{{DISPLAYTITLE:Codeine-''N''-oxide}} {{Chembox | Name = Codeine-''N''-oxide | ImageFile = Codeine-N-oxide.svg | ImageClass = skin-invert-image | ImageSize = 150px | SystematicName = (1''S'',4''S'',5''R'',13''R'',14''S'',17''R'')-10-Methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0<sup>1,13</sup>.0<sup>5,17</sup>.0<sup>7,18</sup>]octadeca-7(18),8,10,15-tetraen-14-ol 4-oxide | OtherNames = |Section1={{Chembox Identifiers | CASNo = 3688-65-1 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = Z32OFX7V17 | PubChem = 5359929 | ChemSpiderID = 4514400 | SMILES = [O-][N@@+]4([C@@H]3Cc5c1c(O[C@@H]2[C@]1([C@H]3/C=C\[C@@H]2O)CC4)c(OC)cc5)C | InChI = 1/C18H21NO4/c1-19(21)8-7-18-11-4-5-13(20)17(18)23-16-14(22-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-,19-/m0/s1 | InChIKey = BDLSDHWCOJPHIE-KFUGMXNIBR | StdInChI = 1S/C18H21NO4/c1-19(21)8-7-18-11-4-5-13(20)17(18)23-16-14(22-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-,19-/m0/s1 | StdInChIKey = BDLSDHWCOJPHIE-KFUGMXNISA-N }} |Section2={{Chembox Properties | C=18 | H=21 | N=1 | O=4 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} |Section4={{Chembox Legal status | legal_AU = | legal_BR = A1 | legal_BR_comment = <ref>{{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}}</ref> | legal_US = | legal_UK = | legal_UN = }} }}
'''Codeine-''N''-oxide''' ('''genocodeine''') is an active metabolite of codeine.<ref>{{Cite journal |author1=Phillipson, J. David |author2=El-Dabbas, Samia W. |author3=Gorrod, John W. | title = In vivo and in vitro N-oxidation of morphine and codeine | journal = Biol. Oxid. Nitrogen, Proc. Int. Symp., 2nd | year = 1978 | pages = 125–30}}</ref> It is an opiate listed as a Schedule I controlled substance.<ref>{{CodeFedReg|21|1308|11}}</ref> It has a DEA ACSCN of 9053 and its annual manufacturing quota for 2013 was 602 grams.
Like morphine-''N''-oxide, it was studied as a potential pharmaceutical drug and is considerably weaker than codeine. The amine oxides of this type form as oxidation products of the parent chemical; virtually every morphine/codeine class opioid has an equivalent nitrogen derivative such as hydromorphone-''N''-oxide.
==References== {{Reflist|2}}
{{Opioidergics}}
Category:Amine oxides Category:Opiates