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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 | | EINECS: | | Product Categories: | Heterocycles;Glutamate;Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives;Neurochemicals;Glutamate receptor | | Mol File: | 52809-07-1.mol |
| 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 | | pka | 2.12±0.10(Predicted) | | form | powder | | 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. |
| QUISQUALIC ACID Usage And Synthesis |
| Description | L-Quisqualic acid is a natural analog of glutamate that acts as an agonist at AMPA-selective and metabotropic glutamate receptors (EC50s = 170, 10, 40, and 29 nM at GluR-A, mGluR1, mGluR3, and mGluR5, respectively), as well as the ionotropic kainate receptor (GRIK4; Ki = 6.43 nM). L-Quisqualic acid is used to study receptor dynamics and as an excitotoxin to selectively destroy neurons in the brain or spinal cord. | | 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. | | Uses | Quisqualic acid has been used to test ligand-gated receptors in spiral ganglion neurons. | | Uses | Quisqualic acid is used to differentiate between mGluR-1 and mGluR-4. L-Quisqualic acid is an activator of GluR. | | 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. | | 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™ . | | Biochem/physiol Actions | Active enantiomer of quisqualic acid; excitatory amino acid at glutamate receptors. | | 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 ACID Preparation Products And Raw materials |
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