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United States Patent Office 3,92, United States Patent Office Paterated June 29, 1965 2 whereas concentrations of 4 to 10% by weight, depend 3,192,111 ing upon the particular fungal species employed, are op METHOD OF ENDUCNG THERAPEUTIC TRAN QUELIZATION WITH PSEELO'CYBE N AND timal for the formation of mycelium and sclerotes. PSLOCEN While daylight is indispensable for the formation of Albert Hofmann, Bottningen, Sasei-Land, Arazir Brack, fruit bodies, it has been found that sclerotes and mycelium Riehen, near Basel, and Haas Kobe, Basel, Switzer are formed in greater profusion if the cultures are incu land, and Roger Heim, Paris, and Roger Caieux, bated in the dark. The largest yields of active fungal Pavillons-sous-Bois, France, assignors to Sandoz Ltd. material (mycelium and sclerotes) are obtained by pre (a/k/a Sandoz A.G.), Base, Switzerlaid paring surface cultures with culture media of malt extract No Drawing. Original application Feb. 16, 1959, Ser. No. O (beerwort or commercial preparations of malt extracts) 793,234. Divided and this application May 4, 1962, containing 4 to 10% by weight of dry substance, and by Ser. No. 194,707 incubation of these cultures in the dark at a constant Claims priority, application Switzerland, Feb. 2, 1958, emperature between 22 and 26° C. Addition of 0.2% 56,443; July 30, 1958, 62,393 by weight of agar to the culture medium enhances good 2 Claims. (C. 167-65) growth. This medium is just sufficiently firm-though it The present application is a division of our copending is still almost liquid-to permit the fungus to grow. application Serial No. 793,234, filed February 16, 1959. quickly, forming a well-knit mycelium layer. Addition of The present invention relates to psilocybin and psilicin ferrous salts is very desirable; addition of zinc, potassium, and to the preparation thereof from the so-called calcium and magnesium salts, of nitrate, phosphate and hallucinogenic fungi: Psilocybe, Stropharia, Panaeolus, 20 sulphate ions as well as of yeast extract or of corn steep Conocybe, Amanita and Russula. It has heretofore been solids is also found to be very advantageous. impossible to isolate the active substance from samples of This process of cultivation is a great technical improve the natural fungi or from artificially cultured fungal ma ment, as it gives a high yield of active starting material; terial; nor has it been possible to culture hallucinogeni the yield is actually ten times greater than that obtained cally active species-starting from natural fungi-under from a culture on natural substrates and the artificial conditions that would produce active material in amounts method takes less time and involves less work. sufficient for obtaining the active substance on a prepara The active fungal material (fruit bodies, sclerotes and tive scale. mycelium) is carefully dried in an air current or under A primary object of the present invention is the em reduced pressure at 20-40 C., finely ground and thor bodiment of an industrially feasible process whereby the 30 oughly extracted with a lower aliphatic alcohol or with hitherto unknown active principles of hallucinogenic a mixture of water and a water-miscible organic solvent fungal species, notably Psilocybe mexicana Heim, at room temperature (20 to 30° C.). The extracts are Psilocybe caerulescens Murrill var. nigripes Heim, Psilo concentrated under reduced pressure at low temperature. cybe zapotecorum Heim, Psilocybe semperviva Heim and The residue is defatted with petroleum ether and ex Cailleux, Psilocybe aztecorum Heim and Stropharia 35 tracted with acetone or chloroform-alcohol to remove in cubensis Earle. active accompanying material. Other ballast material is This object is realized according to the present inven separate off by dissolving the residue in as little water as tion by extracting the active principals either directly from possible and repeated preciptation with absolute ethanol the fungal material of natural origin or from cultures of or acetone; the filtrate is concentrated under reduced pres the fungi or of biological variants or mutants thereof 40 sure at low temperature. which have been grown on natural or artificial substrates Further purification is advantageously carried out by by culture techniques which make it possible to obtain chromatography on cellulose powder in a through-flow sufficient amounts of active material to permit the isola process; elution is performed with water-saturated butanol tion of the latter on a preparative scale. Briefly stated, or another alcohol not miscible with water. The fractions the cultures are incubated in daylight or in the dark at a collected are tested for their content of active substance constant temperature between i8 and 27° C. and, after by means of the Keller reagent (glacial acetic acid con purification, the active substance is separated and freed taining iron chloride