alpha-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID
AMPA · C13672 · AMPA HBR · (RS)-AMPA · (RS)-AMPA hydrobromi · AMPA (ZWITTERION) POTENT EXCITATORY AMI · 5-Methyl-3-hydroxy-α-aminoisoxazole-4-propionic acid · 2-AMINO-3-(3-HYDROXY-5-METHYLISOXAZOL-4-YL)PROPANOIC ACID
Identifiers & Physical Properties
| CAS No. | 77521-29-0 |
|---|---|
| Molecular formula | C7H10N2O4 |
| Average molar mass | 186.17 g/mol |
| Monoisotopic mass | 186.0640568 g/mol |
| SMILES | Cc1o[nH]c(=O)c1CC(N)C(=O)O |
| InChIKey | UUDAMDVQRQNNHZ-UHFFFAOYSA-N |
| PubChem CID | 1221 |
| ChEMBL | CHEMBL13378 |
| ChEBI | CHEBI:34018 |
| DTXSID | DTXSID20868301 |
Chemical & Physical Properties
| XLogP | -3.2 |
|---|---|
| Topological polar surface area | 102 |
| Hydrogen bond donors | 3 |
| Hydrogen bond acceptors | 5 |
| Rotatable bonds | 3 |
| Heavy atoms | 13 |
| Formal charge | 0 |
| Complexity | 284 |
| Ionization Efficiency | Positive0.942.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Melting point | 240 °C |
| Density | 1.386±0.06 g/cm3(Predicted) |
| Storage conditions | 2-8°C |
| Solubility | H2O: 1.2 mg/mLSoluble in water (10mM, gentle warming) |
| pKa (acidity coefficient) | 2.15±0.10(Predicted) |
| Physical state | solid |
| Color | white |
| Stability | Hygroscopic |
| CAS DataBase Reference | 77521-29-0 |
| FDA UNII | J090588E6X |
| EPA Substance Registry System | .alpha.-Amino-2,3-dihydro-5-methyl-3-oxo-4-isoxazolepropanoic acid (77521-29-0) |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H319-H335-H302+H312+H332-H315 |
| GHS precautionary statements | P280 |
| Water hazard class (WGK) | 3 |
| Customs code | 2934999090 |
Safety & Regulations
| Water hazard class (WGK) | 3 |
|---|---|
| Customs code | 2934999090 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| GHS hazard statements | H319-H335-H302+H312+H332-H315 |
| GHS precautionary statements | P280 |
Applications & Uses
Uses
A potent and selective agonist of the excitatory neurotransmitter L-glutamic Acid. AMPA does not interfere with binding sites for kainic acid in vitro, and AMPA- induced neuronal excitation is not significantly affected by NMDA antagonists
Uses
AMPA is the defining agonist for the AMPA subgroup of ionotropic glutamate receptors, which mediate excitatory neurotransmission. Because AMPA does not interfere with binding sites for kainic acid or NMDA , it can be used to distinguish AMPA receptor-specific activity that contributes to a neuronal response. (R,S)-AMPA contains an equal mixture of the active (S)-enantiomer and the inactive (R)-enantiomer.