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N171

Sigma-Aldrich

NBQX hydrate

powder, ≥98% (HPLC)

Sinónimos:

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

Fórmula empírica (notación de Hill):
C12H8N4O6S · xH2O
Número de CAS:
118876-58-7
Peso molecular:
336.28 (anhydrous basis)
MDL number:
MFCD11046016
UNSPSC Code:
12352200
PubChem Substance ID:
329818588
NACRES:
NA.77

Quality Level

100

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

SMILES string

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

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

InChI key

VOYWRRFTJLCIEL-UHFFFAOYSA-N

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.

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
093M4608V
101M4609V
057K46156
057K46155
057K46154

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Visite la Librería de documentos

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)
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
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
Amy M Pooler et al.
EMBO reports, 14(4), 389-394 (2013-02-16)
Propagation of tau pathology is linked with progressive neurodegeneration, but the mechanism underlying trans-synaptic spread of tau is unknown. We show that stimulation of neuronal activity, or AMPA receptor activation, induces tau release from healthy, mature cortical neurons. Notably, phosphorylation
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