3,5-DINITROCATECHOL

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

Structure Search

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

HIDE SMILES / InChI

Molecular Formula	C6H4N2O6
Molecular Weight	200.1058
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3181288

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
Catechol O-methyltransferase 21 Target ID: P21964 Gene ID: 1312.0 Gene Symbol: COMT Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/3181288	Inhibitor 8297		12.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
(-)-Epicatechin elevates nitric oxide in endothelial cells via inhibition of NADPH oxidase.	2007 Aug 3	17560937
Crystal structures of human 108V and 108M catechol O-methyltransferase.	2008 Jun 27	18486144
Inhibitors of catechol-O-methyltransferase sensitize mice to pain.	2010 Dec	20726980

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 Class	Chemical Created by `admin` on `Sat Dec 16 04:48:45 GMT 2023` Edited by `admin` on `Sat Dec 16 04:48:45 GMT 2023`
Record UNII	VK0VA22GY2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

3,5-DINITROCATECHOL

Systematic Name

English

3,5-DINITROPYROCATECHOL

Systematic Name

English

OR-486

Code

English

1,2-BENZENEDIOL, 3,5-DINITRO-

Systematic Name

English

ENTACAPONE IMPURITY E [EP IMPURITY]

Common Name

English

3,5-DINITROBENZENE-1,2-DIOL

Systematic Name

English

3,5-DINITRO-1,2-BENZENEDIOL

Systematic Name

English

OR 486

Code

English

1,2-DIHYDROXY-3,5-DINITROBENZENE

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID00227391