acetylmethadol

{{Short description|Synthetic opioid analgesic}}

{{hatnote|Not to be confused with alphacetylmethadol (α-acetylmethadol) or levacetylmethadol (L-α-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 = (±)-6-(dimethylamino)-4,4-diphenyl-3-heptanyl acetate

| image = Acetylmethadol.svg

| image_class = skin-invert-image

| USAN=methadyl acetate

| CAS_number = 509-74-0

| CAS_number_Ref = {{cascite|correct|CAS}}

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

| UNII = L59OC40KWJ

| KEGG = D04973

| CAS_supplemental =

| ATC_prefix = None

| ATC_suffix =

| PubChem = 10517

| DrugBank = DB01433

| ChemSpiderID = 10080

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

| smiles = O=C(OC(C(c1ccccc1)(c2ccccc2)CC(N(C)C)C)CC)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

| StdInChIKey = XBMIVRRWGCYBTQ-UHFFFAOYSA-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 =

}}

Acetylmethadol, also known as methadyl acetate, 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 }} It is a racemic mixture of alphacetylmethadol (α-acetylmethadol) and betacetylmethadol (β-acetylmethadol), which are in turn racemic mixtures of levacetylmethadol (LAAM; L-α-acetylmethadol) and D-α-acetylmethadol and L-β-acetylmethadol and D-β-acetylmethadol, respectively. Hence, acetylmethadol has four possible optical isomers. All of these isomers have been shown to partially or fully substitute for the discriminative stimulus effects of heroin in rats, and thus it can be inferred that, in addition to LAAM which is used clinically as such, they are all likely to be active opioid analgesics in humans.

In the United States, acetylmethadol and its individual isomers are all Schedule I drugs under the Controlled Substances Act, except LAAM, which is Schedule II and was used clinically until 2003. Acetylmethadol has an ACSCN of 9601. The isomers have individual ACSCNs, which are as follows: Alphacetylmethadol 9603, Betacetylmethadol 9607, LAAM 9648. All of the above have annual manufacturing quotas of 2 grams as of 2013, except LAAM, which is 4 grams.{{uscsub|21|812|b|1}}