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Psilocybin mushrooms

Psilocybin Isn’t the Only Compound in Magic Mushrooms—Here’s What Else There Is

A survey of the alkaloids in psychedelic mushrooms

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Updated July 24, 2021

DoubleBlind Mag is devoted to fair, rigorous reporting by leading experts and journalists in the field of psychedelics. Read more about our editorial process and fact-checking here. Editorially reviewed by Madison Margolin.

With a growing body of research showing psilocybin as an effective mental health treatment, many journalists reporting on these studies have dubbed the lab-made psilocybin capsules used in scientific research as “synthetic magic mushrooms.” However does such a simplification ignore the range of potentially psychoactive compounds found in these mushrooms, most of which we currently know little about? By shining the media spotlight on psilocybin, we may be oversimplifying the effect that magic mushrooms, themselves—as a whole—have on those consuming them. 

The entourage effect is an idea originally coined from the cannabis industry that some have applied to magic mushrooms: It proposes that the sum of a whole plant’s chemical constituents is greater than its parts. In the case of cannabis, it’s believed that cannabinoids other than THC or CBD, such as CBN or CBG, not to mention the plant’s load of aromatic compounds called terpenes, all potentiate each other in a holistic, synergistic effect. In magic mushrooms, the amounts of potentially psychoactive chemical compounds, or “alkaloids” as they’re more commonly known, can vary among species, growing conditions, and even the methods used to analyze them in the lab. So let’s take a look at some of these lesser known alkaloids, and what is currently known about their possible contribution to a magic mushroom experience.

Psilocybin and Psilocin

Psilocybin and Psilocin chemical structures
Psilocybin (left) and Psilocin (right) chemical structures

Psilocybin is the current star of the show in the so-called psychedelic renaissance, as scientists study its effects to treat anxiety, depression, addiction, eating disorders, and more. Psilocybin has been discovered in over 200 species of mushrooms, mostly from the eponymous genus Psilocybe where it’s been found in 116 species. In addition to appearing in fungi, there’s been at least one study indicating that it may be present in a rare lichen (a symbiotic combination of fungi and algae) called Dictyonema huaorani, from Amazonian Ecuador. 

Read: The Definitive History of Psilocybin Mushrooms

While it was Maria Sabina, the Mazatec curandera who first introduced the banker/amateur mycologist Robert Wasson to psilocybin mushrooms in 1955, the chemical itself was first isolated from a sample of lab grown Psilocybe mexicana by Swiss chemist Albert Hofmann in 1959. 

Psilocybin, however, is not actually the compound that directly affects your brain; it is a prodrug, meaning that it is chemically broken down (metabolized) within the body into the active compound psilocin, which then passes from the blood into the brain to act on the 5-HT2A receptor—the mechanism ultimately responsible for the neurological effects described in modern day studies with synthetic psilocybin. 

Compared to psilocybin, psilocin is relatively unstable and, in the presence of oxygen and acidity, breaks down into the characteristic blue color observed in damaged or old mushrooms. Although this bluing reaction has been noted for decades by many mycologists, the chemical pathway that determined psilocin as the cause was not understood until as late as 2020, by Claudius Lenz and other researchers at Leibniz Institute for Natural Product Research and Infection Biology in Germany.

Baeocystin 

Baeocystin chemical structure
Baeocystin chemical structure

Baeocystin is an alkaloid that has a similar chemical structure to psilocybin and is commonly found in many of the same mushroom species, though it is present in much lower concentrations (up to a third of the concentration of psilocybin). Baeocystin was discovered by Albert Leung and Ara Paul in 1968 and, like psilocybin, was named after the mushroom it was first isolated from—Psilocybe baeocystis. Since its discovery, it has been detected in a variety of species including the commonly cultivated Psilocybe cubensis, wood loving species such as Psilocybe cyanescens, and “truffle” producing species such as Psilocybe tampanensis

Although little is known about the effects of baeocystin in isolation, Jochen Gartz, a chemist and mycologist at the Institute for Biotechnology in Germany, made anecdotal references to its psychoactivity being comparable to psilocybin in his book, “Magic Mushrooms Around the World” published in the 1997. In somewhat of a contradiction, famous mycologist Paul Stamets recently reported on The Joe Rogan podcast in 2019 that a pure baeocystin experience during a high state of anxiety didn’t cause psilocybin-like hallucinations, but did dilate his pupils and cause his anxiety to disappear.

While such anecdotes can be useful to guide research, only one study to date has focused on baeocystin’s hallucinatory activity in mice. Conducted by Alexander Sherwood and his colleagues at the Usona Institute in 2020, the study researchers measured the head twitch response (a reliable predictor of hallucinatory effect in humans) of mice exposed to different concentrations of baeocystin and found no effect. This research may support Stamets’ experience of no hallucinations from baeocystin, but more research is needed into claims of the anxiety-reducing properties of this alkaloid, and how these effects may interact with those brought on by the other compounds present in magic mushrooms.    

