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Psilocybin

Psilocybin

Psilocybin
Chemical name	4-Phosphoryloxy- N,N-dimethyl-tryptamine
Chemical formula	C₁₂H₁₇N₂O₄P
Molecular mass	284.25 g/mol
CAS number	520-52-5
SMILES	C[N+](C)([H])CCC1=CNC2= C1C(OP([O-])(O)=O)=CC=C2
Chemical structure of psilocybin

Psilocybin (4-phosphoryloxy-N, N-dimethyl tryptamine) 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.

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.

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.

Pharmacology

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.

Toxicity

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

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 with power taste 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, graduate degree divinity student volunteers who received psilocybin, almost all reported profound religious experiences. (A brief video about the Marsh Chapel experiment can be viewed [http://www.yoism.org/?q=node/52 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 can 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 hallucinogen 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, 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. Tolerance dissipates after a few days, so frequent users often keep doses spaced five to seven days apart to avoid the effect.

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. http://www.freenewmexican.com/news/29120.html Growing hallucinogenic mushrooms not illegal, state appeals court rules Psilocybin mushroom spores are legal to sell and possess in every state except California, Idaho, and Georgia.[http://www.erowid.org/plants/mushrooms/mushrooms_law8.shtml]
- 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.

Media

- [http://www.wired.com/news/medtech/0,1286,65025,00.html Wired News: Long Trip for Psychedelics], September 27, 2004
- [http://www.newscientist.com/article.ns?id=mg18524881.400 Psychedelic medicine: Mind bending, health giving], February 26, 2005

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.

External links

- [http://www.shroomery.org/ The Shroomery] Detailed information about magic mushrooms including identification, cultivation and spores, psychedelic images, trip reports and an active community.
- [http://www.erowid.org/plants/mushrooms/mushrooms.shtml The Vaults of Erowid] Psilocybin mushrooms
- [http://www.erowid.org/psychoactives/faqs/psychedelic_crisis_faq.shtml Erowid Mushroom FAQ] Psychedelic crisis FAQ
- [http://www.erowid.org/psychoactives/health/psychoactives_ld50s.shtml Erowid LD50s] page on various psychoactive LD50s
- [http://www.tripproject.ca/march/drugContent.php?info=mushrooms User-friendly info on Mushrooms], provided by the TRIP! Project, Toronto Canada
- [http://www.mykoweb.com/articles/MindManifestingMushrooms.html The Mechanisms of Mind-Manifesting Mushrooms]
- [http://www.maps.org/research/index.html#PSILOCYBIN MAPS] Psilocybin research
- [http://www.sci-con.org/editorials/20030603.html Science & Consciousness Review] The Neurochemistry of psychedelic experience
- [http://www.thegooddrugsguide.com/mushrooms/basics.htm Good Drugs Guide]
- [http://www.clusterbusters.com Clusterbusters] Psilocybin as cluster headache treatment Category:Alkaloids Category:Schedule I controlled substances Category:Psychedelic tryptamines

Chemical formula

A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. It identifies each type of chemical element by its element symbol and identifies the number of atoms of such element to be found in each discrete molecule of that compound. The number of atoms (if greater than one) is indicated as a subscript. For non-molecular substances the subscripts indicate the ratio of elements in the empirical formula. Chemical formula used for a series of compounds that differ from each other by a constant unit is called general formula. Such a series is called the homologous series, while its members are called homologs.

Elements

In organic chemistry most compounds consist of the following five chemical elements:
- C carbon
- H hydrogen
- N nitrogen
- O oxygen
- S sulfur For other element symbols see list of elements by symbol.

Molecular and structural formulas

For example methane, a simple molecule consisting of one carbon atom bonded to four hydrogen atoms has the chemical formula: : CH₄ and glucose with six carbon atoms, twelve hydrogen atoms and six oxygen atoms has the chemical formula: : C₆H₁₂O₆. A chemical formula may also supply information about the types and spatial arrangement of bonds in the chemical, though it does not necessarily specify the exact isomer. For example ethane consists of two carbon atoms single-bonded to each other, each having three hydrogen atoms bonded to it. Its chemical formula can be rendered as CH₃CH₃. If there were a double bond between the carbon atoms (and thus each carbon only had two hydrogens), the chemical formula may be written: CH₂CH₂, and the fact that there is a double bond between the carbons is assumed. However, a more explicit and correct method is to write H₂C:CH₂ or H₂C=CH₂. The two dots or lines indicate that a double bond connects the atoms on either side of them. A triple bond may be expressed with three dots or lines, and if there may be ambiguity, a single dot or line may be used to indicate a single bond. Molecules with multiple functional groups that are the same may be expressed in the following way: (CH₃)₃CH. However, this implies a different structure from other molecules that can be formed using the same atoms (isomers). The formula (CH₃)₃CH implies a chain of three carbon atoms, with the middle carbon atom bonded to another carbon: Carbon chain and the remaining bonds on the carbons all leading to hydrogen atoms. However, the same number of atoms (10 hydrogens and 4 carbons, or C₄H₁₀) may be used to make a straight chain: CH₃CH₂CH₂CH₃. The alkene 2-butene has two isomers which the chemical formula CH₃CH=CHCH₃ does not identify. The relative position of the two methyl groups must be indicated by additional notation denoting whether the methyl groups are on the same side of the double bond (cis or Z) or on the opposite sides from each other.(trans or E)

