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The Varieties of Psychoactive Fungi

The first step in studying psychoactive fungi is to clarify their forms, functions, and chemistry. Of
the roughly 30,000 documented species of mushrooms, about 200 are known or suspected to be
psychoactive. Most commonly encountered psychoactive fungi can be divided into one of two cat-
egories based on whether their active constituent is psilocin or muscimol. The psilocin-containing
mushrooms are those most commonly used for contemporary practices and constitute the larger
group of the two, while the muscimol-containing fungi have the richest global history.

Psychedelic Chemistry
Psilocin is one of the many tryptamine psychedelic compounds. As with all tryptamines, the central
feature (or “backbone”) of psilocin’s chemical structure is a 3-(2-aminoethyl) indole, itself being
a modified form of the essential amino acid tryptophan. Other tryptamines include the psyche-
delics DMT, 5-MeO-DMT, LSD, ibogaine, and bufotenin. The only chemical differences between
these various compounds are slight modifications in the placement of elements or chemical groups
around this indole. While these adjustments are slight, they make all the difference as each struc-
ture brings about its own characteristic effects in the user. The magic and mystery of psychoactive
chemistry, then, ultimately falls on subtle shifts in the electrical signature of these simple substances.
The phenethylamines are a separate class of chemicals that contain a large number of psyche-
An indole ring is a dual-ring delic substances. It includes many “designer” drugs (e.g. MDMA, 2C-B, 2C-I, MDA, Adderall, and
structure comprised of a ben- mescaline, among others). Some phenethylamines can be biosynthesized from the amino acid
zene ring fused to a pyrrole L-phenylalanine. They tend to affect dopamine levels in the brain.
ring. Compounds that contain
an indole ring are often re- Psychoactive substances can also be classified by how they interact in the brain or by their
ferred to as “indoles.” typical psychological effect on the user. These categories include the dissociatives (e.g. DXM, PCP,
ketamine, and nitrous oxide), the empathogens (e.g. MDMA and 2-CB), and the cannabinoids (e.g.
THC and CBD). A number of other psychoactive substances have unique chemical structures and/
or effects that cannot easily be placed into the above categories. These eclectic compounds include
salvinorin A and B, atropine, scopolamine, harmaline, ibotenic acid, and muscimol.

12 Psilocin (sil-o-sin)
C12H16N2O
4-OH-DMT
4-hydroxy-N, N-dimethyl-
tryptamine
4-hydroxy DMT (i.e. DMT
with a hydroxyl molecule
at the 4-position)
L-Tryptophan DMT Psilocin

404 Radical Mycology
Psilocin-Containing Fungi
Of the roughly 180 species of fungi that contain psilocin, most are in the genus Psilocybe. Psi-
locin-containing fungi are found on every continent except Antarctica. Mexico hosts 75 psi- Psilocybe Species Distribution 1
locin-containing species, the greatest number of any country. Fifty-three of these are Psilocybes. Mexico: 53
US and Canada: 22
On the black market, Psilocybe cubensis dominates due to its ease of cultivation on a variety of Australia and Pacific Islands: 19
simple substrates. Europe: 16
Over a dozen other genera are said to contain species with psilocin and/or the related com- Asia: 15
Africa: 4
pound psilocybin. All of the psilocin-containing species are decomposers; some inhabit grasslands
and lawns, while others prefer riparian areas, animal dung, or the wood chips in manicured gardens
and landscaped areas.

