Structure via PubChem · Public domain (PubChem)
morphine-N-oxide
Sign in to save'Morphine-N-oxide (genomorphine') is an active opioid metabolite of morphine. Morphine itself, in trials with rats, is 11–22 times more potent than morphine-N-oxide subcutaneously and 39–89 times more potent intraperitoneally. However, pretreatment with amiphenazole or tacrine increases the potency of morphine-N-oxide in relation to morphine (intraperitoneally more so than in subcutaneous administration). A possible explanation is that morphine-N-oxide is rapidly inactivated in the liver and impairment of inactivation processes or enzymes increases functionality.
Chemical data
- Formula
- C17H19NO4
- Molecular weight
- 301.34 g/mol
- IUPAC name
- (4R,4aR,7S,7aR,12bS)-3-methyl-3-oxido-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium-7,9-diol
- SMILES
- C[N+]1(CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)O)O[C@H]3[C@H](C=C4)O)[O-]
- InChIKey
- AMAPEXTUMXQULJ-APQDOHRLSA-N
- XLogP
- 0.2
- Polar surface area
- 67.8 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 301.131408
Show 3 more facts
- chemical formula
- C₁₇H₁₉NO₄
- isomeric SMILES
- C[N+]1(CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)O)O[C@H]3[C@H](C=C4)O)[O-]
- canonical SMILES
- C[N+]1(CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(C=C4)O)[O-]
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
'Morphine-N-oxide (genomorphine') is an active opioid metabolite of morphine. Morphine itself, in trials with rats, is 11–22 times more potent than morphine-N-oxide subcutaneously and 39–89 times more potent intraperitoneally. However, pretreatment with amiphenazole or tacrine increases the potency of morphine-N-oxide in relation to morphine (intraperitoneally more so than in subcutaneous administration). A possible explanation is that morphine-N-oxide is rapidly inactivated in the liver and impairment of inactivation processes or enzymes increases functionality.
Morphine-N-oxide can also form as a decomposition product of morphine outside the body and may show up in assays of opium and poppy straw concentrate. Codeine and the semi-synthetics such as heroin, dihydrocodeine, dihydromorphine, hydromorphone, and hydrocodone also have equivalent amine oxide derivatives.
Excerpted from Wikipedia’s “morphine-N-oxide” article, available under the CC BY-SA 4.0 licence.