N-[2-(4-phenoxybenzyl)benzimidazol-5-yl]methanesulfonamide (CHEBI:177876)

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ChEBI Name	N-[2-(4-phenoxybenzyl)benzimidazol-5-yl]methanesulfonamide

ChEBI ID	CHEBI:177876

ChEBI ASCII Name	N-[2-(4-phenoxybenzyl)benzimidazol-5-yl]methanesulfonamide

Definition	A member of the class of benzimidazoles that is 1H-benzimidazole substituted by 4-phenoxybenzyl and (methylsulfonyl)amino groups at positions 2 and 6, respectively. It is a potent antagonist of the GluN2B subunit of the N-methyl-D-aspartate (NMDA) receptor.

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

Submitter	Stan Laulederkind

Supplier Information

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Formula

C21H19N3O3S

Net Charge

Average Mass

393.460

Monoisotopic Mass

393.11471

InChI

InChI=1S/C21H19N3O3S/c1-28(25,26)24-16-9-12-19-20(14-16)23-21(22-19)13-15-7-10-18(11-8-15)27-17-5-3-2-4-6-17/h2-12,14,24H,13H2,1H3,(H,22,23)

InChIKey

YOUFPIVQKJMXMT-UHFFFAOYSA-N

SMILES

CS(=O)(=O)NC1=CC2=C(C=C1)N=C(CC1=CC=C(OC3=CC=CC=C3)C=C1)N2

Roles Classification
Biological Role(s):	NMDA receptor antagonist Any substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs.

Application(s):	neuroprotective agent Any compound that can be used for the treatment of neurodegenerative disorders.

ChEBI Ontology
Outgoing	N-[2-(4-phenoxybenzyl)benzimidazol-5-yl]methanesulfonamide (CHEBI:177876) has role neuroprotective agent (CHEBI:63726) N-[2-(4-phenoxybenzyl)benzimidazol-5-yl]methanesulfonamide (CHEBI:177876) has role NMDA receptor antagonist (CHEBI:60643) N-[2-(4-phenoxybenzyl)benzimidazol-5-yl]methanesulfonamide (CHEBI:177876) is a aromatic ether (CHEBI:35618) N-[2-(4-phenoxybenzyl)benzimidazol-5-yl]methanesulfonamide (CHEBI:177876) is a benzenes (CHEBI:22712) N-[2-(4-phenoxybenzyl)benzimidazol-5-yl]methanesulfonamide (CHEBI:177876) is a benzimidazoles (CHEBI:22715) N-[2-(4-phenoxybenzyl)benzimidazol-5-yl]methanesulfonamide (CHEBI:177876) is a sulfonamide (CHEBI:35358)

IUPAC Name

N-[2-(4-phenoxybenzyl)-1H-benzimidazol-6-yl]methanesulfonamide

Synonyms	Sources
N-[2-(4-phenoxybenzyl)benzimidazol-5-yl]methanesulphonamide	ChEBI
XK2	SUBMITTER

Last Modified

17 September 2021