Alphacetylmethadol

Alphacetylmethadol (INN), or α-acetylmethadol (AAM), is a synthetic opioid analgesic.[2] Its levorotary enantiomer, levacetylmethadol, is an FDA-approved treatment for opioid addiction.[2] 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.[3]

Not to be confused with acetylmethadol[1]
Alphacetylmethadol
Clinical data
ATC code
  • None
Legal status
Legal status
  • AU: S8 (Controlled drug)
  • CA: Schedule I
  • DE: Anlage I (Authorized scientific use only)
  • US: Schedule I
Identifiers
IUPAC name
  • [(3R,6R)-6-(Dimethylamino)-4,4-diphenylheptan-3-yl] acetate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H31NO2
Molar mass353.506 g·mol−1
3D model (JSmol)
SMILES
  • CC[C@H](C(C[C@@H](C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C
InChI
  • 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. 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.
  3. 21 U.S.C. § 812(b)(1)


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