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

ChEBI IDCHEBI:177876
ChEBI NameN-[2-(4-phenoxybenzyl)benzimidazol-5-yl]methanesulfonamide
Stars
ASCII NameN-[2-(4-phenoxybenzyl)benzimidazol-5-yl]methanesulfonamide
DefinitionA 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.
Last Modified17 September 2021
Submitterslaulederkind
DownloadsMolfile
FormulaC21H19N3O3S
Net Charge0
Average Mass393.468
Monoisotopic Mass393.11471
SMILESCS(=O)(=O)Nc1ccc2nc(Cc3ccc(Oc4ccccc4)cc3)nc2c1
InChIInChI=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)
InChIKeyYOUFPIVQKJMXMT-UHFFFAOYSA-N
Roles Classification
Biological Role:
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:
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
ChEBI Ontology
Outgoing Relation(s)
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  Source
XK2SUBMITTER
N-[2-(4-phenoxybenzyl)benzimidazol-5-yl]methanesulphonamideChEBI
Manual XrefsDatabases
WO2001032174Patent
8041057ChemSpider
Citations