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NBQX

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NBQX
File:NBQX.png
Names
IUPAC name 2,3-Dioxo-6-nitro-1,2,3,4-tetrahydrobenzoquinoxaline -7-sulfonamide
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.149.984 Edit this at Wikidata
KEGG
PubChem CID
CompTox Dashboard (EPA)
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)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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

NBQX (2,3-dihydroxy-6-nitro-7-sulfamoyl-benzoquinoxaline-2,3-dione) is an AMPA receptor antagonist.

NBQX blocks AMPA receptors in micromolar concentrations (~10–20 µmol) 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 (<30 mmol).

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.
Glutamate receptor modulators
Ionotropic glutamate receptor modulators
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor
Metabotropic glutamate receptor modulators
Group I
mGluR1Tooltip Metabotropic glutamate receptor 1
mGluR5Tooltip Metabotropic glutamate receptor 5
Group II
mGluR2Tooltip Metabotropic glutamate receptor 2
mGluR3Tooltip Metabotropic glutamate receptor 3
Group III
mGluR4Tooltip Metabotropic glutamate receptor 4
mGluR6Tooltip Metabotropic glutamate receptor 6
mGluR7Tooltip Metabotropic glutamate receptor 7
mGluR8Tooltip Metabotropic glutamate receptor 8
See also: Receptor/signaling modulators • Ionotropic glutamate receptor modulators • Glutamate metabolism/transport modulators


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