Tolcapone

For research use only. Not for therapeutic Use.

  • CAT Number: A000380
  • CAS Number: 134308-13-7
  • Molecular Formula: C14H11NO5
  • Molecular Weight: 273.20
  • Purity: ≥95%
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Tolcapone(Cat No.:A000380)is a potent inhibitor of catechol-O-methyltransferase (COMT), used in the treatment of Parkinson’s disease to improve motor symptoms. By inhibiting COMT, tolcapone reduces the breakdown of dopamine, particularly in the brain, thus enhancing and prolonging dopamine availability when combined with other treatments like levodopa. This mechanism helps alleviate Parkinsonian symptoms by stabilizing dopamine levels, crucial for motor control. Due to its effect on dopamine metabolism, tolcapone is also studied in neurological research, though it requires monitoring for potential liver-related side effects in clinical settings.


Catalog Number A000380
CAS Number 134308-13-7
Synonyms

134308-13-7; Tasmar; Ro 40-7592; (3,4-Dihydroxy-5-nitrophenyl)(4-methylphenyl)methanone; (3,4-dihydroxy-5-nitrophenyl)(p-tolyl)methanone

Molecular Formula C14H11NO5
Purity ≥95%
Target Transferase
Solubility >12mg/mL in DMSO
Storage -20°C
IUPAC Name (3,4-dihydroxy-5-nitrophenyl)-(4-methylphenyl)methanone
InChI 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
InChIKey MIQPIUSUKVNLNT-UHFFFAOYSA-N
SMILES CC1=CC=C(C=C1)C(=O)C2=CC(=C(C(=C2)O)O)[N+](=O)[O-]
Reference

1: Mak A, Kato R, Weston K, Hayes A, Uetrecht J. An Impaired Immune Tolerance
Animal Model Distinguishes the Potential of Troglitazone/Pioglitazone and
Tolcapone/Entacapone to Cause IDILI. Toxicol Sci. 2017 Oct 24. doi:
10.1093/toxsci/kfx219. [Epub ahead of print] PubMed PMID: 29087505.
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2: Bhakta SG, Light GA, Talledo JA, Balvaneda B, Hughes E, Alvarez A, Rana BK,
Young JW, Swerdlow NR. Tolcapone-enhanced neurocognition in healthy adults:
neural basis and predictors. Int J Neuropsychopharmacol. 2017 Aug 21. doi:
10.1093/ijnp/pyx074. [Epub ahead of print] PubMed PMID: 29020372.

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3: Grünig D, Felser A, Bouitbir J, Kr&#228;henbühl S. The catechol-O-methyltransferase
inhibitors tolcapone and entacapone uncouple and inhibit the mitochondrial
respiratory chain in HepaRG cells. Toxicol In Vitro. 2017 Aug;42:337-347. doi:
10.1016/j.tiv.2017.05.013. Epub 2017 May 16. PubMed PMID: 28526448.
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4: Maser T, Rich M, Hayes D, Zhao P, Nagulapally AB, Bond J, Saulnier Sholler G.
Tolcapone induces oxidative stress leading to apoptosis and inhibition of tumor
growth in Neuroblastoma. Cancer Med. 2017 Jun;6(6):1341-1352. doi:
10.1002/cam4.1065. Epub 2017 Apr 21. PubMed PMID: 28429453; PubMed Central PMCID:
PMC5463066.
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5: Kayser AS, Vega T, Weinstein D, Peters J, Mitchell JM. Right inferior frontal
cortex activity correlates with tolcapone responsivity in problem and
pathological gamblers. Neuroimage Clin. 2016 Dec 20;13:339-348. doi:
10.1016/j.nicl.2016.12.022. eCollection 2017. PubMed PMID: 28066708; PubMed
Central PMCID: PMC5200917.

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6: Lv X, Wang XX, Hou J, Fang ZZ, Wu JJ, Cao YF, Liu SW, Ge GB, Yang L.
Comparison of the inhibitory effects of tolcapone and entacapone against human
UDP-glucuronosyltransferases. Toxicol Appl Pharmacol. 2016 Jun 15;301:42-9. doi:
10.1016/j.taap.2016.04.009. Epub 2016 Apr 16. PubMed PMID: 27089846.
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7: Detrait ER, Carr GV, Weinberger DR, Lamberty Y. Brain
catechol-O-methyltransferase (COMT) inhibition by tolcapone counteracts
recognition memory deficits in normal and chronic phencyclidine-treated rats and
in COMT-Val transgenic mice. Behav Pharmacol. 2016 Aug;27(5):415-21. doi:
10.1097/FBP.0000000000000208. PubMed PMID: 26919286; PubMed Central PMCID:
PMC4935608.
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8: Sant/’Anna R, Gallego P, Robinson LZ, Pereira-Henriques A, Ferreira N, Pinheiro
F, Esperante S, Pallares I, Huertas O, Almeida MR, Reixach N, Insa R,
Velazquez-Campoy A, Reverter D, Reig N, Ventura S. Repositioning tolcapone as a
potent inhibitor of transthyretin amyloidogenesis and associated cellular
toxicity. Nat Commun. 2016 Feb 23;7:10787. doi: 10.1038/ncomms10787. PubMed PMID:
26902880; PubMed Central PMCID: PMC4766415.
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9: Longo DM, Yang Y, Watkins PB, Howell BA, Siler SQ. Elucidating Differences in
the Hepatotoxic Potential of Tolcapone and Entacapone With DILIsym(&#174;), a
Mechanistic Model of Drug-Induced Liver Injury. CPT Pharmacometrics Syst
Pharmacol. 2016 Jan;5(1):31-9. doi: 10.1002/psp4.12053. Epub 2016 Jan 13. PubMed
PMID: 26844013; PubMed Central PMCID: PMC4728295.

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10: Forester SC, Lambert JD. The catechol-O-methyltransferase inhibitor,
tolcapone, increases the bioavailability of unmethylated
(-)-epigallocatechin-3-gallate in mice. J Funct Foods. 2015 Aug 1;17:183-188.
PubMed PMID: 26213577; PubMed Central PMCID: PMC4509505.

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