Quisqualic Acid
QUISQUALATE · Quisqualic acid · L-QUISQUALIC ACID · (+)-QuisqualicAci · Quisqualinic acid · ()-QUISQUALIC ACID · (+)-QUISQUALIC ACID · L(+)-QUISQUALIC ACID
Identifiers & Physical Properties
| CAS No. | 52809-07-1 |
|---|---|
| Molecular formula | C5H7N3O5 |
| Average molar mass | 189.13 g/mol |
| Monoisotopic mass | 189.03857032 g/mol |
| SMILES | N[C@@H](Cn1oc(=O)[nH]c1=O)C(=O)O |
| InChIKey | ASNFTDCKZKHJSW-REOHCLBHSA-N |
| PubChem CID | 40539 |
| ChEMBL | CHEMBL168279 |
| ChEBI | CHEBI:8734 |
| EC No. | 637-070-2 |
| DTXSID | DTXSID20896927 |
Chemical & Physical Properties
| XLogP | -3.9 |
|---|---|
| Topological polar surface area | 122 |
| Hydrogen bond donors | 3 |
| Hydrogen bond acceptors | 6 |
| Rotatable bonds | 3 |
| Heavy atoms | 13 |
| Formal charge | 0 |
| Complexity | 265 |
| Drugs | Pharmaceuticals -> Listed in ZINC15 |
| 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 conditions | 2-8°C |
| Solubility | NH4OH 1 M: 20 mg/mL, clear, colorlessSoluble in ethanol, water. Insoluble in organic solvents. |
| pKa (acidity coefficient) | 2.12±0.10(Predicted) |
| Physical state | powder |
| Color | white to off-white |
| Merck | 13,8177 |
| BRN | 1078734 |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| 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| |
| FDA UNII | 8OC22C1B99 |
| UNSPSC Code | 12352106 |
| NACRES | NA.32 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302-H312-H332 |
| GHS precautionary statements | P261-P280h-P301+P312a-P304+P340-P321-P501a |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xn |
| Risk statements (R) | 20/21/22 |
| Safety statements (S) | 26-36 |
| Water hazard class (WGK) | 3 |
| F | 10 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| GHS classification | WarningH302+H312+H332 (41.2%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation]P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 68 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| F | 10 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| Risk statements (R) | 20/21/22 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn |
| Safety statements (S) | 26-36 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H302-H312-H332 |
| GHS precautionary statements | P261-P280h-P301+P312a-P304+P340-P321-P501a |
Applications & Uses
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.
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.