The (Bio)Chemistry of Psiloc(yb)in
While psilocin is the main compound responsible for the effects of these mushrooms, four other
active compounds may be present, depending on the species: psilocybin, baeocystin, norbaeocys-
tin, and aeruginacine. Regardless of species, psilocin and/or psilocybin are typically found in the
highest concentrations.
Psilocin and psilocybin are closely related compounds, differing only by the addition of a
phosphate group to the 4-position of psilocybin’s indole ring. It is believed that this phosphate
group protects psilocybin from oxidation, giving it the ability to remain stable at room temperature
for years and to be boiled with minimal degradation. Psilocin, on the other hand, is very unstable
due to its phenolic hydroxyl group, which rapidly degrades in the presence of oxygen. It is believed
that when psilocybin is ingested it is quickly converted (dephosphorylated) to psilocin in the di-
gestive system, kidneys, liver, and perhaps blood by means of alkaline phosphatases that remove
the phosphate group.2 Thus, it is psilocin, and not psilocybin, that reaches the brain to bring about
the psychedelic experience. However, as psilocybin is easier to synthesize and store, it is more often
referred to in the literature.
Many psilocin mushrooms stain a deep cerulean blue when handled, a reaction presumably
attributed to the oxidation (degradation) of psilocin. In other words, as these mushrooms turn blue,
their potency may be decreasing. Not all psilocin-containing fungi stain blue and many non-psy-
choactive fungi stain blue due to the oxidation or modification of compounds other than psilocin.
For example, Satan’s Bolete (Boletus satanus) rapidly turns blue when cut due to the presence of
(the non-psychedelic compound) variegatic acid.
Baeocystin and norbaeocystin are two compounds that are chemically similar to psiloc(yb)in
and trace amounts of them are often found in certain species of psychoactive fungi. Structurally,
they are psilocybin with one methyl and two methyl groups removed, respectively. While these
compounds seem to influence the effects of psiloc(yb)in, their individual actions on the body are not
well studied. A fifth active compound, aeruginacine, is present in Inocybe aeruginascens. Its chemical
structure has not yet been resolved, but it can be distinguished from the other four compounds
using thin layer chromatography.3 Other, unidentified psychoactive compounds may exist as well. Metol (from photo supply
The different species of psilocin mushrooms have varying amounts of these five alkaloids and houses) enhances the bluing
reaction of psilocin. Mush-
it is hypothesized that variations in their ratio corresponds to the distinct “flavor” of each species’ room pieces added to Metol
psychoactive effect. For example, Psilocybe cubensis is said to create a more body-based, “earthy,” dissolved in 20x their weight in
or “muddy” experience, while P. cyanescens produces a mental, “cleaner,” and “clearer” trip. In all water will turn dark blue-violet
in 30 minutes.
species, the entire mushroom seems to be psychoactive, though studies have shown higher alkaloid
concentrations in the caps of P. cubensis specimens.4
Psilocin mushrooms are some of the only natural psychoactive substances that are both orally
active and produce strong effects in relatively low doses. In comparison, the powerful tryptamine
A bluing reaction should not
be used on its own to identify 12
a psychoactive mushroom.
DMT is found endogenously in many plants and animals yet is not orally active. When DMT is swal- However if that bluing mush-
lowed, a chemical in our stomachs (mono amine oxidase, MAO) quickly neutralizes this substance room also has purple-brown
and prohibits it from being metabolized or producing any psychoactive effect. To be orally active, spores (as with Psilocybes), it
might produce psychoactive
DMT must be mixed with a substance that inhibits this neutralizing compound (i.e. a mono amine effects.
oxidase inhibitor [MAOI] such as the harmaline found in Syrian rue [Peganum harmala] or the

MycoGnosis 405
harmine found in the ayhuasca plant [Banisteriopsis caapi]). It is believed that psilocybin is orally
active due to the same phosphate group that keeps it shelf-stable. The oxygen atom at the 4-position
of psilocybin’s indole ring forms a weak hydrogen-bond with the nitrogen on the molecule’s carbon
“tail.” This bond effectively blocks MAO from neutralizing psilocybin in the gut, thereby allowing
it to enter the bloodstream and to ultimately be dephosphorylated and metabolized as psilocin.5
Like all tryptamines, psilocin is chemically similar to the neurotransmitter serotonin, allowing
it to act as a partial agonist (i.e. it stimulates some neurons and not others) on the brain’s serotoner-
gic receptors 5HT2A, 5HT2C, and 5HT1A.6 Serotonin receptors are found throughout the brain’s cortex
as well as in the raphe system, the thalamus, and abundantly in the locus coeruleus at the base of
the brain. The locus coeruleus is considered a “novelty detector” that notifies the rest of the brain
Psilocybin (sil-o-sybe-in)
of changes in the environment and its stimulation seems to increase one’s ability to process infor-
C12H17N2O4P mation.7 More generally, serotonin receptor excitation has been linked to positive moods, increased
4-OPO4-DMT
4-Phosphoryloxy-N,N-di- motivation, memory, and learning. Serotonin is often said to be the “happiness neurotransmitter,”
methyltryptamine though it is also responsible for many other emotions and physiological activities.
O-phosphoryl-4-hydroxy-N, When psilocin activates these receptors, it produces various psychoactive effects. How this
N- dimethyltryptamine
3-[2-(Dimethylamino)ethyl]- happens is not understood. While scientists have been able to show a relationship between psilocin
1H-indol-4-ol dihydrogen and serotonin receptors, how consciousness is actually produced and modulated in the body is
phosphate ester one of the biggest riddles in science and philosophy. As such, one should not assume that psilocin’s
effects are limited to simple brain chemistry—they may be much more complex than one can even
imagine. Experiments using radiolabeled psilocybin have shown the substance to quickly become
distributed throughout the entire body where its interactions are not well understood.
Psiloc(yb)in has not been shown to cause damage to the brain nor to any other major organ.
Other than exhibiting a slight elevation in blood pressure with some users, the physiological effects
of psilocybin are minimal with infrequent use. Psilocybin is not habit forming and is non-addictive.
When taken in successive sessions, its effect rapidly decreases. While this increased tolerance wears
off within a few days, in the short-term it disables the user from going on a mushroom binge. It is
estimated that a 185-pound adult would have to eat 23.9 grams of pure psilocybin (or about 2,390
grams [5.3 pounds] of dried P. cubensis mushrooms) to die.8 Based on the amount of psilocybin
Norbaeocystin necessary to cause human death, this compound is less toxic than heroin, cocaine, alcohol, nicotine,
(nor-bay-o-sis-tin)
caffeine, and aspirin. As far as I am aware, there is only one human death directly attributed to the
C10H13N2O4P consumption of psiloc(yb)in.9
4-OPO4-T
4-Phosphoryloxytryptamine
1H-Indol-4-ol, 3-[2-am- Effects
inoethyl] dihydrogen
phosphate ester Psilocin fungi can be consumed fresh or dried, whole or powdered, in a variety of food-based
preparations, or their active constituents can be extracted. Fresh mushrooms are generally more
potent due to the higher psilocin content. Dosages vary from 0.1–10+ grams of dried mushrooms
depending on the species consumed and the user’s experience and tolerance level.
Describing any “typical” experience of these mushrooms is not easy. While there are often
similarities among the experiences of users, there is no guarantee that one’s experience will be of
a certain quality. Every person responds differently to their environment and has her or his own
unique relationship with themselves. Both of these dynamics are heightened and modified on the
mushroom trip. As such, it is not possible to know how exactly psychoactive mushrooms will affect
a given individual. Further, attempting to describe the effects of psilocin may actually influence
the user’s experience on a subconscious level, something I find rather ethically challenging. As the
Baeocystin (bay-o-sis-tin) personal significance and long-term psychological, emotional, and attitudinal impacts that can
come from consuming these fungi can be life changing, describing—let alone working with—the
12 C11H15N2O4P
4-OPO4-MT
Desmethyl psilocybine
power of these fungi should not be taken lightly. Factors that tend to influence a person’s experience
on psychoactive fungi include:
4-phosphoryloxy-N-methyl-
tryptamine • The species and dosage consumed.
3-[2-(methylamino)ethyl]- • Personal metabolism and chemical sensitivity.
1H-indol-4-ol dihydrogen
phosphate ester • Preconceptions of drugs and psychedelics gained directly or indirectly from others.
• Personal experience with drugs in general, and psychedelics specifically.

