Psilocin
Encyclopedia
Psilocin an aromatic compound, sometimes also (mis)spelled psilocine, psilocyn, or psilotsin, is a psychedelic
(hallucinogenic
) mushroom
alkaloid
. It is found in most psychedelic mushroom
s together with its phosphorylated counterpart psilocybin
. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances
. The mind altering effects of psilocin are highly variable and subjective. The effects typically last anywhere from 3 to 8 hours depending on certain variables (such as metabolism, food interaction), however the effects can seem to last much longer due to psilocin's ability to distort the perception of time.
of natural psilocybin under strongly acid
ic or under alkaline
conditions (hydrolysis
). Another synthetic
route uses the Speeter-Anthony tryptamine synthesis starting from 4-hydroxyindole.
Psilocin is relatively unstable in solution due to its phenolic
hydroxy
(-OH) group. In the presence of oxygen
it readily forms bluish and dark black degradation products . Similar products are also formed under acidic conditions in the presence of oxygen and Fe3+
ion
s (Keller's reagent
).
analogs are known with a benzothienyl
replacement as well as 4-SH-DMT. N1-methylpsilocin is a functionally 5-HT2C receptor
preferring agonists. 4-fluoro-N,N-dimethyltryptamine is known. O-Acetylpsilocin is an acetylized analog of psilocin, also known as 4-AcO-DMT. Additionally, substitution of a methyl group at the dimethylated Nitrogen
with an isopropyl or ethyl group yields 4-HO-MIPT (4-Hydroxy-N-Methyl-N-Isopropyltryptamine) and 4-HO-MET
(4-Hydroxy-N-Methyl-N-Ethyltryptamine), respectively.
Psilocybin is rapidly dephosphorylated in the body to psilocin which acts as a 5HT2A, 5HT2C and 5HT1A agonist
. Psilocin is structurally similar to serotonin
(5-HT), differing only by the hydroxyl
group being on the 4-position rather than the 5 and the dimethyl
groups on the nitrogen
. Its effects are thought to come from its partial agonist activity at 5-HT2A serotonin receptors in the prefrontal cortex
.
Psilocin has no significant effect on dopamine
receptors (unlike LSD
) and only affects the noradrenergic system at very high dosages.
Psilocin's physiological half-life ranges from 2 to 3 hours.
Its physiological effects are similar to a sympathetic arousal state. Specific effects observed after ingestion
can include but are not limited to tachycardia
, dilated pupil
s, restlessness or arousal, euphoria, open and closed eye visuals (common at medium to high doses), synesthesia
(eg. hearing colours and seeing sounds), increased body temperature, headache
, sweat
ing and chills, and nausea
.
There is virtually no direct lethality associated with psilocin. There is virtually no withdrawal syndrome
when chronic use of this drug
is ceased. There is cross tolerance among psilocin, mescaline
, and DMT
.
Psychedelic drug
A psychedelic substance is a psychoactive drug whose primary action is to alter cognition and perception. Psychedelics are part of a wider class of psychoactive drugs known as hallucinogens, a class that also includes related substances such as dissociatives and deliriants...
(hallucinogenic
Psychedelics, dissociatives and deliriants
This general group of pharmacological agents can be divided into three broad categories: psychedelics, dissociatives, and deliriants. These classes of psychoactive drugs have in common that they can cause subjective changes in perception, thought, emotion and consciousness...
) mushroom
Mushroom
A mushroom is the fleshy, spore-bearing fruiting body of a fungus, typically produced above ground on soil or on its food source. The standard for the name "mushroom" is the cultivated white button mushroom, Agaricus bisporus; hence the word "mushroom" is most often applied to those fungi that...
alkaloid
Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...
. It is found in most psychedelic mushroom
Psychedelic mushroom
Psilocybin mushrooms are fungi that contain the psychoactive compounds psilocybin and psilocin. There are multiple colloquial terms for psilocybin mushrooms, the most common being shrooms or magic mushrooms....
s together with its phosphorylated counterpart psilocybin
Psilocybin
Psilocybin is a naturally occurring psychedelic prodrug, with mind-altering effects similar to those of LSD and mescaline, after it is converted to psilocin. The effects can include altered thinking processes, perceptual distortions, an altered sense of time, and spiritual experiences, as well as...
. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances
Convention on Psychotropic Substances
The Convention on Psychotropic Substances of 1971 is a United Nations treaty designed to control psychoactive drugs such as amphetamines, barbiturates, benzodiazepines, and psychedelics signed at Vienna on February 21, 1971...
