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Q2128

Sigma-Aldrich

Quisqualic acid

powder

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

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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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

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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)
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)
Lennart Bunch et al.
Medicinal research reviews, 29(1), 3-28 (2008-07-16)
(S)-Glutamic acid (Glu) is the major excitatory neurotransmitter in the mammalian central nervous system, activating the plethora of glutamate receptors (GluRs). In broad lines, the GluRs are divided into two major classes: the ionotropic Glu receptors (iGluRs) and the metabotropic
Medical Laboratory Science : Theory And Practice (1990)
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