Kainic acid

Kainic acid
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[citation needed]
Identifiers
CAS number	487-79-6 Y
PubChem	10255
ChemSpider	9837 Y
UNII	SIV03811UC Y
KEGG	C12819 N
MeSH	Kainic+acid
ChEBI	CHEBI:31746 Y
ChEMBL	CHEMBL27527 N
Beilstein Reference	86660
Jmol-3D images	Image 1
SMILES CC(=C)[C@H]1CN[C@@H]([C@H]1CC(=O)O)C(=O)O
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) N Key: VLSMHEGGTFMBBZ-UHFFFAOYSA-N N
Properties
Molecular formula	C10H15NO4
Molar mass	213.23 g mol−1
Melting point	215 °C, 488 K, 419 °F (decomposes)
log P	0.635
Acidity (pKa)	2.031
Basicity (pKb)	11.966
Structure
Crystal structure	Monoclinic
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

• Domoic acid
• Kainate receptor

External links

• Kainate Receptors