Codeine-N-oxide

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Codeine-N-oxide
Codeine-N-oxide.svg
Names
Systematic IUPAC name
(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
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.020.899
Properties
C18H21NO4
Molar mass 315.37 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Codeine-N-oxide (genocodeine) is an active metabolite of codeine.[1] It is an opiate listed as a Schedule I controlled substance.[2] It has a DEA ACSCN of 9053 and its annual manufacturing quota for 2013 was 602 grammes.

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[edit]

  1. ^ 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. 
  2. ^ 21 C.F.R. 1308.11