Alphamethadol

Alphamethadol
Clinical data
ATC code	None;
Legal status
Legal status	AU: S9 (Prohibited substance); CA: Schedule I; DE: Anlage I (Authorized scientific use only); 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;
CompTox Dashboard (EPA)	DTXSID60872467 ;
Chemical and physical data
Formula	C21H29NO
Molar mass	311.461 g/mol g·mol−1
3D model (JSmol)	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),^{[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]

References

Template:Research help

^ 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.
^ ^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.
^ 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.
^ 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.

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[Commission2002-1] 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.

[Crime2006-2] 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.

[pmid60774-3] 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.

[pmid12373424-4] 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.

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See also

References