Recent Articles

Psilocybin

Psilocybin (4-phosphoryloxy-N,N-dimethyltryptamine) is a psychedelic alkaloid of the tryptamine family. It is present in many species of fungi, notably Psilocybe cubensis and Psilocybe semilanceata (Liberty Caps). Psilocybin-containing mushrooms are commonly called magic mushrooms or simply "shrooms". Effects of psilocybin generally resemble a shorter LSD trip. Following standard nomenclature rules, the name is Psilocybine, but this is almost never used in practice.

Chemical data

Chemical Structure of Psilocybin

Psilocin can be derived from psilocybin by removal of the phosphate group. Once ingested, psilocybin is rapidly dephosphorylated (thus converting it into psilocin) by the enzyme alkaline phosphatase. Psilocybin is soluble in about 20 parts water, while psilocin is not particularly soluble in water. Psilocin is very fat-soluble, which explains its affinity for the brain.

• IUPAC names: 4-Hydroxy-N,N-dimethyltryptamine, 3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
• Chemical substance classes: Tryptamines, Indolamines (Indolalkaloides)
• Formula: C₁₂H₁₇N₂O

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.

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.

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, in huge doses, 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 can be mitigated by being cognizant of one's "set and setting."

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, but is also broken down by the enzyme monoamine oxidase (MAO). MAOIs can roughly double the potency of psilocybin — people who are taking an MAOI for a medical condition (or are seeking to potentiate the mushroom experience) must 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 and a less enjoyable experience. Tolerance dissipates after a few days, so frequent users often keep doses spaced 5-7 days apart to avoid the effect.

Chemistry

Psilocybin is distributed fairly evenly throughout the entire fruiting body, with the exception of the spores which are completely free of psilocybin and psilocin. The total potency can vary greatly between species and even between batches of the same species. There should be no drastic difference in potency between stems and caps from the same batch. Younger, smaller mushrooms are relatively higher in alkaloids and have a milder taste than larger, mature mushrooms. Mature mycelium contains some psilocybin, though one generally does not eat or otherwise process it. Young mycelium (recently germinated from spores) does not contain appreciable amounts of psilocybin.

Psilocin, the active metabolite of psilocybin, acts by interaction with neurotransmitter receptors on nerve cells in the brain where it mimicks the action of serotonin (5-HT). Specifically, psilocin is a post-synaptic 5-HT_2A receptor agonist. This is the same mechanism of action as for the other hallucinogens like LSD, mescaline, or 2C-B. LSD and psilocybin show cross-tolerance — after taking one of these substances, the brain quickly develops a tolerance to it, and taking another dose of either soon afterward will require more than usual to achieve the desired effects.

Psilocybin and medicine

Psilocybin has been studied as a treatment for several disorders.

In the US, an FDA-approved study supported by MAPS (Multidisciplinary Association for Psychedelic Studies) 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.

Psilocybin and the 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.

• 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 Florida. In Florida, a court decision ruled that wild psilocybin mushrooms themselves are not illegal to possess as they are not mentioned by law. Since Florida has not decided at this time to change its laws on this matter, they remain presumptively legal.

• In the United Kingdom, possession of unprocessed mushrooms is not illegal. However, when prepared, the product (dried mushrooms, tea or powder) may be construed as illegal. This allows shops in the UK to sell fresh mushrooms on the high street and over the internet.

• In the Netherlands, possession of unprocessed mushrooms is not illegal. 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. The recent ban has been reported to EFTA as a violation of the EEA agreement, since unprocessed mushrooms are legal in the UK and in the Netherlands, and the EEA agreement prohibits banning merchandise which are legally sold in any other EEA country. EFTA is currently (September, 2004) investigating the complaint.