Alphamethadol

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Alphamethadol
Alphamethadol.svg
Systematic (IUPAC) name
(3R,6R)-6-(dimethylamino)-4,4-diphenyl-3-heptanol
Clinical data
Legal status Prohibited (S9) (AU) Schedule I (US)
Identifiers
CAS number 17199-54-1
ATC code None
PubChem CID 62709
ChemSpider 56456
ChEMBL CHEMBL159660
Chemical data
Formula C21H29NO 
Mol. mass 311.461 g/mol

Alphamethadol (INN), or α-methadol, also known as alfametadol, is a synthetic opioid analgesic.[1] It is an isomer of dimepheptanol (methadol), the other being betamethadol (β-methadol).[2] Alphamethadol is composed of two isomers itself, L-α-methadol, and D-α-methadol.[2] The former compound, L-α-methadol, is an important active metabolite of levacetylmethadol (LAAM),[citation needed] an opioid substitute drug that is used clinically. Both of alphamethadol's isomers bind to and activate the μ-opioid receptor and are active as opioid analgesics,[3] similarly to those of alphacetylmethadol (α-acetylmethadol).[4]

Alphamethadol is a Schedule I controlled substance in the United States and has a DEA ACSCN of 9605 and an annual aggregate manufacturing quota of 2 grammes.

See also[edit]

References[edit]

  1. ^ British Pharmacopoeia Commission (1 February 2002). British Approved Names 2002. The Stationery Office. p. 9. ISBN 978-0-11-322558-3. Retrieved 15 May 2012. 
  2. ^ a b United Nations Office on Drugs and Crime (2006). Dictionnaire Multilingue Des Stupéfiants Et Des Substances Psychotropes Placés Sous Contrôle International. United Nations Publications. p. 103. ISBN 978-92-1-048117-5. Retrieved 15 May 2012. 
  3. ^ Horng JS, Smits SE, Wong DT (August 1976). "The binding of the optical isomers of methadone, alpha-methadol, alpha-acetylmethadol and their N-demethylated derivatives to the opiate receptors of rat brain". Research Communications in Chemical Pathology and Pharmacology 14 (4): 621–9. PMID 60774. 
  4. ^ 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.