CHEBI:8874 - rivastigmine

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ChEBI Name rivastigmine
ChEBI ID CHEBI:8874
Definition A carbamate ester obtained by formal condensation of the carboxy group of ethyl(methyl)carbamic acid with the phenolic OH group of 3-[(1S)-1-(dimethylamino)ethyl]phenol. A reversible cholinesterase inhibitor.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C14H22N2O2
Net Charge 0
Average Mass 250.33670
Monoisotopic Mass 250.168
InChI InChI=1S/C14H22N2O2/c1-6-16(5)14(17)18-13-9-7-8-12(10-13)11(2)15(3)4/h7-11H,6H2,1-5H3/t11-/m0/s1
InChIKey XSVMFMHYUFZWBK-NSHDSACASA-N
SMILES CCN(C)C(=O)Oc1cccc(c1)[C@H](C)N(C)C
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 3.1.1.8 (cholinesterase) inhibitor
An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).
cholinergic drug
Any drug used for its actions on cholinergic systems. Included here are agonists and antagonists, drugs that affect the life cycle of acetylcholine, and drugs that affect the survival of cholinergic neurons.
Application(s): neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
cholinergic drug
Any drug used for its actions on cholinergic systems. Included here are agonists and antagonists, drugs that affect the life cycle of acetylcholine, and drugs that affect the survival of cholinergic neurons.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing rivastigmine (CHEBI:8874) has role cholinergic drug (CHEBI:38323)
rivastigmine (CHEBI:8874) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733)
rivastigmine (CHEBI:8874) has role neuroprotective agent (CHEBI:63726)
rivastigmine (CHEBI:8874) is a carbamate ester (CHEBI:23003)
rivastigmine (CHEBI:8874) is a tertiary amino compound (CHEBI:50996)
rivastigmine (CHEBI:8874) is conjugate base of rivastigmine(1+) (CHEBI:64363)
Incoming rivastigmine(1+) (CHEBI:64363) is conjugate acid of rivastigmine (CHEBI:8874)
IUPAC Name
3-[(1S)-1-(dimethylamino)ethyl]phenyl ethyl(methyl)carbamate
INN Source
rivastigmine KEGG DRUG
Synonyms Sources
(S)-3-(1-(Dimethylamino)ethyl)phenyl ethylmethylcarbamate ChemIDplus
m-((S)-1-(Dimethylamino)ethyl)phenyl ethylmethylcarbamate ChemIDplus
Manual Xrefs Databases
2392 DrugCentral
C11766 KEGG COMPOUND
D03822 KEGG DRUG
DB00989 DrugBank
DE3805744 Patent
EP1980552 Patent
EP2233465 Patent
LSM-5280 LINCS
Rivastigmine Wikipedia
US2008255383 Patent
US2009298817 Patent
US5602176 Patent
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Registry Numbers Types Sources
123441-03-2 CAS Registry Number ChemIDplus
7875788 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017