Codeine-N-oxide

Codeine-N-oxide

Names
Systematic IUPAC name (1S,4S,5R,13R,14S,17R)-10-Methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,13.0^5,17.0^7,18]octadeca-7(18),8,10,15-tetraen-14-ol 4-oxide
Identifiers
CAS Number	3688-65-1
ChemSpider	4514400
Jmol interactive 3D	Image
PubChem	5359929
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/s1 Key: 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/s1 Key: BDLSDHWCOJPHIE-KFUGMXNIBR
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
Properties
Chemical formula	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

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