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| Names | |
|---|---|
| IUPAC name (2S,3S,4S)-3-(Carboxymethyl)-4-prop-1-en-2-ylpyrrolidine-2-carboxylic acid | |
| Other names (3S,4S)-3-(Carboxymethyl)-4-prop-1-en-2-yl-L-proline; 2-Carboxy-3-carboxymethyl-4-isopropenyl-pyrrolidine | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| Beilstein Reference | 86660 |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| KEGG | |
| MeSH | Kainic+acid |
| PubChem CID | |
| UNII | |
| CompTox Dashboard (EPA) | |
InChI
| |
SMILES
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| Properties | |
| Chemical formula | C10H15NO4 |
| Molar mass | 213.233 g·mol |
| Melting point | 215 °C (419 °F; 488 K) |
| log P | 0.635 |
| Acidity (pKa) | 2.031 |
| Basicity (pKb) | 11.966 |
| Structure | |
| Crystal structure | Monoclinic |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 N verify (what is ?)
Infobox references
| |
Kainic acid is a natural marine acid present in some seaweed. It is a specific agonist for the kainate receptor used as an ionotropic glutamate receptor which mimics the effect of glutamate. Along with quisqualate, it is used in experiments to distinguish a receptor from the other ionotropic receptors for glutamate such as NMDA and AMPA.
Occurrence
In 1953, kainic acid was originally isolated from the seaweed called "Kainin-sou"(海人草) or "Makuri" (Digenea simplex) in Japan. "Kainin-sou" is used as an anthelmintic in Japan.
Kainic acid is a potent central nervous system stimulant, and has been developed as the prototype neuroexcitatory amino acid for the induction of seizures in experimental animals, at a typical dose of 10-30 mg/kg in mice. Kainic acid is neuroexcitotoxic and epileptogenic, acting through specific kainate receptors. Because of the supply shortage in 2000, the price of kainic acid has risen significantly.
Applications
- antiworming agent
- neuroscience research
- neurodegenerative agent
- modeling of epilepsy
- modeling of Alzheimer's disease
See also
References
- CID 10255 from PubChem
- Moloney, Mark G. (1998). "Excitatory amino acids". Natural Product Reports. 15 (2): 205–219. doi:10.1039/a815205y. PMID 9586226.