Alphacetylmethadol

Alphacetylmethadol (INN), or α-acetylmethadol (AAM), is a synthetic opioid analgesic.[3] Its levorotary enantiomer, levacetylmethadol, is an FDA-approved treatment for opioid addiction.[3] Alphacetylmethadol is very similar in structure to methadone, a widely prescribed treatment for opioid addiction. In the United States, it is a Schedule I controlled substance under the Controlled Substances Act (presumably because it was never marketed in the US, as is the case with other common opiate/opioid medications such as heroin and prodine), with an ACSCN of 9603 and a 2013 annual manufacturing quota of 2 grammes.[4]

Not to be confused with acetylmethadol[1]
Alphacetylmethadol
Skeletal formulas of (R,R)-alphacetylmethadol (left), and (S,S)-alphacetylmethadol (right)
Ball-and-stick models of (R,R)-alphacetylmethadol (left), and (S,S)-alphacetylmethadol (right)
Clinical data
ATC code
  • None
Legal status
Legal status
Identifiers
  • [(3R,6R)-6-(Dimethylamino)-4,4-diphenylheptan-3-yl] acetate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H31NO2
Molar mass353.506 g·mol−1
3D model (JSmol)
  • CC[C@H](C(C[C@@H](C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C
  • InChI=1S/C23H31NO2/c1-6-22(26-19(3)25)23(17-18(2)24(4)5,20-13-9-7-10-14-20)21-15-11-8-12-16-21/h7-16,18,22H,6,17H2,1-5H3/t18-,22-/m1/s1
  • Key:XBMIVRRWGCYBTQ-XMSQKQJNSA-N

See also

References
  1. Richard Lawrence Miller (30 December 2002). The Encyclopedia of Addictive Drugs. Greenwood Publishing Group. p. 222. ISBN 978-0-313-31807-8. Retrieved 15 May 2012.
  2. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  3. Newman JL, Vann RE, May EL, Beardsley PM (October 2002). "Heroin discriminative stimulus effects of methadone, LAAM and other isomers of acetylmethadol in rats". Psychopharmacology. 164 (1): 108–14. doi:10.1007/s00213-002-1198-8. PMID 12373424. S2CID 19815273.
  4. 21 U.S.C. § 812(b)(1)


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