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Merck

SML0654

Entacapone

≥98% (HPLC), COMT inhibitor, powder

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

Product Name

Entacapone, ≥98% (HPLC)

SMILES string

[N+](=O)([O-])c1c(c(cc(c1)\C=C(\C(=O)N(CC)CC)/C#N)O)O

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

assay

≥98% (HPLC)

form

powder

color

white to light brown

solubility

DMSO: 20 mg/mL, clear

storage temp.

room temp

Quality Level

100

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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.
Entacapone is a catechol-O-methyl transferase (COMT) inhibitor. Antiparkinson; anti-Dyskinesia.

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000499697
0000499697
0000486137
0000486140
0000486137

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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
Entacapone in the treatment of Parkinson's disease
Schrag Anette
Lancet Neurology, 4(6), 366-370 (2005)
Principles of Treatment in Parkinson's Disease, 133-133 (2005)
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
Fabrizio Stocchi et al.
Parkinsonism & related disorders, 20(12), 1335-1340 (2014-10-13)
IPX066, an investigational extended-release carbidopa-levodopa (CD-LD) preparation, has demonstrated a rapid attainment and prolonged maintenance of therapeutic LD plasma concentrations in advanced Parkinson's disease (PD). This phase-3 crossover study assessed its efficacy and safety vs. CD-LD plus entacapone (CL + E). At
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