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
[H][C@@]12OC3=C4C(C[C@H]5N(C)CC[C@@]14[C@@]5([H])C=CC2=O)=CC=C3O
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
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 |
|---|---|---|
| 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 Oct 15 |
|
| Crystal structure of bacterial morphinone reductase and properties of the C191A mutant enzyme. | 2002 Aug 23 |
|
| Electrospray tandem mass spectrometric investigations of morphinans. | 2003 Nov |
|
| 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 Nov 7 |
|
| Induction of non-apoptotic cell death by morphinone in human promyelocytic leukemia HL-60 cells. | 2006 Sep-Oct |
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| Mutagenesis of morphinone reductase induces multiple reactive configurations and identifies potential ambiguity in kinetic analysis of enzyme tunneling mechanisms. | 2007 Nov 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 Sep 14 |
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| Correction of pre-steady-state KIEs for isotopic impurities and the consequences of kinetic isotope fractionation. | 2008 Dec 18 |
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| Deep tunneling dominates the biologically important hydride transfer reaction from NADH to FMN in morphinone reductase. | 2008 Jun 4 |
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| Solvent as a probe of active site motion and chemistry during the hydrogen tunnelling reaction in morphinone reductase. | 2008 Sep 15 |
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| Incorporation of hydrostatic pressure into models of hydrogen tunneling highlights a role for pressure-modulated promoting vibrations. | 2008 Sep 16 |
|
| Barrier compression enhances an enzymatic hydrogen-transfer reaction. | 2009 |
|
| Parallel pathways and free-energy landscapes for enzymatic hydride transfer probed by hydrostatic pressure. | 2009 May 25 |
|
| Direct analysis of donor-acceptor distance and relationship to isotope effects and the force constant for barrier compression in enzymatic H-tunneling reactions. | 2010 Aug 18 |
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.
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207-384-0
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ACTIVE MOIETY
