Psilocybin (pronounced /ˌsaɪlɵˈsaɪbɪn/ Sil-lə-SYE-bin) (also known as psilocybine or 4-PO-DMT) is a prodrug for the classical hallucinogen The general group of pharmacological agents commonly known as hallucinogens 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. Unlike other psychoactive drugs, such as - more specifically, psychedelic The term psychedelic is derived from the Greek words ψυχή and δηλοῦν (deloun, "to manifest"), translating to "mind-manifesting". A psychedelic experience is characterized by the perception of aspects of one's mind previously unknown, or by the creative exuberance of the mind liberated from its ostensibly ordinary - psilocin Psilocin , an aromatic compound, sometimes also (mis)spelled psilocine, psilocyn, or psilotsin, is a psychedelic (hallucinogenic) mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. The mind altering, or 4-HO-DMT (4-hydroxyl-dimethyltryptamine), the active metabolite of psilocybin, responsible for all of the psychoactive effect of the drug. Both drugs are members of the indole Indole 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 indole ring are called indoles. Notably, the indolic and tryptamine Tryptamine 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. Tryptamine is found in trace amounts in the brains of mammals and is believed to play a role as a neuromodulator or neurotransmitter classes. Psilocybin-containing mushrooms are used both recreationally Recreational drug use is the use of a psychoactive substance with the intention of creating or enhancing recreational experience. Such use is controversial, however, often being considered to be also drug abuse, and it is often illegal. Also, it may overlap with other uses, such as medicinal , performance enhancement, and entheogenic (spiritual) by drug users, and traditionally, for spiritual purposes, as entheogens An entheogen , in the strict sense, is a psychoactive substance used in a religious, shamanic or spiritual context. Historically, entheogens were mostly derived from plant sources and have been used in a variety of traditional religious contexts. Most entheogens do not produce drug dependency. With the advent of organic chemistry, there now exist, with a history of use spanning millenia. It is produced by hundreds of species Inocybe aeruginascens • Inocybe corydalina var. corydalina • Inocybe tricolor of fungi A fungus is a member of a large group of eukaryotic organisms that includes microorganisms such as yeasts and molds, as well as the more familiar mushrooms. The Fungi (pronounced /ˈfʌndʒaɪ/ or /ˈfʌŋɡaɪ/) are classified as a kingdom that is separate from plants, animals and bacteria. One major difference is that fungal cells have cell, including those of the genus Psilocybe Psilocybe is a genus of small mushrooms growing worldwide. This genus is best known for its species with psychedelic or hallucinogenic properties, widely known as "magic mushrooms", though the majority of species do not contain hallucinogenic compounds. Psilocin and psilocybin are the hallucinogenic compounds responsible for the, such as Psilocybe cubensis Psilocybe cubensis is a species of psychedelic mushroom whose principal active compounds are psilocybin and psilocin. Commonly called Roomeyes, Gold Caps, or Golden Teacher , it belongs to the Strophariaceae family of fungi and was previously known as Stropharia cubensis, Psilocybe semilanceata Psilocybe semilanceata is a psychedelic mushroom that contains the psychoactive compound psilocybin. It grows on grassy meadows and similar; particularly in wet, north-facing fields and other habitats well fertilized by sheep and cattle feces, although unlike Psilocybe cubensis it does not grow directly on the dung itself. It is found in fields and Psilocybe cyanescens Psilocybe cyanescens, also known as wavy caps is a potent psychedelic mushroom whose main active compounds are psilocybin and psilocin. It belongs to the family Strophariaceae and was described from Kew Gardens, United Kingdom, by E. M. Wakefield in the 1940s. This species is closely related to Psilocybe azurescens which can be distinguished by, and has also been reportedly isolated from about a dozen other genera. Collectively known as psilocybin mushrooms Psilocybin mushrooms, are fungi that contain the medicinal compounds psilocybin and psilocin. There are multiple colloquial terms for psilocybin mushrooms, the most common being magic mushrooms or shrooms. Biological genera containing psilocybin mushrooms include Agrocybe, Conocybe, Copelandia, Galerina, Gerronema, Gymnopilus, Hypholoma, Inocybe,, these are commonly called "boomers," "sacred mushrooms," "magic mushrooms," or more simply "'shrooms." Possession, and in some cases usage, of psilocybin or psilocin Psilocin , an aromatic compound, sometimes also (mis)spelled psilocine, psilocyn, or psilotsin, is a psychedelic (hallucinogenic) mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. The mind altering has been outlawed in most countries across the globe.^[1] Proponents of its usage consider it to be an entheogen An entheogen , in the strict sense, is a psychoactive substance used in a religious, shamanic or spiritual context. Historically, entheogens were mostly derived from plant sources and have been used in a variety of traditional religious contexts. Most entheogens do not produce drug dependency. With the advent of organic chemistry, there now exist and a tool A tool is a device that can be used to produce or achieve something, but that is not consumed in the process. Colloquially a tool can also be a procedure or process used for a specific purpose. Tools that are used in particular fields or activities may have different assignations such as Instrument, Utensil, Implement, Machine, Apparatus to supplement various types of practices for transcendence In religion, transcendence is a condition or state of being that surpasses physical existence and in one form is also independent of it. It is affirmed in the concept of the divine in the major religious traditions, and contrasts with the notion of God, or the Absolute, existing exclusively in the physical order , or indistinguishable from it (, including in meditation Meditation is a holistic discipline during which time the practitioner trains his or her mind in order to realize some benefit, psychonautics A psychonaut (deriving from the Greek ψυχή (soul) and ναύτης (sailor), that is, a sailor of the mind/soul) is a person who experiences intentionally induced altered states of consciousness in an attempt to investigate their mind, and possibly address spiritual questions through direct experience. Psychonauts tend to be pluralistic,, and psychedelic psychotherapy Psychedelic therapy refers to therapeutic practices involving the use of psychedelic drugs, particularly serotonergic psychedelics such as LSD, psilocin and DMT. As an alternative to synonyms such as "hallucinogen", "entheogen", "psychotomimetic" and other functionally constructed names, the use of the term. The intensity and duration of entheogenic effects of psilocybin mushrooms are highly variable, depending on species or cultivar of mushrooms, dosage, individual physiology, and set and setting Set and setting describes the context for psychoactive and particularly psychedelic drug experiences: one's mindset and the setting in which the user has the experience. This is especially relevant for psychedelic or hallucinogenic experiences; the term was coined by Timothy Leary.

