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
| 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 |
|---|---|---|
| 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 |
|
| Decoration of the aromatic ring of dihydrocodeinone (hydrocodone) and 14-hydroxydihydrocodeinone (oxycodone). | 2005 Aug 5 |
|
| Mutagenesis of morphinone reductase induces multiple reactive configurations and identifies potential ambiguity in kinetic analysis of enzyme tunneling mechanisms. | 2007 Nov 14 |
|
| Live cell monitoring of mu-opioid receptor-mediated G-protein activation reveals strong biological activity of close morphine biosynthetic precursors. | 2007 Sep 14 |
|
| Deep tunneling dominates the biologically important hydride transfer reaction from NADH to FMN in morphinone reductase. | 2008 Jun 4 |
|
| 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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:39:31 GMT 2023
by
admin
on
Fri Dec 15 18:39:31 GMT 2023
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| Record UNII |
28MBK63MAW
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| Record Status |
Validated (UNII)
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| Record Version |
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207-384-0
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PARENT -> IMPURITY |
Procedure 1
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
For the calculation of contents, multiply the peak areas by 0.5
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
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ACTIVE MOIETY |
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