NBQX

NBQX

Names
IUPAC name 2,3-Dioxo-6-nitro-1,2,3,4-tetrahydrobenzo[f]quinoxaline -7-sulfonamide
Identifiers
CAS Number	118876-58-7
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL222519
ChemSpider	2521927
ECHA InfoCard	100.149.984
IUPHAR/BPS	4264
KEGG	C13667
PubChem	3272524
InChI 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) Key: UQNAFPHGVPVTAL-UHFFFAOYSA-N 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
SMILES [O-][N+](=O)c2cc3c(c1cccc(c12)S(=O)(=O)N)NC(=O)C(=O)N3
Properties
Chemical formula	C12H8N4O6S
Molar mass	336.281
Appearance	brown/red powder
Solubility in water	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).
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Infobox references

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

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).^[3]

See also

• Quinoxalinedione

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.
3. Product information at Tocris