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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
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Quality Level

100

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

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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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
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
Dopamine and the brain-gut axis.
G Flemström et al.
Advances in pharmacology (San Diego, Calif.), 42, 846-851 (1997-11-05)
J E Holden et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 38(10), 1568-1574 (1997-10-23)
Graphical methods to analyze tracer time-course data allow reliable quantitation of the rate of incorporation of tracer from plasma into a "trapped" kinetic component, even when the details of the kinetic model are unknown. Applications of the method over long
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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Global Trade Item Number

SKUGTIN
SML0671-25MG04061832949055
SML0671-5MG04061832949062

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