| Identification | Back Directory | [Name]
QUISQUALIC ACID | [CAS]
52809-07-1 | [Synonyms]
QUISQUALATE
QUISQUALIC ACID
L-QUISQUALIC ACID
(+)-QUISQUALIC ACID
L(+)-QUISQUALIC ACID
3-(3,5-DIOXO-1,2,4-OXADIAZOLIDIN-2-YL)-L-ALANINE
β-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)-l-alanine
L-(+)-a-Amino-3,5-Dioxo-1,2,4-oxadiazolidine-2-pro
BETA-(3,5-DIOXO-1,2,4-OXADIZOLIDIN-2-YL)-L-ALANINE
BETA-[3,5-DIOXO-1,2,4-OXADIAZOLIDIN-2-YL]-L-ALANINE
(αS)-α-Amino-3,5-dioxo-1,2,4-oxadiazolidine-2-propanoic acid
L-(+)-α-Amino-3,5-dioxo-1,2,4-oxadiazolidine-2-propanoic Acid
L-(+)-A-AMINO-3,5-DIOXO-1,2,4-OXADIAZOLIDINE-2-PROPANOIC ACID
1,2,4-Oxadiazolidine-2-propanoicacid, a-aMino-3,5-dioxo-, (aS)-
(S)-2-aMino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid
(αS)-α-Amino-3,5-dioxotetrahydro-1,2,4-oxadiazole-2-propionic acid
(L)-(+)-ALPHA-AMINO-3,5-DIOXO-1,2,4-OXADIAZOLIDINE-2-PROPANOIC ACID
(S)-2-Amino-3-(3,5-dioxotetrahydro-1,2,4-oxadiazole-2-yl)propionic acid
β-(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)-L-alanine, 3-(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)-L-alanine
Quisqualic acid,β-(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)-L-alanine, 3-(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)-L-alanine | [Molecular Formula]
C5H7N3O5 | [MDL Number]
MFCD00069337 | [MOL File]
52809-07-1.mol | [Molecular Weight]
189.13 |
| Chemical Properties | Back Directory | [Appearance]
Off-White Solid | [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 | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [Water Solubility ]
Soluble in ethanol, water. Insoluble in organic solvents. | [Merck ]
13,8177 | [BRN ]
1078734 | [InChI]
InChI=1/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-/s3 | [InChIKey]
ASNFTDCKZKHJSW-NVFNTWQMNA-N | [SMILES]
N1(C[C@H](N)C(=O)O)OC(=O)NC1=O |&1:2,r| |
| Hazard Information | Back Directory | [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™ . | [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. | [Definition]
ChEBI: Quisqualic acid is a non-proteinogenic alpha-amino acid. | [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. | [Biochem/physiol Actions]
Active enantiomer of quisqualic acid; excitatory amino acid at glutamate receptors. | [storage]
Store at RT | [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]. | [References]
[1] HUGUES-OLIVIER BERTRAND. Common and Selective Molecular Determinants Involved in Metabotopic Glutamate Receptor Agonist Activity[J]. Journal of Medicinal Chemistry, 2002, 45 15: 3171-3183. DOI: 10.1021/jm010323l
[2] RAJENDER K. KAMBOJ. Molecular Cloning, Expression, and Pharmacological Characterization of humEAA1, a Human Kainate Receptor Subunit[J]. Journal of Neurochemistry, 1994, 62 1: 1-9. DOI: 10.1046/j.1471-4159.1994.62010001.x
[3] VINCENT MUTEL. Characterization of [3H]Quisqualate Binding to Recombinant Rat Metabotropic Glutamate 1a and 5a Receptors and to Rat and Human Brain Sections[J]. Journal of Neurochemistry, 2008, 75 6: 2590-2601. DOI: 10.1046/j.1471-4159.2000.0752590.x
[4] SHIGEO UCHINO . Mutations in a putative agonist binding region of the AMPA-selective glutamate receptor channel[J]. FEBS Letters, 1992, 308 3: Pages 253-257. DOI: 10.1016/0014-5793(92)81286-u
[5] JEUNG WOON LEE. Prolonged nociceptive responses to hind paw formalin injection in rats with a spinal cord injury[J]. Neuroscience Letters, 2008, 439 2: Pages 212-215. DOI: 10.1016/j.neulet.2008.05.030
[6] JANICE L. MUIR . Excitotoxic lesions of basal forebrain cholinergic neurons: Effects on learning, memory and attention[J]. Behavioural Brain Research, 1993, 57 2: Pages 123-131. DOI: 10.1016/0166-4328(93)90128-d |
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