# Codeine-N-oxide

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Codeine-N-oxide
> Markdown URL: https://mediated.wiki/source/Codeine-N-oxide.md
> Source: https://en.wikipedia.org/wiki/Codeine-N-oxide
> Source revision: 1268793899
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{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](/source/Di%C3%A1rio_Oficial_da_Uni%C3%A3o) |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_US = 
| legal_UK = 
| legal_UN = 
}}
}}

'''Codeine-''N''-oxide''' ('''genocodeine''') is an active [metabolite](/source/metabolite) of [codeine](/source/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](/source/opiate) listed as a [Schedule I](/source/List_of_Schedule_I_drugs_(US)) [controlled substance](/source/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](/source/Morphine-N-oxide), it was studied as a potential pharmaceutical drug and is considerably weaker than codeine.  The [amine oxide](/source/amine_oxide)s 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

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Adapted from the Wikipedia article [Codeine-N-oxide](https://en.wikipedia.org/wiki/Codeine-N-oxide) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Codeine-N-oxide?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.