N171

NBQX hydrate

powder, ≥98% (HPLC)

• Synonym(s): 1,2,3,4-Tetrahydro-6-nitro-2,3-dioxo-benzo[f]quinoxaline-7-sulfonamide hydrate, FG 9202
• Empirical Formula (Hill Notation): C₁₂H₈N₄O₆S · xH₂O
• CAS Number: 118876-58-7
• Molecular Weight: 336.28 (anhydrous basis)
• NACRES: NA.77
• PubChem Substance ID: 329818588
• UNSPSC Code: 12352200
• MDL number: MFCD11046016
• Assay: ≥98% (HPLC)
• Form: powder

Properties

• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: powder
• color: yellow
• solubility: methanol: 0.25 mg/mL, 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.5 mg/mL, DMSO: 4 mg/mL, H₂O: insoluble
• SMILES string: O.NS(=O)(=O)c1cccc2c3NC(=O)C(=O)Nc3cc([N+]([O-])=O)c12
• InChI: 1S/C12H8N4O6S.H2O/c13-23(21,22)8-3-1-2-5-9(8)7(16(19)20)4-6-10(5)15-12(18)11(17)14-6;/h1-4H,(H,14,17)(H,15,18)(H2,13,21,22);1H2
• InChI key: VOYWRRFTJLCIEL-UHFFFAOYSA-N

Description

General description

NBQX [2,3-dihydroxy-6-nitro-7-sulphamoyl-benzo(F)quinoxaline] is a competitive antagonist, which shows high affinity to 2-amino-3-hydroxy-5-methyl-4-isoxazol propionic acid (AMPA) receptor than kainite receptor.

Application

NBQX hydrate has been used:

• as a non-N-methyl-D-aspartate receptor (NMDA) 2-amino-3-hydroxy-5-methyl-4-isoxazol propionic acid (AMPA) receptor antagonist to monitor gonadotropin responses
• α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor (AMPAR) antagonist in monocytes
• AMPA and N-methyl-D-aspartate receptor (NMDA) antagonist in migrating interneurons expressing potassium-chloride cotransporter (shKCC2)

Biochem/physiol Actions

NBQX [2,3-dihydroxy-6-nitro-7-sulphamoyl-benzo(F)quinoxaline], an anticonvulsant provides protection against white matter damage in spinal cord crush injury and also protects oligodendrocyte in experimental autoimmune encephalomyelitis (EAE). However, its role in preventing inflammation in EAE is not yet clear.

Neuroprotective AMPA/kainate glutamate receptor antagonist.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves