cayman’s emerging opioid standards is freely available for download at www.caymanchem.com/CSL. More than 600 Opioid Standards for · Synthetic Opioids · Opiates & Natural Products - Fentanyls - Prescription Drugs - Utopioids - Semi-Synthetic Opiates - AH-, MT-45, & W-Series - Opioid Antagonists - Nitazenes - Emerging Classes Tools to Rapidly Screen for Prevalent Opioids Abundance 10.819 Synthetic Opioid Mixtures 8e+07 7.5e+07 11.294 11.485 7e+07 11.878 GC-MS Opioid Mixture 1 6.5e+07 6e+07 Item No. 23629 5.5e+07 12.369 5e+07 14.030 4.5e+07 A mixture of 7 common synthetic opioids (1 mg/ml 14.306 4e+07 3.5e+07 of each): acetyl fentanyl, acrylfentanyl, butyryl 3e+07 10.643 2.5e+07 fentanyl, cyclopropyl fentanyl, fentanyl, furanyl 2e+07 1.5e+07 fentanyl, and U-47700 1e+07 5000000 Time--> 10.20 10.40 10.60 10.80 11.00 11.20 11.4011.60 11.80 12.00 12.20 12.40 12.60 12.80 13.0013.20 13.40 13.60 13.8014.00 14.2014.40 14.60 14.80 GC-MS Opioid Mixture 2 Representative chromatogram of the compounds Item No. 23876 included in the GC-MS Opioid Mixture 2 A mixture of 8 common synthetic opioids (1 mg/ml Peak order from left to right: U-48800, U-49900, FIBF, ortho-fluorofentanyl, of each): cyclopentyl fentanyl, methoxyacetyl fentanyl, (±)-cis-3-methyl fentanyl, methoxyacetyl fentanyl, cyclopentyl fentanyl, (±)-cis-3-methyl fentanyl, tetrahydrofuran fentanyl, tetrahydrofuran fentanyl ortho-fluorofentanyl, FIBF, U-48800, and U-49900 Custom Opioid Mixtures, Screening Libraries, and Plates Available Email [email protected] to discuss your specific project needs 2020 CAYMAN CHEMICAL · 1180 EAST ELLSWORTH ROAD · ANN ARBOR, MI 48108 · USA · (800) 364-9897 WWW.CAYMANCHEM.COM Fentanyls The basic fentanyl scaffold can be modified in four 13 different regions leading to a myriad of new fentanyl C-Labeled Internal Standards varieties. Cayman now offers more than 380 standards 13 for the identification, confirmation, and quantification 4-ANPP- C6 (CRM) of fentanyls and their metabolites. Our scientists have N Item No. 26313 H also developed a naming convention to help provide N a more unambiguous way to describe substituent 13C H13C 13CH placement on the fentanyl scaffold. Read more about H13C 13CH 13C the standardized naming of substituted fentanyls at H www.caymanchem.com/fentanylnaming. H 13 13C Carfentanil- C (CRM) Parent Compounds H13C 13CH 6 13C 13CH N 13C Item No. 26904 Item No. Product Name O H ISO60128 Acetyl fentanyl (hydrochloride) (CRM) * N O O 23060 Acrylfentanyl (hydrochloride) (CRM) * 25936 Benzyl fentanyl (hydrochloride) (CRM) * 19734 Butyryl fentanyl (hydrochloride) (CRM) * H 13C H13C 13CH para-Fluorobutyryl 19884 Carfentanil (CRM) 13C 13CH 13 N 13C fentanyl- C 26637 Crotonyl fentanyl (CRM) * O H 6 N (hydrochloride) (CRM) 23603 Cyclopropyl fentanyl (hydrochloride) (CRM) * • HCl Item No. 26614 ISO60197 Fentanyl (hydrochloride) (CRM) * 25615 β-methyl Fentanyl (hydrochloride) (CRM) * F 21676 (±)-cis-3-methyl Fentanyl (hydrochloride) (CRM) * View a complete list of our isotopically labeled standards 19795 FIBF (hydrochloride) (CRM) * at www.caymanchem.com/forensics 19826 para-Fluorobutyryl fentanyl (hydrochloride) (CRM) * Metabolites 19633 Furanyl fentanyl (hydrochloride) (CRM) * Item No. Product Name 22750 para-fluoro Furanyl fentanyl (hydrochloride) ISO60130 Acetyl norfentanyl (hydrochloride) (CRM) * 26050 meta-methoxy Furanyl fentanyl 22700 4-ANPP (CRM) * 23540 Methoxyacetyl fentanyl (hydrochloride) (CRM) * 19561 Butyryl norfentanyl (hydrochloride) (CRM) * 19635 Ocfentanil (hydrochloride) (CRM) * 25078 Cyclopropyl norfentanyl (hydrochloride) (CRM) * 25887 