Alphamethadol

Not to be confused with Alphacetylmethadol.
Alphamethadol
Clinical data
ATC code
  • None
Legal status
Legal status
Identifiers
  • (3R,6R)-6-(dimethylamino)-4,4-diphenyl-3-heptanol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H29NO
Molar mass311.469 g·mol−1
3D model (JSmol)
  • O[C@@H](C(c1ccccc1)(c2ccccc2)C[C@H](N(C)C)C)CC
  • InChI=1S/C21H29NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17,20,23H,5,16H2,1-4H3/t17-,20-/m1/s1
  • Key:QIRAYNIFEOXSPW-YLJYHZDGSA-N

Alphamethadol (INN), or α-methadol, also known as alfametadol, is a synthetic opioid analgesic.[2] It is an isomer of dimepheptanol (methadol), the other being betamethadol (β-methadol).[3] Alphamethadol is composed of two isomers itself, L-α-methadol, and D-α-methadol.[3] Both of alphamethadol's isomers bind to and activate the μ-opioid receptor and are active as opioid analgesics,[4] similarly to those of alphacetylmethadol (α-acetylmethadol).[5]

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.