Once ingested, psilocybin is rapidly metabolised to psilocin Psilocin , an aromatic compound, sometimes also (mis)spelled psilocine, psilocyn, or psilotsin, is a psychedelic (hallucinogenic) mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. The mind altering, which then acts as a partial agonist Partial agonists bind and activate a given receptor, but have only partial efficacy at the receptor relative to a full agonist. They may also be considered ligands which display both agonistic and antagonistic effects - when both a full agonist and partial agonist are present, the partial agonist actually acts as a competitive antagonist, at the 5-HT_2A The mammalian 5-HT2A receptor is a subtype of the 5-HT2 receptor that belongs to the serotonin receptor family and is a G protein-coupled receptor . This is the main excitatory receptor subtype among the GPCRs for serotonin (5-HT), although 5-HT2A may also have an inhibitory effect[citation needed] on certain areas such as the visual cortex and and 5-HT_1A The 5-HT1A receptor is a subtype of 5-HT receptor which binds the endogenous neurotransmitter serotonin . It is a G protein-coupled receptor (GPCR) which is coupled to Gi/Go and mediates inhibitory neurotransmission. HTR1A denotes the human gene encoding for the receptor serotonin receptors The serotonin receptors also known as 5-hydroxytryptamine receptors or 5-HT receptors are a group of G protein-coupled receptors and ligand-gated ion channels (LGICs) found in the central and peripheral nervous systems. They mediate both excitatory and inhibitory neurotransmission. The serotonin receptors are activated by the neurotransmitter in the brain. The mind-altering effects of psilocybin typically last anywhere from 3 to 8 hours; however, to individuals under the influence of psilocybin, the effects may seem to last much longer, since the drug can distort the perception of time.

History

The American banker and amateur mycologist R. Gordon Wasson Robert Gordon Wasson was an author, amateur researcher and banker. In the course of independent research, he made contributions to the fields of ethnobotany, botany, and anthropology. Several of his books were self-published in illustrated, limited editions and have never been reprinted and his wife Valentina discovered that the ancient religious practices of the Indians in a remote village of Mexico included ingestion of mushrooms. In 1957, they published an article in Life The Life founded in 1883 was similar to xavier and published for 53 years as a general-interest light entertainment magazine, heavy on illustrations, jokes and social commentary. It featured some of the greatest writers, editors and cartoonists of its era, including Charles Dana Gibson, Norman Rockwell and Harry Oliver. During its later years, magazine (Seeking the Magic Mushroom), where they described the occurrence of hallucinatory experiences during these rituals. They were accompanied on a later expedition by the French mycologist Roger Heim Roger Heim, born February 12, 1900, Paris, died September 17, 1979, was a French botanist specialising in mycology and tropical phytopathology. He was known for his studies describing the anatomy of the mushroom hymenium, the systematics and phylogeny of higher fungi , the mycology of tropical fungi such as Termitomyces, as well as, director of the musée national d'histoire naturelle, when it was possible to identify several of the fungi as Psilocybe species.^[2] Heim was able to successfully cultivate the mushroom in France, and sent samples to the Swiss chemist Albert Hofmann Albert Hofmann was a Swiss scientist known best for being the first person to synthesize, ingest and learn of the psychedelic effects of lysergic acid diethylamide (LSD). He authored more than 100 scientific articles and a number of books, including LSD: My Problem Child for analysis. Hofmann, who had in 1938 created 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. LSD is non-addictive and well known for its psychological effects which can include altered thinking processes, closed and open eye visuals, synaesthesia, a sense of time distortion, in his Sandoz laboratory, was the first to recognize the importance and chemical structure of the pure compounds he called psilocybin and psilocin. Leading a research group that was able to isolate and identify the compounds from Psilocybe mexicana Psilocybe mexicana is a psychedelic mushroom, it was from this species that Dr. Albert Hofmann first isolated and named the active compounds, psilocybin and psilocin in 1958. First used by the early natives of Central America over 2,000 years ago, known to the Aztecs as teonanacatl,^[3] Hofmann was aided in the discovery process by his willingness to ingest mushroom extracts Liquid-liquid extraction, also known as solvent extraction and partitioning, is a method to separate compounds based on their relative solubilities in two different immiscible liquids, usually water and an organic solvent. It is an extraction of a substance from one liquid phase into another liquid phase. Liquid-liquid extraction is a basic.^[4] He and his colleagues later synthesized a number of compounds chemically related to the naturally occurring psilocybin:

These were essentially the same molecules except that: (1) the phosphoryl or hydroxy group at the top of the indole ring was moved around to other ring positions, and (2) different numbers of methyl groups (CH₃) and other carbon chains were added to the side chains and to the nitrogen on the indole ring to see how these changes would affect psychoactivity.^[5]

Two diethyl (two ethyl In chemistry, an ethyl group is an alkyl functional group derived from ethane . It has the formula -C2H5 and is very often abbreviated -Et groups in place of the two methyl In chemistry, a methyl group is a hydrophobic alkyl functional group named after methylene (RC groups) analogs of psilocybin and psilocin were synthesized 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. In modern laboratory usage, this tends to imply that the process is reproducible, reliable, and established to work in multiple by Hofmann, 4-phosphoryloxy-N,N-diethyltryptamine, called CY-19, and 4-hydroxy-N,N-diethyltryptamine 4-HO-DET, also known as 4-hydroxy-diethyl-tryptamine, CZ-74, or ethocin, is a hallucinogenic drug and psychedelic compound of moderate duration. 4-HO-DET is a substituted tryptamine, structurally related to psilocin and 4-HO-DIPT, called CZ-74. Because their effects last only about three and a half hours (compared to roughly double that with psilocybin), they proved more manageable in European clinics using "psycholytic therapy"—psychotherapy in conjunction with the controlled use of psychedelics.^[5]

