alphamethadol

{{Short description|Synthetic opioid analgesic drug}}

{{distinguish|Alphacetylmethadol}}

{{Drugbox

| IUPAC_name = (3R,6R)-6-(dimethylamino)-4,4-diphenyl-3-heptanol

| image = Alphamethadol.svg

| image_class = skin-invert-image

| CAS_number = 17199-54-1

| CAS_supplemental =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = XBD99QNI42

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D12674

| ATC_prefix = None

| ATC_suffix =

| PubChem = 62709

| DrugBank_Ref =

| DrugBank = DB01498

| ChemSpiderID = 56456

| ChEMBL = 159660

| C=21 | H=29 | N=1 | O=1

| smiles = O[C@@H](C(c1ccccc1)(c2ccccc2)C[C@H](N(C)C)C)CC

| StdInChI = 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

| StdInChIKey = QIRAYNIFEOXSPW-YLJYHZDGSA-N

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| pregnancy_category =

| legal_AU = S9

| legal_BR = A1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_CA = Schedule I

| legal_US = Schedule I

| legal_DE = Anlage I

| legal_UK = Class A

| routes_of_administration =

}}

Alphamethadol (INN), or α-methadol, also known as alfametadol, is a synthetic opioid analgesic.{{cite book | author = British Pharmacopoeia Commission | title = British Approved Names 2002 | url = https://books.google.com/books?id=zruxjioUFngC&pg=PA9 | access-date = 15 May 2012 | date = 1 February 2002 | publisher = The Stationery Office | isbn = 978-0-11-322558-3 | page = 9}} It is an isomer of dimepheptanol (methadol), the other being betamethadol (β-methadol).{{cite book | author = United Nations Office on Drugs and Crime | title = Dictionnaire Multilingue Des Stupéfiants Et Des Substances Psychotropes Placés Sous Contrôle International | url = https://books.google.com/books?id=RPAphv7h4-IC&pg=PA103 | access-date = 15 May 2012 | year = 2006 | publisher = United Nations Publications | isbn = 978-92-1-048117-5 | page = 103}} Alphamethadol is composed of two isomers itself, L-α-methadol, and D-α-methadol. Both of alphamethadol's isomers bind to and activate the μ-opioid receptor and are active as opioid analgesics,{{cite journal | vauthors = Horng JS, Smits SE, Wong DT | title = The binding of the optical isomers of methadone, alpha-methadol, alpha-acetylmethadol and their N-demethylated derivatives to the opiate receptors of rat brain | journal = Research Communications in Chemical Pathology and Pharmacology | volume = 14 | issue = 4 | pages = 621–9 |date=August 1976 | pmid = 60774 }} similarly to those of alphacetylmethadol (α-acetylmethadol).{{cite journal | vauthors = Newman JL, Vann RE, May EL, Beardsley PM | title = Heroin discriminative stimulus effects of methadone, LAAM and other isomers of acetylmethadol in rats | journal = Psychopharmacology | volume = 164 | issue = 1 | pages = 108–14 |date=October 2002 | pmid = 12373424 | doi = 10.1007/s00213-002-1198-8 | s2cid = 19815273 }}