Q2128

Quisqualic acid

Name: Quisqualic acid
Brand: SIGMA

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

Beilstein:

1078734

MDL number:

MFCD00069337

UNSPSC Code:

12352106

PubChem Substance ID:

24278004

NACRES:

NA.32

Key Documents

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Product Name

Quisqualic acid, powder

form

powder

Quality Level

200

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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Show Differences

1 of 4

This Item	G1501	G1626	AG374
Sigma-Aldrich Q2128 Quisqualic acid	Sigma-Aldrich G1501 L-Glutamic acid potassium salt monohydrate	Sigma-Aldrich G1626 L-Glutamic acid monosodium salt hydrate	Sigma-Aldrich AG374 Metabotropic Glutamate Receptor 5, control peptide for AB5675
Quality Level 200	Quality Level 300	Quality Level 300	Quality Level 100
form powder	form powder	form powder	form liquid
storage temp. 2-8°C	storage temp. -	storage temp. -	storage temp. -
Gene Information rat ... Gria1(50592), Grik1(29559), Grin2a(24409), Grm1(24414), Grm2(24415), Grm4(24417), Grm5(24418)	Gene Information human ... GRIK1(2897), GRIK2(2898), GRIK3(2899), GRIK4(2900), GRIN1(2902), GRIN2A(2903), GRIN2B(2904), GRIN2C(2905), GRIN2D(2906), GRIN3A(116443), GRIN3B(116444), GRINA(2907) mouse ... GRIK1(14805), GRIK2(14806), GRIK3(14807), GRIK4(110637), GRIN1(14810), GRIN2A(14811), GRIN2B(14812), GRIN2C(14813), GRIN2D(14814), GRIN3A(242443), GRIN3B(170483), GRINA(66168) rat ... GRIK1(29559), GRIK2(54257), GRIK3(298521), GRIK4(24406), GRIN1(24408), GRIN2A(24409), GRIN2B(24410), GRIN2C(24411), GRIN2D(24412), GRIN3A(191573), GRIN3B(170796), GRINA(266668)	Gene Information human ... GRIK1(2897), GRIK2(2898), GRIK3(2899), GRIK4(2900), GRIN1(2902), GRIN2A(2903), GRIN2B(2904), GRIN2C(2905), GRIN2D(2906), GRIN3A(116443), GRIN3B(116444), GRINA(2907) mouse ... GRIK1(14805), GRIK2(14806), GRIK3(14807), GRIK4(110637), GRIN1(14810), GRIN2A(14811), GRIN2B(14812), GRIN2C(14813), GRIN2D(14814), GRIN3A(242443), GRIN3B(170483), GRINA(66168) rat ... GRIK1(29559), GRIK2(54257), GRIK3(298521), GRIK4(24406), GRIN1(24408), GRIN2A(24409), GRIN2B(24410), GRIN2C(24411), GRIN2D(24412), GRIN3A(191573), GRIN3B(170796), GRINA(266668)	Gene Information rat ... Grm5(24418)
color white to off-white	color white	color white to off-white	color -
solubility ethanol: <0.17 mg/mL	solubility -	solubility -	solubility -

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.[1][2]

Application

Quisqualic acid has also been used as a group I metabotropic receptor agonist in neurons.[3]

Quisqualic acid has been used to test ligand-gated receptors in spiral ganglion neurons.[4]

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

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Certificates of Analysis (COA)

Lot/Batch Number

0000492019

0000429456

0000433943

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Optical recordings of Ca2+ signaling activities from identified inner ear cells in cochlear slices and hemicochleae

Xi Lin

Brain Res. Protoc., 11(2) (2003)

Orthosteric and allosteric drug binding sites in the Caenorhabditis elegans mgl-2 metabotropic glutamate receptor.

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

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)

Long-term potentiation in isolated dendritic spines.

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

Functional induction of the cystine-glutamate exchanger system Xc(-) activity in SH-SY5Y cells by unconjugated bilirubin.

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

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