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norcodeine (stereochemistry defined)
Sign in to saveAlso known as N-Norcodeine, N-demethylcodeine
Norcodeine is an opiate analogue that is the N-demethylated derivative of codeine. It has relatively little opioid activity in its own right, but is formed as a metabolite of codeine following ingestion.
Chemical data
- Formula
- C17H19NO3
- Molecular weight
- 285.34 g/mol
- IUPAC name
- (4R,4aR,7S,7aR,12bS)-9-methoxy-1,2,3,4,4a,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
- SMILES
- COC1=C2C3=C(C[C@@H]4[C@H]5[C@]3(CCN4)[C@@H](O2)[C@H](C=C5)O)C=C1
- InChIKey
- HKOIXWVRNLGFOR-KOFBORESSA-N
- XLogP
- 0.7
- Polar surface area
- 50.7 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
Show 5 more facts
- chemical formula
- C₁₇H₁₉NO₃
- canonical SMILES
- COC1=C2C3=C(CC4C5C3(CCN4)C(O2)C(C=C5)O)C=C1
- found in taxon
- Papaver somniferum
- isomeric SMILES
- [C@@]123C4=C5C(=CC=C4C[C@H]([C@@]1(C=C[C@@H]([C@@H]2O5)O)[H])NCC3)OC
- subject has role
- metabolite
Sources (2)
via Wikidata · CC0
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Encyclopedic overview
2 sectionsContents
- See also
- References
Norcodeine is an opiate analogue that is the N-demethylated derivative of codeine. It has relatively little opioid activity in its own right, but is formed as a metabolite of codeine following ingestion.
Norcodeine is a Schedule I Narcotic controlled substance in the US with the ACSCN of 9309 and zero annual manufacturing quota. The salts in use are the acetate (free base conversion ratio 0.826), hydroiodide (0.662), hydrochloride (0.759), nitrate (0.819), platinichloride (0.582), and sulphate (0.744).
Excerpted from Wikipedia’s “norcodeine (stereochemistry defined)” article, available under the CC BY-SA 4.0 licence.