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Tolcapone

CAS No.
134308-13-7
Chemical Name:
Tolcapone
Synonyms
Tasmar;TOLCAPONE;TALCAPONE;ro40-7592;TOLOCAPONE;Tolcapone (200 mg);TolcaponeTolcapone;Tolcapone USP/EP/BP;Tolcapone (1670207);(3,4-Dihydroxy-5-nitrophenyl)
CBNumber:
CB9302569
Molecular Formula:
C14H11NO5
Molecular Weight:
273.24
MDL Number:
MFCD00866569
MOL File:
134308-13-7.mol
Last updated:2023-09-20 16:43:00

Tolcapone Properties

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)
EWG's Food Scores 1
FDA UNII CIF6334OLY
NCI Drug Dictionary Tasmar
ATC code N04BX01

Pharmacokinetic data

Protein binding >99.9%
Excreted unchanged in urine 0.5%
Volume of distribution 9 Litres
Biological half-life 2-3 / Unchanged

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS09
Signal word  Warning
Hazard statements  H400
Precautionary statements  P273
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,

Tolcapone price More Price(43)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML0150 Tolcapone ≥98% (HPLC) 134308-13-7 10mg $77 2024-03-01 Buy
Sigma-Aldrich 1670207 Tolcapone United States Pharmacopeia (USP) Reference Standard 134308-13-7 200mg $436 2024-03-01 Buy
TCI Chemical T3856 Tolcapone 134308-13-7 50MG $138 2024-03-01 Buy
TCI Chemical T3856 Tolcapone 134308-13-7 200MG $346 2024-03-01 Buy
Cayman Chemical 20768 Tolcapone ≥98% 134308-13-7 5mg $38 2024-03-01 Buy
Product number Packaging Price Buy
SML0150 10mg $77 Buy
1670207 200mg $436 Buy
T3856 50MG $138 Buy
T3856 200MG $346 Buy
20768 5mg $38 Buy

Tolcapone Chemical Properties,Uses,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

Global( 214)Suppliers
Supplier Tel Email Country ProdList Advantage
ATK CHEMICAL COMPANY LIMITED
+undefined-21-51877795 ivan@atkchemical.com China 32480 60
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29914 58
Accela ChemBio Inc.
(+1)-858-699-3322 info@accelachem.com United States 19965 58
BOC Sciences
+1-631-485-4226 inquiry@bocsci.com United States 19553 58
Chongqing Chemdad Co., Ltd
+86-023-61398051 +8613650506873 sales@chemdad.com China 39916 58
CONIER CHEM AND PHARMA LIMITED
+8618523575427 sales@conier.com China 47465 58
Antai Fine Chemical Technology Co.,Limited
18503026267 info@antaichem.com CHINA 9641 58
HANGZHOU CLAP TECHNOLOGY CO.,LTD
86-571-88216897,88216896 13588875226 sales@hzclap.com CHINA 6313 58
Xi'an MC Biotech, Co., Ltd.
029-89275612 +8618991951683 mcbio_sales@163.com China 2255 58
Dideu Industries Group Limited
+86-29-89586680 +86-15129568250 1026@dideu.com China 29831 58

View Lastest Price from Tolcapone manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Tolcapone pictures 2019-07-06 Tolcapone
134308-13-7
US $1.00 / KG 1G 98% 100KG Career Henan Chemical Co
  • Tolcapone pictures
  • Tolcapone
    134308-13-7
  • US $1.00 / KG
  • 98%
  • Career Henan Chemical Co

Tolcapone Spectrum

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 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 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) 134308-13-7 Inhibitors API Inhibitor Intermediates & Fine Chemicals Pharmaceuticals Aromatics 134308-13-7