Phenyl fentanyl (hydrochloride) (CRM) * 26427 Despropionyl ortho-Fluorofentanyl (CRM) * 22429 Remifentanil (hydrochloride) (CRM) * 26428 Despropionyl para-Fluorofentanyl (CRM) * 22802 Thiophene fentanyl (hydrochloride) 20789 β-hydroxy Fentanyl (hydrochloride) 19798 Valeryl fentanyl (CRM) * 19559 Furanyl norfentanyl (hydrochloride) (CRM) * * Compound also available as a neat solid 22182 Norcarfentanil (hydrochloride) (CRM) * ISO60195 Norfentanyl (CRM) * Request a copy of our 9001142 Norsufentanil Fentanyl Laboratory Guide wall poster 21926 Remifentanil Acid (trifluoroacetate salt) at www.caymanchem.com/literature * Compound also available as a neat solid 2020 CAYMAN CHEMICAL · 1180 EAST ELLSWORTH ROAD · ANN ARBOR, MI 48108 · USA · (800) 364-9897 WWW.CAYMANCHEM.COM Non-Fentanyl Synthetic Opioids Utopioids & Metabolites Item No. Product Name Utopioid Lab Guide Wall Poster 27925 UF-17 (hydrochloride) In this guide to the identification, naming, and 27924 Furanyl UF-17 (hydrochloride) metabolism of U-type opioids: 19397 U-47700 (CRM) * · Common EI-GC-MS Utopioid Fragments 24289 N,N-didesmethyl U-47700 (trifluoroacetate salt) (CRM) * · Mass Spectrum of U-47700 28689 3,4-difluoro U-47700 · Tips for GC-MS Interpretation 29561 3,4-difluoro Isopropyl U-47700 · Halogen Isotope Patterns 29560 3,4-difluoro-N-desmethyl U-47700 (hydrochloride) · Utopioid Metabolism 24263 Isopropyl U-47700 Common C-MS Halogen sotope atterns Utopioid raments Monochloro 139 T tur d f O Latory d or 111 Cl 37 O C v act N N 31 H H O N N N Cl Br heigh a f MM (111113, 139141) UTOPIOID 141 m/20 m/16 m/13 m/13 m/13 113 O O Idtifica, N, N O O O Cl 20530 U-47931E O Cl O Cl N Cl O 100 110 120 130 140 150 HN U-48520 O Cl F3C O Cl d Metabolism Cl m/16 m/13 m/13 m/166 m/163 m/15 m/15 Dichloro O O O 145 O O Cl Cd w 3 13 a f MM (14147, 17317) N O 14 Br O2N O Cl F3C Cl 15 O Cl m/155 m/153 m/150 m/14 m/14 m/145 m/145 m/13 N N Definin topioids Cl O O U-47700 130 140 150 160 10 10 10 O N O Amide Linker N N NC N O2N HO 29563 4-fluoro U-47931E H H m/13 m/13 m/130 m/125 m/122 m/121 m/121 m/112 U- d, Monobromo U-d U-d, d O T tur d f metabolit acterizd y 81Br v act HN HN trans-clohed ty d 11 Cl 155 13 Cl HN NC NH2 HO their d , linkd heigh a f MM N 15 15 together y d y (117, 18318) m/112 m/112 m/111 m/111 m/102 m/=97 m/3 N O Commonly detected utopioids Cl U-47700, U-48800, U-49900, U-174, N N N NH N 140 150 160 10 10 10 200 HN 3,4-Methdxy U-47700, Br 25522 U-48800 (hydrochloride) (CRM) * m/1 m/4 m/1 m/0 Isoprop U-47700 Phenyl Ring trans-Cyclohexanediamine methyl Common ubstitutions Mass pectrum of R4 Utopioid etabolism and ips for nterpretation O O OH R4 O Cl N NH N B Cl Abundance 4 N N HN O O 600,000 OH m/4 Cl A Cl N N O A O B O R R R N NH 550,000 5 3 3 Cl Cl Cl Cl Cl N N N N NH NH2 N Cl 2 Cl 500,000 R2 R1 R2 R1 U-400 Metabolism 29564 2,4-difluoro U-48800 (hydrochloride) N 450,000 Cl m/32 OH N · r R₁-R₃ d R₅ dt y y bstitutions O Cl Common Metabolite 400,000 m/125 N · R₄ dt ring NH 125 Cl 350,000 (d, oxy , oup, etc.) B O 300,000 O O O Cl C Cl C A N Cl Cl N N N H 250,000 N NH NH Cl Cl NH2 2 A Cl Cl Cl 200,000 O U-400 Metabolism O Cl Cl Cl 150,000 m/145 N H 1 NH 110 145 Cl 100,000 42 5 13 Cl m/13 23999 U-49900 (CRM) * 50,000 98 iotransformation Pathway 32 0 A) N-emethylation ) Hydroxylation C) N-eethylation m/z--> 40 50 60 70 80 90 100 110 120 130 140 150 160 10 10 10 200 210 220 230 240 250 260 20 20 20 300 310 320 330 Tips for GC-MS Interpretation · Utd dg d d d · T 84 d 1 dtiv f O · Hydoxyla cur ver clohe ing thylcyclohe-1,-d ty (right Cl N · U-47700 d U-49900 tabolit, N · Isot tt dtify Cl N-(-clohe)-3,4-d-N-thd ituen hen rimethylcycloheanediamine References · T lar (or M-1 ) Krot, A, Mohr, ALA, P, DM, et al. Drug Test Anal. 10(1), 17-136 (018) 29148 U-50488 (hydrochloride) (CRM) * esen very F, SW, Cooley, J.C, J, L, et al. J. nal. oxicol. 