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Kainic acid



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 disclaimer and references

Kainic acid is a natural marine acid present in some algae. It is a specific agonist for the kainate receptor used as an ionotrophic glutamate receptor which mimicks 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.

Contents

Occurrence

In 1953, kainic acid was originally isolated from the red alga 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 and the neurological damage

caused by it to dendrites, synapses, and long-term memory in mice

    • modeling of Alzheimer's disease

See also

References

  1. ^ Merck Index, 11th Edition, 5157
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Kainic_acid". A list of authors is available in Wikipedia.
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