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Merck
CN

SML0671

Nitecapone

≥98% (HPLC)

Synonym(s):

3-[(3,4-Dihydroxy-5-nitrophenyl)methylene]-2,4-pentanedione, OR-462

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About This Item

Empirical Formula (Hill Notation):
C12H11NO6
CAS Number:
116313-94-1
Molecular Weight:
265.22
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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SMILES string

[N+](=O)([O-])c1c(c(cc(c1)C=C(C(=O)C)C(=O)C)O)O

InChI

1S/C12H11NO6/c1-6(14)9(7(2)15)3-8-4-10(13(18)19)12(17)11(16)5-8/h3-5,16-17H,1-2H3

InChI key

UPMRZALMHVUCIN-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 15 mg/mL, clear

storage temp.

−20°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Nitecapone is a short-acting inhibitor of catechol-O-methyltransferase (COMT).
Nitecapone is a short-acting inhibitor of catechol-O-methyltransferase (COMT). Nitecapone displays in vivo activity in peripheral tissues, but does not pentrate the blood brain barrier. The compound increases mechanical and thermal nociception, and reduces neuropathic pain in diabetic rats and in a spinal nerve ligation model.

Features and Benefits

This compound is featured on the Dopamine and Norepinephrine Metabolism page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000115189
043M4757V

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P Lautala et al.
Pharmaceutical research, 14(10), 1444-1448 (1997-11-14)
Nitrocatechol COMT inhibitors are a new class of bioactive compounds, for which glucuronidation is the most important metabolic pathway. The objective was to characterize the enzyme kinetics of nitrocatechol glucuronidation to improve the understanding and predicting of the pharmacokinetic behavior
L Luukkanen et al.
Bioconjugate chemistry, 10(1), 150-154 (1999-01-20)
Enzyme-assisted synthesis and characterization are described for 3-O-beta-D-glucuronides 1b-4b of the aglycons E- and Z-2-cyano-N, N-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)propenamide (entacapone), 1a and 2a, respectively, 3-(3,4-dihydroxy-5-nitrobenzylidene)-2, 4-pentanedione (nitecapone) 3a and 4'-methyl-3, 4-dihydroxy-5-nitrobenzophenone (tolcapone) 4a, and 1-o- and 2-o-glucuronides 5b and 6b of the aglycon
Dopamine and the brain-gut axis.
G Flemström et al.
Advances in pharmacology (San Diego, Calif.), 42, 846-851 (1997-11-05)
A E Vento et al.
The Annals of thoracic surgery, 68(2), 413-420 (1999-09-04)
Nitecapone has been shown to have a protective effect against ischemia-reperfusion injury in experimental heart transplantation and in Langendorff preparations. This prospective, randomized study assessed the effects of nitecapone in patients who had coronary artery bypass grafting. Thirty patients with
A Pertovaara et al.
Experimental neurology, 167(2), 425-434 (2001-02-13)
We attempted to characterize a spinal neuronal correlate of painful neuropathy induced by diabetes mellitus (DM). Pain behavior and response properties of spinal dorsal horn neurons were determined in rats with a streptozocin-induced DM. A catechol-O-methyltransferase inhibitor with potent antioxidant
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