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NBQX

From Wikipedia, the free encyclopedia
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 InfoCard100.149.984Edit 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 mass336.281
Appearancebrown/red powder
Soluble to 100 mM in DMSO
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

NBQX (2,3-dioxo-6-nitro-7-sulfamoyl-benzo[f]quinoxaline) is anantagonist of theAMPA receptor.

NBQX blocks AMPA receptors in micromolar concentrations (~10–20 μM) and also blockskainate receptors. In experiments, it is used to counterglutamateexcitotoxicity.[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.
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor
Receptor
(ligands)
GlyRTooltip Glycine receptor
NMDARTooltip N-Methyl-D-aspartate receptor
Transporter
(blockers)
GlyT1Tooltip Glycine transporter 1
GlyT2Tooltip Glycine transporter 2


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