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United States Patent Office Patented May 11, 1965 1 3,183,172 United States Patent Office Patented May 11, 1965 1. 2 fruit bodies, it has been found that sclerotes and mycel 3,183,172 . ium are formed in greater profusion if the cultures are in OBTANING PSLOCYBEN AND PSLOCN FROM FUNGALMATERIAL cubated in the dark. The largest yields of active fungal Roger Heim, Paris, France, Albert Hofmann, Bottmingen, material (mycelium and sclerotes) are obtained by pre Basel-Land, Artur Brack, Riehen, near Basel, and Hans 5 paring surface cultures with culture media of malt ex Kobel, Basel, Switzerland, and Roger Cailleux, Pavi tract (beerwort or commercial preparations of malt ex lons-sous-Bois, France, assignors to Sandoz Ltd., tracts) containing 4 to 10% by weight of dry substance, Basel, Switzerland, a Swiss firm and by incubation of these cultures in the dark at a No Drawing. Filed Feb. 16, 1959, Ser. No. 793,234 constant temperature between 22 and 26 C. Addition of Claims priority, application Switzerland, Feb. 21, 1958, 10 0.2% by weight of agar to the culture medium enhances 56,143; July 30, 1958, 62,393 good growth. This medium is just sufficiently firm 21 Claims. (CI, 195-80) though it is still almost liquid-to permit the fungus to The present invention relates to psilocybin and psilocin grow quickly, forming a well-knit mycelium layer. Addi and to the preparation thereof from the so-called hallu tion of ferrous salts is very desirable; addition of zinc, po cinogenic fungi: Psilocybe, Stropharia, Panaeolus, Cono 15 tassium, calcium and magnesium salts, of nitrate, phos cybe, Amanita and Russula. It has heretofore been im phate and sulphate ions as well as of yeast extract or of possible to isolate the active substance from samples of corn steep solids is also found to be very advantageous. the natural fungi or from artificially cultured fungal mate This process of cultivation is a great technical improve rial; nor has it been possible to culture hallucinogenically ment, as it gives a high yield of active starting material; active species-starting from natural fungi-under condi 20 the yield is actually ten times greater than that obtained tions that would produce active material in amounts suffi from a culture on natural substrates and the artificial cient for obtaining the active substance on a preparative method takes less time and involves less work. scale. The active fungal material (fruit bodies, sclerotes and A primary object of the present invention is the em mycelium) is carefully dried in an air current or under bodiment of an industrially feasible process whereby the 25 reduced pressure at 20-40 C., finely ground and hitherto unknown active principles of hallucinogenic fun thoroughly extracted with a lower aliphatic alcohol or gal species, notably Psilocybe mexicana Heim, Psilocybe with a mixture of water and a water-miscible organic calerulescens Murrill var. nigripes Heim, Psilocybe zapo solvent at room temperature (20 to 30° C.). The ex tecorum Heim, Psilocybe semperviva Heim and Cailleux, tracts are concentrated under reduced pressure at low tem Psilocybe aztecorum Heim and Stropharia cubensis Earle, 30 perature. The residue is defatted with petroleum ether are obtained free from halogen. and extracted with acetone or chloroform-alcohol to re This object is realized according to the present inven move inactive accompanying material. Other ballast tion by extracting the active principles either directly from material is separated off by dissolving the residue in as the fungal material of natural origin or from cultures of little water as possible and repeated precipitation with the fungi or of biological variants or mutants thereof 35 absolute ethanol or acetone; the filtrate is concentrated which have been grown on natural or artificial substrates under reduced pressure at low temperature. by culture techniques which make it possible to obtain Further purification is advantageously carried out by sufficient amounts of active material to permit the isola chromatography on cellulose powder in a through-flow tion of the latter on a preparative scale. Briefly stated, process; elution is performed with water-saturated butanol the cultures are incubated in daylight or in the dark at a 40 or another alcohol not miscible with water. The frac constant temperature between 18 and 27 C. and, after tions collected are tested for their content of active sub purification, the active substance is separated and freed stance by means of the Keller reagent (glacial acetic acid from halogen, where present. containing iron chloride and concentrated sulphuric acid). The process, more specifically, may be carried out as The fractions showing a positive color reaction are com follows: For a culture on a natural substrate, a compost 45 bined and, if necessary, chromatographed again on a consisting of fermented wheat straw and a mixture of corn column of cellulose powder. From the through-flow leaves and corn