ChemicalBook > CAS DataBase List > Tolcapone

Tolcapone

Product Name
Tolcapone
CAS No.
134308-13-7
Chemical Name
Tolcapone
Synonyms
Tasmar;ro40-7592;TOLCAPONE;TALCAPONE;TOLOCAPONE;TolcaponeTolcapone;Tolcapone (200 mg);Tolcapone USP/EP/BP;Tolcapone (1670207);(3,4-Dihydroxy-5-nitrophenyl)
CBNumber
CB9302569
Molecular Formula
C14H11NO5
Formula Weight
273.24
MOL File
134308-13-7.mol
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Tolcapone Property

Melting point:
126-1280C
Boiling point:
485.6±45.0 °C(Predicted)
Density 
1.419±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: ≥15mg/mL
pka
4.78±0.38(Predicted)
form 
powder
color 
yellow
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.
CAS DataBase Reference
134308-13-7(CAS DataBase Reference)
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Safety

Hazard Codes 
N
Risk Statements 
50
Safety Statements 
61
RIDADR 
UN 3077 9 / PGIII
RTECS 
PC4952500
HS Code 
2914710000
Toxicity
mouse,LD50,oral,1600mg/kg (1600mg/kg),BEHAVIORAL: ATAXIABEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION,Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 24(Suppl,
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H400Very toxic to aquatic life

Precautionary statements

P273Avoid release to the environment.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0150
Product name
Tolcapone
Purity
≥98% (HPLC)
Packaging
10mg
Price
$77
Updated
2024/03/01
Sigma-Aldrich
Product number
1670207
Product name
Tolcapone
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
TCI Chemical
Product number
T3856
Product name
Tolcapone
Packaging
50MG
Price
$138
Updated
2024/03/01
TCI Chemical
Product number
T3856
Product name
Tolcapone
Packaging
200MG
Price
$346
Updated
2024/03/01
Cayman Chemical
Product number
20768
Product name
Tolcapone
Purity
≥98%
Packaging
5mg
Price
$38
Updated
2024/03/01
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Tolcapone Chemical Properties,Usage,Production

Description

Tolcapone (134308-13-7) is a catechol O-methyltransferase inhibitor (COMT), inhibiting both brain and peripheral enzymes.1?Potent inhibitor of alpha-synuclein and beta-amyloid oligomerization and fibrillogenesis protecting against extracellular toxicity.2?Binds to transthyretin (TTR) with high affinity (21 to 58 nM) and inhibits TTR aggregation in human plasma and prevents TTR-induced cytotoxicity?in vitro. Stabilizes TTR in mice and humans?in vivo.3?Inhibits O-methylation of exogenous polyphenols such as EGCG.4?Cell permeable. Orally bioavailable.

Chemical Properties

Yellow Solid

Originator

Tasmar,Roche

Uses

Orally active inhibitor of central and peripheral catechol-O-methyltransferase (COMT). Antiparkinsonian

Uses

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

Preparation

preparation by demethylation of 4-hydroxy-3-methoxy-4′-methyl-5-nitrobenzophenone with hydrobromic acid in refluxing aque-ous acetic acid.

Definition

ChEBI: Tolcapone is benzophenone substituted on one of the phenyl rings at C-3 and C-4 by hydroxy groups and at C-5 by a nitro group, and on the other phenyl ring by a methyl group at C-4. It is an inhibitor of catechol O-methyltransferase. It has a role as an EC 2.1.1.6 (catechol O-methyltransferase) inhibitor and an antiparkinson drug. It is a member of benzophenones, a member of 2-nitrophenols and a member of catechols.

Manufacturing Process

Condensation of 4-benzyloxy-3-methoxybenzaldehyde with 4-lithium-toluene (prepared from 4-bromotoluene and butyl lithium) leads to the corresponding benzhydrole. Oxidation of the new formed hydroxyl in benzhydrole gives the 4-benzyloxy-3-methoxyphenyl)-p-tolylmethanone. Treatment of this compound with hydrogen bromide selectively removes the benzyl ether that is additionally activated by the transannular carbonyl group. The intermediate is then nitrated under standart conditions to give the (4-hydroxy-3-methoxy-5- nitrophenyl)-p-tolylmethanone. A second treatment of the last compound with hydrogen bromide cleaves the ether group, which is now activated by the adjacent nitro group. This last step affords the (3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)methanone.

