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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
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.
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