Edited by Eskatari, 06 June 2010 - 04:13 PM.
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Posted 06 June 2010 - 04:08 PM
Edited by Eskatari, 06 June 2010 - 04:13 PM.
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The active fungal material (fruit bodies, sclerotia and mycelium) is
carefully dried in an air current or under reduced pressure at 20-40
centigrade, finely ground and thoroughly extracted with a lower aliphatic
alcohol or with a mixture of water and a water-miscible organic solvent at
room temperature (20 to 30 centigrade). The extracts are concentrated under
reduced pressure at low temperature. The residue is defatted with petroleum
ether and extracted with acetone or chloroform-alcohol to remove inactive
accompanying material. Other ballast material is separated off by dissolving
the residue in as little water as possible and repeated precipitation with
absolute ethanol or acetone; the filtrate is concentrated under reduced
pressure at low temperature.
Further purification is advantageously carried out by chromatography on
cellulose powder in a through-flow process; elution is performed with water
saturated butanol or another alcohol not miscible with water. The fractions
collected are tested for their content of active substance by means of the
Keller reagent (glacial acetic acid containing iron chloride and
concentrated sulphuric acid). The fractions showing a positive colour
reaction are combined and, if necessary, chromatographed again on a column
of cellulose powder. From the through-flow chromatogram a rather rapidly
travelling zone is eluted.
This yields a product containing an active substance, "psilocin,"
characterized by a clear blue Keller reaction, while from a zone travelling
more slowly, a product containing a second active substance, "psilocybin,"
is obtained in larger amounts.
The active substances are obtained in a fairly pure state from the column
but contain halogen and do not crystallize out as Psilocybin and psilocin.
The halogen may be removed only by chemical treatment, crystalline compounds
being thereby obtained. For this purpose, an aqueous solution of the active
material is treated with silver carbonate or silver oxide. Excess silver
ions are removed with hydrogen sulphide and the remaining solution is
concentrated under reduced pressure at low temperature, the substances
crystallizing out from the concentrated solution.
For analysis, Psilocybin is recrystallized from methanol or water.
Recrystallization from water yields very fine white needles; from methanol
colourless hexagonal plates or prisms are produced; these contain methanol
and melt at 195-200 centigrade (with decomposition). The compound dissolves
in 120 parts by weight of boiling methanol or in 20 parts by weight of
boiling water; it dissolves difficulty in higher alcohols and other organic
solvents. The crystals are dried in a high vacuum at 100 centigrade, a
decrease in weight of 10.4% taking place. The results of elementary analysis
give the empirical formula C12H17O4N2P (molecular weight 284.2). Psilocybin
is an amphoteric compound. It is optically inactive and readily soluble in
dilute aqueous mineral acids and in dilute aqueous alkalis with which it
forms salts. A solution of Psilocybin in 80% (by weight) aqueous ethanol has
a faintly acid reaction (pH 5.2). The UV-spectrum in a methanolic solution
shows maxima at 222, 267 and 290 m~.
For analysis, the Psilocin is purified by another chromatographic operation
on a column of cellulose powder, using water-saturated butanol or by
treatment with potassium bi-carbonate in an aqueous solution and extraction
with ether or an organic solvent. The results of elementary analysis give
the empirical formula C12H16NO2. Psilocin crystallizes from methanol or
acetone; it is moderately soluble in water but dissolves readily in dilute
acid. M.P. 173-176 centigrade. (with decomposition). Psilocybin is the
phosphoric acid ester of Psilocin 4-hydroxy-dimethyl tryptamine
(Experientia, vol. 14, 1958, pages 397-399).
Psilocin is characterized by an UV-spectrum in a methanolic solution with
maxima at 222, 260, 267, 283 and 293 m~ and by the Keller colour reaction
which shows-unlike psilocybin-a clear blue colour.
The products of the present invention are psychotropically active and find
use in therapy as tranquillisers. Subcutaneous injection or oral
administration of 2 to 8 mg. of Psilocybin produces a pronounced euphoric
mood accompanied by a lack of spontaneity and a feeling of indifference.
When administered in higher dosage, there occur changes in perception
together with autonomic symptoms.
Edited by whatchamacallit, 08 June 2010 - 06:13 AM.
Posted 08 June 2010 - 05:42 PM