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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.

Additional recommended knowledge

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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