normethadone

{{Short description|Synthetic opioid}}

{{Distinguish|normethandrone}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 462263227

| IUPAC_name = 6-dimethylamino-4,4-diphenyl-hexan-3-one

| image = Normethadone.png

| image_class = skin-invert-image

| tradename = Cophylac

| pregnancy_AU =

| pregnancy_US =

| 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_DE = Anlage III

| legal_UK =

| legal_US = Schedule I

| legal_status =

| routes_of_administration =

| bioavailability = 100%

| protein_bound =

| metabolism = liver

| elimination_half-life = 14 days

| excretion = Urine

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 467-85-6

| CAS_supplemental =
847-84-7 (HCl)

| ATC_prefix = R05

| ATC_suffix = DA06

| PubChem = 10090

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 9687

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

| UNII = KR2L2A68XL

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

| KEGG = D07384

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 346331

| C=20 | H=25 | N=1 | O=1

| smiles = O=C(C(c1ccccc1)(c2ccccc2)CCN(C)C)CC

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C20H25NO/c1-4-19(22)20(15-16-21(2)3,17-11-7-5-8-12-17)18-13-9-6-10-14-18/h5-14H,4,15-16H2,1-3H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = WCJFBSYALHQBSK-UHFFFAOYSA-N

}}

Normethadone (INN, BAN; brand names Ticarda, Cophylac, Dacartil, Eucopon, Mepidon, Noramidone, Normedon, and others), also known as desmethylmethadone or phenyldimazone, is a synthetic opioid analgesic and antitussive agent.{{citation needed|date=September 2015}}

Normethadone is listed under the Single Convention on Narcotic Drugs 1961 and is a Schedule I Narcotic controlled substance in the United States, with a DEA ACSCN of 9635 and an annual manufacturing quota of 2 grams. It has an effective span of action for about 14 days, and is 12 to 20 times stronger than morphine. {{cite web | title = Quotas - 2014 | url = http://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm | publisher = U.S. Department of Justice, Drug Enforcement Administration | work = Diversion Control Division | access-date = 2016-02-27 | archive-date = 2016-03-04 | archive-url = https://web.archive.org/web/20160304053357/http://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm | url-status = dead }} The salts in use are the hydrobromide (free base conversion ratio 0.785), hydrochloride (0.890), methyliodide (0.675), oxalate (0.766), picrate (0.563), and the 2,6-ditertbutylnapthalindisulphonate (0.480).{{cite book | vauthors = Nordegren T | chapter = Normethadone | chapter-url = https://books.google.com/books?id=4yaGePenGKgC&q=Normethadone&pg=PA469 |title=The A-Z encyclopedia of alcohol and drug abuse |date=2002 |publisher=Brown Walker Press |location=Parkland, Fla. |isbn=978-1-58112-404-0 | page = 470 }}