Alphacetylmethadol

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
  • 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
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H31NO2
Molar mass353.506 g·mol−1
3D model (JSmol)
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

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]

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. 1 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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