NBQX

NBQX
Names
	IUPAC name 6-Nitro-2,3-dioxo-1,2,3,4-tetrahydrobenzo[f]quinoxaline-7-sulfonamide
Identifiers
CAS Number	118876-58-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL222519 ;
ChemSpider	2521927 ;
ECHA InfoCard	100.149.984
IUPHAR/BPS	4264;
KEGG	C13667 ;
PubChem CID	3272524;
CompTox Dashboard (EPA)	DTXSID60152256 ;
	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).

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).^[3]

References

^ Pitt, D.; Werner, P.; Raine, C. S. (2000). "Glutamate excitotoxicity in a model of multiple sclerosis". Nat Med. 6 (1): 67–70.
^ 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.
^ Vendor product information

[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] Vendor product information

[1]

[2]

[3]

Names


IUPAC name 6-Nitro-2,3-dioxo-1,2,3,4-tetrahydrobenzo[f]quinoxaline-7-sulfonamide
Identifiers
CAS Number	118876-58-7
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL222519
ChemSpider	2521927
ECHA InfoCard	100.149.984
IUPHAR/BPS	4264
KEGG	C13667
PubChem CID	3272524
CompTox Dashboard (EPA)	DTXSID60152256
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).

NBQX

See also

References