CHEBI:132050 - norverapamil

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ChEBI Name norverapamil
ChEBI ID CHEBI:132050
Definition A racemate comprising equimolar amounts of (R)- and (S)-norverapamil. The major active metabolite of verapamil.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C26H36N2O4
Net Charge 0
Average Mass 440.576
Monoisotopic Mass 440.26751
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) See: MetaboLights Study
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): drug metabolite

calcium channel blocker
One of a class of drugs that acts by selective inhibition of calcium influx through cell membranes or on the release and binding of calcium in intracellular pools.
EC 1.2.3.1 (aldehyde oxidase) inhibitor
An EC 1.2.3.* (oxidoreductase acting on donor aldehyde/oxo group with oxygen as acceptor) inhibitor which interferes with the action of aldehyde oxidase (EC 1.2.3.1).
EC 3.4.24.18 (meprin A) inhibitor
An EC 3.4.24.* (metalloendopeptidase) inhibitor that inhibits the action of meprin A (EC 3.4.24.18).
EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor
An EC 3.4.24.* (metalloendopeptidase) inhibitor that interferes with the action of anthrax lethal factor endopeptidase (EC 3.4.24.83).
EC 3.6.3.1 (phospholipid-translocating ATPase) inhibitor
An EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of phospholipid-translocating ATPase (EC 3.6.3.1).
EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor
An EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of xenobiotic-transporting ATPase (EC 3.6.3.44).
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): anti-arrhythmia drug
A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
vasodilator agent
A drug used to cause dilation of the blood vessels.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing norverapamil (CHEBI:132050) has part (R)-norverapamil (CHEBI:134082)
norverapamil (CHEBI:132050) has part (S)-norverapamil (CHEBI:134081)
norverapamil (CHEBI:132050) has role anti-arrhythmia drug (CHEBI:38070)
norverapamil (CHEBI:132050) has role antihypertensive agent (CHEBI:35674)
norverapamil (CHEBI:132050) has role calcium channel blocker (CHEBI:38215)
norverapamil (CHEBI:132050) has role drug metabolite (CHEBI:49103)
norverapamil (CHEBI:132050) has role EC 1.2.3.1 (aldehyde oxidase) inhibitor (CHEBI:62872)
norverapamil (CHEBI:132050) has role EC 3.4.24.18 (meprin A) inhibitor (CHEBI:77745)
norverapamil (CHEBI:132050) has role EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor (CHEBI:77255)
norverapamil (CHEBI:132050) has role EC 3.6.3.1 (phospholipid-translocating ATPase) inhibitor (CHEBI:77747)
norverapamil (CHEBI:132050) has role EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor (CHEBI:77748)
norverapamil (CHEBI:132050) has role environmental contaminant (CHEBI:78298)
norverapamil (CHEBI:132050) has role vasodilator agent (CHEBI:35620)
norverapamil (CHEBI:132050) has role xenobiotic (CHEBI:35703)
norverapamil (CHEBI:132050) is a racemate (CHEBI:60911)
IUPAC Name
rac-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl]amino}-2-(propan-2-yl)pentanenitrile
Synonyms Sources
(±)-norverapamil ChEBI
(RS)-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl]amino}-2-(propan-2-yl)pentanenitrile ChEBI
(RS)-norverapamil ChEBI
5-((3,4-Dimethoxyphenethyl)amino)-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile ChemIDplus
alpha-(3-((2-(3,4-Dimethoxyphenyl)ethyl)amino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)benzeneacetonitrile ChemIDplus
desmethylverapamil ChEBI
rac-norverapamil ChEBI
Manual Xrefs Databases
94724 ChemSpider
HMDB0060540 HMDB
Norverapamil Wikipedia
View more database links
Registry Numbers Types Sources
5458977 Reaxys Registry Number Reaxys
67018-85-3 CAS Registry Number NIST Chemistry WebBook
67018-85-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
07 December 2016
General Comment
2016-12-07 This is the entry for racemic material. There are separate entries for the individual enantiomers [(R)-norverapamil and (S)-norverapamil] and for the entity with unspecified stereochemistry (2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl]amino}-2-(propan-2-yl)pentanenitrile)