41(3), 173-180 (017) L d or ddd www.caymanchem.com/utopioids 019 C Ccal 29566 3,4-difluoro U-50488 (hydrochloride) Request a physical copy of this wall poster at 24264 U-51754 (hydrochloride) (CRM) * www.caymanchem.com/literature * Compound also available as a neat solid AH-, MT-45, & W-Series Opioids & Metabolites Nitazenes & Other Synthetic Opioids & Metabolites Item No. Product Name Item No. Product Name 19732 AH 7921 (CRM) * 27816 Brorphine (hydrochloride) 20280 N-desmethyl AH 7921 (hydrochloride) ISO60143 EDDP (perchlorate) (CRM) 19336 AH 8533 27255 Isotonitazene 19737 MT-45 (hydrochloride) (CRM) * 19406 Meperidine (hydrochloride) (CRM) 25288 2-fluoro MT-45 (hydrochloride) ISO60145 (±)-Methadone (hydrochloride) (CRM) * 25290 4-fluoro MT-45 (hydrochloride) 26398 Metonitazene 19482 W-15 (CRM) * 20899 Normeperidine (hydrochloride) (CRM) * 20413 W-15-d4 (CRM) 15912 (−)-Pentazocine 19483 W-18 (CRM) * 26335 Piperidylthiambutene (hydrochloride) 20366 W-18-d4 (CRM) ISO60184 (+)-Propoxyphene (hydrochloride) (CRM) 19713 nor-W-18 18660 Tapentadol (hydrochloride) (CRM) * 20317 nor-W-18-d4 25950 Tianeptine (sodium salt) 19484 W-19 (hydrochloride) ISO60149 cis-Tramadol (hydrochloride) (CRM) * 19487 W-19-d4 (hydrochloride) 18751 O-Desmethyl-cis-tramadol (hydrochloride) (CRM) * * Compound also available as a neat solid * Compound also available as a neat solid Be the first to know about novel synthetic opioids showing up in casework.
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    ©2014 Mahta Samizadeh ALL RIGHTS RESERVED ANTI-HIV DRUG CONJUGATES FOR ENHANCED MUCOSAL PRE-EXPOSURE PROPHYLAXIS By MAHTA SAMIZADEH A dissertation submitted to the Graduate School-New Brunswick Rutgers, The State University of New Jersey In partial fulfillment of the requirements For the degree of Doctor of Philosophy Graduate Program in Pharmaceutical Science Written under the direction of Professor Patrick J. Sinko And approved by ____________________________ ____________________________ ____________________________ ____________________________ New Brunswick, New Jersey May, 2014 ABSTRACT OF THE DISSERTATION ANTI-HIV DRUG CONJUGATES FOR ENHANCED MUCOSAL PRE-EXPOSURE PROPHYLAXIS By Mahta Samizadeh Dissertation Director: Professor Patrick J. Sinko To combat HIV pandemic, targeting HIV mucosal transmission appears to be more effective than targeting later stages of the infection owing to the viral vulnerability and higher efficacy of antiretrovirals at this very early stage of HIV infection. The objective of the current project is to investigate the complementary benefits of combining an anti-HIV drug (amprenavir, APV), a cell-penetrating peptide (bactenicin 7, Bac7 CPP) and poly (ethylene glycol) (PEG) together as a nanocarrier conjugate for fast and efficient cytosolic delivery of the drug. The nanocarrier is to be incorporated into an alcohol-free thermosensitive foam for colonic/rectal delivery. In the initial studies, APV-PEG conjugates were prepared using 2 to 30 kDa PEGs and protease inhibition properties were assessed in buffer using FRET-based protease inhibition assay. The results suggested that PEG size between 2 and 5 kDa is the optimum range for maintaining the protease inhibition activity. For further studies, APV- PEG3.4-FITC (APF) and a PEGylated APV conjugated with Bac7 CPP (APV-PEG3.4- Bac7 CPP; APB) were prepared.