stems or stalks of wild grasses is washed chromatogram a rather rapidly travelling zone is eluted. well under running water, poured into earthenware dishes This yields a product containing an active substance, and sterilized in an autoclave. The compost is inoculated "psilocin,' characterized by a clear blue Keller reaction, with mycelium from primary cultures and incubated for 50 while from a zone travelling more slowly, a product approximately two weeks at 24-27 C. The cultures containing a second active substance, "psilocybin,” is ob are then covered with sterile sand and left undisturbed tained in larger amounts. in a glass box in the daylight at a temperature of 18-27 The active substances are obtained in a fairly pure state C., the moisture content being kept constant. The fruit from the column but contain halogen and do not crystal bodies appear after 4 to 5 weeks. They are harvested 55 lize out as psilocybin and psilocin. The halogen may be from time to time for a period of 1 or 2 months as soon removed only by chemical treatment, crystalline com as the formation of the spores has started. pounds being thereby obtained. For this purpose, an In developing an alternative process which is better aqueous solution of the active material is treated with sil adapted for large scale operation, it was found quite ver carbonate or silver oxide. Excess silver ions are re unexpectedly that, grown in vitro on substrates rich in 60 moved with hydrogen sulphide and the remaining solution nutritive material, the fungi produce active mycelium and is concentrated under reduced pressure at low tempera sclerotes in large quantities and only a very small number ture, the substances crystallizing out from the concen of fruit bodies, on substrates poor in nutrients, however, trated solution. the familiar fruit bodies are produced. On an agar medi For analysis, psilocybin is recrystallized from methanol um containing 1.5% by weight of agar, a concentration 65 or water. Recrystallization from water yields very fine of 0.2 to 0.7% by weight of dry substance of malt ex white needles; from methanol colorless hexagonal plates tract is the optimum for the formation of fruit bodies, or prisms are produced; these contain methanol and melt whereas concentrations of 4 to 10% by weight, depending at 195-200° C. (with decomposition). The compound upon the particular fungal species employed, are optimal dissolves in 120 parts by weight of boiling methanol or for the formation of mycelium and sclerotes. 70 in 20 parts by weight of boiling water; it dissolves dif While daylight is indispensable for the formation of ficulty in higher alcohols and other organic solvents. The 3,183,172 3 --- 4 crystals are dried in a high vacuum at 100° C., a decrease methanol and the solution treated with 20 parts by in weight of 10.4% taking place. The results of elemen weight of cellulose powder containing 5% of water. The tary analysis give the empirical formula C12HONP methanol is evaporated off under reduced pressure and (molecular weight 248.2). Psilocybin is an amphoteric the cellulose powder bearing the active material is poured compound. It is optically inactive and readily soluble in onto a column of 100 parts by weight of cellulose pow dilute aqueous mineral acids and in dilute aqueous alkalis der containing 5% of water, the column having previously with which it forms salts. A solution of psilocybin in been washed with water-saturated butanol. The column 80% (by weight) aqueous ethanol has a faintly acid re is eluted with water-saturated butanoi and fractions of 20 action (pH 5.2). The UV-spectrum in a methanolic parts by volume are collected. The evaporation residues solution shows maxima at 222, 267 and 290 mp. 10 from the individual fractions are tested for their content For analysis, the psilocin is purified by another of active material by means of the Keller color reaction. chromatographic operation on a column of cellulose pow For this purpose, 2 milliliters of Keller reagent are added der, using water-saturated butanol or by treatment with to samples of 0.25 milligram of evaporation residue. potassium bicarbonate in an aqueous solution and extrac The fractions showing a positive color reaction are tion with ether or an organic solvent. The results of ele 15 combined. The amorphous powder is dissolved in 20 mentary analysis give the empirical formula C12H1NO2. parts by volume of water and shaken with 0.5 part by Psilocin crystallizes from methanol or acetone; it is mod weight of silver carbonate. The solution is filtered and erately soluble in water but dissolves readily in dilute acid. desilverized with hydrogen sulphide and then carefully . M.P., 173-176 C. (with decomposition). concentrated. Psilocybin crystallizes from the concen- . Psilocin is characterized by an UV-spectrum in a 20 trated solution in the form of fine colorless needles (yield methanolic solution with maxima at 222, 260, 267, 283 200 parts by weight).
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