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SML0671

Sigma-Aldrich

Nitecapone

≥98% (HPLC)

Synonym(s):

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

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5 MG
$54.30
25 MG
$309.00

About This Item

Empirical Formula (Hill Notation):
C12H11NO6
CAS Number:
Molecular Weight:
265.22
UNSPSC Code:
12352200
NACRES:
NA.77

$54.30


Available to ship onApril 30, 2025Details


Request a Bulk Order

Quality Level

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 15 mg/mL, clear

storage temp.

−20°C

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

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

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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E J Pesonen et al.
Anesthesiology, 91(2), 355-361 (1999-08-12)
To study the effect of nitecapone, a novel antioxidant, on cardiac neutrophil activation during cardiopulmonary bypass in patients. In a double-blind, placebo controlled trial, 30 male patients undergoing coronary artery bypass grafting were randomly assigned to control (crystalloid cardioplegia, n
J Höök-Nikanne et al.
Scandinavian journal of gastroenterology, 31(4), 334-338 (1996-04-01)
The aims of the present study were to assess the usefulness of the Helicobacter felis mouse model in the evaluation of antimicrobial therapies and the effect of Helicobacter infection on gastric mucosal prostaglandin E2 release. Barrier-maintained BALB/c mice were infected
T Vainikka et al.
Scandinavian cardiovascular journal : SCJ, 34(4), 415-420 (2000-09-13)
Nitecapone is an antioxidant molecule which has been shown to protect the heart against ischemia-reperfusion injury. We investigated whether a similar effect could be detected on lung graft preservation in a porcine model of single lung transplantation. Donors received either
L Nagy et al.
American journal of physiology. Gastrointestinal and liver physiology, 279(6), G1201-G1208 (2000-11-30)
We tested the hypothesis that recognized gastroprotective agents exert direct protection against ethanol-induced injury in isolated rat gastric mucosal cells in vitro. If protection exists, we also wanted to identify subcellular targets in the reversible and/or irreversible stages of cell
A C Eklöf et al.
Kidney international, 52(3), 742-747 (1997-09-18)
The enzyme catechol-O-methyltransferase (COMT), which plays an important role for dopamine metabolism, is abundantly expressed in the kidney. To test whether the natriuretic effects of dopamine may be related to the rate of dopamine metabolism, rats were treated with nitecapone

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