NBQX

NBQX
Space-filling model of the NBQX molecule
Names
Preferred IUPAC name
6-Nitro-2,3-dioxo-1,2,3,4-tetrahydrobenzo[f]quinoxaline-7-sulfonamide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.149.984 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C12H8N4O6S/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) checkY
    Key: UQNAFPHGVPVTAL-UHFFFAOYSA-N checkY
  • InChI=1/C12H8N4O6S/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)
    Key: UQNAFPHGVPVTAL-UHFFFAOYAI
  • [O-][N+](=O)c2cc3c(c1cccc(c12)S(=O)(=O)N)NC(=O)C(=O)N3
Properties
C12H8N4O6S
Molar mass 336.281
Appearance brown/red powder
Soluble to 100 mM in DMSO
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkYX markN ?)

NBQX (2,3-dioxo-6-nitro-7-sulfamoyl-benzo[f]quinoxaline) is an antagonist of the AMPA receptor.

NBQX blocks AMPA receptors in micromolar concentrations (~10–20 μM) and also blocks kainate receptors. In experiments, it is used to counter glutamate excitotoxicity. NBQX was found to have anticonvulsant activity in rodent seizure models.

As the disodium salt, NBQX is soluble in water at high concentrations (at least up to 100 mM).

See also

References

  1. ↑ Pitt, D.; Werner, P.; Raine, C. S. (2000). "Glutamate excitotoxicity in a model of multiple sclerosis". Nat Med. 6 (1): 67–70.
  2. ↑ Yamaguchi, S.; Donevan, S.D.; Rogawski, M.A. (1993). Anticonvulsant activity of AMPA/kainate antagonists: comparison of GYKI 52466 and NBOX in maximal electroshock and chemoconvulsant seizure models. Epilepsy Res. 15:179–184.