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Codeine-N-oxide

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Codeine-N-oxide
Names
Systematic IUPAC name (1S,4S,5R,13R,14S,17R)-10-Methoxy-4-methyl-12-oxa-4-azapentacyclooctadeca-7(18),8,10,15-tetraen-14-ol 4-oxide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.020.899 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=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/s1Key: BDLSDHWCOJPHIE-KFUGMXNISA-N
  • 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/s1Key: BDLSDHWCOJPHIE-KFUGMXNIBR
SMILES
  • 4(3Cc5c1c(O21(3/C=C\2O)CC4)c(OC)cc5)C
Properties
Chemical formula C18H21NO4
Molar mass 315.369 g·mol
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Codeine-N-oxide (genocodeine) is an active metabolite of codeine. It is an opiate listed as a Schedule I controlled substance. 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

  1. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. Phillipson, J. David; El-Dabbas, Samia W.; Gorrod, John W. (1978). "In vivo and in vitro N-oxidation of morphine and codeine". Biol. Oxid. Nitrogen, Proc. Int. Symp., 2nd: 125–30.
  3. 21 CFR 1308.11
Opioid receptor modulators
μ-opioid
(MOR)
Agonists
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full list)
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δ-opioid
(DOR)
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κ-opioid
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Nociceptin
(NOP)
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Others
  • Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)
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