Α-Methylacetylfentanyl

α-Methylacetylfentanyl
Clinical data
Other namesα-methylacetylfentanyl, acetyl-α-methylfentanyl
ATC code
  • none
Legal status
Legal status
Identifiers
IUPAC name
  • N-Phenyl-N-[1-(1-phenylpropan-2-yl)-4-piperidyl]acetamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
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 checkY
  • Key:OKTLVZBUKMRPLL-UHFFFAOYSA-N checkY
  (verify)

α-Methylacetylfentanyl (or alphamethylacetylfentanyl) is an opioid analgesic and an analog of fentanyl. It is classified as a Schedule I controlled substance in many jurisdictions.

History

The drug appeared briefly on the black market in the early 1980s, prior to the enactment of the Federal Analog Act, which sought to regulate entire classes of substances based on structural similarity rather than scheduling each one individually as it emerged.[6] Fentanyl analogs have been responsible for hundreds of fatalities across Europe and the former Soviet republics since their re-emergence in Estonia in the early 2000s, and new derivatives continue to appear.[7] In 2013, the Drug Enforcement Administration (DEA) established an aggregate production quota of 2 grams (0.071 oz) for acetyl-alpha-methylfentanyl.[8]

Pharmacology

Pharmacologically, α-methylacetylfentanyl acts as a mu-opioid receptor agonist and produces effects similar to those of fentanyl.[9]

Adverse effects

The adverse effects of fentanyl analogs are also similar to those of fentanyl itself, including itching, nausea, and severe respiratory depression, which may be life-threatening.[9]

Synthesis

α-Methylacetylfentanyl can be synthesized by the same method as α-methylfentanyl, except that the more readily available acetic anhydride is used in place of the less accessible propionic anhydride.[10]

References

  1. ↑ Anvisa (2024-05-28). "RDC Nº 877 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 877 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União. Archived from the original on 2024-09-25. Retrieved 2024-09-25.
  2. ↑ "Controlled Drugs and Substances Act (S.C. 1996, c. 19)". 2016-11-30. Archived from the original on 3 April 2011. Retrieved 17 November 2013.
  3. ↑ "Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz - BtMG) Anlage I (zu § 1 Abs. 1) (nicht verkehrsfähige Betäubungsmittel)" (in German). Bundesministerium für Justiz und Verbraucherschutz.
  4. ↑ "Misuse of Drugs Act 1971 (c. 38): SCHEDULE 2: Controlled Drugs". Office of Public Sector Information. Retrieved 15 June 2009.
  5. ↑ 52 FR 20070
  6. ↑ Henderson G (March 1988). "Designer drugs: past history and future prospects". Journal of Forensic Sciences. 33 (2): 569–575. doi:10.1520/JFS11976J. PMID 3286815.
  7. ↑ 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): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.
  8. ↑ 78 FR 37238
  9. 1 2 "Acetyl-alpha-methylfentanyl". Expert Committee on Drug Dependence Information Repository. World Health Organization. Retrieved 25 September 2025. Acetyl-alpha-methylfentanyl has been classified pharmacologically as a mu-type opioid receptor agonist with a profile similar to that of fentanyl. As a mu-type opioid agonist it possesses analgesic activity and produces morphine-like euphoric effects. Its analgesic potency is ten times that of morphine. Like other mu-opioids, acetyl-alpha-methylfentanyl can depress respiration, and its effects on the central nervous system can be reversed by narcotic antagonists such as naloxone.
  10. ↑ "α-Methylacetylfentanyl". DrugBank. DB01532.
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