Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H4N2O6 |
| Molecular Weight | 200.1058 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC(=CC(=C1O)[N+]([O-])=O)[N+]([O-])=O
InChI
InChIKey=VDCDWNDTNSWDFJ-UHFFFAOYSA-N
InChI=1S/C6H4N2O6/c9-5-2-3(7(11)12)1-4(6(5)10)8(13)14/h1-2,9-10H
3,5-Dinitrocatechol (OR-486) is a selective inhibitor of catechol O-methyl transferase (COMT). COMT is an enzyme that plays a major role in catechol neurotransmitter deactivation. Inhibition of COMT can increase neurotransmitter levels, which provides a means of treatment for Parkinson's disease, schizophrenia, and depression.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effects of tolcapone upon soluble and membrane-bound brain and liver catechol-O-methyltransferase. | 1999 Mar 6 |
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| Role of adenosine in drug-induced catatonia in mice. | 2002 Aug |
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| Characterization of catechol glucuronidation in rat liver. | 2002 Feb |
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| Quercetin metabolism in the lens: role in inhibition of hydrogen peroxide induced cataract. | 2002 Jul 1 |
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| Quercetin potentiates L-Dopa reversal of drug-induced catalepsy in rats: possible COMT/MAO inhibition. | 2003 Jun |
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| Molecular modeling and metabolic studies of the interaction of catechol-O-methyltransferase and a new nitrocatechol inhibitor. | 2003 Mar |
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| Catecholamines block the antimitogenic effect of estradiol on human coronary artery smooth muscle cells. | 2004 Aug |
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| Cytochromes 1A1/1B1- and catechol-O-methyltransferase-derived metabolites mediate estradiol-induced antimitogenesis in human cardiac fibroblast. | 2005 Jan |
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| Redox properties of novel antioxidant 5,8-Dihydroxycoumarin: implications for its prooxidant cytotoxicity. | 2005 Nov-Dec |
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| Quantitative structure-activity relationships in prooxidant cytotoxicity of polyphenols: role of potential of phenoxyl radical/phenol redox couple. | 2005 Sep 15 |
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| (-)-Epicatechin elevates nitric oxide in endothelial cells via inhibition of NADPH oxidase. | 2007 Aug 3 |
|
| Crystal structures of human 108V and 108M catechol O-methyltransferase. | 2008 Jun 27 |
|
| Inhibitors of catechol-O-methyltransferase sensitize mice to pain. | 2010 Dec |
Sample Use Guides
in rat: orally administered OR-486 (3,5-DINITROCATECHOL) were more effective in reducing the formation of 3-O-methyldopa from levodopa than was the levodopa-carbidopa treatment alone. These results indicate that OR-486 is effective and long-lasting inhibitors of COMT activity.
Route of Administration:
Oral
Two novel COMT inhibitors, OR-462 and OR-486 (3,5-DINITROCATECHOL), were highly effective (IC50 = 18 and 12 nM, respectively) and selective in inhibiting COMT activity in vitro. Tyrosine hydroxylase was not inhibited until micromolar concentrations of these compounds were used: the IC50 values for OR-462 and OR-486 were 10 and 14 microM, respectively.
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DTXSID00227391
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VK0VA22GY2
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7659-29-2
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3870203
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DB02105
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SUBSTANCE RECORD
