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{{drugbox || IUPAC_name = 4-Phosphoryloxy-N,N-dimethyl-tryptamine| image = Psilocybin.png| image2=Psilocybin3d.png| width=200| CAS_number = 520-52-5| ATC_prefix =| ATC_suffix =| PubChem =| C=12 | H=17 | N=2 | O=4 | P=1| molecular_weight = 284.25 g/mol| smiles = C(C)()CCC1=CNC2=C1C(OP()(O)=O)=CC=C2| bioavailability =| protein_bound =| metabolism =| elimination_half-life =| excretion =| pregnancy_AU =| pregnancy_US =| pregnancy_category =| legal_AU = S9| legal_CA = Schedule III| legal_UK = Class A| legal_US = Schedule I| legal_status =| routes_of_administration =-->
Psilocybin (also known as
psilocybine) is a
psychedelic drug alkaloid of the
tryptamine family, found in psilocybin mushrooms. It is considered mostly to be an
entheogen and a
tool in use to supplement various types of practices for
transcendence including in
meditation,
psychonautics, and illicit psychedelic psychotherapy whether self administered or not. It can also be used as a recreational drug. Though Psilocybin rarely attracts much attention from mainstream media, when it does, the focus tends to be on the recreational use to the exclusion of any other purpose. It is present in hundreds of species of fungi, including those of the genus
Psilocybe, such as
Psilocybe cubensis and
liberty cap (mushroom), but also reportedly isolated from a dozen or so other genera.
Psilocybin mushrooms are commonly called "magic mushrooms" or more simply "shrooms". The intensity and duration of entheogenic and recreational use of psilocybin mushrooms vary depending on species of mushrooms, dosage, individual physiology, and set and setting.
Chemistry
Psilocybin is a
prodrug that is converted into the Pharmacology active compound psilocin in the body by dephosphorylation.Horita, A. and L.J. Weber. "Dephosphorylation of psilocybin to psilocin by alkaline phosphatase." Proceedings of the Society for Experimental Biology 106(1): 32-34 (1961) This
chemical reaction takes place under strongly
acidic conditions or
Enzyme 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.
Albert Hofmann was the first to recognize the importance and chemical structure of the pure compounds psilocybin and psilocin. Hofmann was aided in this process by his willingness to ingest Liquid-liquid extraction isolated from
Psilocybe. Hofmann's colleagues at the
University of Delaware were also trying to isolate the active principle, but were unsuccessful.http://www.stainblue.com/ah.html
Biology
Psilocybin is a naturally-occurring compound found in high concentrations in some species of
Psilocybe and
Panaeolus (collectively called "psilocybin mushrooms" or "psilocybian mushrooms"), and at low levels in a large number of species of the Agaricales. The spores of these mushrooms 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 though bruising is not a definitive method of determining a mushrooms potency.
Pharmacology
Psilocybin is rapidly dephosphorylated in the body to
psilocin which then acts as a
partial agonist at the 5-HT2A receptor serotonin receptor in the brain where it mimics the effects of serotonin (5-HT). Psilocin is an 5-HT1A and 5-HT2A/2C agonist.
Medicine
Psilocybin has been studied as a 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.
In the United States, an
Food and Drug Administration-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.http://www.maps.org/research/psilo/azproto.html Effects of Psilocybin in 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 group of cluster headache sufferers.http://www.maps.org/research/cluster/psilo-lsd/#cluster Research into psilocybin and LSD as potential treatments for people with cluster headaches In 2006, the MAPS study found psilocybin effective in relieving obsessive compulsive disorder symptoms, in some cases for more than a few days.
In a current study of psilocybin, led by Charles Grob, 12 subjects are being administered with either the hallucinogen or a placebo in two separate sessions. Grob hopes to reduce the psychological distress that is associated with death by treating patients with psilocybin.http://www.clinicaltrials.gov/ct/show/NCT00481325?order=31hhtp://http://psychedelics.com/psilocybe/psilocybin.html The Hallucinogenic Way of DyingLewis, Judith. "The Hallucinogenic Way to Die." LA Weekly. Mar. 2004:AlterNet
Toxicity
The
toxicity of psilocybin is relatively low; in rats, the oral LD50 is 280mg/kg — almost one and a half times that of the LD50 of caffeine. When administered intravenously in
rabbits, Psilocybin's LD50 is approximately 12.5mg/kg. NLM (click on "toxicity" on the left side) Death from psilocybin intake alone is unknown at recreational or medicinal levels.
The psilocybin content of psychoactive mushrooms is quite variable and depends on species, growth and drying conditions, and mushroom size.
Effects
Psilocybin is absorbed through the lining of the mouth and stomach. Effects begin 10-40 minutes after ingestion of psilocybin-containing mushrooms if held in mouth for 20-60 minutes or if swallowed on an empty stomach, and last from 2-6 hours depending on dose, species, and individual metabolism.http://www.erowid.org/plants/mushrooms/mushrooms_dose.htlm Typical recreational dosage is from 10-50mg psilocybin, approximately 1-5g dried mushroom or 10-50g wet mushrooms.
The effects of psilocybin are often pleasant, even ecstatic, including a deep sense of connection to others, confusion, hilarity, and a general feeling of connection to nature and the universe.
