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Merck
CN

D131

Sigma-Aldrich

3,5-Dinitrocatechol

solid

Synonym(s):

3,5-Dinitro-1,2-benzenediol, OR-486

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About This Item

Empirical Formula (Hill Notation):
C6H4N2O6
CAS Number:
7659-29-2
Molecular Weight:
200.11
MDL number:
MFCD00069263
UNSPSC Code:
12352202
PubChem Substance ID:
24278158
NACRES:
NA.77

Key Documents

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biological source

synthetic (organic)

Assay

≥98% (HPLC)

form

solid

color

yellow

mp

168-170  °C

solubility

H2O: slightly soluble 0.17 mg/mL
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 2.8 mg/mL
0.1 M HCl: slightly soluble
DMSO: soluble
aqueous buffer pH > 5: soluble
ethanol: soluble

storage temp.

2-8°C

SMILES string

Oc1cc(cc(c1O)[N+]([O-])=O)[N+]([O-])=O

InChI

1S/C6H4N2O6/c9-5-2-3(7(11)12)1-4(6(5)10)8(13)14/h1-2,9-10H

InChI key

VDCDWNDTNSWDFJ-UHFFFAOYSA-N

Gene Information

human ... COMT(1312)

Related Categories

Application

3,5-Dinitrocatechol (3,5-DNC) has been used in the preparation of the molybdenum (VI)-(3,5-DNC) complex. It has also been used as a catechol-O-methyltransferase (COMT) inhibitor and as a positive control for screening human COMT inhibition.
Chelating reagent used in a sensitive (μM) assay for vanadium.

Biochem/physiol Actions

Selective inhibitor of catechol O-methyl transferase (COMT); penetrates the blood brain barrier and is useful both orally and parenteraly in experiments where inhibition of COMT in the central nervous system is required.

Analysis Note

Solutions may be stored for several days at 4 °C.

Disclaimer

Photosensitive

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000287895
0000287895
SLCP5279
SLCF6118
SLBT2326

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E Nissinen et al.
European journal of pharmacology, 153(2-3), 263-269 (1988-08-24)
Catechol-O-methyltransferase (COMT) has an important role in the extraneuronal inactivation of catecholamine neurotransmitters and drugs with a catechol structure. Two novel COMT inhibitors, OR-462 and OR-486, were highly effective (IC50 = 18 and 12 nM, respectively) and selective in inhibiting
Raghvendra K Dubey et al.
The Journal of clinical endocrinology and metabolism, 89(8), 3922-3931 (2004-08-05)
Sequential conversion of estradiol to catecholestradiols and methoxyestradiols by cytochrome-P(450) (CYP450) and catechol-O-methyltransferase (COMT), respectively, contributes to the antimitogenic effects of estradiol on vascular smooth muscle cell (SMC) growth via estrogen receptor-independent mechanisms. Because catecholamines are also substrates for COMT
O Kambur et al.
British journal of pharmacology, 161(7), 1553-1565 (2010-08-24)
Catechol-O-methyltransferase (COMT) inhibitors are used in Parkinson's disease in which pain is an important symptom. COMT polymorphisms modulate pain and opioid analgesia in humans. In rats, COMT inhibitors have been shown to be pro-nociceptive in acute pain models, but also
Raghvendra K Dubey et al.
Hypertension (Dallas, Tex. : 1979), 42(3), 349-355 (2003-08-13)
Local sequential conversion of estradiol to hydroxyestradiols and methoxyestradiols by CYP450 and catechol-O-methyltransferase, respectively, contributes to the antimitogenic effects of estradiol on glomerular mesangial cell growth via estrogen receptor-independent mechanisms. Catecholamines are also substrates for catechol-O-methyltransferase and therefore, might abrogate
C Wiese et al.
Naunyn-Schmiedeberg's archives of pharmacology, 348(6), 582-585 (1993-12-01)
Organotypic primary cell cultures of fetal rat brain were used as a model system to study the effect of COMT inhibitors on the cerebral metabolic conversions of fluoro-DOPA enantiomers. The selective COMT inhibitors OR 486 and CGP 28014 were used
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