Compound: Morphine N-oxide
SMILES: O1c2c(O)ccc3c2[C@@]45[C@@H]1[C@@H](O)C=C[C@H]4[C@H]([N+]([O-])(C)CC5)C3
InChIKey: AMAPEXTUMXQULJ-APQDOHRLSA-N
Synonyms: Morphine N-oxide, MORPHINE-N-OXIDE, 639-46-3, DEA No. 9307, EINECS 211-355-8, 9E77NL2Y9I, MORPHINE, N-OXIDE, IDS-NM-012, DTXSID301018237, Morphinan-3,6-alpha-diol, 7,8-didehydro-4,5-alpha-epoxy-17-methyl-, 17-oxide, Morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-methyl-, (5-alpha,6-alpha)-, 17-oxide, MORPHINE SULFATE IMPURITY F [EP IMPURITY], (17S)-7,8-DIDEHYDRO-4,5.ALPHA.-EPOXY-17-METHYLMORPHINAN-3,6.ALPHA.-DIOL 17-OXIDE, MORPHINE SULFATE IMPURITY F (EP IMPURITY), RefChem:392625, DTXCID301476471, (4R,4aR,7S,7aR,12bS)-3-methyl-3-oxido-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinoline-3-ium-7,9-diol, (4R,4aR,7S,7aR,12bS)-3-methyl-3-oxido-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-3-ium-7,9-diol, (17S)-7,8-Didehydro-4,5alpha-epoxy-17-methylmorphinan-3,6alpha-diol 17-oxide, MORPHINAN-3,6-DIOL, 7,8-DIDEHYDRO-4,5-EPOXY-17-METHYL-(5ALPHA,6ALPHA)-, 17-OXIDE, MORPHINAN-3,6-DIOL, 7,8-DIDEHYDRO-4,5-EPOXY-17-METHYL-(5.ALPHA.,6.ALPHA.)-, 17-OXIDE, Morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-methyl-, (5-alpha,6-alpha)-, 17-oxide (9CI), Genomorphine, Genomorphin, Morphine oxide, Morphine N-Oxide (100?g/ml in Methanol), UNII-9E77NL2Y9I, (S)-2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]-propanoic Acid Methyl Ester;, SCHEMBL619646, CHEBI:7002, SCHEMBL29449358, AMAPEXTUMXQULJ-APQDOHRLSA-N, Morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-methyl- (5.alpha.,6.alpha.)-, 17-oxide, NS00042110, Q6913407, MORPHINE HYDROCHLORIDE IMPURITY F [EP IMPURITY], (5?,6?)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol 17-Oxide;, (17S)-7,8-Didehydro-4,5alpha-epoxy-17-methylmorphinan-3,6alpha-diol 17-Oxide (Morphine N-Oxide), (3R,4R,4aR,7S,7aR,12bS)-3-Methyl-3-oxo-2,3,4,4a,7,7a-hexahydro-1H-4,12-methano-3lambda~5~-[1]benzofuro[3,2-e]isoquinoline-7,9-diol
Theoretical properties:
molecular_formula: C17H19NO4
molecular_weight: 301.34 g/mol
exact_mass: 301.13140809 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 0
heavy_atom_count: 22
topological_polar_surface_area: 67.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Morphine N-oxide is a tertiary amine oxide and a morphinane alkaloid.
wikipedia: 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.
Morphine-N-oxide has a DEA ACSCN of 9307 and annual production quota of 655 grams in 2013.  It is a Schedule I controlled substance in the US.