N171

NBQX hydrate

Name: NBQX hydrate
Brand: SIGMA

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

Product Name

NBQX hydrate, powder, ≥98% (HPLC)

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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Glutamate excitotoxicity in a model of multiple sclerosis.

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

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.

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

Glutamate excitotoxicity in a model of multiple sclerosis

Pitt D, et al.

Nature Medicine, 6(1), 67-70 (2000)

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.

Wanda Nowak et al.

EBioMedicine, 50, 290-305 (2019-11-23)

Depression is a highly prevalent disorder that is one of the leading causes of disability worldwide. Despite an unknown aetiology, evidence suggests that the innate and adaptive immune systems play a significant role in the development and maintenance of major

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