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Psilocybin

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Psilocybin
General
Systematic name 4-Phosphoryloxy-N,N-
dimethyl-tryptamine
Molecular formula C12H17N2O4P
SMILES C[N+](C)([H])CCC1=CNC2=

C1C(OP([O-])(O)=O)=CC=C2
Molar mass 284.25 g/mol
CAS number [520-52-5]
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and references

Psilocybin (4-phosphoryloxy-N, N-dimethyltryptamine) 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 generally resemble a shorter LSD trip.


Contents

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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. He first noted that they had adverse effects on the human cerebal system if they were to be used long term, due to their interaction with the body's sodium-potassium ion concentrations. 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

In the fruitbody, psilocybin and psilocin tend to accumulate in the caps more than in the stems. 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. Most psilocybin mushrooms bruise blue when handled.

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Pharmacology

Psilocybin acts as an agonist for the neurotransmitter serotonin (5-hydroxytryptamine, or 5-HT). It binds to 5-HT receptors in the brain, and mimics the effects of serotonin.

While psilocybin may deliver a stronger impulse to the postsynaptic receptor than serotonin does, mostly the effect is a product of the fact that there is now both serotonin and a serotonin agonist in the synapse (this is equivalent to having twice as much serotonin in the synapse). Compare this effect to that of MDMA, which increases the amount of actual serotonin in the synapse at any given moment.

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Medicine

Psilocybin has been studied as a treatment for several disorders.

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. 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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Law

Spores of Psilocybe mushrooms can be legally purchased from several mail order sources; however, cultivation and consumption of the mushrooms are illegal in many jurisdictions.

Internationally, psilocybin is a Schedule I drug under the Convention on Psychotropic Substances. Parties to the treaty are required to restrict use of the drug to medical and scientific purposes.

  • In Japan, it was legal to possess and sell psilocybin mushrooms until June 2002. Possession was made illegal in 2002, possibly in preparation for the World Cup and in response to a widely reported case of mushroom poisoning.
  • In Denmark, sale, possession and consumption of psilocybine/psilocine mushrooms were legal up until 2002, where the governmental purge of what they called "designer drugs" outlawed them along with a number of other hallucinogens and empathogens.
  • In the United States, psilocybin and psilocybe mushrooms are regulated under DEA Schedule 1, making them illegal to possess under federal law. (Researchers and their subjects are granted exemptions by the DEA.) Under state law, it is illegal to possess psilocybin and psilocybin mushrooms in all states except New Mexico. New Mexico appeals court ruled on June 16, 2005, that growing psilocybin mushrooms for personal consumption could not be considered "manufacturing a controlled substance" under state law. [1] Psilocybin mushroom spores are legal to sell and possess in every state except California, Idaho, and Georgia.[2]
  • In the United Kingdom, possession of unprocessed mushrooms is illegal. As a result of new laws unveiled on January 18, 2005, psilocybin-containing mushrooms are now classified as a Class A substance under UK law.
  • In the Netherlands, possession of unprocessed mushrooms is legal. However, when prepared, the product (dried mushrooms, tea or powder) may be construed as illegal. Because of this there are a lot of drug shops selling fresh mushrooms in the Netherlands, especially in Amsterdam.
  • In Norway, possession of the indigenous Liberty cap (Psilocybe semilanceata) has been illegal since 1977. In 2004, all mushrooms containing psilocybin and psilocin, and specifically Psilocybe cubensis, were outlawed.
  • In the British Virgin Islands, where the mushrooms grow naturally, it is legal to possess and consume psilocybin mushrooms, however their sale is illegal.
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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.
  • 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



Psychedelic tryptamines edit

4-Acetoxy-DET | 4-Acetoxy-DIPT | α-ET | α-MT | Baeocystin | Bufotenin | DET | DIPT | DMT | DPT | EIPT | Ethocin | Iprocin | MET | MIPT |5-MeO-α-ET | 5-MeO-α-MT | 5-MeO-DALT | 5-MeO-DET | 5-MeO-DIPT | 5-MeO-DMT | 5-MeO-DPT | 5-MeO-MIPT | Miprocin | Norbaeocystin | Psilocin | Psilocybin |
Tryptamines edit
4-Acetoxy-DET | 4-Acetoxy-DIPT | 5-MeO-α-ET | 5-MeO-α-MT | 5-MeO-DALT | 5-MeO-DET | 5-MeO-DIPT | 5-MeO-DMT | 5-MeO-DPT | 5-MeO-MIPT | α-ET | α-MT | Baeocystin | Bufotenin | DET | DIPT | DMT | DPT | EIPT | Ethocin | Ibogaine | Iprocin | MET | MIPT | Miprocin | Melatonin | NMT | Norbaeocystin | Psilocin | Psilocybin | Rizatriptan | Serotonin | Sumatriptan | Tryptamine | Tryptophan
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