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SML0150

Sigma-Aldrich

Tolcapone

≥98% (HPLC)

Synonym(s):

3,4-Dihydroxy-4′-methyl-5-nitrobenzophenone, Ro 40-7592

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About This Item

Empirical Formula (Hill Notation):
C14H11NO5
CAS Number:
134308-13-7
Molecular Weight:
273.24
MDL number:
MFCD00866569
UNSPSC Code:
12352200
PubChem Substance ID:
329825198
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

yellow

solubility

DMSO: ≥15 mg/mL

originator

Roche

storage temp.

2-8°C

SMILES string

Cc1ccc(cc1)C(=O)c2cc(O)c(O)c(c2)[N+]([O-])=O

InChI

1S/C14H11NO5/c1-8-2-4-9(5-3-8)13(17)10-6-11(15(19)20)14(18)12(16)7-10/h2-7,16,18H,1H3

InChI key

MIQPIUSUKVNLNT-UHFFFAOYSA-N

Gene Information

human ... COMT(1312)

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Application

Tolcapone may be used in COMT-mediated cell signaling studies.
Tolcapone has been used in methyltransferase assay in human embryonic kidney 293 cells.

Biochem/physiol Actions

Inhibition of catechol-O-methyltransferase by tolcapone increases the half-life and bioavailabilty of levodopa. It therefore is an effective adjunctive therapy in patients with Parkinson′s disease with motor response fluctuations.
Orally active catechol-O-methyltransferase (COMT) inhibitor: inhibits both central and peripheral COMT.
Tolcapone is an orally active catechol-O-methyltransferase (COMT) inhibitor. It inhibits both central and peripheral COMT. Tolcapone crosses the blood-brain barrier, and has been used for L-DOPA adjunct therapy in the treatment of Parkinson′s Disease.

Features and Benefits

This compound was developed by Roche. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H400

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000385901
0000385900
0000340108
0000340108
0000385900

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H Baas et al.
Journal of neurology, neurosurgery, and psychiatry, 63(4), 421-428 (1997-10-29)
More than 50% of patients with Parkinson's disease develop motor response fluctuations (the "wearing off" phenomenon) after more than five years of levodopa therapy. Inhibition of catechol-O-methyltransferase by tolcapone has been shown to increase levodopa bioavailability and plasma elimination half
Gillian M Keating et al.
CNS drugs, 19(2), 165-184 (2005-02-09)
Tolcapone (Tasmar) is a selective, reversible inhibitor of peripheral and central catechol-O-methyltransferase (COMT). Results of well designed studies indicate that oral tolcapone is an effective adjunct to levodopa plus a peripheral dopa-decarboxylase inhibitor (DDCI) in patients with fluctuating Parkinson's disease.
Jenny J Fischer et al.
Toxicological sciences : an official journal of the Society of Toxicology, 113(1), 243-253 (2009-09-29)
Capture compound mass spectrometry (CCMS) is a novel technology that helps understand the molecular mechanism of the mode of action of small molecules. The Capture Compounds are trifunctional probes: A selectivity function (the drug) interacts with the proteins in a
Saviana Di Giovanni et al.
The Journal of biological chemistry, 285(20), 14941-14954 (2010-02-13)
Parkinson disease (PD) is the second most common neurodegenerative disorder after Alzheimer disease (AD). There is considerable consensus that the increased production and/or aggregation of alpha-synuclein (alpha-syn) plays a central role in the pathogenesis of PD and related synucleinopathies. Current
Inès Khsime et al.
International journal of molecular sciences, 24(19) (2023-10-14)
L-DOPA, the precursor of catecholamines, exerts a pro-locomotor action in several vertebrate species, including newborn rats. Here, we tested the hypothesis that decreasing the degradation of monoamines can promote the pro-locomotor action of a low, subthreshold dose of L-DOPA in
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