Alphacetylmethadol

{{Short description|Synthetic opioid analgesic drug}}

{{hatnote|Not to be confused with acetylmethadol{{cite book | author = Richard Lawrence Miller | title = The Encyclopedia of Addictive Drugs | url = https://books.google.com/books?id=G7As-qawdzMC&pg=PA222 | accessdate = 15 May 2012 | date = 30 December 2002 | publisher = Greenwood Publishing Group | isbn = 978-0-313-31807-8 | page = 222}}}}

{{Drugbox

| IUPAC_name = [(3R,6R)-6-(Dimethylamino)-4,4-diphenylheptan-3-yl] acetate

| image = Alphacetylmethadol Enantiomers V1.svg

| image_class = skin-invert-image

| alt = Skeletal formulas of (R,R)-alphacetylmethadol (left), and (S,S)-alphacetylmethadol (right)

| image2 = (R,R) and (S,S)-Alphacetylmethadol isomers ball.png

| alt2 = Ball-and-stick models of (R,R)-alphacetylmethadol (left), and (S,S)-alphacetylmethadol (right)

| width = 320

| CAS_number = 17199-58-5

| CAS_supplemental =

| ATC_prefix = None

| ATC_suffix =

| PubChem = 22308

| DrugBank_Ref =

| DrugBank = DB01555

| ChEMBL = 2107793

| ChemSpiderID = 20937

| UNII = BXF83S0HEL

| KEGG = D12660

| C = 23 | H=31 | N=1 | O=2

| smiles = CC[C@H](C(C[C@@H](C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C

| StdInChI = 1S/C23H31NO2/c1-6-22(26-19(3)25)23(17-18(2)24(4)5,20-13-9-7-10-14-20)21-15-11-8-12-16-21/h7-16,18,22H,6,17H2,1-5H3/t18-,22-/m1/s1

| StdInChIKey = XBMIVRRWGCYBTQ-XMSQKQJNSA-N

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| pregnancy_category =

| legal_AU = S8

| 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

| routes_of_administration =

}}

Alphacetylmethadol (INN), or α-acetylmethadol (AAM), is a synthetic opioid analgesic.{{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 }} Its levorotary enantiomer, levacetylmethadol, is an FDA-approved treatment for opioid addiction; however as of 2003 it is no longer used in the United States for this purpose. Alphacetylmethadol is very similar in structure to methadone, a widely prescribed treatment for opioid addiction. In the United States, it is a Schedule I controlled substance under the Controlled Substances Act (presumably because it was never marketed in the US, as is the case with other common opiate/opioid medications such as heroin and prodine),{{uscsub|21|812|b|1}} with an ACSCN of 9603 and a 2013 annual manufacturing quota of 2 grammes.{{cn|date=October 2023}}