Codeine-N-oxide
{{DISPLAYTITLE:Codeine-N-oxide}}
{{Chembox
| Name = Codeine-N-oxide
| ImageFile = Codeine-N-oxide.svg
| ImageClass = skin-invert-image
| ImageSize = 150px
| SystematicName = (1S,4S,5R,13R,14S,17R)-10-Methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]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
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|Section3={{Chembox Hazards
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|Section4={{Chembox Legal status
| legal_AU =
| 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_US =
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}}
Codeine-N-oxide (genocodeine) is an active metabolite of codeine.{{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}} It is an opiate listed as a Schedule I controlled substance.{{CodeFedReg|21|1308|11}} 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.