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Butyrfentanyl (Butyrylfentanyl) Critical Review Report Agenda Item 4.2

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Butyrfentanyl (Butyrylfentanyl) Critical Review Report Agenda Item 4.2 Butyrfentanyl (Butyrylfentanyl) Critical Review Report Agenda item 4.2 Expert Committee on Drug Dependence Thirty-eighth Meeting Geneva, 14-18 November 2016 38th ECDD (2016) Agenda item 4.2 Butyrfentanyl Page 2 of 17 38th ECDD (2016) Agenda item 4.2 Butyrfentanyl Contents Acknowledgements .......................................................................................................................... 5 Summary .......................................................................................................................................... 6 1. Substance identification .................................................................................................... 7 A. International Nonproprietary Name (INN) ........................................................................ 7 B. Chemical Abstract Service (CAS) Registry Number .......................................................... 7 C. Other Chemical Names ...................................................................................................... 7 D. Trade Names ...................................................................................................................... 7 E. Street Names ...................................................................................................................... 7 F. Physical Appearance .......................................................................................................... 7 G. WHO Review History ......................................................................................................... 7 2. Chemistry ........................................................................................................................... 7 A. Chemical Name .................................................................................................................. 7 B. Chemical Structure ............................................................................................................ 7 C. Stereoisomers ..................................................................................................................... 8 D. Methods and Ease of Illicit Manufacturing ....................................................................... 8 E. Chemical Properties .......................................................................................................... 8 F. Identification and Analysis ................................................................................................. 8 3. Ease of Convertibility Into Controlled Substances .......................................................... 8 4. General Pharmacology ..................................................................................................... 8 A. Routes of administration and dosage ................................................................................. 8 B. Pharmacokinetics ............................................................................................................... 8 C. Pharmacodynamics ............................................................................................................ 9 5. Toxicology ......................................................................................................................... 9 6. Adverse Reactions in Humans .......................................................................................... 9 7. Dependence Potential ...................................................................................................... 10 A. Animal Studies .................................................................................................................. 10 B. Human Studies ................................................................................................................. 10 8. Abuse Potential ................................................................................................................ 11 A. Animal Studies .................................................................................................................. 11 B. Human Studies ................................................................................................................. 11 9. Therapeutic Applications and Extent of Therapeutic Use and Epidemiology of Medical Use ................................................................................................................................... 11 10. Listing on the WHO Model List of Essential Medicines ............................................... 11 11. Marketing Authorizations (as a Medicinal Product) ..................................................... 11 12. Industrial Use .................................................................................................................. 11 13. Non-Medical Use, Abuse and Dependence .................................................................... 11 Page 3 of 17 38th ECDD (2016) Agenda item 4.2 Butyrfentanyl 14. Nature and Magnitude of Public Health Problems Related to Misuse, Abuse and Dependence ..................................................................................................................... 11 15. Licit Production, Consumption and International Trade ............................................. 12 16. Illicit Manufacture and Traffic and Related Information ............................................ 12 17. Current International Controls and Their Impact ........................................................ 13 18. Current and Past National Controls............................................................................... 13 19. Other Medical and Scientific Matters Relevant for a Recommendation on the Scheduling of the Substance ........................................................................................... 13 References ...................................................................................................................................... 14 Annex 1: Report on WHO Questionnaire for Review of Psychoactive Substances for the 38th ECDD: Evaluation of Butyrfentanyl ........................................................................................... 16 Page 4 of 17 38th ECDD (2016) Agenda item 4.2 Butyrfentanyl Acknowledgements This report has been drafted under the responsibility of the WHO Secretariat, Essential Medicines and Health Products, Policy Access and Use team. The WHO Secretariat would like to thank the following people for their contribution in producing this critical review report: Mr. Justin Matheson, PhD Candidate, Ontario, Canada (literature search), Professor Bruna Brands, Ontario, Canada (literature search, review and drafting) and Dr. Stephanie Kershaw, Geneva, Switzerland (editing and questionnaire report drafting). Page 5 of 17 38th ECDD (2016) Agenda item 4.2 Butyrfentanyl Summary Butyrfentanyl is a potent, short-acting mu opioid receptor agonist, and an analogue of fentanyl, differing by only one methyl group. It has no approved medical indications, but is being used for recreational purposes, with cases of fatal overdoses reported in Europe and the United States. In the United States, butyrfentanyl has been temporarily scheduled as a Schedule 1 controlled substance under the Controlled Substances Act, and the DEA has confirmed at least 40 fatalities as of May 2016. It is sold over the Internet, often as a “research chemical”, and a number of online drug forums contain information on common routes of administration, dosing, and reported effects. The actual extent of abuse and mortality associated with butyrfentanyl is not known because it is not tested for in routine toxicological analyses. Case studies and drug forums have suggested that butyrfentanyl is typically used as a nasal spray, snorted as a white power, or injected intravenously, and doses range from 0.5 to 3 mg. Clinical studies of the pharmacological effects of butyrfentanyl in humans are not available, but the effects appear to be similar to the effects of fentanyl, including euphoria, altered mood states, drowsiness, and respiratory depression. Studies in non-human primates have found that butyrfentanyl is associated with body and jaw sag, ataxia, slowed movement, and scratching. Pre-clinical studies of butyrfentanyl are scarce; however, the few available studies suggest that butyrfentanyl is about 30 times less potent than fentanyl itself, and has significant antinociceptive properties, as demonstrated by the acetic acid writhing test in rodents. Butyrfentanyl is being abused for its opioid effects. As with other mu opioid agonists, it can induce respiratory depression which may lead to death and numerous deaths have been reported. No accepted medical purpose has been identified. Page 6 of 17 38th ECDD (2016) Agenda item 4.2 Butyrfentanyl 1. Substance identification A. International Nonproprietary Name (INN) Not applicable B. Chemical Abstract Service (CAS) Registry Number 1169-70-6 (base); 1443-52-3 (hydrochloride) C. Other Chemical Names N-(1-phenethylpiperidin-4-yl)-N-phenylbutyramide, N-(1-phenethylpiperidin-4- yl)-N-phenylbutanamide, butyryl fentanyl, NIH 10486 D. Trade Names None E. Street Names bf or b-f F. Physical Appearance White/yellow powder G. WHO Review History Not previously reviewed 2. Chemistry A. Chemical Name IUPAC Name: N-(1-phenethylpiperidin-4-yl)-N-phenylbutyramide CA Index Name: not available B. Chemical Structure Free base: Molecular Formula: C23H30N2O; C23H30N2O·HCl (for HCl salt) Molecular Weight: 350.503 g/mol (base); 386.9639 (HCl) Page 7 of 17 38th ECDD (2016) Agenda item 4.2
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