Baeocystin – an Ignored Psilocybin Derivative

Baeocystin – A Psilocybin Derivative

Baeocystin is a chemical compound found in so-called “magic mushrooms.”

From a chemical standpoint, baeocystin is closely related to psilocybin.  The two molecules differ by one methyl group. Baeocystin is [3-(2-methylaminoethyl)-1H-indol-4-yl] dihydrogen phosphate. Psilocybin is 3-(2-dimethylaminoethyl)-1H-indol-4-yl] dihydrogen phosphate.  Below are two pictures showing this structural difference.

Psilocybin is the most abundant psychoactive compound in psychoactive mushrooms. Note the TWO methyl groups on the ethylamino group.

 

Baeocystin is a minor component found in psychoactive mushrooms. It is reported to be active. But no conclusive studies have documented its activity. Note the ONE methyl group on the ethylamino group.

Baeocystin is a psilocybin derivative or analog.  It is often described as either (1) the N-demethylated derivative of psilocybin or (B) the phosphorylated derivative of 4-HO-NMT (4-hydroxy-N-methyltryptamine).  It was first isolated from the mushroom Psilocybe baeocystis (hence the name). Others later isolated it from P. semilanceata, Panaeolus renenosus, Panaeolus subbalteatus, and Copelandia chlorocystis. It was prepared synthetically in 1959.

What we Know About Baeocystin

The scientific community has virtually no data on baeocystin or its human pharmacology.  At best, we have anecdotal reports by people taking the drug. For example, in the book Magic Mushrooms Around the World, author Jochen Gartz refers to a report that “10 mg of baeocystin were found to be about as psychoactive as a similar amount of psilocybin.”  The same author also reported that his experience taking 4 mg of pure drug caused “a gentle hallucinogenic experience”.

Aside from the above accounts, no one has quantified the effects of this molecule– alone or in combination with other active species.

Although the presence or absence of a methyl group seems like a small structural change, those sorts of changes 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 activity 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 an methyl group to amphetamine (to make methamphetamine) changes how the molecule is metabolized by monoamine oxidase enzymes.

Future Research

Future research in this area will benefit from shifting our focus from “magic mushrooms” to the active molecules within them.  See Psilocybin ChemistryThe current state of the art for psilocybin technology 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.