IBOTENIC ACID

Химические свойства

Crystalline solid; forms monohydrate; mp151°C (303.8°F) (anhydrous), 145°C (293°F)(monohydrate); soluble in water and alcohol.

Использование

Ibotenic acid is a neuroexcitatory amino acid originally isolated from Amanita species that functions as a NMDA and metabotropic glutamate receptor agonist. As a neurotoxin, ibotenic acid is often used to induce brain lesions in animals that model cognitive dysfunctions resulting from neurodegenerative diseases, traumatic brain injury, and stroke.

Подготовка

Isolated from the Japanese fly mushroom. The acid can be produced synthetically.

Определение

A isoxazole which, together with muscimol, is largely responsible for the toxicities of a number of mushrooms including those of the genus Amanita. It is a potent excitatory amino acid.

Опасность

Neurotoxic; causes motor depression, ataxia, changes in mood, perceptions and feelings.

Угроза здоровью

Ibotenic acid is a potent neurologic aminoacid. It exhibits neuroexcitatory activity andcauses sedative actions on spinal neurons.High doses can cause sleep, hallucinations,distorted perceptions, and nausea. In humansthe symptoms above may be manifested fromingestion of 6–8 mg of ibotenic acid.
LD50 value, oral (mice): 38 mg/kg
LD50 value, intraperitoneal (mice): 15 mg/kg.

Биологическая активность

NMDA and metabotropic glutamate receptor agonist.

Методы очистки

It has been converted to the ammonium salt (m 121-123o dec) dissolved in H2O, passed through an Amberlite IR 120 resin (H+ form) and eluted with H2O. The acidic fractions are collected, evaporated to dryness and the residue recrystallises from H2O as the monohydrate (m 144-146o). The anhydrous acid is obtained by making a slurry with MeOH, decanting and evaporating to dryness, and repeating the process twice more to give the anhydrous acid (m 151-152o). Recrystallisation from H2O gives the monohydrate. [Nakamura Chem Pharm Bull Jpn 19 46 1971.] The ethyl ester forms needles when crystallised from a small volume of Et2O and has m 78-79o and IR (CHCl3) with max 35002300 (OH), 1742 (ester C=O), 1628, 1528cm-1, and UV with λmax (EtOH) at 206nm (ε 7,080). The hydrazide has m 174-175o (from MeOH) with IR (KBr) 1656 (C=O)cm-1.