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NBQX

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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 checkY☒N ?)

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.[1] NBQX was found to have anticonvulsant activity in rodent seizure models.[2]

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

See also

[edit]

References

[edit]
  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.


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