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Prescription & Illicit Drug Certified Reference Materials

Many analgesics clinically prescribed to manage chronic pain carry warranted concerns over safety and abuse liability. Further complications can arise from drug-drug interactions when stimulants or other illicit compounds are also abused. Cayman Chemical offers Certified Reference Materials (CRMs) to help identify, confirm, and quantify many of the major opioids, , psychoactive drugs, and other controlled substances. Our CRMs meet ISO/IEC 17025 and ISO 17034 standards and are sold as quantitative solutions in sealed ampules.

Opioid CRMs CRMs Item No. Product Name Item No. Product Name

ISO60128 Acetyl fentanyl (hydrochloride) (CRM) ISO60185 (CRM)

23060 Acrylfentanyl (hydrochloride) (CRM) ISO60181 (CRM)

25936 Benzyl fentanyl (hydrochloride) (CRM) 25614 (CRM)

ISO60178 Buprenorphine (hydrochloride) (CRM) ISO60177 (CRM)

19734 Butyryl fentanyl (hydrochloride) (CRM) 28623 (CRM)

19884 Carfentanil (CRM) 20991 (CRM)

26637 Crotonyl fentanyl (CRM) 25577 (CRM)

23603 Cyclopropyl fentanyl (hydrochloride) (CRM) 26352 (CRM)

ISO60197 Fentanyl (hydrochloride) (CRM) 18160 (CRM)

25615 β-methyl Fentanyl (hydrochloride) (CRM) 19391 (CRM)

19795 FIBF (hydrochloride) (CRM) 19206 (CRM)

19826 para-Fluorobutyryl fentanyl (hydrochloride) (CRM) ISO60172 (CRM)

19633 Furanyl fentanyl (hydrochloride) (CRM) ISO60182 (CRM)

ISO60187 Heroin (CRM) Common benzodiazepines listed, more benzodiazepines and their metabolites and internal standards available online 23540 Methoxyacetyl fentanyl (hydrochloride) (CRM) 18567 Mitragynine (CRM) Request a physical copy of the 19635 Ocfentanil (hydrochloride) (CRM) Benzodiazepine Metabolism 25887 Phenyl fentanyl (hydrochloride) (CRM)

22429 Remifentanil (hydrochloride) (CRM) Wall Poster for your lab!

18660 Tapentadol (hydrochloride) (CRM) BENZODIAZEPINE METABOLISM LAB GUIDE

7-Halogenated-1,4-Benzodiazepines 7-Nitro-1,4-Benzodiazepines Half-Life of Common Benzodiazepines

H H O O H O O O Drug (Brand Name) Half-Life (h)+Half-LifePrimary (hr) Metabolite+ (half-life, h)+ N N N N N O O Long Half-Life (effective >24 h)hr) 19397 U-47700 (CRM) OH OH OH R N B O2N N H2N N N N N N Diazepam (Valium) 20-100 20-100Nordiazepam (36-200) A H H R' R CE R R B R (Librium) (Librium) 5-30 5-30Nordiazepam (36-200) H 1 O O (Tranxene) * * Nordiazepam (36-200) N N Biotransformation Pathway (Centrax) * * Nordiazepam (36-200) OH 7 4 R N R N B H H Flurazepam (Dalmane) * * Desalkylflurazepam (40-250) R' R' Intermediate to Short Half-Life (effective 5-24 h)hr) H H Drug O O 1 O O O (Alodorm) 15-38 15-387-Aminonitrazepam N N N N N OH (Rohypnol) 20-30 20-307-Aminoflunitrazepam B O N N O N 7 N 4 H N N H N N R N A 2 2 2 2 Temazepam (Restoril) 8-22 8-22Oxazepam (4-15) 25522 U-48800 (hydrochloride) (CRM) R' R A R CE R B R (Lectopam) 10-20 10-203-hydroxy Bromazepam (Ativan) 10-20 10-20Lorazepam Glucuronide H CH CO H CO R NO Drug Primary Metabolite 3 2 2 2 Alprazolam (Xanax) 6-20 6-20α-hydroxy Alprazolam Examples CE B (Serax) 4-15 4-15Oxazepam Glucuronide

O O O H O Etizolam (Etizest) 3.4-7.1 3.4-7.1α-hydroxy Etizolam A B C D E N N N N Examples H Ultra-Short Half-Life (effective <5 h)hr) Cl N Cl N Cl N Br N O H O H O O O N N N N N Midazolam (Versed) <5 <5α-hydroxy Midazolam Cl F Cl

OH O2N N O2N N O2N N (Halcion) <5 <5α-hydroxy Triazolam N N Phase I Metabolite Diazepam* Diclazepam Phenazepam H2N O2N F Cl

+ H O H O H O O R R Approximate half-life data adapted from Greenblatt, D.J., Shader, R.I., Divoll, M., et al. Br. J. Clin. Pharmacol. N N N N Flunitrazepam Nitrazepam Clonazepam 11 (Suppl 1), 11S-16S (1981) and Manchester, K.R., Lomas, E.C., Waters, L., et al. Drug Test Anal. 10(1), 37-53 (2018). OH OH OH *Indicates or drug precursors that do not reach the systemic circulation in clinically important amounts. Cl N Cl N Cl N Cl N

23999 U-49900 (CRM) Cl

Nordiazepam Lorazepam Oxazepam Temazepam OH H H CO2H NH2 *The primary metabolite of diazepam is nordiazepam Benzodiazepine Prodrugs via phase I demethylation. N N N H O H O H O F G H HO N N N N N N N N N CO2Et CO2H H H H H A A OH Cl N D Cl N CE Cl N R N R N R N Phase II Metabolite F F F R' R' R' Loflazepate Desalkylflurazepam 24264 U-51754 (hydrochloride) (CRM) N N N HO N N N S N S N HO S N H Examples H O O H O N N N N N N O NH CO2H H N N N N OH H H OH H3C R A R A R N N N N O O N N N N Cl N Cl N Cl N

