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QUISQUALIC ACID

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QUISQUALIC ACID Basic information

Product Name:
QUISQUALIC ACID
Synonyms:
  • 3-(3,5-DIOXO-1,2,4-OXADIAZOLIDIN-2-YL)-L-ALANINE
  • L(+)-QUISQUALIC ACID
  • L-QUISQUALIC ACID
  • L-(+)-A-AMINO-3,5-DIOXO-1,2,4-OXADIAZOLIDINE-2-PROPANOIC ACID
  • (L)-(+)-ALPHA-AMINO-3,5-DIOXO-1,2,4-OXADIAZOLIDINE-2-PROPANOIC ACID
  • BETA-[3,5-DIOXO-1,2,4-OXADIAZOLIDIN-2-YL]-L-ALANINE
  • BETA-(3,5-DIOXO-1,2,4-OXADIZOLIDIN-2-YL)-L-ALANINE
  • (+)-QUISQUALIC ACID
CAS:
52809-07-1
MF:
C5H7N3O5
MW:
189.13
Product Categories:
  • Heterocycles
  • Glutamate
  • Amino Acids 13C, 2H, 15N
  • Amino Acids & Derivatives
  • Neurochemicals
  • Glutamate receptor
Mol File:
52809-07-1.mol
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QUISQUALIC ACID Chemical Properties

Melting point:
185-187°C dec.
alpha 
D20 +17.0° (c = 2.0 in 6M HCl)
Boiling point:
324.36°C (rough estimate)
Density 
1.6649 (rough estimate)
refractive index 
1.6190 (estimate)
storage temp. 
2-8°C
solubility 
NH4OH 1 M: 20 mg/mL, clear, colorless
form 
powder
pka
2.12±0.10(Predicted)
color 
white to off-white
Water Solubility 
Soluble in ethanol, water. Insoluble in organic solvents.
Merck 
13,8177
BRN 
1078734
Stability:
Stable. Incompatible with strong oxidizing agents.
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Safety Information

Hazard Codes 
Xn
Risk Statements 
20/21/22
Safety Statements 
26-36
WGK Germany 
3
10

MSDS

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QUISQUALIC ACID Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

An amino acid that is able to function as an agonist at multiple excitatory amino acid receptor substrates in the central nervous system. It also has high affinity for the kainate, AMPA and the metabotropic receptors. Inhibits the Ca2+/Cl-dependent glutamic acid uptake system in brain synaptic plasma membrane preparations.

Biological Activity

Glutamate receptor agonist acting at AMPA receptors and metabotropic glutamate receptors positively linked to phosphoinositide hydrolysis. Sensitizes neurons in hippocampus to depolarization by L-AP6 (the so called 'quis' effect). Also available as part of the Group I mGlu Receptor Tocriset™ .

Purification Methods

It has been purified by ion-exchange chromatography on Dowex 50W (x 8, H+ form); the desired fractions are lyophilised and recrystallised from H2O/EtOH. It has IR (KBr) : 3400-2750br, 1830s, 1775s, 1745s and 1605s cm-1;maxand 1H NMR (NaOD/D2O, pH 13) : 3.55-3.57 (1H m, X of ABX, H-2), 3.72-3.85 (2H, AB of ABX, H-3), 1 3C NMR (D2O) : 50.1t, 53.4d, 154.8s, 159.7s and 171.3s. [Baldwin et al. J Chem Soc, Chem Commun 256 1985.] It is a quasiqualate receptor agonist [Joels et al. Proc Natl Acad Sci USA 86 3404 1989].

QUISQUALIC ACIDSupplier

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