Structure via PubChem · Public domain (PubChem)
normorphine
Sign in to saveAlso known as demethylmorphine, desmethylmorphine, N-normorphine, (-)-normorphine
Normorphine is an opiate analogue, the N-demethylated derivative of morphine, that was first described in the 1950s when a large group of N-substituted morphine analogues were characterized for activity. The compound has relatively little opioid activity in its own right, but is a useful intermediate which can be used to produce both opioid antagonists such as nalorphine, and also potent opioid agonists such as N-phenethylnormorphine. with its formation from morphine catalyzed by the liver enzymes CYP3A4 and CYP2C8.
Chemical data
- Formula
- C16H17NO3
- Molecular weight
- 271.31 g/mol
- IUPAC name
- (4R,4aR,7S,7aR,12bS)-1,2,3,4,4a,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol
- SMILES
- C1CN[C@@H]2CC3=C4[C@@]15[C@H]2C=C[C@@H]([C@@H]5OC4=C(C=C3)O)O
- InChIKey
- ONBWJWYUHXVEJS-ZTYRTETDSA-N
- XLogP
- 0.3
- Polar surface area
- 61.7 Ų
- H-bond donors
- 3
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Has part
- carbon
- Mass
- 271.120843
Show 4 more facts
- isomeric SMILES
- Oc1ccc2c3c1O[C@H]1[C@@H](O)C=C[C@H]4[C@@H](C2)NCC[C@]314
- chemical formula
- C₁₆H₁₇NO₃
- found in taxon
- Valsa sordida
- canonical SMILES
- C1CNC2CC3=C4C15C2C=CC(C5OC4=C(C=C3)O)O
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Normorphine is an opiate analogue, the N-demethylated derivative of morphine, that was first described in the 1950s when a large group of N-substituted morphine analogues were characterized for activity. The compound has relatively little opioid activity in its own right, but is a useful intermediate which can be used to produce both opioid antagonists such as nalorphine, and also potent opioid agonists such as N-phenethylnormorphine. with its formation from morphine catalyzed by the liver enzymes CYP3A4 and CYP2C8.
Normorphine is a controlled substance listed under the Single Convention On Narcotic Drugs 1961 and the laws in various states implementing it; for example, in the United States it is a Schedule I Narcotic controlled substance, with an ACSCN of 9313 and an annual aggregate manufacturing quota of 18 grams in 2014, unchanged from the prior year. The salts in use are the free base hexahydrate (free base conversion ratio 0.715), and hydrochloride (0.833).
Excerpted from Wikipedia’s “normorphine” article, available under the CC BY-SA 4.0 licence.