and concentrated sulphuric acid). from halogen, where present. The fractions showing a positive color reaction are com The process, more specifically, may be carried out as bined and, if necessary, chromatographed again on a follows: For a culture on a natural substrate, a compost 50 column of cellulose powder. From the through-flow consisting of fermented wheat straw and a mixture of chromatogram a rather rapidly travelling Zone is eluted. corn leaves and corn stems or stalks of wild grasses is This yields a product containing an active substance, washed well under running water, poured into earthen “psilocin,” characterized by a clear blue Keller reaction, ware dishes and sterilized in an autoclave. The compost while from a zone travelling more slowly, a product con is inoculated with mycelium from primary cultures and 5 5 taining a second active substance, "psilocybin,” is ob incubated for approx. two weeks at 24-27 C. The tained in larger amounts. cultures are then covered with sterile Sand and left un The active substances are obtained in a fairly pure state disturbed in a glass box in the daylight at a temperature from the column but contain halogen and do not crystal of 18-27 C., the moisture content being kept constant. lize out as psilocybin and psilocin. The halogen may be re The fruit bodies appear after 4 to 5 weeks. They are 60 moved only by chemical treatment, crystalline compounds harvested from time to time for a period of 1 or 2 months being thereby obtained. For this purpose, an aqueous so as soon as the formation of the spores has started. lution of the active material is treated with silver car In developing an alternative process which is better bonate. Excess silver ions are removed with hydrogen - adapted for large scale operation, it was found quite un sulphide and the remaining solution is concentrated under expectedly that, grown in vitro on Substrates rich in nutri 65 reduced pressure at low temperature, the substances crys tive material, the fungi produce active mycelium and talizing out from the concentrated solution. sclerotes in large quantities and only a very small nun For analysis, psilocybin is recrystallized from methanol ber of fruit bodies; on substrates poor in nutrients, how or water. Recrystallization from water yields very fine ever, the familiar fruit bodies are produced. On an agar white needles; from methanol colorless hexagonal plates or medium containing 1.5% by weight of agar, a concentra 70 prisms are produced; these contain methanol and melt at tion of 0.2 to 0.7% by weight of dry substance of malt 195-200 C. (with decomposition). The compound dis extract is the optimum for the formation of fruit bodies, solves in 120 parts by weight of boiling methanol or in 20 3,193,111 es s 4. parts by weight of boiling water; it dissolves difficulty in treated with 20 parts by weight of cellulose powder con higher alcohols and other organic solvents. The crystals taining 5% of water. The methanol is evaporated off are dried in a high vacuum at 100° C., a decrease in Weight under reduced pressure and the cellulose powder bearing of 10.4% taking place. The results of elementary analysis the active material is poured onto a column of 100 parts give the empirical formula C12H4O4N2P (molecular by weight cellulose powder containing 5% of water, the weight 284.2). Psilocybin is an amphoteric compound. column having previously been washed with Water-Satu It is optically inactive and readily soluble in dilute aqueous rated butanol. The column is eluted with water-saturated mineral acids and in dilute aqueous alkalis with which it butanol and fractions of 20 parts by volume are collected. forms salts. A solution of psilocybin in 80% (by weight) The evaporation residues from the individual fractions are aqueous ethanol has a faintly acid reaction (pH 5.2). The O tested for their content of active material by means of the UV-spectrum in a methanolic solution shows maxima at Keller color reaction. For this purpose, 2 milliliters of 222, 267 and 290 mu. Keller reagent are added to samples of 0.25 milligram of For analysis, the psilocin is purified by another chroma evaporation residue. tographic operation on a column of cellulose powder, using The fractions showing a positive color reaction are com water-saturated butanoi or by treatment with potassium bi bined. The amorphous powder is dissolved in 20 parts by carbonate in an aqueous solution and extraction with ether volume of water and shaken with 0.5 part by weight of or an organic solvent. The results of elementary analysis silver carbonate. The solution is filtered and desilverized give the empirical formula C12HNO2. Psilocybin crys with hydrogen sulphide and then carefully concentrated. tallizes from methanol or acetone; it is moderately soluble Psilocybin crystallizes from the concentrated solution in in water but dissolves readily in dilute acid.
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