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]

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-di(phenyl)heptan-3-yl] acetate
CAS Number	1553-31-7
ChEMBL	ChEMBL2107793
CompTox Dashboard (EPA)	DTXSID70169198
Chemical and physical data
Formula	C23H31NO2
Molar mass	353.506 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CN(C)[C@H](C)CC(c1ccccc1)(c1ccccc1)[C@H](OC(=O)C)CC.CN(C)[C@@H](C)CC(c1ccccc1)(c1ccccc1)[C@@H](OC(=O)C)CC
InChI InChI=InChI=1S/2C23H31NO2/c2*1-6-22(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/h2*7-16,18,22H,6,17H2,1-5H3/t2*18-,22+/m10/s1 Key:HYAUQUUCBMIXJW-UAILNNRFSA-N

See also

• Levacetylmethadol
• Acetylmethadol
• Betacetylmethadol
• Alphamethadol

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)