Alphamethadol

Alphamethadol

Clinical data
ATC code	None
Legal status
Legal status	AU: S9 (Prohibited) CA: Schedule I DE: Anlage I (Controlled) US: Schedule I
Identifiers
IUPAC name (3R,6R)-6-(dimethylamino)-4,4-diphenyl-3-heptanol
CAS Number	17199-54-1
PubChem (CID)	62709
ChemSpider	56456
ChEMBL	CHEMBL159660
Chemical and physical data
Formula	C21H29NO
Molar mass	311.461 g/mol
3D model (Jmol)	Interactive image
SMILES O[C@@H](C(c1ccccc1)(c2ccccc2)C[C@H](N(C)C)C)CC
InChI 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.^[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), 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]

See also

• Dimepheptanol
• Betamethadol
• Alphacetylmethadol

References

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. 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.