. The mind altering effects of psilocin are highly variable and subjective. The effects typically last anywhere from 3 to 8 hours depending on certain variables (such as metabolism, food interaction), however the effects can seem to last much longer due to psilocin's ability to distort the perception of time.
Chemistry
Psilocin can be obtained by dephosphorylationPhosphorylation
Phosphorylation is the addition of a phosphate group to a protein or other organic molecule. Phosphorylation activates or deactivates many protein enzymes....
of natural psilocybin under strongly acid
Acid
An acid is a substance which reacts with a base. Commonly, acids can be identified as tasting sour, reacting with metals such as calcium, and bases like sodium carbonate. Aqueous acids have a pH of less than 7, where an acid of lower pH is typically stronger, and turn blue litmus paper red...
ic or under alkaline
Base (chemistry)
For the term in genetics, see base A base in chemistry is a substance that can accept hydrogen ions or more generally, donate electron pairs. A soluble base is referred to as an alkali if it contains and releases hydroxide ions quantitatively...
conditions (hydrolysis
Hydrolysis
Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...
). Another synthetic
Chemical synthesis
In chemistry, chemical synthesis is purposeful execution of chemical reactions to get a product, or several products. This happens by physical and chemical manipulations usually involving one or more reactions...
route uses the Speeter-Anthony tryptamine synthesis starting from 4-hydroxyindole.
Psilocin is relatively unstable in solution due to its phenolic
Phenols
In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl group bonded directly to an aromatic hydrocarbon group...
hydroxy
Hydroxy
Hydroxy can refer to:* In chemical nomenclature, the prefix "hydroxy-" shows the presence of a hydroxyl functional group '* An abbreviation for the medication hydroxyzine, which is commonly sold under the brand names Atarax, Ucerax, Serecid, and Vistaril* Hydroxy gas: A nickname for oxyhydrogen, a...
(-OH) group. In the presence of oxygen
Oxygen
Oxygen is the element with atomic number 8 and represented by the symbol O. Its name derives from the Greek roots ὀξύς and -γενής , because at the time of naming, it was mistakenly thought that all acids required oxygen in their composition...
it readily forms bluish and dark black degradation products . Similar products are also formed under acidic conditions in the presence of oxygen and Fe3+
Iron
Iron is a chemical element with the symbol Fe and atomic number 26. It is a metal in the first transition series. It is the most common element forming the planet Earth as a whole, forming much of Earth's outer and inner core. It is the fourth most common element in the Earth's crust...
ion
Ion
An ion is an atom or molecule in which the total number of electrons is not equal to the total number of protons, giving it a net positive or negative electrical charge. The name was given by physicist Michael Faraday for the substances that allow a current to pass between electrodes in a...
s (Keller's reagent
Keller's reagent
Keller's reagent can refer to either of two different mixtures of acids.In metallurgy, Keller's reagent is a mixture of nitric acid, hydrochloric acid, and hydrofluoric acid, used to etch aluminum alloys to reveal their grain boundaries and orientations. It is also sometimes called Dix–Keller...
).
Structural analogs
SulfurSulfur
Sulfur or sulphur is the chemical element with atomic number 16. In the periodic table it is represented by the symbol S. It is an abundant, multivalent non-metal. Under normal conditions, sulfur atoms form cyclic octatomic molecules with chemical formula S8. Elemental sulfur is a bright yellow...
analogs are known with a benzothienyl
Benzothiophene
Benzothiophene is an aromatic organic compound with a molecular formula C8H6S and an odor similar to naphthalene . It occurs naturally as a constituent of petroleum-related deposits such as lignite tar. Benzothiophene has no household use...
replacement as well as 4-SH-DMT. N1-methylpsilocin is a functionally 5-HT2C receptor
5-HT2C receptor
The 5-HT2C receptor is a subtype of 5-HT receptor that binds the endogenous neurotransmitter serotonin . It is a G protein-coupled receptor that is coupled to Gq/G11 and mediates excitatory neurotransmission. HTR2C denotes the human gene encoding for the receptor, that in humans is located at the...
preferring agonists. 4-fluoro-N,N-dimethyltryptamine is known. O-Acetylpsilocin is an acetylized analog of psilocin, also known as 4-AcO-DMT. Additionally, substitution of a methyl group at the dimethylated Nitrogen
Nitrogen
Nitrogen is a chemical element that has the symbol N, atomic number of 7 and atomic mass 14.00674 u. Elemental nitrogen is a colorless, odorless, tasteless, and mostly inert diatomic gas at standard conditions, constituting 78.08% by volume of Earth's atmosphere...
with an isopropyl or ethyl group yields 4-HO-MIPT (4-Hydroxy-N-Methyl-N-Isopropyltryptamine) and 4-HO-MET
4-HO-MET
4-HO-MET, or 4-hydroxy-N-methyl-N-ethyltryptamine, also known as metocin, is a lesser-known psychedelic drug. It is a structural− and functional analog of psilocin as well the 4-hydroxyl analog of MET. 4-HO-MET was first synthesized by Alexander Shulgin...