In the early 1960s, Harvard University Harvard University is a private university located in Cambridge, Massachusetts, and a member of the Ivy League. Established in 1636 by the colonial Massachusetts legislature, Harvard is the first corporation chartered in the United States and oldest institution of higher learning in the United States became the testing ground of psilocybin, through the efforts of Timothy Leary Dr. Timothy Francis Leary was an American writer, psychologist, futurist, and advocate of psychedelic drug research. An icon of 1960s counterculture, Leary is most famous as a proponent of the therapeutic, spiritual and emotional benefits of LSD. He coined and popularized the catch phrase "Turn on, tune in, drop out" and his associate Richard Alpert (now known as Ram Dass Richard Alpert , also known as Baba Ram Dass, is a contemporary spiritual teacher who wrote the 1971 bestseller Remember Be Here Now. He is well known for his personal and professional association with Timothy Leary at Harvard University in the early 1960s. He is also known for his travels to India and his relationship with the Hindu guru Neem). Leary was able to obtain synthesized psilocybin from Hofmann through Hofmann's employer, Sandoz pharmaceutical (now Novartis Novartis International AG is a multinational pharmaceutical company based in Basel, Switzerland, ranking number three in sales, which accounted 36.173 billon in 2008. It is currently the 6th largest Pharmaceutical company in terms of revenue with a profit margin of about 20%, which is the same as its industry competitors. Their profits were down). Although a number of experiments in the early 1960s demonstrated positive results using psilocybin in clinical psychiatry, the 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. LSD is non-addictive and well known for its psychological effects which can include altered thinking processes, closed and open eye visuals, synaesthesia, a sense of time distortion, hysteria of the times swept psilocybin along with it into the Schedule I category of illicit drugs in 1970. The 1970s would witness the emergence of psilocybin as the "entheogen of choice".^[6] This was due in large part to a wide dissemination of information on the topic, which even included fictional works such as those by Carlos Castaneda Carlos Castaneda was a Peruvian-born American anthropologist and author. Starting with The Teachings of Don Juan in 1968, Castaneda wrote a series of books that describe his purported training in traditional Mesoamerican shamanism. His 12 books have sold more than 8 million copies in 17 languages. The books and Castaneda, who rarely spoke in, and several books that taught the technique of growing one's own psilocybin mushrooms. One of the most popular of these books was produced under the pseudonyms O.T. Oss and O.N. Oeric by J. Bigwood, D.J. McKenna, K. Harrison McKenna and T.K. McKenna, entitled Psilocybin: Magic Mushroom Grower's Guide. Over 100,000 copies had been sold by 1981:^[7]

These authors adapted San Antonio's technique (for producing edible mushrooms by casing mycelial cultures on a rye grain substrate; San Antonio 1971) to the production of Psilocybe [Stropharia] cubensis. The new technique involved the use of ordinary kitchen implements, and for the first time the layperson was able to produce a potent entheogen in his own home, without access to sophisticated technology, equipment or chemical supplies.^[8]

Biology

Psilocybin is a naturally occurring compound found in varying concentrations in over 200 species of Basidiomycota Basidiomycota is one of two large phyla that, together with the Ascomycota, comprise the subkingdom Dikarya (often referred to as the "higher fungi") within the Kingdom Fungi. More specifically the Basidiomycota include mushrooms, puffballs, stinkhorns, bracket fungi, other polypores, jelly fungi, boletes, chanterelles, earth stars, mushrooms, distributed amongst the following genera In biology, a genus is a low-level taxonomic rank (a taxon) used in the classification of living and fossil organisms, which is an example of definition by genus and differentia. The term comes from Latin genus "descent, family, type, gender", cognate with Greek: γένος – genos, "race, stock, kin": Psilocybe Psilocybe is a genus of small mushrooms growing worldwide. This genus is best known for its species with psychedelic or hallucinogenic properties, widely known as "magic mushrooms", though the majority of species do not contain hallucinogenic compounds. Psilocin and psilocybin are the hallucinogenic compounds responsible for the (116 species), Gymnopilus Gymnopilus is a genus of gilled mushrooms within the fungal family Cortinariaceae containing over 150 rusty-orange spored mushroom species formerly divided among Pholiota and the defunct genus Flammula. The fruiting body is typically reddish brown to rusty orange to yellow, medium to large, often with a well developed veil. Most members of (14), Panaeolus Panaeolus is a genus of small, black-spored, saprotrophic agarics. The word Panaeolus is Greek for "all variegated", alluding to the spotted gills of the mushrooms produced (13), Copelandia (12), Hypholoma (6), Pluteus (6) Inocybe (6), Conocybe (4), Panaeolina (4), Gerronema (2) and Agrocybe, Galerina and Mycena (1 species each).^[9] The spores of these mushrooms do not contain psilocybin or psilocin. Mushroom caps tend to contain more of the psychoactive compounds than the stems.^[10][11][12] The total potency varies greatly between species and even between specimens of one species in the same batch.^[13] Younger, smaller mushrooms have a higher concentration of alkaloids and have a milder taste than larger, mature mushrooms. In general, the psilocybin content of mushrooms is quite variable (approximately 0.5–2% dry weight) and depends on species, growth and drying conditions, and mushroom size.^[14] Mature mycelium contains some psilocybin, while young mycelium (recently germinated from spores) does not contain appreciable amounts of alkaloids.^[15] Many species of mushrooms containing psilocybin also contain small amounts of the psilocybin analogs baeocystin and norbaeocystin.^[16][17][18] Most species of psilocybin-containing mushrooms bruise blue when handled or damaged^[19] due to the oxidization of phenolic compounds. This reaction, however, is not a definitive method of identification or determining a mushroom's potency.