  • Analysis of Oxycodone and Its Metabolites-Noroxycodone, Oxymorphone, and Noroxymorphone in Plasma by LC/MS with an Agilent ZORBAX Stablebond SB -C18 LC Column

    Analysis of Oxycodone and Its Metabolites-Noroxycodone, Oxymorphone, and Noroxymorphone in Plasma by LC/MS with an Agilent ZORBAX Stablebond SB -C18 LC Column

    Analysis of Oxycodone and Its Metabolites-Noroxycodone, Oxymorphone, and Noroxymorphone in Plasma by LC/MS with an Agilent ZORBAX StableBond SB -C18 LC Column Application Note Pharmaceutical Authors Abstract Linda L. Risler Oxycodone and its oxidative metabolites (noroxycodone, oxymorphone, and Fred Hutchinson Cancer Research noroxymorphone) were analyzed by high performance liquid chromatography/mass Center, spectrometry (HPLC/MS), coupled with chromatographic separation by an Agilent Seattle, WA 98109 ZORBAX Rapid Resolution High Throughput (RRHT) StableBond SB-C18 column. The method used an ammonium acetate/acetonitrile gradient with detection by a mass Anne E. Mack spectrometer in electrospray mode with positive polarity. Spiked human plasma Agilent Technologies, Inc. samples underwent solid phase extraction (SPE) prior to LC/MS analysis. This method provided good linearity (R 2 > 0.9900) and reproducibility (< 10% difference between duplicates) for all compounds, while increasing productivity with a fast, efficient analysis and minimal solvent usage. Introduction Experimental Oxycodone was developed in 1916 as an opioid analgesic An Agilent 1100 Series LC/MS was used for this work: medication intended to replace the far too addictive analgesic at the time, heroin. Today, oxycodone is a Schedule II drug in • Agilent G1312A Binary Pump. Mobile phase A: 20 mM the US, which means, while it has proven medical uses, it is ammonium acetate, pH 4.0 and B: acetonitrile. Flow rate still considered highly addictive with the possibility of both was 0.300 mL/min. Hold 5% B for 2.33 minutes, then physical and psychological dependencies. Figure 1 shows increase B from 5% to 20% from 2.33 to 4.33 minutes, stop oxycodone and its metabolic scheme, yielding noroxycodone, time is 6 minutes, and post time is 4 minutes.
  • Benzimidazole-Opioids June 2021

    Benzimidazole-Opioids June 2021

    Drug Enforcement Administration Diversion Control Division Drug & Chemical Evaluation Section Benzimidazole-Opioids June 2021 Introduction: metonitazene, metodesnitazene, and protonitazene involved interaction with β-arrestin-2. Mu-opioid receptor and β-arrestin-2 Recently, several synthetic substances of benzimidazole interaction has been implicated in adverse health effects of many structural class are being trafficked and abused for their opioid- opioid analgesics. It is well established that mu-opioid receptor like effects. In the late 1950s, the pharmaceutical research agonists have a high potential for addiction and can produce dose- laboratories of the Swiss chemical company CIBA dependent respiratory depression and arrest. Abuse of these Aktiengesellschaft synthesized numerous benzimidazole- benzimidazole-opioids has led to their positive identification in opioids to include butonitazene, etodesnitazene, flunitazene, several toxicological cases in the United States. Specifically, metonitazene, metodesnitazene, and protonitazene. Since metonitazene has been identified in twenty post-mortem cases. 2019, the abuse of benzimidazole-opioids as evidenced by their identification in toxicology cases, similar to other synthetic opioids, has resulted in adverse health effects including deaths. User Population: As the United States continues to experience an unprecedented The population likely to abuse benzimidazole-opioids appears to be epidemic of opioid misuse and abuse, the continued evolution the same as those abusing prescription opioid analgesics, heroin, and increased trafficking and popularity of new and deadly and other synthetic opioid substances. This is evidenced by the synthetic opioids including benzimidazole-opioids with no types of other drugs co-identified in isotonitazene seizures and in approved medical use are of public health concern. fatal overdose cases. Toxicology analyses co-identified some of these benzimidazole-opioids with other opioids, stimulants, and Chemistry: benzodiazepines.