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D131 Sigma

3,5-Dinitrocatechol

solid

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

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Properties

Related Categories Biochemicals and Reagents, Enzyme Inhibitors, Enzyme Inhibitors by Type, Enzymes, Inhibitors, and Substrates, Substrate Analogs More...
form   solid
color   yellow
solubility   H2O: slightly soluble0.17 mg/mL
  45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble2.8 mg/mL
  0.1 M HCl: slightly soluble
  DMSO: soluble
  aqueous buffer pH > 5: soluble
  ethanol: soluble
storage temp.   2-8°C
Gene Information   human ... COMT(1312)

Description

Application

Chelating reagent used in a sensitive (μM) assay for vanadium.1

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.

Caution

Photosensitive

Packaging

250 mg in poly bottle

50 mg in glass bottle

Quality

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

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®,1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Price and Availability

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Safety & Documentation

Safety Information

WGK Germany 
3
RTECS 
CZ8947010

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

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1. Extraction-spectrophotometric determination of vanadium with 3,5-dinitrocatechol and Brilliant Green Marczenko, Z., and Lobinski, R. Talanta 35, 1001-1004, (1988)

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Catechol-O-methyltransferase inhibition increases pain sensitivity through activation of both beta2- and beta3-adrenergic receptors. Nackley AG, Tan KS, Fecho K, et al. Pain 128(3), 199-208, (2007)

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Ultraviolet resonance Raman study of drug binding in dihydrofolate reductase, gyrase, and catechol O-methyltransferase. Couling VW, Fischer P, Klenerman D, et al. Biophys. J. 75(2), 1097-106, (1998)

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Inhibitors of catechol-O-methyltransferase sensitize mice to pain. Kambur O, Talka R, Ansah OB, et al. Br. J. Pharmacol. 161(7), 1553-65, (2010)

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Oxidative deamination of noradrenaline in human blood vessels. Osswald W J. Neural Transm. Suppl. 32, 395-404, (1990)

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Role of adenosine in drug-induced catatonia in mice. Singh A and Kulkarni SK Indian J. Exp. Biol. 40(8), 882-8, (2002)

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Catecholamines block the antimitogenic effect of estradiol on human glomerular mesangial cells. Dubey RK, Zacharia LC, Gillespie DG, et al. Hypertension 42(3), 349-55, (2003)

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Catecholamines block the antimitogenic effect of estradiol on human coronary artery smooth muscle cells. Dubey RK, Jackson EK, Gillespie DG, et al. J. Clin. Endocrinol. Metab. 89(8), 3922-31, (2004)

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Microdialysis with radiometric monitoring of L-[β-11C]DOPA to assess dopaminergic metabolism: effect of inhibitors of L-amino acid decarboxylase, monoamine oxidase, and catechol-O-methyltransferase on rat striatal dialysate. Okada M, Nakao R, Hosoi R, et al. J. Cereb. Blood Flow Metab. 31(1), 124-31, (2011)

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Properties of novel effective and highly selective inhibitors of catechol-O-methyl-transferase. Mannisto, et al. Life Sci. 43, 1465, (1988)

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Catechol-O-methyltransferase (COMT) inhibition reduces spinal nociceptive activity. Jacobsen LM, Eriksen GS, Pedersen LM, et al. Neurosci. Lett. 473(3), 212-5, (2010)

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Pharmacological analysis of monoamine synthesis and catabolism in the scallop, Placopecten magellanicus. Pani AK and Croll RP Gen. Pharmacol. 31(1), 67-73, (1998)

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Regulation of heme oxygenase-1 expression by dopamine in cultured C6 glioma and primary astrocytes. Schmidt J, Mertz K, and Morgan JI Brain Res. Mol. Brain Res. 73(1-2), 50-9, (1999)

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Plasma clearances and extractions of four catecholamines in the anesthetized rabbit: the role of amine removal by blood cells. Friedgen B, Halbrügge T, and Graefe KH J. Cardiovasc. Pharmacol. 21(1), 21-8, (1993)

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COMT-dependent protection of dopaminergic neurons by methionine, dimethionine and S-adenosylmethionine (SAM) against L-dopa toxicity in vitro. Werner P, Di Rocco A, Prikhojan A, et al. Brain Res. 893(1-2), 278-81, (2001)

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Inhibition of catechol-O-methyltransferase activity by two novel disubstituted catechols in the rat. Nissinen, et al. Eur. J. Pharmacol. 153, 263, (1988)

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Catechol-O-methyltransferase inhibition increases the uptake of 11C-3-(3,4-dihydroxyphenyl)-L-alanine in the rat pancreas. Bergström M, Lu L, Marquez M, et al. Scand. J. Gastroenterol. 31(12), 1216-22, (1996)

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Extraneuronal uptake and O-methylation of 3H-adrenaline in the rabbit aorta. Martel F, Azevedo I, and Osswald W Naunyn Schmiedebergs Arch. Pharmacol. 347(4), 363-70, (1993)

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A method for the covalent capture and screening of diverse small molecules in a microarray format. Bradner, J.E., et al. Nat. Protoc. 1, 2344-52, (2006)

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COMT inhibitors and metabolism of fluorodopa enantiomers in aggregating cell cultures. Wiese C, Cogoli-Greuter M, Weinreich R, et al. Naunyn Schmiedebergs Arch. Pharmacol. 348(6), 582-5, (1993)

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