Psilocybin

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Psilocybin, sometimes misspelled psilocybine, is a psychedelic alkaloid of the tryptamine family. It is present in many species of fungi, notoriously those of the genus Psilocybe, such as Psilocybe cubensis and Psilocybe semilanceata (Liberty Caps), but also reportedly isolated from a dozen or so other genera. Psilocybin-containing mushrooms are commonly called magic mushrooms or simply "shrooms." Effects of psilocybin are comparable to those of a shorter LSD trip, although intensity and duration vary depending on dosage, individual physiology, and set and setting.

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Chemistry

Psilocybin is a prodrug that is converted into the pharmacologically active compound psilocin in the body by dephosphorylation. This chemical reaction takes place under strongly acidic conditions or enzymatically by phosphatases in the body. Psilocybin is a zwitterionic alkaloid that is soluble in water, moderately soluble in methanol and ethanol, and insoluble in most organic solvents. Psilocybin can be synthesized in the laboratory from psilocin by a two-step procedure, but this is rarely done since psilocin is the actual pharmacologically active compound.

Albert Hofmann was first to recognize the importance and chemical structure of the pure compounds psilocybin and psilocin, largely because he ingested fractions isolated from the mushroom and subsequently named the active fractions. Hofmann's colleagues at the University of Delaware, who were funded by the Central Intelligence Agency, were also trying to figure out why the mushrooms had a psychotropic effect, but could not figure out the active principles, despite interloping on at least one of Hofmann's visits to Mexico. Hofmann also had Roger Heim and R. Gordon Wasson working with him.

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Biology

The spores are completely free of both psilocybin and psilocin. The total potency varies greatly between species and even between specimens of one species in the same batch. Younger, smaller mushrooms are relatively higher in alkaloids and have a milder taste than larger, mature mushrooms. Mature mycelium contains some amount of psilocybin, which can be extracted with an acidic solution, usually of citric acid or ascorbic acid (Vitamin C). Young mycelium (recently germinated from spores) does not contain appreciable amounts of alkaloids. Most species of hallucinogenic mushrooms also contain small amounts of the psilocybin analogs baeocystin and norbaeocystin. Many types of psilocybin mushrooms bruise blue when handled or damaged - this is due to the oxidization of active compounds and is most notable in mushrooms with a high psilocin content. Several other non-psychoactive (and in some cases toxic) mushrooms also bruise blue.

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Pharmacology

Psilocybin is rapidly dephosphorylated in the body to psilocin which then acts as an agonist at the 5-HT2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT).

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Medicine

Psilocybin has been studied as a treatment for several disorders. In the early 1960s, 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.

More recently, in the US, an FDA-approved study supported by Multidisciplinary Association for Psychedelic Studies (MAPS) began in 2001 to study the effects of psilocybin on patients with obsessive-compulsive disorder. MAPS has also proposed studying psilocybin's potential application for the treatment of cluster headaches based on anecdotal evidence presented to them by a cluster headache sufferer.

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Toxicity

Psilocybin has a fairly high LD50, signifying very low toxicity — less than half that of caffeine when administered intravenously in rats. Death from psilocybin intake alone is unknown at most recreational or medicinal levels.

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Effects

Psilocybin is absorbed through the lining of the mouth and stomach. Effects begin 20-45 minutes after ingestion of psilocybin-containing mushrooms, and last from 2-6 hours depending on dose, species, and individual metabolism. If mushrooms are chewed and held in the mouth, or taken as mushroom tea, effects begin slightly sooner and are usually noticeable within 15 minutes. This is typically done in combination with orange juice or another drink to dilute the unpleasant taste of Psilocybe mushrooms. Nausea is not uncommon when ingesting Psilocybe mushrooms, but typically subsides within an hour of appearing or less. Sometimes vomiting will occur. Some users have also been known to induce vomiting after psilocybin begins to take effect as the drug is already in the system and this will relieve the nausea which can be mild to very unpleasant.

At low doses, hallucinatory effects occur, including walls that seem to breathe, a vivid enhancement of colors and the animation of organic shapes. At higher doses, experiences tend to be less social and more entheogenic, often catalyzing intense spiritual experiences. 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. (A brief video about the Marsh Chapel experiment can be viewed here.) In fact, some people who have eaten the mushrooms without knowing of their hallucinatory effects typically believe they have had an unprovoked religious experience.

The effects are often pleasant, even ecstatic, including a deep sense of connection to others, and a general feeling of connection to nature and the universe. However, as with all psychedelic chemicals, not all experiences are positive. This is especially true when they are taken with other drugs, during times of mental instability, or by people with psychoemotional problems. In such situations, "bad trips" are much more likely to occur. Anxiety, frightening hallucinations, confronting (symbolically or literally) past or deep-seated internal conflicts, and feelings of permanent disconnection from reality and the Self can be quite intense and cause panic if the user is unprepared. Thus, the possibility of such experiences may be mitigated by being cognizant of one's set and setting.

A non-physiologically induced dreaminess is present up to 24 hours following administration, presumably representing the need to reflect and integrate the content of a profound hallucinogenic experience well into the next day.

A very small number of people are unusually sensitive to psilocybin's effects, where doses as little as 0.25 grams of dried Psilocybe cubensis mushrooms (normally a threshold dose of around 2 mg 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 plays a large role in determining a person's response to psilocybin.

Psilocybin is probably metabolized mostly in the liver where it becomes Psilocin, but is also 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 (or are seeking to potentiate the mushroom experience) should be careful.

Mental and physical tolerance to psilocybin builds and dissipates quickly. Taking psilocybin more than three or four times in a week (especially two days in a row) 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.

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Social and legal aspects

Psilocybin and psilocin are listed as Schedule I drugs under the United Nations 1971 Convention on Psychotropic Substances.[1] 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 psilocybian 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 psilocybian mushrooms and the spores of these mushrooms, as well as a strong element of selective enforcement in some places. For more details on the legal status of psilocybian mushrooms and Psilocybe spores, see: Psilocybe: Social_and_legal_aspects.

Because of the ease of cultivating psilocybian mushrooms or gathering wild species, purified psilocybin is practically nonexistent on the illegal drug market.

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Media

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References in popular culture

  • The American stand-up comedian, satirist and social critic Bill Hicks has used his psilocybin experiences as themes in his act.
  • Terence McKenna has written extensively on the psychopharmacology of psilocybin, as well as authoring a popular and authoritative growing guide, written under the pseudonym Oss and Oeric.
  • Comedian Lewis Black talks about a psilocybin experience in his 2005 album Luther Burbank Performing Arts Center Blues.
  • The film Super Troopers features a scene in which a young male character ingests a large quantity of mushrooms and cannabis, immediately before being questioned by police officers.
  • The American rock band Finch featured a song called Dreams of Psilocybin on their 2005 album Say Hello to Sunshine.
  • The American rock band Incubus features a song called Psychopsilocybin on their 1995 album Fungus Amongus. Both the song title and the album title are references to psilocybin, and a picture of one species of hallucinogenic mushroom is on the album cover. The mushroom that appears is a 'fly agaric' mushroom (Amanita muscaria) which does not contain psilocybin.
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External links


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