Ibotenic Acid
Structural Formula Vector Image
Title: Ibotenic Acid
CAS Registry Number: 2552-55-8
CAS Name: a-Amino-2,3-dihydro-3-oxo-5-isoxazoleacetic acid
Additional Names: a-amino-3-hydroxy-5-isoxazoleacetic acid; amino-(3-hydroxy-5-isoxazolyl)acetic acid
Molecular Formula: C5H6N2O4
Molecular Weight: 158.11
Percent Composition: C 37.98%, H 3.82%, N 17.72%, O 40.48%
Literature References: Fly-killing and narcosis-potentiating amino acid structurally similar to kainic acid, q.v., extracted from poisonous mushroom species. Isoln from Amanita pantherina (DC.) Fr., and A. muscaria (L.) Fr., Agaricaceae: Takemoto et al., J. Pharm. Soc. Jpn. 84, 1233 (1964); Eugster et al., Tetrahedron Lett. 1965, 1813. Structure: Takemoto et al., J. Pharm. Soc. Jpn. 84, 1186, 1232 (1964). Syntheses: Gagneux et al., Tetrahedron Lett. 1965, 2081; Sirakawa et al., Chem. Pharm. Bull. 14, 89 (1966); Kishida et al., ibid. 14, 92 (1966); 15, 1025 (1967). Improved synthesis: Nakamura, ibid. 19, 46 (1971). Industrial pats: BE 665249 C.A. 65, 2266e (1966); Gagneux et al., US 3459862 (1965, 1969 both to Geigy); Kishida et al., JP 68 15975; JP 69 25780 (1968, 1969 both to Sankyo), C.A. 70, 77944p (1969); 72, 13054g (1970). Pharmacology: Theobald et al., Arzneim.-Forsch. 18, 311 (1968); Johnston et al., Biochem. Pharmacol. 17, 2488 (1968). Exhibits potent neuroexcitatory activity: eidem, Nature 248, 804 (1974). Chemistry review: Eugster, Fortschr. Chem. Org. Naturst. 27, 261-321 (1969); Catalfomo, Eugster, Bull. Narc. 22, 33-41 (1970). Excitatory and possible sedative actions on spinal neurons: D. R. Curtis et al., J. Physiol. 291, 19 (1979); in cerebral cortex: E. Puil, Can. J. Physiol. Pharmacol. 59, 1025 (1981). Use as experimental neurotoxic agent: A. Contestabile et al., Experientia 40, 524 (1984).
Properties: Crystals from water or methanol, mp 151-152° (anhydrous); mp 144-146° (monohydrate). LD50 in mice, rats (mg/kg): 15, 42 i.v.; 38, 129 orally (Theobald).
Melting point: mp 151-152° (anhydrous); mp 144-146° (monohydrate)
Toxicity data: LD50 in mice, rats (mg/kg): 15, 42 i.v.; 38, 129 orally (Theobald)
Use: Neurobiological tool.

Other Monographs:
Amberlyst 15®MocimycinScilliroside3,4-Diaminopyridine
LunacridineZincn-Propyl NitriteEthoxyquin
AncymidolCalcium ThiosulfateMADULysalbinic Acid
Polymerized Pyridoxylated HemoglobinEntprolCymoxanilEthyl β-Carboline-3-carboxylate
©2006-2017 DrugFuture->Chemical Index Database