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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

Key Documents

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Product Name

Nitecapone, ≥98% (HPLC)

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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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
G Léger et al.
Synapse (New York, N.Y.), 30(4), 351-361 (1998-11-24)
The efficacy of levo-DOPA in the treatment of Parkinson's disease is potentiated by blockade of its peripheral metabolism with inhibitors of catechol-O-methyltransferase (COMT). Some COMT inhibitors may act entirely in the periphery (nitecapone, OR-462), while others may also have some
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
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
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
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