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Merck

N171

NBQX hydrate

powder, ≥98% (HPLC)

Synonym(s):

1,2,3,4-Tetrahydro-6-nitro-2,3-dioxo-benzo[f]quinoxaline-7-sulfonamide hydrate, FG 9202

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About This Item

Empirical Formula (Hill Notation):
C12H8N4O6S · xH2O
CAS Number:
118876-58-7
Molecular Weight:
336.28 (anhydrous basis)
NACRES:
NA.77
PubChem Substance ID:
329818588
UNSPSC Code:
12352200
MDL number:
MFCD11046016
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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InChI

1S/C12H8N4O6S.H2O/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);1H2

SMILES string

O.NS(=O)(=O)c1cccc2c3NC(=O)C(=O)Nc3cc([N+]([O-])=O)c12

InChI key

VOYWRRFTJLCIEL-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

yellow

solubility

methanol: 0.25 mg/mL, 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.5 mg/mL, DMSO: 4 mg/mL, H2O: insoluble

Quality Level

100

Application

NBQX hydrate has been used:
  • as a non-N-methyl-D-aspartate receptor (NMDA) 2-amino-3-hydroxy-5-methyl-4-isoxazol propionic acid (AMPA) receptor antagonist to monitor gonadotropin responses
  • α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor (AMPAR) antagonist in monocytes
  • AMPA and N-methyl-D-aspartate receptor (NMDA) antagonist in migrating interneurons expressing potassium-chloride cotransporter (shKCC2)

Biochem/physiol Actions

NBQX [2,3-dihydroxy-6-nitro-7-sulphamoyl-benzo(F)quinoxaline], an anticonvulsant provides protection against white matter damage in spinal cord crush injury and also protects oligodendrocyte in experimental autoimmune encephalomyelitis (EAE). However, its role in preventing inflammation in EAE is not yet clear.
Neuroprotective AMPA/kainate glutamate receptor antagonist.

General description

NBQX [2,3-dihydroxy-6-nitro-7-sulphamoyl-benzo(F)quinoxaline] is a competitive antagonist, which shows high affinity to 2-amino-3-hydroxy-5-methyl-4-isoxazol propionic acid (AMPA) receptor than kainite receptor.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000217411
0000217411
0000141762
0000127988
0000127989

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D Pitt et al.
Nature medicine, 6(1), 67-70 (1999-12-29)
Glutamate excitotoxicity mediated by the AMPA/kainate type of glutamate receptors damages not only neurons but also the myelin-producing cell of the central nervous system, the oligodendrocyte. In multiple sclerosis, myelin, oligodendrocytes and some axons are lost as a result of
Jane E Libbey et al.
Experimental neurology, 280, 89-96 (2016-04-14)
Seizures occur due to an imbalance between excitation and inhibition, with the balance tipping towards excitation, and glutamate is the predominant excitatory neurotransmitter in the central nervous system of mammals. Since upregulation of expression and/or function of glutamate receptors can
Pro-inflammatory monocyte profile in patients with major depressive disorder and suicide behaviour and how ketamine induces anti-inflammatory M2 macrophages by NMDAR and mTOR
Nowak W, et al.
EBioMedicine, 50, 290-305 (2019)
NBQX, a highly selective competitive antagonist of AMPA and KA ionotropic glutamate receptors, increases seizures and mortality following picornavirus infection
Libbey JE, et al.
Experimental Neurology, 280, 89-96 (2016)
Sandra Jurado et al.
Neuron, 77(3), 542-558 (2013-02-12)
Membrane fusion during exocytosis is mediated by assemblies of SNARE (soluble NSF-attachment protein receptor) and SM (Sec1/Munc18-like) proteins. The SNARE/SM proteins involved in vesicle fusion during neurotransmitter release are well understood, whereas little is known about the protein machinery that
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