amisulpride (CHEBI:64045)

ChEBI > Main

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	amisulpride

ChEBI ID	CHEBI:64045

Definition	A member of the class of benzamides resulting from the formal condensation of the carboxy group of 4-amino-5-(ethylsulfonyl)-2-methoxybenzoic acid with the primary amino group of 2-(aminomethyl)-1-ethylpyrrolidine. It is a potent, selective dopamine D₂ and D₃ receptor antagonist. It is an atypical antipsychotic/antischizophrenic agent with limited extrapyrimidal side effects.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Wikipedia	License

Read full article at Wikipedia

Formula

C17H27N3O4S

Net Charge

Average Mass

369.47900

Monoisotopic Mass

369.17223

InChI

InChI=1S/C17H27N3O4S/c1-4-20-8-6-7-12(20)11-19-17(21)13-9-16(25(22,23)5-2)14(18)10-15(13)24-3/h9-10,12H,4-8,11,18H2,1-3H3,(H,19,21)

InChIKey

NTJOBXMMWNYJFB-UHFFFAOYSA-N

SMILES

CCN1CCCC1CNC(=O)c1cc(c(N)cc1OC)S(=O)(=O)CC

Roles Classification
Chemical Role(s):	environmental contaminant Any minor or unwanted substance introduced into the environment that can have undesired effects. Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	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):	second generation antipsychotic Antipsychotic drugs which can have different modes of action but which tend to be less likely than first generation antipsychotics to cause extrapyramidal motor control disabilities such as body rigidity or Parkinson's disease-type movements.

ChEBI Ontology
Outgoing	amisulpride (CHEBI:64045) has role environmental contaminant (CHEBI:78298) amisulpride (CHEBI:64045) has role second generation antipsychotic (CHEBI:65191) amisulpride (CHEBI:64045) has role xenobiotic (CHEBI:35703) amisulpride (CHEBI:64045) is a aromatic amide (CHEBI:62733) amisulpride (CHEBI:64045) is a aromatic amine (CHEBI:33860) amisulpride (CHEBI:64045) is a benzamides (CHEBI:22702) amisulpride (CHEBI:64045) is a pyrrolidines (CHEBI:38260) amisulpride (CHEBI:64045) is a sulfone (CHEBI:35850)

IUPAC Name

4-amino-N-[(1-ethylpyrrolidin-2-yl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide

Synonyms	Sources
4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide	ChemIDplus
4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-o-anisamide	ChemIDplus
Aminosultopride	DrugBank

Last Modified

22 February 2017

General Comment
2014-10-29	Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag