Structure via PubChem · Public domain (PubChem)
Codeine-N-oxide
Sign in to save'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.
Chemical data
- Formula
- C18H21NO4
- Molecular weight
- 315.4 g/mol
- IUPAC name
- (3S,4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-3-oxido-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium-7-ol
- SMILES
- C[N@@+]1(CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O)[O-]
- InChIKey
- BDLSDHWCOJPHIE-KFUGMXNISA-N
- XLogP
- 0.6
- Polar surface area
- 56.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 315.147058
Show 3 more facts
- chemical formula
- C₁₈H₂₁NO₄
- canonical SMILES
- C[N+]1(CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O)[O-]
- isomeric SMILES
- C[N@@+]1(CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O)[O-]
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
'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.
Excerpted from Wikipedia’s “Codeine-N-oxide” article, available under the CC BY-SA 4.0 licence.