Polymers

For polymers, parentheses are placed around the repeating unit. For example, a hydrocarbon molecule that is described as: CH₃(CH₂)₅₀CH₃, is a molecule with 50 repeating units. If the number of repeating units is unknown or variable, the letter n may be used to indicate this: CH₃(CH₂)_nCH₃.

Ions

For ions, the charge on a particular atom may be denoted with a right-hand superscript. For example Na⁺, or Cu²⁺. The total charge on a charged molecule or a polyatomic ion may also be shown in this way. For example: hydronium, H₃O⁺ or sulfate, SO₄^2-.

Isotopes

Although isotopes are more relevant to nuclear chemistry or stable isotope chemistry than to conventional chemistry, different isotopes may be indicated with a left-hand superscript in a chemical formula. For example, the phosphate ion containing radioactive phosphorus-32 is ³²PO₄^3-. Also a study involving stable isotope ratios might include ¹⁸O:¹⁶O. A left-hand subscript is sometimes used to indicate redundantly, for convenience, the atomic number.

Empirical formula

In chemistry, the empirical formula of a chemical is a simple expression of the relative number of each type of atom or ratio of the elements in it. Empirical formulas are the standard for ionic compounds, such as CaCl₂, and for macromolecules, such as SiO₂. An empirical formula makes no reference to isomerism, structure, or absolute number of atoms. The term empirical refers to the process of elemental analysis, a technique of analytical chemistry used to determine the relative percent composition of a pure chemical substance by element. For example, hexane could have a chemical formula of CH₃CH₂CH₂CH₂CH₂CH₃, implying that it has a straight chain structure, 6 carbon atoms, and 14 hydrogen atoms. However the empirical formula for the same molecule would be C₃H₇.

CAS number

CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. They are also referred to as CAS numbers, CAS RNs or CAS #s. Chemical Abstracts Service (CAS), a division of the American Chemical Society, assigns these identifiers to every chemical that has been described in the literature. The intention is to make database searches more convenient, as chemicals often have many names. Almost all molecule databases today allow searching by CAS number. As of Dec 4, 2005, there were 27,028,944 substances in the CAS registry — the current number is published [http://www.cas.org/cgi-bin/regreport.pl here]. About 4,000 new numbers are added each day. CAS also maintains and sells a database of these chemicals, known as the CAS registry.

Format

A CAS registry number is separated by hyphens into three parts, the first consisting of up to 6 digits, the second consisting of two digits, and the third consisting of a single digit serving as a check digit. The numbers are assigned in increasing order and do not have any inherent meaning. The checksum is calculated by taking the last digit times 1, the next digit times 2, the next digit times 3 etc., adding all these up and computing the sum modulo 10. For example, the CAS number of water is 7732-18-5, and the checksum is calculated as (8×1 + 1×2 + 2×3 + 3×4 + 7×5 + 7×6) mod 10 = 105 mod 10 = 5.

Isomers, enzymes, and mixtures

Different isomers of a molecule receive different CAS numbers: D-glucose has 50-99-7, L-glucose has 921-60-8, α-D-glucose has 26655-34-5, etc. Occasionally, whole classes of molecules receive a single CAS number: the group of alcohol dehydrogenases has 9031-72-5. An example of a mixture with a CAS number is mustard oil (8007-40-7).

Searches

When using CAS numbers for database searches, it is useful to include the numbers of closely related compounds. For instance, to search for information about cocaine (CAS 50-36-2), one should include cocaine hydrochloride (CAS 53-21-4), since that is the most common form of cocaine when used as a drug.