(4-Hydroxy-N-Methyl-N-Ethyltryptamine), respectively.
Pharmacology
Psilocin is the pharmacologically active agent in the body after ingestion of psilocybin or some species of psychedelic mushrooms.Psilocybin is rapidly dephosphorylated in the body to psilocin which acts as a 5HT2A, 5HT2C and 5HT1A agonist
Agonist
An agonist is a chemical that binds to a receptor of a cell and triggers a response by that cell. Agonists often mimic the action of a naturally occurring substance...
. Psilocin is structurally similar to serotonin
Serotonin
Serotonin or 5-hydroxytryptamine is a monoamine neurotransmitter. Biochemically derived from tryptophan, serotonin is primarily found in the gastrointestinal tract, platelets, and in the central nervous system of animals including humans...
(5-HT), differing only by the hydroxyl
Hydroxyl
A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...
group being on the 4-position rather than the 5 and the dimethyl
Methyl group
Methyl group is a functional group derived from methane, containing one carbon atom bonded to three hydrogen atoms —CH3. The group is often abbreviated Me. Such hydrocarbon groups occur in many organic compounds. The methyl group can be found in three forms: anion, cation and radical. The anion...
groups on the nitrogen
Nitrogen
Nitrogen is a chemical element that has the symbol N, atomic number of 7 and atomic mass 14.00674 u. Elemental nitrogen is a colorless, odorless, tasteless, and mostly inert diatomic gas at standard conditions, constituting 78.08% by volume of Earth's atmosphere...
. Its effects are thought to come from its partial agonist activity at 5-HT2A serotonin receptors in the prefrontal cortex
Prefrontal cortex
The prefrontal cortex is the anterior part of the frontal lobes of the brain, lying in front of the motor and premotor areas.This brain region has been implicated in planning complex cognitive behaviors, personality expression, decision making and moderating correct social behavior...
.
Psilocin has no significant effect on dopamine
Dopamine
Dopamine is a catecholamine neurotransmitter present in a wide variety of animals, including both vertebrates and invertebrates. In the brain, this substituted phenethylamine functions as a neurotransmitter, activating the five known types of dopamine receptors—D1, D2, D3, D4, and D5—and their...
receptors (unlike LSD
LSD
Lysergic acid diethylamide, abbreviated LSD or LSD-25, also known as lysergide and colloquially as acid, is a semisynthetic psychedelic drug of the ergoline family, well known for its psychological effects which can include altered thinking processes, closed and open eye visuals, synaesthesia, an...
) and only affects the noradrenergic system at very high dosages.
Psilocin's physiological half-life ranges from 2 to 3 hours.
- See psilocybinPsilocybinPsilocybin is a naturally occurring psychedelic prodrug, with mind-altering effects similar to those of LSD and mescaline, after it is converted to psilocin. The effects can include altered thinking processes, perceptual distortions, an altered sense of time, and spiritual experiences, as well as...
for more details
Behavioral and non-behavioral effects
Ingestion
Ingestion is the consumption of a substance by an organism. In animals, it normally is accomplished by taking in the substance through the mouth into the gastrointestinal tract, such as through eating or drinking...
can include but are not limited to tachycardia
Tachycardia
Tachycardia comes from the Greek words tachys and kardia . Tachycardia typically refers to a heart rate that exceeds the normal range for a resting heart rate...
, dilated pupil
Pupil
The pupil is a hole located in the center of the iris of the eye that allows light to enter the retina. It appears black because most of the light entering the pupil is absorbed by the tissues inside the eye. In humans the pupil is round, but other species, such as some cats, have slit pupils. In...
s, restlessness or arousal, euphoria, open and closed eye visuals (common at medium to high doses), synesthesia
Synesthesia
Synesthesia , from the ancient Greek , "together," and , "sensation," is a neurologically based condition in which stimulation of one sensory or cognitive pathway leads to automatic, involuntary experiences in a second sensory or cognitive pathway...