Chemistry

Psilocybin (O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine) is a prodrug that is converted into the pharmacologically active compound psilocin in the body by a dephosphorylation reaction.^[20] This chemical reaction takes place under strongly acidic conditions, or under physiological conditions in the body, through the action of enzymes called phosphatases. Psilocybin is a tryptamine compound having a chemical structure derived from tryptophan and containing a ring configuration called an indole linked to an ethylamine substituent. It bears a close structural resemblance to the neurotransmitter serotonin (5-hydroxytryptamine). Psilocybin is a zwitterionic alkaloid that is soluble in water, moderately soluble in methanol and ethanol, and insoluble in most organic solvents. Exposure to light is detrimental to the stability of aqueous solutions of psilocybin, and will cause it to rapidly oxidize—an important consideration when using it as an analytical standard.^[21] A method for the large-scale synthesis of psilocybin was reported by a Japanese group in 2003.^[22]

Analytical methods

Many analytical techniques have been used to identify and evaluate the quantity of psilocybin in mushroom material. These techniques include thin layer chromatography,^[23] gas chromatography coupled to mass spectrometry (GC-MS),^[24] ion mobility spectrometry,^[25] capillary zone electrophoresis,^[26] ultraviolet spectroscopy,^[27] infrared spectroscopy^[28], high performance liquid chromatography (HPLC) with ultraviolet,^[21] fluorescence,^[29] electrochemical,^[30] or electrospray mass spectrometric detection methods.^[31] The earliest techniques used gas chromatography, however, a problem with this method is that psilocybin dephosphorylates to psilocin prior to analysis, complicating the analysis.^[32][33]

Various chromatographic methods have been developed to detect psilocin in body fluids: the rapid emergency drug identification system (REMEDi HS), a drug screening method based on HPLC;^[34] HPLC with electrochemical detection;^[35][36] GC-MS;^[34][37] and liquid chromatography coupled to mass spectrometry.^[38] Although the determination of psilocin levels in urine can be performed without sample clean-up, the analysis in plasma or serum requires a preliminary extraction, followed by derivatization of the extracts in the case of GC-MS. A specific immunoassay has also been developed to detect psilocin in whole blood samples.^[39]

Concentrations in body fluids

Psilocin concentrations in the plasma of adult volunteers averaged about 8 µg/L within 2 hours after ingestion of a single 15 mg oral psilocybin dose. A young man arrested for driving under the influence of psilocybin mushrooms had serum and urine psilocin levels of 18 and 52 µg/L, respectively.^[40]

Pharmacology

Psilocybin is rapidly dephosphorylated in the body to psilocin which then acts as a partial agonist at the 5-HT_2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT). Psilocin is a 5-HT_1A and 5-HT_2A/2C agonist.^[41] The psychotomimetic effects of psilocin can be blocked in a dose-dependent fashion by the 5-HT2A antagonists ketanserin and risperidone.^[42] Psilocybin and psilocybin analogues have been used to help model the structure of the 5-HT_2C G-protein coupled receptor.^[43]

Medicine

Psilocybin has been investigated as an experimental treatment for several disorders.

In 1961, Timothy Leary and Richard Alpert ran the Harvard Psilocybin Project, carrying out a number of experiments concerning the use of psilocybin in the treatment of personality disorders and other uses in psychological counseling.^[44]

A pilot study led by Francisco Moreno at the University of Arizona and supported by Multidisciplinary Association for Psychedelic Studies studied the effects of psilocybin on nine patients with obsessive-compulsive disorder (OCD).^[45] The study found that psilocybin could be safely given to patients with OCD, and it was associated with substantial reductions in OCD symptoms in several of the patients.^[46]

Two current studies are investigating the possibility that psilocybin can ease the psychological suffering associated with cancer. One study, led by Charles Grob, involves 12 subjects with terminal cancer being administered the hallucinogen or a placebo in two separate sessions.^[47] A second study, led by Roland Griffiths at Johns Hopkins, will administer psilocybin on two occasions to people "with a current or past diagnosis of cancer who have some anxiety or are feeling down about their cancer".^[48] In 2008, the Johns Hopkins research team published guidelines for responsibly conducting medical research trials with psilocybin and other hallucinogens in humans.^[49]

Additionally, psilocybin has shown promise to ease the pain caused by cluster headaches, often considered not only the most painful of all types of headaches,^[50] but "one of the worst pain syndromes known to mankind."^[51] In a 2006 study, 22 of 26 cluster headache patients reported successfully using psilocybin to abort the attacks, and 18 of 19 psilocybin users reported longer attack-free periods.^[52]

Toxicity

The toxicity of psilocybin is low; in rats, the oral LD₅₀ is 280 mg/kg, approximately one and a half times that of caffeine. When administered intravenously in rabbits, psilocybin's LD₅₀ is approximately 12.5 mg/kg^[53] (however rabbits are extremely intolerant to the effects of most psychoactive drugs). The lethal dose from psilocybin toxicity alone is unknown at recreational or medicinal levels, and has never been documented; a 2008 case report noted "Death from psilocybin intake alone is unknown at recreational or medicinal levels."^[54] Psilocybin makes up roughly 1% of the weight of Psilocybe cubensis mushrooms, and so nearly 1.7 kilograms of dried mushrooms, or 17 kilograms of fresh mushrooms, would be required for a 60 kg person to reach the 280 mg/kg LD50 rate of rats.