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Norbaeocystin

Norbaeocystin chemical structure
Norbaeocystin chemical structure

Norbaeocystin was discovered simultaneously to baeocystin, by the same researchers and in the same species of mushroom. However if we know little about the effects of baeocystin, we know even less about norbaeocystin. Although scientists at the Usona Institute have found ways to synthesize this alkaloid, to date no studies have been conducted on its psychoactive effects, leaving this area of research wide open for further study. 

Norpsilocin

Norpsilocin chemical structure
Norpsilocin chemical structure

Norpsilocin is one of the more recently discovered alkaloids, also discovered by Claudius Lenz and colleagues in 2017. The researchers from the Leibniz Institute for Natural Product Research and Infection Biology isolated this alkaloid from Psilocybe cubensis, the most commonly cultivated species by homegrowers. Norpsilocin is currently thought to be the metabolized equivalent of baeocystin, with researchers comparing the chemical relationship of these two alkaloids to that of psilocybin and psilocin (i.e. psilocybin and baeocystin both represent the unmetabolized equivalents of psilocin and norpsilocin, respectively). However in a 2020 study, researchers at the Usona Institute found that unlike psilocin, norpsilocin may be incapable of crossing from the blood into the brain to exert a hallucinogenic effect. However when norpsilocin was used in tests that measure a compound’s effect on the 5-HT2A receptor directly, it was found to be even more potent than psilocin. Putting these pieces of research together indicates that although norpsilocin may be more potent than psilocin, it is chemically unable to pass from the blood into the brain to exert its effect. While this alkaloid may not act upon the same receptors in the brain as psilocin, it is not currently known if there are other receptors or chemical pathways in the body that norpsilocin may act on instead.

Aeruginascin

Aeruginascin chemical structure
Aeruginascin chemical structure

On the timeline of mushroom alkaloid discovery, aeruginascin sits somewhere in the middle. It was first discovered by Jochen Gartz in 1989 in Inocybe aeruginascens (hopefully you’re noticing the trend of naming alkaloids after the mushrooms they’re found in by now!), though recent research in late 2020 by Klára Gotvaldová and colleagues at University of Chemistry and Technology, Czech Republic discovered the presence of this alkaloid in Psilocybe cubensis, suggesting it may be more common than was once thought.

Read: Beyond Psilocybe Cubensis: 10 Magic Mushroom Species You Should Know About

As well as being chemically similar to other mushroom alkaloids, aeruginascin also shares a similar structure to bufotenidine, a chemical found in the venom of some toads. In the same paper from 1989, Jochen Gartz analysed 23 cases of accidental ingestion of Inocybe aeruginascens and found that the effects always resulted in euphoria, however as with other alkaloids described here, little is known about the effects of pure formulations of aeruginascin.   

ß-carbolines

ß-carbolines chemical structure
ß-carbolines chemical structure

From a chemical point of view, the discovery of ß-carbolines in four species of Psilocybe (P. cyanescens, P. cubensis, P. semilanceata and P. mexicana) by Felix Blei and other researchers at the Leibniz Institute for Natural Product Research and Infection Biology in 2019, was quite the surprise. ß-carbolines are a general class of chemical compounds that includes the chemicals found in Psychotria viridis and Banisteriopsis caapi (two plant ingredients used in traditional ayahuasca brews) called monoamine oxidase inhibitors (MAOI). In the context of ayahuasca, monoamine oxidase is the enzyme that breaks down DMT in the gut. Through the inclusion of an MAOI, the activity of these enzymes is reduced, ultimately increasing and prolonging the effects of DMT in the brew. Due to the structural similarity of psilocybin and DMT, MAOIs could also play a role in boosting the effect of psilocybin a magic mushroom experience, raising some interesting questions as to how a clinical experience with pure psilocybin may perceptually differ from a whole-mushroom experience. 

Although psilocybin is currently having its moment in the spotlight, it appears there is a lot more to learn about the interaction and potential entourage effect of the naturally occurring compounds in magic mushrooms. Whether or not the entourage effect can be applied to magic mushrooms, both historical and modern scientific studies have shown that from a chemical perspective there’s more to shrooms than just psilocybin.      

If you or a loved one is struggling with substance use, contact the Substance Abuse and Mental Health Services Administration (SAMHSA) National Helpline at 1-800-662-4357 for support. If you’re looking for peer support during or after a psychedelic experience, contact Fireside Project by calling or texting 6-2FIRESIDE.
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