Description
Kainic acid (487-79-6) is a conformationally restricted glutamate analog which acts as a selective agonist at kainate receptors. CNS stimulant and neurotoxin. Kainic acid is a classic neuroexcitatory agent for induction of seizures in laboratory animals (typical dose 10-30 mg/kg).
Chemical Properties
soluble in 0.1 M NaOH
Uses
excitory amino acid, neurotoxin, neurobiology tool
Uses
glutamate receptor agonist, anthelmintic
Uses
Neurobiological tool.
Definition
ChEBI: Kainic acid is a dicarboxylic acid, a pyrrolidinecarboxylic acid, a L-proline derivative and a non-proteinogenic L-alpha-amino acid. It has a role as an antinematodal drug and an excitatory amino acid agonist. It is a conjugate acid of a kainate(1-).
Biological Activity
Selective agonist at kainate receptors. Potent excitant and neurotoxin. Also available as part of the Kainate Receptor Tocriset™ .
Purification Methods
Purify the acid by adsorbing on to a strongly acidic ion-exchange resin (Merck), elute the diacid with aqueous M NaOH, the eluate is evaporated, H2O is added, and filtered through a weakly acidic ion-exchange resin (Merck). The filtrate is then evaporated and recrystallised from EtOH. Its solubility is 0.1g in 1mL of 0.5N HCl. (±)--Kainic acid is recrystallised from H2O with m 230-260o. UV (MeOH): 219 (log 3.9); max 1HNMR (CCl4, 100MHz, Me4Si standard) : 1.64 (s 1H), 1.70 (s 3H), 3.24 (d J 7.5, 2H), 3.3-4.2 (1H), 3.70 (s 3H), 3.83 (s 3H), 4.35 (dd J 7.5, J 14.5, 1H), 5.21 (t J 7.5, 1H), 7.26 (t J 7.5, 1H). [Oppolzer & Andres Helv Chim Acta 62 2282 1979, Beilstein 22 III/IV 1523.]
References
1) Watkins et al. (1981), Excitatory amino acid transmitters; Ann. Rev. Pharmacol. Toxicol., 21 165