Therapeutic Function

Antiparkinsonian

General Description

Tolcapone, 3,4-dihydroxy-4'-methyl-5-nitrobenzophenone (Tasmar), is a yellow, odorless, nonhygroscopic,crystalline compound (pKa＝4.78). Tolcapone israpidly absorbed after oral administration. Tolcapone ishighly bound to plasma albumin (＞98%), and its distributionis therefore restricted. Tolcapone has low first-pass metabolism.It is almost completely metabolized in the liver before excretion, and 60% is excreted by the kidney. The majormetabolite of tolcapone is an inactive glucuronide conjugate.COMT inhibitors increase chronotropic and arrhythmogeniceffects of epinephrine.Tolcapone is indicated as an adjunctto levodopa/carbidopa for the management of signs andsymptoms of PD.

Biochem/physiol Actions

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.

Clinical Use

Catechol-o-methyltransferase inhibitor:
Treatment of Parkinson’s disease

Drug interactions

Potentially hazardous interactions with other drugs
Antidepressants: avoid with MAOIs.

Metabolism

Extensively metabolised, mainly by conjugation to the inactive glucuronide, but methylation by catecholO-methyltransferase to 3-O-methyltolcapone and metabolism by cytochrome P450 isoenzymes CYP3A4 and CYP2A6 also occurs. Approximately 60
% of a dose is excreted in the urine with the remainder appearing in the faeces.

storage

Store at +4°C

References

1) Manisto?et al.?(1992),?Different in vivo properties of three new inhibitors of catechol O-methyltransferase in the rat; Br, J. Pharmacol.,?105?569 2) Giovanni?et al.?(2010),?Entacapone and tolcapone, two catechol O-methyltransferase inhibitors, block fibril formation of alpha-synuclein and beta-amyloid and protect against amyloid-induced toxicity;?J. Biol. Chem.,?285?14941 3) Sant’Anna?et al.?(2016),?Repositioning tolcapone as a potent inhibitor of transthyretin amyloidogenesis and associated cellular toxicity; Nat. Commun.,?7?10787 4) Forester and Lambert (2015),?The catechol-O-methyltransferase inhibitor, tolcapone, increases the bioavailability of unmethylated (-)-epigallocatechin-3-gallate in mice; Funct. Foods,?17?183

Tolcapone Preparation Products And Raw materials

Raw materials

Preparation Products

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Tolcapone Suppliers

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View Lastest Price from Tolcapone manufacturers

Career Henan Chemical Co
Product
Tolcapone 134308-13-7
Price
US $1.00/KG
Min. Order
1G
Purity
98%
Supply Ability
100KG
Release date
2018-08-20

134308-13-7, TolcaponeRelated Search:

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  • 3,4-DIHYDROXYL-5-NITROBENZYL,4'-METHYLBENZENYL KETONE
  • (3,4-Dihydroxy-5-nitrophenyl)
  • TALCAPONE
  • TOLCAPONE
  • (3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)-methanon
  • (3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)methanone
  • 3,4-dihydroxy-4’-methyl-5-nitrobenzophenone
  • ro40-7592
  • TolcaponeTolcapone
  • Tasmar
  • TOLOCAPONE
  • 3,4-DIHYDROXYL-5-NITROBENZENYL,4-METHYLBENZENYL KETONE, TALCAPONE
  • Tolcapone (200 mg)
  • Methanone, (3,4-dihydroxy-5-nitrophenyl)(4-Methylphenyl)-
  • (3,4-Dihydroxy-5-nitrophenyl)(p-tolyl)methanone
  • Tolcapone USP/EP/BP
  • TolcaponeQ: What is Tolcapone Q: What is the CAS Number of Tolcapone Q: What is the storage condition of Tolcapone Q: What are the applications of Tolcapone
  • Tolcapone (1670207)
  • 3,4-Dihydroxy-4'-methyl-5-nitrobenzophenone
  • 134308-13-7
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