External links

- [http://www.cas.org/EO/regsys.html CAS registry description], by the Chemical Abstracts Service To find the CAS number of a compound given its name, formula or structure, the following free resources can be used:
- [http://pubchem.ncbi.nlm.nih.gov PubChem]
- [http://chem2.sis.nlm.nih.gov/chemidplus/chemidlite.jsp NIH ChemIDplus]
- [http://webbook.nist.gov/chemistry/ NIST Chemistry WebBook]
- [http://cactvs.cit.nih.gov/ NCI Database Browser]
- [http://chemfinder.cambridgesoft.com/ Chemfinder]
- [http://ecb.jrc.it/esis/esis.php European chemical Substances Information System (ESIS)] - useful for finding EC# Category:Chemical numbering schemes ja:CAS登録番号

Simplified molecular input line entry specification

The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. SMILES strings can be imported by most molecule editors for conversion back into two-dimensional drawings or three-dimensional models of the molecules. The original SMILES specification was developed by Arthur Weininger and David Weininger in the late 1980s. It has since been modified and extended by others, most notably by Daylight Chemical Information Systems Inc. Other 'linear' notations include the Wiswesser Line Notation (WLN), ROSDAL and SLN (Tripos Inc). Recently, the IUPAC has introduced the InChI as a standard for formula representation.

Canonical SMILES and Isomeric SMILES

The term Canonical SMILES refers to the version of the SMILES specification that includes rules for ensuring that each chemical molecule has a single SMILES representation. A common application of Canonical SMILES is for indexing molecules in a database. The term Isomeric SMILES refers to the version of the SMILES specification that includes extensions to support the specification of isotopes, chirality, and configuration about double bonds. A notable feature of these rules is that they allow rigorous partial specification of chirality.

Graph-based definition

In terms of a graph-based computational procedure, SMILES is a string obtained by printing the symbol nodes encountered in a depth-first tree-traversal of a chemical graph. The chemical graph is first trimmed to remove hydrogen atoms and cycles are broken to make it into a spanning tree. Where cycles have been broken, numeric suffix labels are included to indicate the connected nodes. Parentheses are used to indicate points of branching on the tree.

Examples

Atoms are represented by the standard abbreviation of the chemical elements, in square brackets, such as [Au] for gold. The hydroxide anion is [OH-]. Brackets can be omitted for the "organic subset" of C, N, O, P, S, Br, Cl, I. All other elements must be enclosed in brackets. If the brackets are omitted, the proper number of implicit hydrogen atoms is assumed; for instance the SMILES for water is simply O and that for ethanol is CCO. The double-bonded carbon dioxide is represented as O=C=O and the triple-bonded hydrogen cyanide as C#N. Cyclohexane is represented as C1CCCCC1, the idea being that the two ones label the same position in the molecule, thus forming a ring with six carbons. Note that the label is the numeral (in this case the 1) rather than the combination of 'C1'. Expanded notation for clarification: (C1)-(C)-(C)-(C)-(C)-(C)-1 rather than (C1)-(C)-(C)-(C)-(C)-(C)-(C1). Aromatic C, O, S and N atoms are shown in their lower case 'c', 'o', 's' and 'n' respectively. Branches are described with parentheses, as in CCC(=O)O for propionic acid and C(F)(F)F for fluoroform, which could also be described by the non-canonical formula: FC(F)F.

Isomeric SMILES

fluoroform Configuration around double bonds is specified using the characters "/" and "\". For example, F/C=C/F is one representation of trans-difluoroethene, in which the Fs are on opposite sides of the double bond, whereas F/C=C\F is one possible representation of cis-difluoroethene, in which the Fs are on the same side of the double bond, as shown in the figure.

Extensions

SMARTS is a modification of SMILES that allows, in addition to the SMILES elements, the specification of wildcard atoms and bonds. This is used in specifying search structures and is widely used in chemical database search applications. This practise has led to a common misconception that chemical substructure search is achieved computationally by matching SMILES/SMARTS strings, when in fact it is achieved by the computationally more intensive search for subgraph isomorphism in the graphs reconstructed from the SMILES representations.

Conversion

SMILES can be converted back to 2-dimensional representations using Structure Diagram Generation algorithms. This conversion is not always unambiguous. Conversion to 3-dimensional representation is achieved by energy minimization approaches.

