3-O-Methyltolcapone

3-O-Methyltolcapone (Ro 40-7591) is a metabolite of Tolcapone (HY-17406) . Tolcapone (Ro 40-7592) is a selective, potent and orally active COMT inhibitor with an IC50of 773 nM. Tolcapone can inhibits α-syn and Aβ42 oligomerization and fibrillogenesis. Tolcapone can cause oxidative stress and induce cancer cells apoptosis and ROS production. Tolcapone can be used for the researches of cancer and neurological disease, such as Parkinson disease and neuroblastoma[1][2][3][4][5][6].

Product Specifications

CAS Number

[134612-80-9]

Product Name Alternative

Ro 40-7591

UNSPSC

12352005

Hazard Statement

H315, H319, H335

Target

Amyloid-β; Apoptosis; COMT; Drug Metabolite; Reactive Oxygen Species (ROS)

Type

Reference compound

Related Pathways

Apoptosis; Immunology/Inflammation; Metabolic Enzyme/Protease; Neuronal Signaling; NF-κB

Applications

Neuroscience-Neurodegeneration

Field of Research

Cancer; Neurological Disease

Assay Protocol

https://www.medchemexpress.com/3-o-methyltolcapone.html

Purity

99.95

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

O=C(C1=CC([N+]([O-])=O)=C(O)C(OC)=C1)C2=CC=C(C)C=C2

Molecular Formula

C15H13NO5

Molecular Weight

287.27

Precautions

H315, H319, H335

References & Citations

[1]De Santi C, et al. Catechol-O-methyltransferase: variation in enzyme activity and inhibition by entacapone and tolcapone. Eur J Clin Pharmacol. 1998 May;54 (3) :215-9.|[2]Di Giovanni S, et al. 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. 2010 May 14;285 (20) :14941-14954. |[3]Ceravolo R, et al. 18F-dopa PET evidence that tolcapone acts as a central COMT inhibitor in Parkinson's disease. Synapse. 2002 Mar 1;43 (3) :201-7.|[4]Maser T, et al. Tolcapone induces oxidative stress leading to apoptosis and inhibition of tumor growth in Neuroblastoma. Cancer Med. 2017 Jun;6 (6) :1341-1352. |[5]Jorga K, et al. Metabolism and excretion of tolcapone, a novel inhibitor of catechol-O-methyltransferase. Br J Clin Pharmacol. 1999 Oct;48 (4) :513-20.|[6]Poonsiri T, et al. 3-O-Methyltolcapone and Its Lipophilic Analogues Are Potent Inhibitors of Transthyretin Amyloidogenesis with High Permeability and Low Toxicity. Int J Mol Sci. 2023 Dec 29;25 (1) :479.