Alphamethadol information

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;
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] 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,^[4] similarly to those of alphacetylmethadol (α-acetylmethadol).^[5]

^ 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.

[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.

Alphamethadol information

and 15 Related for: Alphamethadol information

Alphamethadol

Dimepheptanol

Brazilian Controlled Drugs and Substances Act

Alphacetylmethadol

Drug policy of India

Betamethadol

Drugs controlled by the UK Misuse of Drugs Act

C21H29NO

Opium Law

Single Convention on Narcotic Drugs

Controlled Drugs and Substances Act

List of opioids

Misuse of Drugs Act 1977

Methade

List of compounds with carbon number 21

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
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