NBQX

{{chembox

| verifiedrevid = 408765621

| ImageFile=NBQX.svg

| ImageSize=

| ImageFile1 = NBQX molecule spacefill.png

| ImageSize1 = 220

| ImageAlt1 = Space-filling model of the NBQX molecule

| PIN=6-Nitro-2,3-dioxo-1,2,3,4-tetrahydrobenzo[f]quinoxaline-7-sulfonamide

| OtherNames=

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 4264

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2521927

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C13667

| 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)

| InChIKey = UQNAFPHGVPVTAL-UHFFFAOYAI

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 222519

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = UQNAFPHGVPVTAL-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 118876-58-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 8LZ6Q43V2S

| PubChem=3272524

| SMILES = [O-][N+](=O)c2cc3c(c1cccc(c12)S(=O)(=O)N)NC(=O)C(=O)N3

}}

|Section2={{Chembox Properties

| Formula=C₁₂H₈N₄O₆S

| MolarMass=336.281

| Appearance=brown/red powder

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=Soluble to 100 mM in DMSO

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

}}

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.Pitt, D.; Werner, P.; Raine, C. S. (2000). "Glutamate excitotoxicity in a model of multiple sclerosis". Nat Med. 6 (1): 67–70. NBQX was found to have anticonvulsant activity in rodent seizure models.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.

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