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Merck
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D131

Sigma-Aldrich

3,5-Dinitrocatechol

solid

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C6H4N2O6
Número de CAS:
7659-29-2
Peso molecular:
200.11
MDL number:
MFCD00069263
UNSPSC Code:
12352202
PubChem Substance ID:
24278158
NACRES:
NA.77

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)

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.

Quality

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

Caution

Photosensitive

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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A K Pani et al.
General pharmacology, 31(1), 67-73 (1998-05-22)
1. The efficacies of various agents that affect monoamine synthesis, oxidation and methylation were evaluated in the scallop, Placopecten magellanicus, through the use of high performance liquid chromatography with electrochemical detection. 2. Central ganglia, labial palps and feet from animals
V W Couling et al.
Biophysical journal, 75(2), 1097-1106 (1998-07-24)
This paper presents a study of the use of ultraviolet resonance Raman (UVRR) spectroscopic methods as a means of elucidating aspects of drug-protein interactions. Some of the RR vibrational bands of the aromatic amino acids tyrosine and tryptophan are sensitive
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
P T Männistö et al.
Life sciences, 43(18), 1465-1471 (1988-01-01)
Novel bisubstituted catechols were found to be potent and highly selective COMT inhibitors in vitro. One of them, OR-462 (3-(3,4-dihydroxy-5-benzylidene)-2,4-pentanedione), was studied also in vivo. When administered to rats orally together with levodopa and carbidopa, OR-462 greatly improved the bioavailability
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
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