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NBQX
Names
Preferred IUPAC name
6-Nitro-2,3-dioxo-1,2,3,4-tetrahydrobenzo[f ]quinoxaline-7-sulfonamide
Identifiers
ChEMBL
ChemSpider
ECHA InfoCard 100.149.984
KEGG
UNII
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)
Y Key: UQNAFPHGVPVTAL-UHFFFAOYSA-N
Y 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
[O-][N+](=O)c2cc3c(c1cccc(c12)S(=O)(=O)N)NC(=O)C(=O)N3
Properties
C12 H8 N4 O6 S
Molar mass
336.281
Appearance
brown/red powder
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).
Chemical compound
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] [ 2]
As the disodium salt, NBQX is soluble in water at high concentrations (at least up to 100 mM).
^ 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.
AMPAR Tooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor KAR Tooltip Kainate receptor NMDAR Tooltip N-Methyl-D-aspartate receptor
Receptor (ligands )
GlyR Tooltip Glycine receptor
Positive modulators: Alcohols (e.g., brometone , chlorobutanol (chloretone) , ethanol (alcohol) , tert -butanol (2M2P)tribromoethanol , trichloroethanol , trifluoroethanol )Alkylbenzene sulfonate Anandamide Barbiturates (e.g., pentobarbital , sodium thiopental )Chlormethiazole D12-116 Dihydropyridines (e.g., nicardipine )Etomidate Ginseng constituents (e.g., ginsenosides (e.g., ginsenoside-Rf ))Glutamic acid (glutamate) Ivermectin Ketamine Neuroactive steroids (e.g., alfaxolone , pregnenolone (eltanolone) , pregnenolone acetate , minaxolone , ORG-20599 )Nitrous oxide Penicillin G Propofol Tamoxifen Tetrahydrocannabinol Triclofos Tropeines (e.g., atropine , bemesetron , cocaine , LY-278584 , tropisetron , zatosetron )Volatiles /gases (e.g., chloral hydrate , chloroform , desflurane , diethyl ether (ether) , enflurane , halothane , isoflurane , methoxyflurane , sevoflurane , toluene , trichloroethane (methyl chloroform) , trichloroethylene )Xenon Zinc Antagonists: 2-Aminostrychnine 2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine Diaboline Endocannabinoids (e.g., 2-AG , anandamide (AEA) )Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline N-Methylstrychnine N,N-Dimethylmuscimol Nipecotic acid Pitrazepin Pseudostrychnine Quinolines (e.g., 4-hydroxyquinoline , 4-hydroxyquinoline-3-carboxylic acid , 5,7-CIQA , 7-CIQ , 7-TFQ , 7-TFQA )RU-5135 Sinomenine Strychnine Thiocolchicoside Tutin Negative modulators: Amiloride Benzodiazepines (e.g., bromazepam , clonazepam , diazepam , flunitrazepam , flurazepam )Corymine Cyanotriphenylborate Daidzein Dihydropyridines (e.g., nicardipine , nifedipine , nitrendipine )Furosemide Genistein Ginkgo constituents (e.g., bilobalide , ginkgolides (e.g., ginkgolide A , ginkgolide B , ginkgolide C , ginkgolide J , ginkgolide M ))Imipramine NBQX Neuroactive steroids (e.g., 3α-androsterone sulfate , 3β-androsterone sulfate , deoxycorticosterone , DHEA sulfate , pregnenolone sulfate , progesterone )Opioids (e.g., codeine , dextromethorphan , dextrorphan , levomethadone , levorphanol , morphine , oripavine , pethidine , thebaine )Picrotoxin (i.e., picrotin and picrotoxinin )PMBA Riluzole Tropeines (e.g., bemesetron , LY-278584 , tropisetron , zatosetron )Verapamil Zinc NMDAR Tooltip N-Methyl-D-aspartate receptor
Transporter (blockers )
GlyT1 Tooltip Glycine transporter 1 GlyT2 Tooltip Glycine transporter 2
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