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Shulgin Online
ARCHIVE: March 5, 2003
Psilocybe Mushroom Extractions
Dear Dr. Shulgin:
A friend of mine performed a Soxhlet extraction of 12 grams of powdered Psilocybe
cubensis, using 95% ethanol. When the 60 mL of extract cooled to room
temperature, many small transparent, colorless crystals had formed on the bottom
of the container and did not redissolve on agitation. Do you know what these
crystals are? -- Journeyman

Dear Journeyman:
There is a fascinating report in the literature that gives a quantitative
measurement of the efficiency of extraction of both psilocybin and psilocin from the
mushroom Psilocybe bohemica. The citation to the article is Kysilka, R. and Wurst,
M., Planta Med. Vol. 56 pp. 327-328 (1990). These Czechoslovakian scientists
studied the efficiency of both methanol and ethanol as solvents, each containing
varying amounts of water. The results were, to me, both unexpected and most
provocative.
The isolation of psilocybin seemed to be quite reasonable. This alkaloid is
reasonably soluble in boiling water from which it can be nicely crystallized. It is less
soluble in boiling methanol, and almost insoluble in boiling ethanol. And the
extraction efficiency is optimum with methanol and almost as good with ethanol.
With both, the less water present, the better. The compound is, after all, a perfect
example of a zwitterion, the internal salt of a phosphoric acid and an amine base.
But the numbers with psilocin are strange. With aqueous ethanol, the optimum
extraction was with a 70% ethanol concentration, and the extraction efficiency
dropped almost to zero when there was no water present. But methanol was
extremely inefficient regardless of the amount of water present in it. These
researchers were apparently surprised by these findings, as they explored further
and uncovered other clues. Time is a factor. Psilocin is extracted at a much slower
rate than is psilocybin because it is contained intracellularly in the plant, and thus
slower to be gotten out. They conclude that many of the low psilocin assays of
mushrooms are due to this difficulty of getting the alkaloid out of the plant and into
the extracting solvent. Using this information they determined that the levels of
psilocybin and psilocin are substantially the same in Psilocybe bohemica, in conflict
with the published literature values where very small amounts of psilocin were
observed.
Efficient extraction apparently requires patience.
As to the identity of the crystals that were drifting around in the cooled Soxhlet
receiver, from their being insoluble in ethanol, and white, and transparent, I would
guess that you are seeing pure psilocybin.
-- Dr. Shulgin