Description and references

Alkaloid from the red variety of Amanita muscaria (L.) Pers., Agaricaceae, the fly fungus, a poisonous mushroom. Also found in some other fungi: Inocybe patouillardi; I. fastigiata, I. umbrina; I. rimosa. Isoln procedure for the naturally occurring l-(+)-form: Kuehl et al., J. Am. Chem. Soc. 77, 6663 (1955); Eugster, Helv. Chim. Acta 39, 1002 (1956). Structure and synthesis of racemate: K"ogl et al., Rec. Trav. Chim. 76, 109 (1957); K"ogl et al., Experientia 13, 137, 138 (1957); Cox et al., Helv. Chim. Acta 41, 229 (1958). Alternate syntheses: GB 828395 (1960 to Hoffmann-La Roche); Matsumoto et al., Tetrahedron 25, 5889 (1969); W. C. Still, J. A. Schneider, J. Org. Chem. 45, 3375 (1980). Synthesis of muscarine: Whiting et al., Can. J. Chem. 50, 3322 (1972); A. M. Mubarak, D. M. Brown, Tetrahedron Lett. 21, 2453 (1980); eidem, J. Chem. Soc. Perkin Trans. 1 1982, 809; S. Pochet, T. Huynhdinh, J. Org. Chem. 47, 193 (1982). Chemistry and pharmacology: Waser, Pharmacol. Rev. 13, 465-515 (1961). Toxicity study: P. J. Fraser, Br. J. Pharmacol. 12, 47 (1957). Reviews: C. H. Eugster, Adv. Org. Chem. 2, 427-455 (1960); S. Wilkinson, Q. Rev. Chem. Soc. 15, 153-171 (1961). Configurational relationship in the muscarine series: Bollinger, Eugster, Helv. Chim. Acta 54, 2704 (1971).

Derivative

Caution