(eg. hearing colours and seeing sounds), increased body temperature, headache
Headache
A headache or cephalalgia is pain anywhere in the region of the head or neck. It can be a symptom of a number of different conditions of the head and neck. The brain tissue itself is not sensitive to pain because it lacks pain receptors. Rather, the pain is caused by disturbance of the...
, sweat
SWEAT
SWEAT is an OLN/TSN show hosted by Julie Zwillich that aired in 2003-2004.Each of the 13 half-hour episodes of SWEAT features a different outdoor sport: kayaking, mountain biking, ice hockey, beach volleyball, soccer, windsurfing, rowing, Ultimate, triathlon, wakeboarding, snowboarding, telemark...
ing and chills, and nausea
Nausea
Nausea , is a sensation of unease and discomfort in the upper stomach with an involuntary urge to vomit. It often, but not always, precedes vomiting...
.
There is virtually no direct lethality associated with psilocin. There is virtually no withdrawal syndrome
Withdrawal syndrome
A withdrawal syndrome, also called a discontinuation syndrome, occurs when a person suddenly stops taking or reduces the dosage of some types of medications...
when chronic use of this drug
Drug
A drug, broadly speaking, is any substance that, when absorbed into the body of a living organism, alters normal bodily function. There is no single, precise definition, as there are different meanings in drug control law, government regulations, medicine, and colloquial usage.In pharmacology, a...
is ceased. There is cross tolerance among psilocin, mescaline
Mescaline
Mescaline or 3,4,5-trimethoxyphenethylamine is a naturally occurring psychedelic alkaloid of the phenethylamine class used mainly as an entheogen....
, and DMT
Dimethyltryptamine
N,N-Dimethyltryptamine is a naturally occurring psychedelic compound of the tryptamine family. DMT is found in several plants, and also in trace amounts in humans and other mammals, where it is originally derived from the essential amino acid tryptophan, and ultimately produced by the enzyme INMT...
.
See also
- Psychedelic mushroomPsychedelic mushroomPsilocybin mushrooms are fungi that contain the psychoactive compounds psilocybin and psilocin. There are multiple colloquial terms for psilocybin mushrooms, the most common being shrooms or magic mushrooms....
s - PsilocybinPsilocybinPsilocybin is a naturally occurring psychedelic prodrug, with mind-altering effects similar to those of LSD and mescaline, after it is converted to psilocin. The effects can include altered thinking processes, perceptual distortions, an altered sense of time, and spiritual experiences, as well as...
- TryptamineTryptamineTryptamine is a monoamine alkaloid found in plants, fungi, and animals. It is based around the indole ring structure, and is chemically related to the amino acid tryptophan, from which its name is derived...
- O-Acetylpsilocin
- MiprocinMiprocinMiprocin is a substituted aromatic compound and a lesser-known psychedelic drug from the tryptamine family. Miprocin is part of the class of drugs known as serotonergic psychedelics , and its effects and molecular structure resemble that of the tryptamine psilocin...
- Metocin4-HO-MET4-HO-MET, or 4-hydroxy-N-methyl-N-ethyltryptamine, also known as metocin, is a lesser-known psychedelic drug. It is a structural− and functional analog of psilocin as well the 4-hydroxyl analog of MET. 4-HO-MET was first synthesized by Alexander Shulgin...
- IndoleIndoleIndole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Indole is a popular component of fragrances and the precursor to many pharmaceuticals. Compounds that contain an...
- Psychedelic drugPsychedelic drugA psychedelic substance is a psychoactive drug whose primary action is to alter cognition and perception. Psychedelics are part of a wider class of psychoactive drugs known as hallucinogens, a class that also includes related substances such as dissociatives and deliriants...
- Psychoactive drugPsychoactive drugA psychoactive drug, psychopharmaceutical, or psychotropic is a chemical substance that crosses the blood–brain barrier and acts primarily upon the central nervous system where it affects brain function, resulting in changes in perception, mood, consciousness, cognition, and behavior...
External links
- The Ones That Stain Blue Studies in ethnomycology including the contributions of Maria Sabina, Dr. Albert Hofmann and Dr. Gaston Guzman.
- The Shroomery Detailed information about Psilocybin mushrooms including identification, cultivation and spores, psychedelic images, trip reports, a dosage calculator and an active community.
- 4-HO-DMT entry in TiHKAL