Aeruginascin: An Understudied Psilocybin Derivative

Seldom mentioned in scientific literature, Aeruginascin is closely structurally related to psilocybin, the most well-known psychoactive compound in "magic" mushrooms.

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Aeruginascin is a compound present in some species of “magic mushrooms.”  Structurally, it is closely related to psilocybin.  However, aeruginascin is seldom mentioned in the contemporary or scientific literature. Psilocybin is the most discussed compound in so-called “magic mushrooms.” (Technically, psilocybin is not the active molecule in magic mushrooms.  It is a prodrug of psilocin, which is the active molecule.  When ingested, psilocybin is readily converted into psilocin, providing the psychoactive effects.)

Because of its potential utility in medical treatments, scientists have become increasingly interested in psilocybin and psilocin. Scientists would also benefit from investigating other psilocybin derivatives, such as baeocystin, norbaeocystin, and aeruginascin.

What is Aeruginascin?

Like baeocystin and norbaeocystin, aeruginascin is a compound that is structurally similar to psilocybin. Aeruginascin is described by at least three chemical names:

  • 3-(2-trimethylaminoethyl) indol-4-yl dihydrogen phosphate
  • N, N, N-trimethyl-4-phosphoryloxytryptamine
  • 4-phosphoryloxy-N,N,N-trimethyltryptamine

Aeruginascin occurs naturally in the psychoactive mushroom Inocybe aeruginascens.In 1989, scientist J.Gartz found that the fruit bodies of Inocybe aeruginascens were rich in aeruginascin.  Scientists have also synthesized aeruginascin in the laboratory.

Structurally, the molecule aeruginascin resembles psilocybin and baeocystin. It differs by having three methyl groups (instead of one or two) on the ethylamine moiety.

Aeruginascin – Effect on Humans

Aeruginascin’s specific mode of action remains unstudied. In contrast to psilocybin and psilocin, ingesting aeruginascin produces only euphoria, as opposed to hallucinations.1

Because it is a quaternary amine, scientists hypothesize that aeruginascin cannot cross the blood-brain barrier, except when it is metabolically demethylated or when is accompanied by a specific transporter. Penetrating the blood-brain barrier is important to generating the psychoactivity observed for the dimethylated analogs psilocybin and psilocin.  One would expect similar logic to apply to aeruginascin.