Bad trips may occur when psychedelic compounds are taken in a non-supportive or inadequate environment, by an inexperienced person, in an unexpectedly high dose (see:
set and setting), or when the substance triggers difficult areas of one's psyche.
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 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 active placebo; the tests were double-blind, with neither the subject nor the administrator knowing which drug was being administered. 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. This research was widely covered in the major media outlets.. Most people who have used psilocybin report that if you believe you will have a "bad trip" then you will. The same people, also report the best way to have a "good trip" is respect the mushroom, believe it will be a "good trip", and use it more for spiritual enhancement, rather than taking the psilocybin just to get "messed up".
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 metabolized mostly in the liver where it becomes psilocin. It is broken down by the enzyme monoamine oxidase. MAOI 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.
Adverse effects
Individuals that have relatives with schizophrenia should be very careful about consuming psilocybin or any hallucinogenic drug at all due to the risk of triggering a psychosis. http://www.erowid.org/mushrooms/mushrooms_basics.html
In extremely rare cases the use of hallucinogens may trigger a malady called Hallucinogen persisting perception disorder. (HPPD).Espiard ML. et al. (2005): "HPPD after psilocybin consumption: a case study.", Eur. Psychiatry 20(5-6):458-60. Abstract
Social and legal aspects
Psilocybin and psilocin are listed as
Controlled Substances Act drugs under the United Nations 1971 Convention on Psychotropic Substances. 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 Prohibition (drugs) 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. For more details on the legal status of psilocybin mushrooms and
Psilocybe spores, see: Psilocybe#Social and legal aspects.
Because of the ease of cultivating psilocybin mushrooms or gathering wild species, purified psilocybin is practically nonexistent on the illegal drug market.
See also
References
2006 Johns Hopkins experiment
- Griffiths RR, Richards WA, McCann U, Jesse R. (2006). Psilocybin can occasion mystical-type experiences having substantial and sustained personal meaning and spiritual significance. Psychopharmacology (online edition): July 11, 2006. (PDF) – Original paper.
- 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, New Scientist 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.
External links
- Report by the Dutch Government Stating Psilocybin's Harmlessness
- The Shroomery Detailed information about magic mushrooms including identification, cultivation and spores, psychedelic images, trip reports and an active community.
- Erowid Psilocybin & Psilocin Vault
- Erowid Psilocybin Mushroom Vault
- Erowid Psychedelic Crisis FAQ
- Erowid LD50s page on various psychoactive LD50s
- User-friendly info on Mushrooms, provided by the TRIP! Project, Toronto Canada
- Media reports of 2006 Johns Hopkins Research including ABC News video, The Wall Street Journal, The Washington Post, and The New York Times
- Visionary Mushrooms
- The Mechanisms of Mind-Manifesting Mushrooms
- MAPS Psilocybin research
- Science & Consciousness Review The Neurochemistry of psychedelic experience
- Good Drugs Guide
- Clusterbusters Psilocybin as cluster headache treatment
- "Psychedelic medicine: Mind bending, health giving." New Scientist, February 26, 2005 - contains information on cluster headache research
- Wired News: Long Trip for Psychedelics, September 27, 2004
- Czech Parliament approved growing of psychoactive magic mushrooms December 20, 2005
- EMCDDA Thematic Papers — Hallucinogenic mushrooms: an emerging trend case study , European Monitoring Centre for Drugs and Drug Addiction, June, 2006.
Psilocybin
What is psilocybin?
Psilocybin - Wikipedia, the free encyclopedia
Psilocybin (IPA: /saɪləˈsaɪbɪn/)(also known as psilocybine) is a psychedelic indole of the tryptamine family, found in psilocybin mushrooms. It is present in hundreds of ...
Psilocybin mushrooms - Wikipedia, the free encyclopedia
Psilocybin mushrooms (also called psilocybian mushrooms) are fungi that contain the psychedelic substances psilocybin and psilocin, and occasionally other psychoactive tryptamines.
Psilocybin
What does psilocybin do? ... 5-HT modulation of dopamine release in basal ganglia in psilocybin-induced psychosis in man--a PET study with [11C]raclopride
Psilocybin - Molecule of the Month
Psilocybin and Mescaline. Paul May University of Bristol, School of Chemistry Molecule of the Month - October 1999 Chime enhanced, VRML and Chemsymphony (java) versions
Psilocybin for the dying
Source: AlterNet Date: 22 March 2004 The Hallucinogenic Way of Dying By Judith Lewis, LA Weekly. Almost as soon as Dr. Charles Grob secured approval to study the effects of ...
It07:Psilocybin - ChemWiki
3] Psilocybin (a.k.a. psilocybine) is a psychedelic alkaloid (naturally occurring amine) of the tryptamine family, found in psilocybin (magic mushrooms).
Erowid Psilocybin Mushroom (Psychedelic / Magic Mushrooms) Vault
An extensive collection of information about psilocybin-containing mushrooms (psychoactive 'magic' mushrooms). Includes images, information, and links on historical, spiritual ...
Psilocybin : magic and medicine
Source: Independent Date: 30 November 2004 Magical and medicinal We all know about the psychedelic 'benefits' of some types of fungus. But could they also be a miracle cure for ...
Psilocybin
What is psilocybin? Psilocybin is produced synthetically or extracted from the psilocybe mexicana mushroom and other mushroom species.