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Merck

Q2128

Quisqualic acid

L-glutamate agonist, powder

Synonym(s):

β-(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)-L-alanine, 3-(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)-L-alanine

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About This Item

Empirical Formula (Hill Notation):
C5H7N3O5
CAS Number:
52809-07-1
Molecular Weight:
189.13
NACRES:
NA.32
PubChem Substance ID:
24278004
UNSPSC Code:
12352106
MDL number:
MFCD00069337
Beilstein/REAXYS Number:
1078734

Key Documents

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Product Name

Quisqualic acid, powder

InChI

1S/C5H7N3O5/c6-2(3(9)10)1-8-4(11)7-5(12)13-8/h2H,1,6H2,(H,9,10)(H,7,11,12)/t2-/m0/s1

SMILES string

N[C@@H](CN1OC(=O)NC1=O)C(O)=O

InChI key

ASNFTDCKZKHJSW-REOHCLBHSA-N

form

powder

color

white to off-white

solubility

ethanol: <0.17 mg/mL, H2O: 0.5 mg/mL, 0.1 M HCl: 1.4 mg/mL, 1 M NH4OH: 20 mg/mL, organic solvents: insoluble

storage temp.

2-8°C

Quality Level

200

Gene Information

rat ... Gria1(50592), Grik1(29559), Grin2a(24409), Grm1(24414), Grm2(24415), Grm4(24417), Grm5(24418)

Related Categories

General description

Quisqualate/ Quisqualic acid is obtained from the fruits and seeds of Quisqualis chinensis. It is an agonist at two subsets of excitatory amino acid receptors metabotropic receptors that indirectly mediate calcium mobilization from intracellular stores and, ionotropic receptors that directly control membrane channels. L-quisqualic acid is an agonist of the neurotransmitter L-glutamate.

Application

Quisqualic acid has also been used as a group I metabotropic receptor agonist in neurons.
Quisqualic acid has been used to test ligand-gated receptors in spiral ganglion neurons.

Biochem/physiol Actions

Active enantiomer of quisqualic acid; excitatory amino acid at glutamate receptors.

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
0000492019
0000492019
0000429456
0000429456
0000433943

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Pablo J Giraudi et al.
PloS one, 6(12), e29078-e29078 (2012-01-05)
We have previously reported that exposure of SH-SY5Y neuroblastoma cells to unconjugated bilirubin (UCB) resulted in a marked up-regulation of the mRNA encoding for the Na(+)-independent cystine∶glutamate exchanger System X(c)(-) (SLC7A11 and SLC3A2 genes). In this study we demonstrate that
Chinese Drugs of Plant Origin: Chemistry, Pharmacology, and Use in Traditional and Modern Medicine null
Thibault Collin et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 29(29), 9281-9291 (2009-07-25)
Little is known about the generation of slow rhythms in brain neuronal circuits. Nevertheless, a few studies, both from reconstituted systems and from hippocampal slices, indicate that activation of metabotropic glutamate receptors (mGluRs) could generate such rhythms. Here we show
Impaired cellular bioenergetics caused by GBA1 depletion sensitizes neurons to calcium overload
Plotegher N, et al.
Cell Death and Differentiation, 27(5), 1588-1603 (2020)
Optical recordings of Ca2+ signaling activities from identified inner ear cells in cochlear slices and hemicochleae
Xi Lin
Brain Res. Protoc., 11(2) (2003)
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