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N183

Sigma-Aldrich

NBQX disodium salt hydrate

≥98% (HPLC), lyophilized powder, neuroprotective AMPA/kainate glutamate receptor antagonist

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C12H6N4Na2O6S · xH2O
CAS Number:
118876-58-7
Molecular Weight:
380.24 (anhydrous basis)
MDL number:
MFCD12910445
UNSPSC Code:
12352200
PubChem Substance ID:
24277996
NACRES:
NA.77

product name

NBQX disodium salt hydrate, ≥98% (HPLC)

Quality Level

100

Assay

≥98% (HPLC)

form

lyophilized powder

storage condition

desiccated

color

, brown to dark red-brown

solubility

H2O: >10 mg/mL

storage temp.

2-8°C

SMILES string

O.[Na+].[Na+].NS(=O)(=O)c1cccc2c1c(cc3nc([O-])c([O-])nc23)[N+]([O-])=O

InChI

1S/C12H8N4O6S.2Na.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/q;2*+1;/p-2

InChI key

LQSCHRKYVVVUFA-UHFFFAOYSA-L

Gene Information

human ... GRIA1(2890) , GRIA2(2891) , GRIA3(2892) , GRIA4(2893) , GRIK1(2897) , GRIK2(2898) , GRIK3(2899) , GRIK4(2900) , GRIK5(2901)

Application

NBQX disodium salt hydrate has been used:
  • in N-methyl-D-aspartate receptor (NMDAR) kinetic studies
  • as an α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor antagonist for the electrophysiological studies cultured neurons
  • in the extracellular solution for current/voltage (I/V) relationship and rectification index experiments in excitatory postsynaptic currents (EPSCs) mediated by NMDA receptors (EPSCNMDAR)

Biochem/physiol Actions

NBQX disodium salt hydrate is a neuroprotective AMPA/kainate glutamate receptor antagonist.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Glutamate Receptors (Ion Channel Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

N183-25MG:
N183-IP:
N183-VAR:
N183-100MG:
N183-BULK:
N183-5MG:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Predicting the functional states of human iPSC-derived neurons with single-cell RNA-seq and electrophysiology
Bardy C, et al.
Molecular Psychiatry, 21(11), 1573-1573 (2016)
Cross-modal reinstatement of thalamocortical plasticity accelerates ocular dominance plasticity in adult mice
Rodriguez G, et al.
Cell Reports, 24(13), 3433-3440 (2018)
The C-terminal tails of endogenous GluA1 and GluA2 differentially contribute to hippocampal synaptic plasticity and learning
Zhou Z, et al.
Nature Neuroscience, 21(1), 50-50 (2018)
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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