Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C17H17NO3 |
| Molecular Weight | 283.3218 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CC[C@@]23[C@H]4OC5=C2C(C[C@@H]1[C@@H]3C=CC4=O)=CC=C5O
InChI
InChIKey=PFBSOANQDDTNGJ-YNHQPCIGSA-N
InChI=1S/C17H17NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,16,19H,6-8H2,1H3/t10-,11+,16-,17-/m0/s1
| Molecular Formula | C17H17NO3 |
| Molecular Weight | 283.3218 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/17094451 | https://www.ncbi.nlm.nih.gov/pubmed/1688995 | https://www.ncbi.nlm.nih.gov/pubmed/6135574 | https://www.ncbi.nlm.nih.gov/pubmed/7078349
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/17094451 | https://www.ncbi.nlm.nih.gov/pubmed/1688995 | https://www.ncbi.nlm.nih.gov/pubmed/6135574 | https://www.ncbi.nlm.nih.gov/pubmed/7078349
Morphinone is an oxidation product of morphine with weak agonistic activity toward mu opioid receptor. Morphinone is the intermediate when morphine is being converted to hydromorphone. Morphinone is toxic compound, subcutaneous administration of morphinone produced a reduction of hepatic non-protein sulfhydryl concentration. Glutathione or cysteine significantly decrease Morphinone toxicity.
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Direct analysis of donor-acceptor distance and relationship to isotope effects and the force constant for barrier compression in enzymatic H-tunneling reactions. | 2010-08-18 |
|
| Parallel pathways and free-energy landscapes for enzymatic hydride transfer probed by hydrostatic pressure. | 2009-05-25 |
|
| Barrier compression enhances an enzymatic hydrogen-transfer reaction. | 2009 |
|
| Correction of pre-steady-state KIEs for isotopic impurities and the consequences of kinetic isotope fractionation. | 2008-12-18 |
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| Incorporation of hydrostatic pressure into models of hydrogen tunneling highlights a role for pressure-modulated promoting vibrations. | 2008-09-16 |
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| Solvent as a probe of active site motion and chemistry during the hydrogen tunnelling reaction in morphinone reductase. | 2008-09-15 |
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| Deep tunneling dominates the biologically important hydride transfer reaction from NADH to FMN in morphinone reductase. | 2008-06-04 |
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| Mutagenesis of morphinone reductase induces multiple reactive configurations and identifies potential ambiguity in kinetic analysis of enzyme tunneling mechanisms. | 2007-11-14 |
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| Live cell monitoring of mu-opioid receptor-mediated G-protein activation reveals strong biological activity of close morphine biosynthetic precursors. | 2007-09-14 |
|
| Induction of non-apoptotic cell death by morphinone in human promyelocytic leukemia HL-60 cells. | 2006-11-11 |
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| Alpha-secondary isotope effects as probes of "tunneling-ready" configurations in enzymatic H-tunneling: insight from environmentally coupled tunneling models. | 2006-11-01 |
|
| Hydrogen tunnelling in enzyme-catalysed H-transfer reactions: flavoprotein and quinoprotein systems. | 2006-08-29 |
|
| Pharmacological action of Panax ginseng on the behavioral toxicities induced by psychotropic agents. | 2005-09 |
|
| Decoration of the aromatic ring of dihydrocodeinone (hydrocodone) and 14-hydroxydihydrocodeinone (oxycodone). | 2005-08-05 |
|
| Role of active site residues and solvent in proton transfer and the modulation of flavin reduction potential in bacterial morphinone reductase. | 2005-07-22 |
|
| Bioactivation of morphine in human liver: isolation and identification of morphinone, a toxic metabolite. | 2005-07 |
|
| Reaction of morphinone reductase with 2-cyclohexen-1-one and 1-nitrocyclohexene: proton donation, ligand binding, and the role of residues Histidine 186 and Asparagine 189. | 2005-03-18 |
|
| H-tunneling in the multiple H-transfers of the catalytic cycle of morphinone reductase and in the reductive half-reaction of the homologous pentaerythritol tetranitrate reductase. | 2003-11-07 |
|
| Electrospray tandem mass spectrometric investigations of morphinans. | 2003-11 |
|
| [Combined use of intrathecal morphine and diclofenac suppository for postoperative analgesia after caesarean section]. | 2003-10 |
|
| Crystal structure of bacterial morphinone reductase and properties of the C191A mutant enzyme. | 2002-08-23 |
|
| Effects of environment on flavin reactivity in morphinone reductase: analysis of enzymes displaying differential charge near the N-1 atom and C-2 carbonyl region of the active-site flavin. | 2001-10-15 |
Patents
Sample Use Guides
The analgesic effects of morphinone and morphine in mice were determined by the acetic acid writhing test. Each group of I0 male mice was subcutaneously administered a solution of morphine or morphinone (0.25, 0.5, 1.0 and 1.5 mg/kg) in a volume of I0 ml solution per kg, 30 min prior to the intraperltoneal injection of I0 ml/kg of 0.7% acetic acid in the saline.
Route of Administration:
Other
HL-60 cells were inoculated at 1.0x10^6 cells/well in 96-microwell (Becton Dickinson Labware, NJ, USA), unless otherwise stated. After 24 h, the medium was removed with an aspirator and replaced with 0.1 mL of fresh medium containing the 0-100mkM of morphinone. Cells were incubated for another 24 h and the relative viable cell number was then determined by the MTT method.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:18:36 GMT 2025
by
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on
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| Record UNII |
28MBK63MAW
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| Record Status |
Validated (UNII)
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