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SML0671

Sigma-Aldrich

Nitecapone

≥98% (HPLC)

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C12H11NO6
CAS-Nummer:
116313-94-1
Molekulargewicht:
265.22
UNSPSC-Code:
12352200
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Farbe

white to beige

Löslichkeit

DMSO: 15 mg/mL, clear

Lagertemp.

−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

InChIKey

UPMRZALMHVUCIN-UHFFFAOYSA-N

Biochem./physiol. Wirkung

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.

Leistungsmerkmale und Vorteile

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.

Piktogramme

Skull and crossbones
GHS06

Signalwort

Danger

H-Sätze

H301

Gefahreneinstufungen

Acute Tox. 3 Oral

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

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Analysenzertifikate (COA)

Lot/Batch Number
043M4757V

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P Martínez-Martín et al.
Neurology, 50(6 Suppl 6), S27-S32 (1998-06-20)
Degradation of levodopa in the periphery is known to be associated with motor fluctuations and dyskinesia in Parkinson's disease (PD) patients. The enzyme catechol-O-methyltransferase (COMT) is responsible for much of this degradation. Therefore, inhibiting COMT activity is one method of
M A Lal et al.
Diabetes, 49(8), 1381-1389 (2000-08-03)
The development and progression of diabetic nephropathy is dependent on glucose homeostasis and many other contributing factors. In the present study, we examined the effect of nitecapone, an inhibitor of the dopamine-metabolizing enzyme catechol-O-methyl transferase (COMT) and a potent antioxidant
J Petäjä et al.
The Journal of thoracic and cardiovascular surgery, 118(3), 422-429 (1999-09-02)
We hypothesized that antithrombotic plasma-activated protein C plays a defensive antithrombotic role during coronary ischemia and postischemic reperfusion. We evaluated protein C activation during cardiopulmonary bypass and coronary reperfusion in 20 patients undergoing coronary bypass surgery. During cardiopulmonary bypass and
A E Vento et al.
Research in experimental medicine. Zeitschrift fur die gesamte experimentelle Medizin einschliesslich experimenteller Chirurgie, 198(6), 299-306 (1999-06-16)
Nitecapone (NC) has been shown to have beneficial effects on the functional recovery of rat hearts in Langendorff-preparation. The present study was executed to evaluate the effect of NC on preservation of grafts in heart transplantation and the role of
H Brismar et al.
Proceedings of the National Academy of Sciences of the United States of America, 95(10), 5573-5578 (1998-05-20)
The recruitment of G protein-coupled receptors from the cytoplasm to the plasma membrane generally is believed to be a constitutive process. We show here by the use of both confocal microscopy and subcellular fractionation that, for at least one such
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