People taking lithium should exercise caution with psilocybin as the combination has led to seizures in several anecdotal reports.^[55]

Physiology

Psilocybin is absorbed through the lining of the mouth and stomach. Effects begin 10–40 minutes after ingestion of psilocybin-containing mushrooms, and last from 2–6 hours depending on dose, species, and individual metabolism. A typical recreational dosage is from 10–50 mg psilocybin. However, a very small number of people are unusually sensitive to psilocybin's effects, where a normal threshold dose of around 2 mg of psilocybin can result in effects usually associated with medium and high doses. Likewise, there are some people who require relatively high doses of psilocybin to gain low-dose effects. Individual brain chemistry and metabolism play a large role in determining a person's response to psilocybin.^[56]

Psilocybin is metabolized mostly in the liver where it becomes psilocin. It is broken down by the enzyme monoamine oxidase. MAO inhibitors have been known to sustain the effects of psilocybin for longer periods of time; people who are taking an MAOI for a medical condition may experience highly potentiated effects.

Mental and physical tolerance to psilocybin builds and dissipates quickly. Taking psilocybin more than three or four times in a week (especially on consecutive days) can result in diminished effects. Tolerance dissipates after a few days, so frequent users often keep doses spaced five to seven days apart to avoid the effect.

One study reported in 2008 concluded that, based on US data from the period 2000–2, adolescent-onset (defined here as ages 11–17) usage of hallucinogenic drugs (including psilocybin) did not increase the risk of drug dependence in adulthood; this was in contrast to adolescent usage of cannabis, cocaine, inhalants, anxiolytic medicines, and stimulants, all of which were associated with "an excess risk of developing clinical features associated with drug dependence".^[57]

Effects

The effects of psilocybin are highly variable and dependent on the current mood and overall sense of well-being by the individual. Initially the subject may begin to feel somewhat disoriented, lethargic, and euphoric or sometimes depressed. At low doses, hallucinatory effects may occur, including enhancement of colors and the animation of geometric shapes. Closed-eye hallucination may occur, where the affected individual may see multi-colored geometric shapes and vivid imaginative sequences. At higher doses, hallucinatory effects increase and experiences tend to be less social and more introspective or entheogenic. Open-eye visuals are more common, and may be very detailed although rarely confused with reality.^[58] Based on a study of 27 hospital admissions of patients (ages ranging from 12 to 24 years) who consumed Psilocybe semilanceata, a 1980 clinical report summarized the distribution of clinical symptoms of psilocybin overdose as follows: perceptual disorder (23 patients), mydriasis (pupil dilation) (20), dysphoria (an unpleasant mood) (13), hyperreflexia (twitching) (12), tachycardia (increased heart rate) (10), drowsiness (7), and euphoria (elation) (5).^[59] These clinical responses are similar to results obtained in several earlier studies where pure psilocybin was administered to human volunteers.^{[60][61][62][63][64]}

Perceptual distortions

Distortions in the experience of time in psilocybin-induced states have been subjectively reported,^[65] and objectively measured.^[66] In these studies, psilocybin significantly decreased subjects’ reproduction of time intervals longer than 2.5 seconds, impaired their ability to synchronize to inter-beat intervals longer than 2 seconds, and reduced their preferred tapping rate. Recent studies into the effects of psilocybin on time interval reproduction may shed light on qualitative alterations of time experience in experimentally-induced altered states of consciousness, mystical states, or in psychopathology.^[67]

Users having a pleasant experience can feel ecstatic, a sense of connection to others, nature, the universe, and other feelings/emotions are often intensified. The vernacular term "bad trip" describes a reaction accompanied by fear of varying degrees, other substantial unpleasant feelings or sometimes dangerous behavior. Bad trip is generally used to describe a reaction which is primarily characterized by fear or other unpleasant emotions, not just transitory experience of such feelings. A variety of reasons may contribute to a psilocybin user experiencing a bad trip, including "tripping" during an emotional or physical low, or in a non-supportive/inadequate/etc. environment (see: set and setting); ingesting psilocybin in combination with other drugs or with alcohol can also induce a bad trip.^[68] Latent psychological issues may be triggered by the strong emotional components of the experience.^[69]

Mystical experiences

Some of these individuals report that they have experienced a 'spiritual' episode. For example, in the Marsh Chapel Experiment, which was run by a graduate student at Harvard Divinity School under the supervision of Timothy Leary, almost all of the graduate degree divinity student volunteers who received psilocybin reported profound religious experiences.^{[citation needed]}

In 2006, a group of researchers from Johns Hopkins School of Medicine led by Roland R Griffiths conducted an experiment assessing the degree of mystical experience and attitudinal effects of the psilocybin experience; this report was published in the journal Psychopharmacology. Thirty-six volunteers without prior experience with hallucinogens were given psilocybin and methylphenidate (Ritalin) in separate sessions, the methylphenidate sessions serving as a control and psychoactive placebo; the tests were double-blind. The degree of mystical experience was measured using a questionnaire on mystical experience developed by Ralph W Hood; 61% of subjects reported a "complete mystical experience" after their psilocybin session, while only 13% reported such an outcome after their experience with methylphenidate. Two months after taking psilocybin, 79% of the participants reported moderately to greatly increased life satisfaction and sense of well-being. About 36% of participants also had a strong to extreme “experience of fear” or dysphoria (i.e., a “bad trip”) at some point during the psilocybin session (which was not reported by any subject during the methylphenidate session), with about one-third of these (13% of the total) reporting that this dysphoria dominated the entire session. These negative effects were reported to be easily managed by the researchers and did not have a lasting negative effect on the subject’s sense of well-being.^[70] Further measures at 14 months after the psilocybin experience confirmed that participants continued to attribute deep personal meaning to the experience.

