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{{chembox {{chembox
| verifiedrevid = 408765621 | verifiedrevid = 408765621
|ImageFile=NBQX.png | ImageFile=NBQX.svg
|ImageSize= | ImageSize=
| ImageFile1 = NBQX molecule spacefill.png
⚫ |IUPACName=2,3-Dioxo-6-nitro-1,2,3,4-tetrahydrobenzoquinoxaline -7-sulfonamide
| ImageSize1 = 220
⚫ |OtherNames=
| ImageAlt1 = Space-filling model of the NBQX molecule
⚫ |Section1= {{Chembox Identifiers
⚫ | PIN=6-Nitro-2,3-dioxo-1,2,3,4-tetrahydrobenzoquinoxaline-7-sulfonamide
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | OtherNames=
⚫ |Section1={{Chembox Identifiers
| IUPHAR_ligand = 4264
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2521927 | ChemSpiderID = 2521927
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
Line 18: Line 22:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UQNAFPHGVPVTAL-UHFFFAOYSA-N | StdInChIKey = UQNAFPHGVPVTAL-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=118876-58-7 | CASNo = 118876-58-7
⚫ | PubChem=3272524
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | SMILES = (=O)c2cc3c(c1cccc(c12)S(=O)(=O)N)NC(=O)C(=O)N3
| UNII = 8LZ6Q43V2S
⚫ | PubChem=3272524
⚫ | SMILES = (=O)c2cc3c(c1cccc(c12)S(=O)(=O)N)NC(=O)C(=O)N3
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>12</sub>H<sub>8</sub>N<sub>4</sub>O<sub>6</sub>S | Formula=C<sub>12</sub>H<sub>8</sub>N<sub>4</sub>O<sub>6</sub>S
| MolarMass=336.281 | MolarMass=336.281
| Appearance=brown/red powder | Appearance=brown/red powder
| Density= | Density=
| MeltingPt= | MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility=Soluble to 100 mM in DMSO | Solubility=Soluble to 100 mM in DMSO
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}
⚫ '''NBQX''' (2,3-dihydroxy-6-nitro-7-sulfamoyl-benzoquinoxaline-2,3-dione) is an ] ].


⚫ '''NBQX''' (2,3-dioxo-6-nitro-7-sulfamoyl-benzoquinoxaline) is an ] of the ].
⚫ NBQX blocks ]s in micromolar concentrations (~10–20 µmol) and also blocks kainate receptors. In experiments, it is used to counter ] ].<ref>Pitt, D.; Werner, P.; Raine, C. S. (2000). "Glutamate excitotoxicity in a model of multiple sclerosis". ''Nat Med.'' '''6''' (1): 67–70.</ref> NBQX was found to have anticonvulsant activity in rodent seizure models. <ref>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.</ref>


⚫ NBQX blocks AMPA receptors in micromolar concentrations (~10–20 μM) and also blocks ]s. In experiments, it is used to counter ] ].<ref>Pitt, D.; Werner, P.; Raine, C. S. (2000). "Glutamate excitotoxicity in a model of multiple sclerosis". ''Nat Med.'' '''6''' (1): 67–70.</ref> NBQX was found to have anticonvulsant activity in rodent seizure models.<ref>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.</ref>
⚫ As the disodium salt, NBQX is soluble in water at high concentrations (<30 mmol).{{Fact|date=August 2010}}

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

==See also==
*]
*]
*] (MPQX)
*]


==References== ==References==
{{reflist}} {{Reflist}}


{{Ionotropic glutamate receptor modulators}}
{{Glutamate_receptor_ligands}}
{{Glycine receptor modulators}}


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{{biochem-stub}} {{biochem-stub}}

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Latest revision as of 20:14, 5 April 2024

NBQX
Space-filling model of the NBQX molecule
Names
Preferred IUPAC name 6-Nitro-2,3-dioxo-1,2,3,4-tetrahydrobenzoquinoxaline-7-sulfonamide
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.149.984 Edit this at Wikidata
IUPHAR/BPS
KEGG
PubChem CID
UNII
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). checkY verify (what is  ?) Infobox references
Chemical compound

NBQX (2,3-dioxo-6-nitro-7-sulfamoyl-benzoquinoxaline) 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. NBQX was found to have anticonvulsant activity in rodent seizure models.

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

See also

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.
Ionotropic glutamate receptor modulators
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor
Glycine receptor modulators
Receptor
(ligands)
GlyRTooltip Glycine receptor
NMDARTooltip N-Methyl-D-aspartate receptor
Transporter
(blockers)
GlyT1Tooltip Glycine transporter 1
GlyT2Tooltip Glycine transporter 2
See also
Receptor/signaling modulators
GABA receptor modulators
GABAA receptor positive modulators
Ionotropic glutamate receptor modulators


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