Acetylmethadol

Not to be confused with alphacetylmethadol (α-acetylmethadol) or levacetylmethadol (L-α-acetylmethadol).^[1]

Acetylmethadol, also known as methadyl acetate, is a synthetic opioid analgesic.^[3] It is a racemic mixture of alphacetylmethadol (α-acetylmethadol) and betacetylmethadol (β-acetylmethadol), which are in turn racemic mixtures of levacetylmethadol (LAAM; L-α-acetylmethadol) and D-α-acetylmethadol and L-β-acetylmethadol and D-β-acetylmethadol, respectively.^[3] Hence, acetylmethadol has four possible optical isomers.^[3] All of these isomers have been shown to partially or fully substitute for the discriminative stimulus effects of heroin in rats, and thus it can be inferred that, in addition to LAAM which is used clinically as such, they are all likely to be active opioid analgesics in humans.^[3]

Acetylmethadol

Clinical data
Other names	methadyl acetate (USAN US)
ATC code	None
Legal status
Legal status	AU: S8 (Controlled drug) BR: Class A1 (Narcotic drugs)[2] CA: Schedule I DE: Anlage I (Authorized scientific use only) US: Schedule I
Identifiers
IUPAC name (±)-6-(dimethylamino)-4,4-diphenyl-3-heptanyl acetate
CAS Number	509-74-0 Y
PubChem CID	10517
DrugBank	DB01433
ChemSpider	10080
UNII	L59OC40KWJ
KEGG	D04973
CompTox Dashboard (EPA)	DTXSID2023274
ECHA InfoCard	100.007.368
Chemical and physical data
Formula	C23H31NO2
Molar mass	353.506 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(OC(C(c1ccccc1)(c2ccccc2)CC(N(C)C)C)CC)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 Key:XBMIVRRWGCYBTQ-UHFFFAOYSA-N

In the United States, acetylmethadol and its individual isomers are all Schedule I drugs under the Controlled Substances Act, except LAAM, which is Schedule II and was used clinically until 2003. Acetylmethadol has an ACSCN of 9601. The isomers have individual ACSCNs, which are as follows: Alphacetylmethadol 9603, Betacetylmethadol 9607, LAAM 9648. All of the above have annual manufacturing quotas of 2 grams as of 2013, except LAAM, which is 4 grams.^[4]

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)