KAINIC ACID Chemical Properties

Melting point:

253-254 C

alpha 

D24 -14.8° (c = 1.01)

Boiling point:

353.22°C (rough estimate)

Density 

1.2177 (rough estimate)

refractive index 

1.4368 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

H₂O: soluble

form 

White to off-white solid.

pka

2.03±0.60(Predicted)

color 

White

Water Solubility 

Soluble to 25 mM in water

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20° for up to 3 months.

InChI

InChI=1S/C10H15NO4/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13/h6-7,9,11H,1,3-4H2,2H3,(H,12,13)(H,14,15)/t6-,7+,9-/m0/s1

InChIKey

VLSMHEGGTFMBBZ-OOZYFLPDSA-N

SMILES

N1C[C@H](C(C)=C)[C@H](CC(O)=O)[C@H]1C(O)=O

EPA Substance Registry System

3-Pyrrolidineacetic acid, 2-carboxy-4-(1-methylethenyl)-, (2S,3S,4S)- (487-79-6)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22

Safety Statements 

22-24/25-36

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

KAINIC ACID Usage And Synthesis

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

Neurobiological tool.

Uses

glutamate receptor agonist, anthelmintic

Uses

(-)-α-Kainic Acid is a naturally occurring neuroexcitatory chemical that is an selective agonist for a subtype of ionotropic glutamate receptor. Administration of (-)-α-Kainic Acid has been shown to increase production of reactive oxygen species, mitochondrial dysfunction, and apoptosis in neurons in many regions of the brain, particularly in the hippocampal subregions and in the hilus of dentate gyrus.

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™ .

storage

Room temperature

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

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