Acetylmethadol

Acetylmethadol
Clinical data
ATC code	None;
Legal status
Legal status	AU: S8 (Controlled drug); 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;
PubChem CID	10517;
DrugBank	DB01433;
ChemSpider	10080;
CompTox Dashboard (EPA)	DTXSID2023274 ;
ECHA InfoCard	100.007.368
Chemical and physical data
Formula	C23H31NO2
Molar mass	353.498 g/mol 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;

Acetylmethadol (INN), also known as methadyl acetate (USAN), is a synthetic opioid analgesic.^[2] 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.^[2] Hence, acetylmethadol has four possible optical isomers.^[2] 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.^[2]

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 1993. 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 grammes as of 2013, except LAAM, which is 4 grammes.^[3]

References

Template:Research help

^ 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.
^ ^a ^b ^c ^d 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 21 U.S.C. § 812(b)(1)

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[Miller2002-1] 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.

[pmid12373424-2] 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[3] 21 U.S.C. § 812(b)(1)

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