406 Radical Mycology
• Personal belief systems, motivations, and life desires.
Average Dose Sizes of
• The specific collection (psiloc[yb]in content can vary dramatically from harvest to Psilocybe cubensis
harvest), method of preparation, and age of specimens.
Threshold: 0–0.25 grams
• The “set” and “setting” of the session. Light: 0.25–1.0 grams
• Intentions and desires for the experience. Average: 1.0–2.5 grams
• Post-experience integration and processing strategy. Strong: 2.5–5.0 grams
Heavy: 5.0+ grams

Experience “Levels”
That said, it is helpful for the reader inexperienced with psilocin mushrooms to have a sense of how
their effects are often described. Based on the above, I find it easier to separate standard dosages
from the different intensity “levels” of experience one may have on any dosage.
• Level 1 (Spore): Unusual bodily sensations (a body high) are felt and some mild
visual enhancement is observed.
• Level 2 (Hyphal): Greater visual enhancement coincides with the sensation that
objects are alive. Creativity increases along with 2-D, closed-eye visuals.
• Level 3 (Mycelial): Strong open-eye visuals (curving, warped, flowing, or kaleido-
scopic patterns) and 3-D closed-eye visuals manifest. The physical senses and the
sense of time behave unusually. Behavior regresses as childhood or other repressed Past Names for Psychedelics
memories are recalled. Empathy toward others is significantly heightened. Deliriants
• Level 4 (Ecosystemic): Very strong visuals coincide with the destruction or split- Delusionogens
Eidetics
ting of the ego. Communication with objects becomes possible as time loses mean- Hallucinogens
ing. Out-of-body experiences or E.S.P.-type phenomena are sensed. Misperceptonogens
• Level 5 (Universal): All sense of an ego and any visual connection with reality is Mysticomimetics
Phanerothymes
completely lost as the psilophile merges with objects or the entire universe. Access- Phantasticants
ing the akashik records/genetic database is reported. This level defies description. Psychotics
Psychoticants
Physiological changes such as increased heart rate vary by user and their state of calmness and Psychogens
Psychosomimetics
agitation. Chewing the mushrooms thoroughly and holding them in one’s mouth increase the rate Psychodysleptics
of effectiveness, which typically begins in the first one to two hours. The peak of the experience Psychotaraxics
can come on about two hours later, crest for one to two hours, and then taper off over another one Psychotogens
Psychotomimetics
to three hours. The whole experience often lasts four to six hours, with physiological aftereffects Schizogens
noticeable for up to eight hours afterword. Insights from the experience can linger for a lifetime.

But Why?
The mere fact that some fungi even produce these compounds is quite remarkable. Psilocin and
its related alkaloids are considered secondary metabolites that are not crucial to the fungus’ sur-
vival. Why do these fungi produce these compounds in such abundant quantities (sometimes in
excess of 1% of the dried weight of the mushroom)? This question has never been adequately an-
swered. Some argue that it is a defense mechanism, others say it is a spore dispersal strategy that
attracts certain animals. Others suggest that the coevolution of psychoactive fungi and humans
was and is an intertwined relationship and that these fungi have evolved to provide information
to their human counterpart through unique means of communicating with Nature.
Some psychoactive species appear almost exclusively in areas of human settlement, leading
to the suggestion that the trailing of these fungi into the landscapes of modernity are subtle

12
reminders of the eternal potential to connect with Nature, regardless of context or constraint.

MycoGnosis 407