Baeocystin

When it comes to the compounds in psilocybin mushrooms (aka magic mushrooms), psilocybin is usually the center of attention. However, there are additional compounds found in magic mushrooms that probably play a role in the overall psychedelic experience for the user.

Baeocystin is a psilocybin derivative or analog. It was first isolated from Psilocybe baeocystis by Leung and Paul in 1968.1 Later, other researchers isolated it from other species such as Psilocybe semilanceataPanaeolus renenosusPanaeolus subbalteatus2 and Pluteus salicinus.3

The Chemistry of Baeocystin

Baeocystin was first prepared synthetically in the lab by Troxler, Sailor, and Albert Hofmann in 1959.4 Chemically, baeocystin differs from psilocybin by one methyl group (Figure 1). Baeocystin is [3-(2-methylaminoethyl)-1H-indol-4-yl] dihydrogen phosphate whereas psilocybin is [3-(2-dimethylaminoethyl)-1H-indol-4-yl] dihydrogen phosphate. Baeocystin is often described as either the N-demethylated derivative of psilocybin or the phosphorylated derivative of 4-HO-NMT (4-hydroxy-N-methyltryptamine).

Figure 1: The chemical structures of psilocybin and baeocystin.

Although the presence or absence of a methyl group seems like a small structural change, those sorts of differences often result in significant changes in pharmacology. For example, amphetamine and methamphetamine differ “only” by one methyl group on their respective ethylamino groups. That difference results in dramatically different activities between the two molecules.  In many cases, the presence or absence of alkyl groups on the amino nitrogen affects the metabolism of the molecule. For example, adding a methyl group to amphetamine (to make methamphetamine) changes how the molecule is metabolized by monoamine oxidase enzymes.

The Pharmacology of Baeocystin

The scientific community has very little data on baeocystin or its human pharmacology. At best, there are anecdotal reports from people taking the drug. For example, in the book Magic Mushrooms Around the World, author Jochen Gartz refers to a report that describes “10 mg of baeocystin were found to be about as psychoactive as a similar amount of psilocybin.” 5 Gartz also reported that his experience taking 4 mg of the pure drug caused “a gentle hallucinogenic experience.”

Although there are scattered instances of people like Gartz obtaining pure baeocystin, access to this compound is difficult. Accordingly, progress towards understanding the properties of pure baeocystin will likely come from better access to the molecule via separation techniques, synthetic methods, or both.

Aside from these accounts, no one has quantified the effects of this molecule–alone or in combination with other active magic mushroom compounds.

The Applications and Potential of Baeocystin

Overall, nothing is known about the possible therapeutic effects of baeocystin either by itself or in combination with other magic mushroom compounds. And on top of this, scientists are not actively studying baeocystin, resulting in an empty research pipeline. Future research in this area will benefit from shifting the focus from magic mushrooms to the active molecules within them.

Based on what is known from studying the compounds in other naturally-occurring organisms such as cannabis, it is conceivable that there is also an entourage effect with magic mushrooms. Baeocystin may be very important for generating and modulating specific psychedelic effects. The current state of the art for baeocystin (and psilocybin) can be improved by isolating each of the individual molecules and studying how they affect cellular receptors (e.g., serotonin) alone and in combination with other molecules.

    References
  1. Leung AY, Paul AG. Baeocystin and norbaeocystin: New analogs of psilocybin from Psilocybe baeocystis. Journal of Pharmaceutical Sciences. 1968;57(10):1667-1671. doi:10.1002/jps.2600571007
  2. Repke DB, Leslie DT, Guzmán G. Baeocystin in psilocybe, conocybe and panaeolus. Lloydia. 1977;40(6):566-578.
  3. Gartz J. Occurrence of Psilocybin and Baeocystin in Fruit Bodies of Pluteus salicinus. Planta Med. 1987;53(3):290-291. doi:10.1055/s-2006-962710
  4. Troxler F, Seemann F, Hofmann A. Abwandlungsprodukte von Psilocybin und Psilocin. 2. Mitteilung über synthetische Indolverbindungen. Helvetica Chimica Acta. 1959;42(6):2073-2103. doi:10.1002/hlca.19590420638
  5. Gartz J. Magic Mushrooms Around the World. Los Angeles: LIS publs.; 1996.