rivastigmine (CHEBI:8874)

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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

Average Mass

250.33670

Monoisotopic Mass

250.16813

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.

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

Last Modified

22 February 2017