Further studies by this group have investigated the relationship of psilocybin dose to likelihood of mystical experience in healthy volunteers. A double-blind study showed that psychedelic mushrooms could provide people an experience with substantial personal meaning and spiritual significance. In the study, one third of the subjects reported that ingestion of psychedelic mushrooms was the single most spiritually significant event of their lives, and over two-thirds reported it among their five most meaningful and spiritually significant events. On the other hand, one-third of the subjects reported extreme anxiety.^[71][72] Related research being conducted by this group is investigating whether mystical experiences in volunteers given psilocybin can help with anxiety and poor mood due to cancer.^[73]

There has been 1 case report of psilocybin and cannabis possibly causing Hallucinogen Persisting Perception Disorder;^[74] the recent clinical study showed no such side effects.^[71]

Cardiovascular abnormalities

Some reports have described cardiac complications that have occurred after the consumption of psychoactive fungi. A 1998 report described an 18-year old male suffering from arrhythmias and heart attack after eating P. semilanceata.^[14] A 2007 report described a male who developed symptoms similar to Takotsubo cardiomyopathy, characterized by a sudden temporary weakening of the myocardium (cardiac muscle).^[54]

Psychiatric Adverse Effects

Panic reactions can occur after consumption of psilocybin-containing mushrooms, especially if the ingestion is accidental or otherwise unexpected. For example, reactions such as violence, aggression, homicidal and suicidal attempts,^[75], prolonged schizophrenia-like psychosis^[42][76] and convulsions^[77] have been reported in the literature. The similarity of psilocybin-induced symptoms to those of schizophrenia has led to the drug being used in both behavioral and neuroimaging studies of this psychotic disorder. In both cases, psychotic symptoms are thought to arise from a "deficient gating of sensory and cognitive information" in the brain that ultimately lead to "cognitive fragmentation and psychosis".^[78]

Social and legal aspects

In the United States, psilocybin (and psilocin) were first subjected to federal regulation by a law that is commonly referred to as "the Drug Abuse Control Amendments of 1965". This law, a product of a bill sponsored by Senator Thomas J. Dodd, was passed in July 1965 and took effect on February 1, 1966. The law was an amendment to the federal Food, Drug and Cosmetic Act and was intended to regulate the unlicensed "possession, manufacture, or sale of depressant, stimulant and hallucinogenic drugs”.^[79] The statutes themselves, however, did not list the "hallucinogenic drugs" that were being regulated.^[79] Instead the term "hallucinogenic drugs" was meant to refer to those substances that supposedly have a "hallucinogenic effect on the central nervous system".^[79]

Despite the seemingly strict provisions of the law, many people were exempt from prosecution. Specifically the statutes "permit[ted]… people to possess such drugs so long as they were for the personal use of the possessor, a member of his household, or for administration to an animal".^[79] The federal law that specifically banned psilocybin and psilocin was enacted on October 24, 1968. The latter substances were said to have "a high potential for abuse", "no currently accepted medical use" and "a lack of accepted safety".^[80] And, finally, on October 27, 1970, both psilocybin and psilocin became classified as Schedule I and were simultaneously labeled "hallucinogens" under a section of the “Comprehensive Drug Abuse Prevention and Control Act” known as the "Controlled Substances Act".^[81] Schedule I drugs are illicit drugs that are claimed to have no known therapeutic benefit. Parties to the treaty are required to restrict use of the drug to medical and scientific research under strictly controlled conditions. Most national drug laws have been amended to reflect this convention (for example, the US Psychotropic Substances Act, the UK Misuse of Drugs Act 1971, and the Canadian Controlled Drugs and Substances Act), with possession and use of psilocybin and psilocin being prohibited under almost all circumstances, and often carrying severe legal penalties.

Possession and use of psilocybin mushrooms, including the bluing species of Psilocybe, is therefore prohibited by extension. However, in many national, state, and provincial drug laws, there is a great deal of ambiguity about the legal status of psilocybin mushrooms and the spores of these mushrooms, as well as a strong element of selective enforcement in some places. Additionally, there has been a general shift in attitudes regarding research with psilocybin and other hallucingenic agents; after a long moratorium on the use of these drugs, many countries are revising their positions and have started to approve studies to test the physiological and therapeutic effects of hallucinogens.^[82] For more details on the legal status of psilocybin mushrooms and Psilocybe spores, see: Legal status of psilocybin mushrooms.

See also

• Ayahuasca
• List of Entheogens
• Psychedelic drug
• Psychedelic plants
• Psychoactive drug
• Psychotropic
• Soma
• O-Acetylpsilocin

External links

• Hopkins/CSP research findings and media reports, 2006 and 2008
• Report by the Dutch Government Stating Psilocybin's Harmlessness
• MAPS Psilocybin research
• Clusterbusters Psilocybin as cluster headache treatment
• Hallucinogenic mushrooms EMCDDA, Lisbon, June 2006
• Hallucinogenic mushrooms: the challenge of responding to naturally occurring substances in an electronic age EMCDDA, Drugs in Focus 15

