State of the Art of Aeruginascin – July 2019

Aeruginascin remains an understudied compound in psychedelic research.

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This year, PSR published articles about aeruginascin in January and April. The January article was a brief overview, and in April the discussion extended to its possible role in Wood Lover Paralysis. The interest in psychedelic drug research is continuing to increase. Therefore, it is important to take a moment and review the state of the art for this compound and discuss any new information coming out since our last publication.

Aeruginascin is one of several compounds found in so-called magic mushrooms. It’s seldom mentioned in the scientific literature, psychedelic discussion boards, or even experience reports. Interestingly, Inocybe aeruginascens is the only species of mushroom in which aeruginascin has been detected.

The Chemistry of Aeruginascin

The German chemist Jochen Gartz was the first to isolate aeruginascin from extracts of I. aeruginascens.1 He found from further analysis that the concentration of aeruginascin in the mushrooms was comparable to that of psilocybin and baeocystin.2 The quaternary trimethylammonium structure of aeruginascin was confirmed using 1H-NMR in 2004.3

From a chemical structure standpoint, aeruginascin is similar to baeocystin and norbaeocystin.  It is also closely related to a compound in toad secretions (aka venom) called bufotenidine. Specifically, aeruginascin has three methyl groups on the ethylamine moiety. In contrast, psilocybin has two methyl groups, and baeocystin has just one.

Based on its chemistry, scientists don’t think that aeruginascin can cross the blood-brain barrier.3  Similar compounds entering the human body would have to be demethylated to become metabolically active or be attached to a transporter protein or other molecule.

The Effects of Aeruginascin on Humans

The only morsel of information in the scientific literature about the effects of aeruginascin is from a 1989 study published by Gartz.2 In this work, he analyzed 23 cases of the accidental hallucinogenic mushroom poisonings. He noticed that people who had ingested Inocybe aeruginascens reported only euphoric experiences. Dr. Gartz described the experiences of those ingesting mushrooms without aeruginascin (and high in psilocybin and psilocin) as an “often slight and in some cases deep dysphoric mood” accompanied by psychosis, panic, and anxiety. He hypothesized that aeruginascin modified the overall psychedelic effect of the compounds in the mushrooms, culminating in an overall euphoric feeling. Specifically, he stated:

It seems that the significant amounts of the indole derivative aeruginascin can modify the pharmacological action of psilocybin to give an (sic) euphoric mood during psychosis with hallucinations due to ingestion of I. aeruginascens.

The Importance of the Entourage Effect

At this point in psychedelic research, there’s little doubt that psilocybin (more accurately, it’s active metabolite psilocin) has therapeutic benefits for treating several mental conditions. However considering the multiple compounds found in psychedelic mushrooms and the different effects that are reported from ingesting entire mushrooms as opposed to a single chemical, several questions emerge. What are the effects and the specific pharmacology of each compound found in magic mushrooms? How do these compounds work together to give the overall psychedelic effect for the user? Can modulating the amount of some of these compounds lead to more effective therapies and perhaps new therapies yet undiscovered? Are some combinations of magic mushroom compounds more effective than others? The presence of the entourage effect in nature is evidence of the likelihood that more than one compound is involved in the full psychedelic effect.

Looking Forward

The groundbreaking and promising work being done using psilocybin for treating a variety of mental conditions is challenging the paradigms of psychotherapy. Aeruginascin, however, remains an understudied psilocybin derivative that may have important contributions to make to psychedelic therapy. It appears that the last published study on aeruginascin was a 2006 paper that analyzed the extracts from I. aeruginascens.4

As Jochen Gartz has stated:

In order to establish the specific action of aeruginascin, investigations of human ingestion of aeruginascin with and without additional application of psilocybin should be done.

A search of the literature reveals no recent research being done on this compound, its chemistry, or its effects in combination with the other chemicals and magic mushrooms. Aeruginascin is a wide-open area of investigation for the curious researcher. Additional knowledge about aeruginascin, it’s chemistry, and pharmacology will contribute to a better understanding of its use in therapeutic formulations.

Barb Bauer Headshot

Barb is the former Editor and one of the founders of Psychedelic Science Review. She is currently a contributing writer. Her goal is making accurate and concise psychedelic science research assessable so that researchers and private citizens can make informed decisions.

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Bernard Lerer
4 years ago

Thank you for this fascinating article.
One point is not clear. If aeruginascin does not cross the blood brain barrier, how does it induce the euphoriant effects described by Garz and how could it modify the effects of psilocybin?

jonas
4 years ago

hi !

seems it is metabolized to 4-ho-tmt which than can cross the bbb.

there is a firm that is researching aeruginascin, there site is caam.tech

    References
  1. Gartz J. Variation der Alkaloidmengen in Fruchtkörpern von Inocybe aeruginascens. Planta medica. 1987;53(06):539-541. doi:10.1055/s-2006-962805
  2. Gartz J. Analysis of aeruginascin in fruit bodies of the mushroom Inocybe aeruginascens. International Journal of Crude Drug Research. 1989;27(3):141-144. doi:10.3109/13880208909053954
  3. Jensen N. Tryptamines as Ligands and Modulators of the Serotonin 5‑HT 2A Receptor and the Isolation of Aeruginascin from the Hallucinogenic Mushroom Inocybe aeruginascens. 2004. http://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.632.9308&rep=rep1&type=pdf.
  4. Jensen N, Gartz J, Laatsch H, Biotransformations F. Aeruginascin, a trimethylammonium analogue of psilocybin from the hallucinogenic mushroom Inocybe aeruginascens. Planta Medica. 2006;72(7):665. doi:10.1055/s-2006-931576