Psilocybe cubensis – Pharmacology

Alkaloids

The mushrooms used during ceremonies in Mexico were called Psilocybe mexicana Heim, as Heim collected samples of these mushrooms and sent them to Hofmann in order to identify the intoxicating ingredients (Hofmann et al., 1959). Hofmann also discovered LSD, a structurally related drug. He identified the two alkaloids psilocybin and psilocin, which can be found in all mushrooms of the genus Psilocybe. The alkaloid content of different Psilocybe species (dry weight) varies between 0.2% for Psilocybe mexicana Heim, 0.7% for Psilocybe cubensis and the highest Psilocybin concentration ever found in a fungus was 2% by dry weight (Beug and Bigwood, 1982).

Chemical formula of psilocybin and psilocin

The hallucinogenic substances of Psilocybe cubensis was identified in 1958 by Hofmann et al.. He found out that its active substance is 0-phosphoryl-4-hydroxy-N-dimethyl tryptamine, what is also known under the name ‚psilocybin‘. In the body psilocybin is converted into psilocin within an hour, a substance, which is also found in Psilocybe cubensis (Horita and Weber, 1961). The structural formula of Psilocin is 4-hydroxy-N: N-dimethyltryptamine, which mainly is a dephosphorylated psilocybin (Hofmann and Troxler, 1959). During the conversion in the body, the phosphoric acid group of psilocybin is oxidized and converted to a hydroxyl group. Due to the methyl groups of the indole ring it can penetrate the central nervous system. Psilocybin and psilocin are closely related and it is thought that psilocin is the active substance of psilocybin. In the brain, psilocin behaves as a neurotransmitter since it has the typical indole ring. Therefore, psilocybin and psilocin can bind to specific receptors and with this causes an over-stimulation. This happens because the cotico-striato-thalamo-cotrical (shortly CSTC) loop is stopped. This loop is responsible to ensure that the external stimuli and information cannot access the ceberum unfiltered and thus triggering a sensory overload. Through the activation of certain serotonin receptors by psilocybin, the CSTC loop becomes decoupled and thus opening the filter for the thalamus. Then, the sensory information are no longer compared with the memory and thus interpreted, but the information can access unfiltered, leading to a fundamentally altered self-environmental-awareness. This over-stimulation is then experienced as a characteristic trip. Psilocybin acts as an agonist of serotonin (5-hydroxytryptamine or 5-HT) and binds to the 5-HT receptor in the brain. Psilocybin and psilocin are evenly distributed in all organs, whereas about 25% are excreted unmetabolized by the kidneys and about 10% are stored for several days in adipose tissue. The remainder is metabolized within hours.

Psilocybin and psilocin are sensitive to temperature and at temperatures between 50 – 100 °C decomposes easily. Therefore, the mushrooms should never be dried with application of high temperature. In addition, the atmospheric oxygen also causes a reduction of the two substances. Therefore, fresh mushrooms should be air dried and stored air tight and at cool temperature (in the freezer), which makes them durable for month or even for years.

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