Chemistry:Alphamethadol

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Short description: Synthetic opioid analgesic drug
Alphamethadol
Alphamethadol.svg
Clinical data
ATC code
  • None
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC21H29NO
Molar mass311.469 g·mol−1
3D model (JSmol)

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]

Legal status

Australia

Alphamethadol is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (February 2017).[5] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.[5]

See also

References

  1. British Pharmacopoeia Commission (1 February 2002). British Approved Names 2002. The Stationery Office. p. 9. ISBN 978-0-11-322558-3. https://books.google.com/books?id=zruxjioUFngC&pg=PA9. Retrieved 15 May 2012. 
  2. 2.0 2.1 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. https://books.google.com/books?id=RPAphv7h4-IC&pg=PA103. Retrieved 15 May 2012. 
  3. "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. August 1976. PMID 60774. 
  4. "Heroin discriminative stimulus effects of methadone, LAAM and other isomers of acetylmethadol in rats". Psychopharmacology 164 (1): 108–14. October 2002. doi:10.1007/s00213-002-1198-8. PMID 12373424. 
  5. 5.0 5.1 Poisons Standard October 2015 https://www.legislation.gov.au/Details/F2017L00057