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Q2128

Sigma-Aldrich

Quisqualic acid

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
Beilstein:
1078734
MDL number:
MFCD00069337
UNSPSC Code:
12352106
PubChem Substance ID:
24278004
NACRES:
NA.32

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

SMILES string

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

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

InChI key

ASNFTDCKZKHJSW-REOHCLBHSA-N

Gene Information

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

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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 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

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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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
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Xi Lin
Brain Res. Protoc., 11(2) (2003)
Sujeenthar Tharmalingam et al.
Neuropharmacology, 63(4), 667-674 (2012-06-02)
The metabotropic glutamate receptors (mGluRs) are evolutionarily conserved from nematodes to vertebrates. The Caenorhabditis elegans (C. elegans) genome contains three mGluR genes referred to as mgl-1, mgl-2, and mgl-3. The aim of this study was to characterize the pharmacological profiles
Amadou T Corera et al.
PloS one, 4(6), e6021-e6021 (2009-06-24)
In brain, N-methyl-D-aspartate (NMDA) receptor (NMDAR) activation can induce long-lasting changes in synaptic alpha-amino-3-hydroxy-5-methylisoxazole-4-propionate (AMPA) receptor (AMPAR) levels. These changes are believed to underlie the expression of several forms of synaptic plasticity, including long-term potentiation (LTP). Such plasticity is generally
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