Alphamethadol

Alphamethadol
Clinical data
ATC code	None;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class A1 (Narcotic drugs); CA: Schedule I; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule I;
Identifiers
	IUPAC name (3R,6R)-6-(dimethylamino)-4,4-diphenyl-3-heptanol;
CAS Number	17199-54-1;
PubChem CID	62709;
DrugBank	DB01498;
ChemSpider	56456;
UNII	XBD99QNI42;
KEGG	D12674 ;
ChEMBL	ChEMBL159660;
CompTox Dashboard (EPA)	DTXSID60872467 ;
Chemical and physical data
Formula	C21H29NO
Molar mass	311.469 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.^[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]

Legal status

Australia

Alphamethadol is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (February 2017).^[6] 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.^[6]

References

^ 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.
^ 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. S2CID 19815273.
^ ^a ^b Poisons Standard October 2015 https://www.legislation.gov.au/Details/F2017L00057

This analgesic-related article is a stub. You can help Wikipedia by expanding it.

[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.

[Commission2002-2] 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.

[Crime2006-3] 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.

[pmid60774-4] 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.

[pmid12373424-5] 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.

[Poisons_Standard-6] Poisons Standard October 2015 https://www.legislation.gov.au/Details/F2017L00057

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Clinical data

ATC code	None
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class A1 (Narcotic drugs)^[1] CA: Schedule I DE: Anlage I (Authorized scientific use only) UK: Class A US: Schedule I
Identifiers
IUPAC name (3R,6R)-6-(dimethylamino)-4,4-diphenyl-3-heptanol
CAS Number	17199-54-1
PubChem CID	62709
DrugBank	DB01498
ChemSpider	56456
UNII	XBD99QNI42
KEGG	D12674^Y
ChEMBL	ChEMBL159660
CompTox Dashboard (EPA)	DTXSID60872467
Chemical and physical data
Formula	C₂₁H₂₉NO
Molar mass	311.469 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