noracymethadol

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 6-(Methylamino)-4,4-diphenyl-3-heptanyl acetate

| image = Noracymethadol.svg

| image_class = skin-invert-image

| CAS_number = 1477-39-0

| CAS_supplemental =
5633-25-0 (hydrochloride)
7645-01-4 (gluconate)

| ATC_prefix = None

| ATC_suffix =

| PubChem = 15129

| ChemSpiderID = 14400

| C=22 | H=29 | N=1 | O=2

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

| StdInChI = 1S/C22H29NO2/c1-5-21(25-18(3)24)22(16-17(2)23-4,19-12-8-6-9-13-19)20-14-10-7-11-15-20/h6-15,17,21,23H,5,16H2,1-4H3

| StdInChIKey = VWCUGCYZZGRKEE-UHFFFAOYSA-N

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| pregnancy_category =

| 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_DE = Anlage I

| legal_US = Schedule I

| routes_of_administration =

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

| UNII = KU5U13XY7J

| KEGG = D05203

}}

Noracymethadol (INN) is a synthetic opioid analgesic related to methadone that was never marketed.{{cite book | vauthors = Macdonald F | title = Dictionary of Pharmacological Agents | date = 21 November 1996 | url = https://books.google.com/books?id=DeX7jgInYFMC&pg=PA47 | access-date = 11 May 2012 | publisher = CRC Press | isbn = 978-0-412-46630-4 | page = 1447}} In a clinical trial of postpartum patients it was reported to produce analgesia comparable to that of morphine but with less nausea, dizziness, and drowsiness.{{cite journal | vauthors = Gruber CM, Baptisti A | title = Estimating the acceptability of morphine and noracymethadol in postpartum patients | journal = Clinical Pharmacology and Therapeutics | volume = 4 | issue = 2| pages = 172–81 | year = 1963 | pmid = 13950878 | doi = 10.1002/cpt196342172 | s2cid = 19919842 }}{{cite journal | vauthors = Lister RE | title = The toxicity of some of the newer narcotic analgesics | journal = The Journal of Pharmacy and Pharmacology | volume = 18 | issue = 6 | pages = 364–83 | date = June 1966 | pmid = 4381372 | doi = 10.1111/j.2042-7158.1966.tb07890.x | s2cid = 32896981 }} Other side effects included salivation, ataxia, and respiratory depression that was reversible by naloxone. Similarly to many of its analogues, noracymethadol is a Schedule I controlled substance in the United States with an ACSCN of 9633 and 2013 annual manufacturing quota of 12 grammes. {{cite web | title = Controlled Substances in Schedule I | publisher = Drug Enforcement Administration - Office of Diversion Control | url = http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm | access-date = 2012-05-11 }} and is also controlled internationally under the United Nations Single Convention on Narcotic Drugs of 1961.{{cite book | first = Thomas | last = Nordegren | name-list-style = vanc | title = The A-Z Encyclopedia of Alcohol and Drug Abuse | url = https://books.google.com/books?id=4yaGePenGKgC&pg=PA468 | access-date = 11 May 2012 | date = 1 March 2002 | publisher = Universal-Publishers | isbn = 978-1-58112-404-0 | page = 468}} The salts known are the gluconate (free base conversion ratio 0.633) and hydrochloride (0.903).

Noracymethadol is an acetyl ester of methadol and it can be said with some precision that it is either the heroin or 6-monoacetylmorphine analogue of methadol, and being a methadol it exhibits optical isomerism. The other methadols (acetylmethadol, methadol &c) have at least four optical isomers (see Orlaam).