α-Methylacetylfentanyl

α-Methylacetylfentanyl (or alphamethylacetylfentanyl) is an opioid analgesic that is an analog of fentanyl. It is a Schedule I controlled substance in the United States, with a DEA ACSCN of 9815.

α-Methylacetylfentanyl
Clinical data
Other namesα-methylacetylfentanyl, acetyl-α-methylfentanyl
ATC code
  • none
Legal status
Legal status
  • CA: Schedule I
  • DE: Anlage I (Authorized scientific use only)
  • UK: Class A
  • US: Schedule I
Identifiers
IUPAC name
  • N-Phenyl-N-[1-(1-phenylpropan-2-yl)-4-piperidyl]acetamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ECHA InfoCard100.288.948
Chemical and physical data
FormulaC22H28N2O
Molar mass336.479 g·mol−1
3D model (JSmol)
SMILES
  • O=C(N(c1ccccc1)C3CCN(C(Cc2ccccc2)C)CC3)C
InChI
  • InChI=1S/C22H28N2O/c1-18(17-20-9-5-3-6-10-20)23-15-13-22(14-16-23)24(19(2)25)21-11-7-4-8-12-21/h3-12,18,22H,13-17H2,1-2H3 Y
  • Key:OKTLVZBUKMRPLL-UHFFFAOYSA-N Y
  (verify)

α-Methylacetylfentanyl was sold briefly on the black market in the early 1980s, before the introduction of the Federal Analog Act which for the first time attempted to control entire families of drugs based on their structural similarity rather than scheduling each drug individually as they appeared.[1] α-Methylacetylfentanyl is made with the same synthetic route as α-methylfentanyl, but by substituting the relatively common acetic anhydride for the more difficult to obtain chemical propionic anhydride in the synthesis.

α-Methylacetylfentanyl has similar effects to fentanyl. Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear.[2]

The 2013 DEA production quota for acetyl-alpha-methylfentanyl is 2 grammes.[3]

References
  1. Henderson GL (March 1988). "Designer drugs: past history and future prospects". Journal of Forensic Sciences. 33 (2): 569–75. doi:10.1520/JFS11976J. PMID 3286815.
  2. Mounteney J, Giraudon I, Denissov G, Griffiths P (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal on Drug Policy. 26 (7): 626–31. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.
  3. "Quotas - 2013". Diversion Control Division. Drug Enforcement Administration, U.S. Department of Justice. 20 June 2013.
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