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Hofmann A, Heim R, Brack A, Kobel H, Frey A, Ott H, Petrzilka T, Troxler F.
“Psilocybin und Psilocin, zwei psychotrope Wirkstoffe aus mexikanischen Rauschpilzen”.
Helv. chim. Acta. 1959;42:1557-1572.
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Abstract
The psychotropically active principles of the Mexican hallucinogenic fungus Psilocybe mexicana Heim have been isolated and obtained in crystalline form. The two new substances, which have been called Psilocybin and Psilocin, are present in the fruit bodies, the artificially cultivated mycelium and in the aclerotia. The dried mushroom contains 0.2 to 0.4 percent Psilocybin. Psilocin is present, at the most, in trace amounts only. . The same active principles were also found in other mushrooms of the genus Psilocybe and Stropharia which are used to produce states of intoxication. . Oral doses of 4 to 6 mg. Psilocybin and Psilocin elicit vegetative symptoms and mental changes lasting several hours. These effects are identical with those elicited by the fresh or dried mushroom. . The structural formulae of the two substances have been elucidated and confirmed by synthesis. Psilocybin is o-phosphoryl-4-hydroxy-w-N,N-dimethyl-tryptamine. Psilocin is dephosphorylated Psilocybin, i.c. 4- hydroxy-w-N-,N-dimethyl-tryptamine. . Psilocybin and Psilocin are the first natural indole derivatives found which possess a hydroxyl group in position 4. In addition, Psilocybin is the first natural indole derivative found to contain Phosphoric.
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