| 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.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 12.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
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.
SUBSTANCE RECORD