Cl N Cl N O N N Br N HO2C OH 2 CE A OH Cl Cl F Clorazepate Nordiazepam Oxazepam Examples Alprazolam Triazolam Clonazolam Flubromazolam

N N N O N N N 8-Nitrotriazolobenzodiazepines can also undergo Hydroxylation Reduction N N N N A E S S S S 19798 Valeryl fentanyl (hydrochloride) (CRM) (MW plus 16) (MW minus 30) Cl Br reduction to 8-aminotriazolobenzodiazepines. O N N N N N Dealkylation What is a ? Demethylation Sulfation Cl Cl F Cl B F Cl N A prodrug is a drug substance that needs to be (MW minus 14) (MW plus 80) Etizolam Fluclotizolam converted into the pharmacologically active agent Decarboxylation Glucuronidation View a complete list of parent compounds, metabolites, by metabolic or physiochemical transformation.1 C G Thienodiazepines contain a thiophene ring in place of the (MW minus 44) (MW plus 176) and labeled standards at www.caymanchem.com 1. Drago, D., Pacifici, E., and Bain, S. Chapter 3 Drugs. An overview of FDA regulated products: From Drugs ring of a standard benzodiazepine but exhibit Prazepam and cosmetics to food and tobacco. Pacifici, E. and Bain, S., editors, 1st edition, Academic Press (2018). Acetylation similar activity and pharmacological effects. D Hydrolysis H Common opioids listed, more opioids and their metabolites and internal standards (MW plus 42) © Cayman Chemical Company · Created June 2019 available online Visit www.caymanchem.com/literature

2020 CAYMAN CHEMICAL · 1180 EAST ELLSWORTH ROAD · ANN ARBOR, MI 48108 · USA · (800) 364-9897 WWW.CAYMANCHEM.COM Stimulant and Hallucinogen CRMs Item No. Product Name Item No. Product Name

ISO60188 (±)-Amphetamine (hydrochloride) (CRM) 26615 (+)-Methamphetamine (hydrochloride) (CRM)

25523 BZP (hydrochloride) (CRM) 20891 Methylone (hydrochloride) (CRM)

ISO60176 Cocaine (CRM) 26279 Mexedrone (hydrochloride) (CRM)

25688 Deschloroketamine (hydrochloride) (CRM) ISO60194 PCP (hydrochloride) (CRM)

27239 bk-DMBDB (hydrochloride) (CRM) 28958 3-methoxy PCP (hydrochloride) (CRM)

29672 Eutylone (hydrochloride) (CRM) 25670 4-methyl Pentedrone (hydrochloride) (CRM)

19389 Ketamine (hydrochloride) (CRM) 27504 Pentylone (hydrochloride) (CRM)

ISO60189 (±)-MDA (hydrochloride) (CRM) 24337 N-ethyl Pentylone (hydrochloride) (CRM)

27240 bk-MDEA (hydrochloride) (CRM) 22808 α-Pyrrolidinopentiophenone (hydrochloride) (CRM)

ISO60190 3,4-MDMA (hydrochloride) (CRM) 28879 4'-chloro-α-Pyrrolidinovalerophenone (hydrochloride) (CRM)

Common psychoactives listed, more psychoactive drugs and their metabolites and internal standards available online Synthetic Cannabinoid CRMs Item No. Product Name Item No. Product Name

27237 AB-CHMINACA (CRM) 17726 5-fluoro CUMYL-PINACA (CRM)

ISO60211 AB-FUBINACA (CRM) 27973 JWH 018 (CRM)

19805 4-fluoro ADB (CRM) 22047 MAB-CHMINACA (CRM)

25012 (S)-5-fluoro ADB (CRM) 28186 4-fluoro MDMB-BUTINACA (CRM)

27043 AM2201 (CRM) 18203 PB-22 (CRM)

28624 APP-BUTINACA (CRM) ISO60059 XLR11 (CRM)

Common synthetic cannabinoids listed, more synthetic cannabinoids and their metabolites and internal standards available online and CRMs CRMs Item No. Product Name Item No. Product Name

ISO60206 (CRM) 22912 (CRM)

ISO60141 Dextromethorphan (CRM) 22854 (CRM)

20283 (CRM) 20091 (CRM)

20411 (CRM) 20966 (CRM)

20648 (CRM) 20987 (CRM)

20397 (CRM) 21707 (CRM)

View a full list of internal standards online View a full list of internal standards online CRMs Performance-Enhancing Drug CRMs Item No. Product Name Item No. Product Name

19031 (hydrochloride) (CRM) ISO60161 Androstenedione (CRM)

25576 (hydrochloride) (CRM) 19247 Lorcaserin (hydrochloride) (CRM)

23981 Quetiapine (hemifumarate) (CRM) 21677 Methyldienolone (CRM)

19049 (hydrochloride) (CRM) ISO60154 (CRM)

25524 (hydrochloride) (CRM) 9002564 11-keto Testosterone (CRM)

View a full list of internal standards online To view a complete list of our Certified Reference Materials, visit us online at www.caymanchem.com/forensics

2020 CAYMAN CHEMICAL · 1180 EAST ELLSWORTH ROAD · ANN ARBOR, MI 48108 · USA · (800) 364-9897 WWW.CAYMANCHEM.COM