Notes

1. ^ "List of psychotropic substances under international control" (PDF). Vienna, Austria: International Narcotics Control Board. August 2003. http://www.incb.org/pdf/e/list/green.pdf. Retrieved 2009-11-11.
2. ^ Heim R. (1957). "Notes preliminaires sur lee Agaric hallucinogenes du Mexique [Preliminary notes on the hallucination-producing Agarics of Mexico]" (in French). Revue de Mycologie 22 (1): 58–79.
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5. ^ ^{a b} Stafford, p. 237.
6. ^ Ott, p. 276.
7. ^ Oeric OT, Os ON. (1991). Psilocybin: Magic Mushroom Grower's Guide. 2nd ed. Quick American Archives. ISBN 978-0932551061.
8. ^ Ott, p. 290.
9. ^ Guzmán G, Allen JW, Gartz J. (1998). "A worldwide geographical distribution of the neurotropic fungi, an analysis and discussion". Ann. Mus. Civ. Rovereto Sez. 14: 189–280. http://www.museocivico.rovereto.tn.it/UploadDocs/104_art09-Guzman%20&%20C.pdf.
10. ^ Wurst MM, Semerdzieva M, Vokoun J. (1984). "Analysis of psychotropic compounds in fungi of the genus Psilocybe by reversed-phase high performance liquid chromatography". Journal of chromatography 286: 229–35. doi:10.1016/S0021-9673(01)99190-3.
11. ^ Kysilka R, Wurst M. (1989). "High-performance liquid chromatographic determination of some psychotropic indole derivatives". Journal of Chromatography 464 (2): 434–37. PMID 2722990.
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25. ^ Keller T, Schneider A, Regenscheit P, Dirnhofer R, Rucker T, Jaspers J, Kisser W. (1999). "Analysis of psilocybin and psilocin in Psilocybe subcubensis GUZMAN by ion mobility spectrometry and gas chromatography-mass spectrometry". Forensis Science International 99: 93–105. doi:10.1016/S0379-0738(98)00168-6.
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31. ^ Rodriguez-Cruz S. (2005). "Analysis and characterization of psilocybin and psilocin using liquid chromatography-electrospray ionization mass spectrometry (LC-ESI-MS) with collision-induced-dissociation (CID) and source-induced dissociation (SID)". Microgram Journal 3: 175–82.
32. ^ Repke D, Leslie D, Mandell D, Kish N. (1977). "GLC-mass spectral analysis of psilocin and psilocybin". Journal of Pharmaceutical Sciences 66: 743–44. doi:10.1002/jps.2600660539.
33. ^ Christiansen AL, Rasmussen KE, Tonnesen F. (1981). "Determination of psilocybin in Psilocybe semilanceata using high performance liquid chromatography on a silica column". Journal of Chromatography 214: 163–67.
34. ^ ^{a b} Sticht G, Käferstein H. (2000). "Detection of psilocin in body fluids". Forensic Science International 113 (1-3): 403–7. doi:10.1016/S0379-0738(00)00213-9. PMID 10978655. http://linkinghub.elsevier.com/retrieve/pii/S0379073800002139. Retrieved 2009-11-15.
35. ^ Kysilka R. (1990). "Determination of psilocin in rat urine by high-performance liquid chromatography with electrochemical detection". Journal of Chromatography 534: 287–90. doi:10.1016/S0378-4347(00)82176-3. PMID 2094720.
36. ^ Lindenblatt H, Krämer E, Holzmann-Erens P, Gouzoulis-Mayfrank E, Kovar KA. (1998). "Quantitation of psilocin in human plasma by high-performance liquid chromatography and electrochemical detection: comparison of liquid-liquid extraction with automated on-line solid-phase extraction". Journal of Chromatography. B, Biomedical Sciences and Applications 709 (2): 255–63. doi:10.1016/S0378-4347(98)00067-X. PMID 9657222.
37. ^ Grieshaber AF, Moore KA, Levine B. (2001). "The detection of psilocin in human urine". Journal of Forensic Sciences 46 (3): 627–30. PMID 11373000.
38. ^ Kamata T, Nishikawa M, Katagi M, Tsuchihashi H. (2003). "Optimized glucuronide hydrolysis for the detection of psilocin in human urine samples". The Journal of Chromatography B - Analytical Technologies in the Biomedical and Life Sciences 792: 421–27.
39. ^ Albers C, Köhler H, Lehr M, Brinkmann B, Beike J. (2004). "Development of a psilocin immunoassay for serum and blood samples". International Journal of Legal Medicine 118 (6): 326–31. doi:10.1007/s00414-004-0469-9. PMID 15526212.
40. ^ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 1346-1348.
41. ^ Passie T, Seifert J, Schneider U, Emrich HM. (2002). "The pharmacology of psilocybin.". Addiction Biology 7 (4): 357–64. doi:10.1080/1355621021000005937. PMID 14578010.
42. ^ ^{a b} Vollenweider FX, Vollenweider-Scherpenhuyzen MF, Babler A, Vogel H, Hell D. (1998). "Psilocybin induces schizophrenia-like psychosis in humans via a serotonin-2 agonist action". NeuroReport 9 (17): 3897–902. doi:10.1097/00001756-199812010-00024. PMID 9875725.
43. ^ Bray JK, Goddard III WA. (2008). "The structure of human serotonin 2c G-protein coupled receptor bound to agonists and antagonists". Journal of Molecular Graphics and Modelling 27 (1): 66–81. doi:10.1016/j.jmgm.2008.02.006. PMID 18499489.
44. ^ Wark C, Galliher JF. (Sept 2009). "Timothy Leary, Richard Alpert (Ram Dass) and the changing definition of psilocybin". The International Journal on Drug Policy 21 (3): Epub ahead of print. doi:10.1016/j.drugpo.2009.08.004. PMID 19744846.
45. ^ Moreno FA, Delgado P, Gelenberg AJ. "Effects of Psilocybin in Obsessive-Compulsive Disorder". Multidisciplinary Association for Psychedelic Studies (MAPS). http://www.maps.org/research/psilo/azproto.html. Retrieved 2009-09-29.
46. ^ Moreno FA, Wiegand CB, Taitano EK, Delgado PL. (2006). "Safety, tolerability, and efficacy of psilocybin in 9 patients with obsessive-compulsive disorder". Journal of Clinical Psychiatry 67 (11): 1735–40. doi:10.4088/JCP.v67n1110. PMID 17196053.
47. ^ "Psychopharmacology of Psilocybin in Cancer Patients - ClinicalTrials.gov". U.S. National Institutes of Health. 2009. http://www.clinicaltrials.gov/ct2/show/NCT00465595. Retrieved 2009-09-29.
48. ^ [http://www.bpru.org/cancer/ "Seeking Volunteers with a Cancer Diagnosis to participate in a scientific study of self-exploration and personal meaning"]. Recruitment notice for psilocybin clinical trial. John Hopkins School of Medicine. http://www.bpru.org/cancer/. Retrieved 2009-09-29.
49. ^ Johnson MW, Richards WA, Griffiths RR. (2008). "Human hallucinogen research: guidelines for safety" (PDF). Journal of Psychopharmacology 22 (6): 603–20. doi:10.1177/0269881108093587. PMID 18593734. http://csp.org/psilocybin/HopkinsHallucinogenSafety2008.pdf.
50. ^ Dodick DW, Rozen TD, Gaodsby PJ, Silberstein SD. (2000). "Cluster headache". Cephalgia 20: 787–803. doi:10.1046/j.1468-2982.2000.00118.x.
51. ^ Husid MS. (2007). "Cluster headache: A case-based review of diagnostic and treatment approaches". Current Pain and Headache Reports 10 (2): 117–25. doi:10.1007/s11916-006-0022-2. PMID 16539864.
52. ^ Sewell RA, Halpern JH, Pope HG Jr. (2006). "Response of cluster headache to psilocybin and LSD". Neurology 66 (12): 1920–22. doi:10.1212/01.wnl.0000219761.05466.43. PMID 16801660.
53. ^ NLM (click on "toxicity" on the left side)
54. ^ ^{a b} Nef HM, Möllmann H, Hilpert P, Krause N, Troidl C, Weber M, Rolf A, Dill T, Hamm C, Elsässer A. (2008). "Apical regional wall motion abnormalities reminiscent to Tako-Tsubo cardiomyopathy following consumption of psychoactive fungi". International Journal of Cardiology 134 (1): e39–e41. doi:10.1016/j.ijcard.2007.12.064. PMID 18378018.
55. ^ Jerome I. "Warning/Caution". Entheogenic Treatments of Cluster Headaches. Clusterbusters Inc. http://www.clusterbusters.com/warning.htm. Retrieved 2009-10-15.
56. ^ Stamets P. (1996). Psilocybin Mushrooms of the World: An Identification Guide. Berkeley, California: Ten Speed Press. pp. 36–41. ISBN 0-89815-839-7. http://books.google.com/?id=10HiGVo94FUC&lpg=PP1&dq=stamets%20psilocybin&pg=PA36#v=onepage&q=. Retrieved 2009-11-11.
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62. ^ Hollister LE, Prusmack JJ, Paulsen A, Rosenquist N. (1960). "Comparison of three psychotropic drugs (psilocybin, JB-329, and IT-290) in volunteer subjects". Journal of Nervous and Mental Disease 131: 428–34. doi:10.1097/00005053-196011000-00007. PMID 13715375.
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66. ^ Wittmann M, Carter O, Hasler F, Cahn BR, Grimberg U, Spring P, Hell D, Flohr H, Vollenweider FX. (2007). "Effects of psilocybin on time perception and temporal control of behaviour in humans". Journal of Psychopharmacology (Oxford) 21 (1): 50–64. doi:10.1177/0269881106065859. PMID 16714323.
67. ^ Wackermann J, Wittmann M, Hasler F, Vollenweider FX. (2008). "Effects of varied doses of psilocybin on time interval reproduction in human subjects". Neuroscience Letters 435 (1): 51–55. doi:10.1016/j.neulet.2008.02.006. PMID 18325673. http://linkinghub.elsevier.com/retrieve/pii/S0304-3940(08)00179-1.
68. ^ Attema-de Jonge ME, Portier CB, Franssen EJF. (2007). "Automutilation after consumption of hallucinogenic mushrooms" (in Dutch). Nederlands Tijdschrift voor Geneeskunde 151 (52): 2869–872.
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71. ^ ^{a b} Griffiths R, Richards W, Johnson M, McCann U, Jesse R. (2008). "Mystical-type experiences occasioned by psilocybin mediate the attribution of personal meaning and spiritual significance 14 months later". Journal of Psychopharmacology 22 (6): 621–32. doi:10.1177/0269881108094300. PMID 18593735. http://www.csp.org/psilocybin/Hopkins-CSP-Psilocybin2008.pdf. Retrieved 2009-09-30.
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73. ^ Recruitment page for Hopkins cancer study
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80. ^ Boire, p. 26.
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References

