6312. Muscimol

Nomenclature

CAS number: 2763-96-4
5-(Aminomethyl)-3(2H)-isoxazolone; 5-(aminomethyl)-3-isoxazolol; 5-aminomethyl-3-hydroxyisoxazole; 3-hydroxy-5-aminomethylisoxazole; agarin; pantherine.
C4H6N2O2; mol wt 114.10.
C 42.11%, H 5.30%, N 24.55%, O 28.04%.

Description and references

Potent CNS depressant and GABA agonist isolated from Amanita muscaria (L.) Fr., Agaricaceae. Structural identity with the insecticidal substances, pantherine and agarin: Onda et al., Chem. Pharm. Bull. 12, 751 (1964); Eugster et al., Tetrahedron Lett. 1965, 1813; Bowden, Drysdale, ibid. 727. Synthesis: Gagneux et al., ibid. 2077; G"oth et al., Helv. Chim. Acta 50, 137 (1967); Bowden et al., J. Chem. Soc. C 1968, 172. Improved syntheses: Nakamura, Chem. Pharm. Bull. 19, 46 (1971); P. Krogsgaard-Larsen, S. B. Christensen, Acta Chem. Scand. B B30, 281 (1976); A. Barco et al., J. Chem. Res. Synop. 1979, 176; B. E. McCarry, M. Savard, Tetrahedron Lett. 22, 5153 (1981); V. Jager, M. Frey, Ann. 1982, 817. Conformational structure: L. Brehm et al., ibid. 26, 1298 (1972). Industrial patents: Hafliger, Gagneux, US 3242190, US 3397209 (1966, 1968 both to Geigy). Pharmacology: Theobald et al., Arzneim.-Forsch. 18, 311 (1968). Review of pharmacology: F. V. DeFeudis, Neurochem. Res. 5, 1047-1068 (1980).

Chemical structure

Properties

Crystals, mp 175° (dec). LD50 in mice (mg/kg): 3.8 s.c., 2.5 i.p.; in rats (mg/kg): 4.5 i.v., 45 orally (Theobald).

Use

As a molecular probe to study GABA receptors.