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SML0654

Sigma-Aldrich

Entacapone

≥98% (HPLC)

Synonym(s):

2-Cyano-N,N-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)propenamide

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About This Item

Empirical Formula (Hill Notation):
C14H15N3O5
CAS Number:
130929-57-6
Molecular Weight:
305.29
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to light brown

solubility

DMSO: 20 mg/mL, clear

storage temp.

room temp

InChI

1S/C14H15N3O5/c1-3-16(4-2)14(20)10(8-15)5-9-6-11(17(21)22)13(19)12(18)7-9/h5-7,18-19H,3-4H2,1-2H3/b10-5+

InChI key

JRURYQJSLYLRLN-BJMVGYQFSA-N

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Application

Entacapone has been used in high-performance bioaffinity chromatography.

Biochem/physiol Actions

Entacapone acts predominantly in the intestine. It increases the bioavailability of levodopa. Levodopa is known to be associated with many complications such as motor fluctuations. COMT inhibitors have been used to overcome these adverse effects of levodopa by reducing its metabolism. Entacapone exhibits its inhibition action on COMT in the peripheral nervous system.
Entacapone is a catechol-O-methyl transferase (COMT) inhibitor. Used in treatment of Parkinson′s disease, entacapone is administered with L-DOPA to inihibit COMT from converting L-DOPA into a compound that cannot cross the blood brain barrier.

Features and Benefits

This compound is featured on the Dopamine and Norepinephrine Metabolism page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Alice Petty et al.
Molecular imaging and biology, 25(6), 1054-1062 (2023-10-24)
There is robust evidence that people with schizophrenia show elevated dopamine (DA) synthesis capacity in the striatum. This finding comes from positron emission tomography (PET) studies using radiolabelled l-3,4-dihydroxyphenylalanine (18F-DOPA). DA synthesis capacity also appears to be elevated in the
Els F Halff et al.
Molecular imaging, 2022, 4419221-4419221 (2023-02-02)
Positron emission tomography (PET) using the radiotracer [18F]-FDOPA provides a tool for studying brain dopamine synthesis capacity in animals and humans. We have previously standardised a micro-PET methodology in mice by intravenously administering [18F]-FDOPA via jugular vein cannulation and assessment
Principles of Treatment in Parkinson's Disease, 133-133 (2005)
Paul E Polak et al.
Journal of neuroimmunology, 276(1-2), 135-141 (2014-09-23)
Reduced levels of noradrenaline (NA) in CNS of multiple sclerosis patients could be due to metabolism by catechol-O-methyltransferase (COMT). In mice immunized with myelin oligodendrocyte glycoprotein peptide, the BBB-permeable COMT inhibitor dinitrocatechol (DNC) reduced clinical signs, while entacapone, a non-BBB-permeable
Michelle Kokkinou et al.
Molecular psychiatry (2020-05-10)
Patients with schizophrenia show increased striatal dopamine synthesis capacity in imaging studies. The mechanism underlying this is unclear but may be due to N-methyl-D-aspartate receptor (NMDAR) hypofunction and parvalbumin (PV) neuronal dysfunction leading to disinhibition of mesostriatal dopamine neurons. Here
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