• Boire RG. (2002). Sacred Mushrooms and the Law. Ronin Publishing. ISBN 978-1579510619.
• Ott J. (1993). Pharmacotheon Entheogenic Drugs Their Plant Sources and Histories. Natural Products Company. ISBN 978-0961423438.

2006 Johns Hopkins experiment

• Schuster C; Kleber H; Snyder S; Nichols D; de Wit H. (2006). Commentaries and Editorial on Article by Griffiths et al. Psychopharmacology (online edition): July 11, 2006. (PDF)
  • "Hopkins Scientists Show Hallucinogen in Mushrooms Creates Universal 'Mystical' Experience", Johns Hopkins Medicine news release, July 11, 2006.
  • "Q&A is with Roland Griffiths, the study’s lead researcher", Johns Hopkins Medicine news release, July 11, 2006.
  • "Psilocybin Viewed as Therapy or Research Tool" by Michael Smith, Medpagetoday.com, July 12, 2006.
  • "Magic mushrooms really cause 'spiritual' experiences" by Roxanne Khamsi, NewScientist.com news service, July 11, 2006.
  • "Drug's Mystical Properties Confirmed" by David Brown, Washington Post, July 11, 2006.
  • "Mushroom Drug Produces Mystical Experience", Associated Press, July 11, 2006.
  • "Counterculture Drug Provides Spiritual Boost" by Denise Gellene, Los Angeles Times, July 11, 2006.
  • "Tripping Out: Scientists Study Mystical Effects of Mushrooms" by Joy Victory, Bharathi Radhakrishnan, and Andrea Carter, ABC News (online), July 11, 2006. ABC News video report of the study.

2008 Follow-up to Johns Hopkins experiment

• "A Very Memorable Trip", by Greg Miller, ScienceNOW Daily News, July 1, 2008
• "Spiritual Effects of Hallucinogens Persist, Johns Hopkins Researchers Report", Johns Hopkins Medicine news release, July 1, 2008.
• "Psilocybin Study Hints at Rebirth of Hallucinogen Research", by Brandon Keim, "Wired," July 1, 2008

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