Kainic acid

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Kainic acid[1]
IUPAC name	(2S,3S,4S)-3-(carboxymethyl)-4-prop-1-en-2-ylpyrrolidine-2-carboxylic acid
Other names	2-Carboxy-3-carboxymethyl-4-isopropenyl-pyrrolidine
Identifiers
CAS number	[487-79-6]
PubChem	10255
SMILES	CC(=C)[C@H]1CN[C@@H]([C@H]1CC(=O)O)C(=O)O
Properties
Molecular formula	C10H15NO4
Molar mass	213.23 g/mol
Appearance	Crystalline needles
Melting point	215 °C (decomp.)
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 ionotrophic glutamate receptor which mimics the effect of glutamate. It is used in experiments to distinguish a receptor from the other ionotropic receptors for glutamate such as NMDA and AMPA, a.k.a. quisqualate.

[edit] Occurrence

In 1953, kainic acid was originally isolated from the seaweed^[2] 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.

[edit] Applications

• antiworming agent
• neuroscience research
  • neurodegenerative agent
  • modeling of epilepsy
  • modeling of Alzheimer's disease

[edit] See also

• Domoic acid

• Kainate receptor

[edit] References

1. ^ Merck Index, 11th Edition, 5157
2. ^ Moloney, M. G.; Natural Product Reports; 1998; pp. 208

[edit] External links

• Kainate Receptors