norcodeine (stereochemistry defined)

Also 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.

In the Vinony graph

Vinony's link graph records 17 inbound references to norcodeine (stereochemistry defined), and connects out to (+)-catechin, butorphanol and medication.

It sits within the topics 4,5-Epoxymorphinans, Chemical pages without DrugBank identifier and Drugboxes which contain changes to verified fields.

Vinony links it to 10 Wikipedia language editions.

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 Å²
H-bond donors: 2
H-bond acceptors: 4
Formal charge: 0

via PubChem

Wikidata facts

Has part: carbon
Mass: 285.136493
Has use: drug

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)

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Encyclopedic overview

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Contents

See also
References

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.