External links

- [http://www.daylight.com/dayhtml/doc/theory/theory.smiles.html "SMILES - A Simplified Chemical Language"]
- [http://www.daylight.com/smiles/smiles-intro.html Daylight SMILES tutorial]
- Web-based applications capable of converting SMILES strings to 2D structure images
- [http://www.daylight.com/daycgi/depict Daylight Depict]
- [http://cactus.nci.nih.gov/services/gifcreator/ CACTVS at NCI] GIF/PNG converter with more controls
- [http://pubchem.ncbi.nlm.nih.gov/edit/index.html PubChem online molecule editor] that supports SMILES/SMARTS, InChI and all common chemical file formats
- [http://www.molinspiration.com/jme/index.html JME molecule editor] applet that can create SMILES
- [http://www.dalkescientific.com/writings/diary/archive/2004/01/05/tokens.html Parsing SMILES]
- [http://www.acdlabs.com/download/chemsk.html ACD/ChemSketch] freeware
- [http://jmol.sourceforge.net Jmol] molecule viewer for SMILES
- [http://www.chemaxon.com/ ChemAxon] SMILES aware Java based molecule editor and 2D/3D viewer (Marvin), database and complete cheminformatics toolkit (JChem) with API, free for teaching, academic research and for free public access web sites
- [http://www.hungry.com/~alves/smormoed/ Smormo-Ed] Molecule editor for Linux which can read and write SMILES Category:Chemical nomenclature Category:Encodings ja:SMILES記法

Methyl

In chemistry, a methyl group is a hydrophobic alkyl functional group derived from methane (₄). It has the formula -₃ and is very often abbreviated -Me. This hydrocarbon unit can be found in many organic compounds, such as biodiesel (methyl ester). When a methyl group is substituted as the R group in an amino acid, it forms alanine. See methanol history for its etymology.

Tryptamine

Tryptamine
Chemical name	3-(2-Aminoethyl)indole
Chemical formula	C₁₀H₁₂N₂
Molecular mass	160.22 g/mol
SMILES	NCCC1=CNC2=C1C=CC=C2
Chemical structure of Tryptamine

Tryptamine (3-(2-amino ethyl)indole) is a monoamine compound that is widespread in nature. Biosynthesis generally proceeds from the amino acid tryptophan, with tryptamine in turn acting as a precursor for other compounds including indole, beta-carboline and ergoline alkaloids and auxins. Substitutions to the tryptamine molecule give rise to a group of compounds collectively known as tryptamines. The most well-known tryptamines are serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine alkaloids found in fungi, plants and animals are commonly used by humans for their psychoactive effects, which tend to be psychedelic in nature. Prominent examples include psilocybin (from "magic mushrooms") and DMT (from numerous plant sources, e.g. ayahuasca). Many synthetic tryptamines have also been made, including the migraine drug sumatriptan and its relatives. The table below lists some commonly encountered substituted tryptamines. The tryptamine backbone can also be identified as part of the structure of some more complex compounds, for example: ergoline alkaloids, LSD, ibogaine and yohimbine. A thorough investigation of dozens of tryptamine compounds was published by Ann and Alexander Shulgin under the title TiHKAL. TiHKAL

External links

- [http://www.erowid.org/psychoactives/faqs/faqs_tryptamine.shtml Tryptamine FAQ]
- [http://www.lysergicbook.com Lysergic book], describes several tryptamine journeys
- [http://www.tripproject.ca/march/drugContent.php?info=researchchemicals User-friendly info on Tryptamines], provided by the TRIP! Project, Toronto Canada Category:Indole compounds
-

Psychedelic

:For "psychedelics," see psychedelic drug. The word psychedelic is a neologism coined from the Greek words for "mind," ψυχη (psyche), and "manifest," δηλειν (delein). 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 ordinary fetters. Psychedelic states are one of the stations on the spectrum of experiences elicited by psychedelic substances. On that same spectrum will be found hallucinations, distortions of perception, synaesthesia, altered states of awareness, mystical states, and occasionally states resembling psychosis. The term was first coined as a noun in 1956 by psychiatrist Humphry Osmond, as an alternative descriptor for hallucinogenic drugs in the context of psychedelic psychotherapy. The term featured in a now-famous exchange with Aldous Huxley, in which the ill-fated term phanerothyme was suggested: :To make this trivial world sublime, :take half a gram of phanerothyme. Osmond responded: :To fathom Hell or soar angelic, :just take a pinch of psychedelic. The use of psychedelic drugs became widespread in the mid-1960s. Timothy Leary, who was largely responsible for the popularization of the term "psychedelic", was a well known proponent of their use, as was Aldous Huxley. The fashion for psychedelic drugs gave its name to the visual style of psychedelia, and to a rock music style that became known as psychedelic music. The impact of psychedelic drugs on western culture in the 1960s led to meaning drift in the use of the word "psychedelic", and it is now frequently applied to describe any brightly patterned or coloured object. In objection to this new meaning, and to the pejorative meanings of other synonyms such as "hallucinogen" and "psychotomimetic", the term "entheogen" was proposed and is seeing increasing use. However, many consider the term "entheogen" best reserved for religious and spiritual usage, such as certain Native American churches do with the peyote sacrament, and "psychedelic" left to describe those who are using these drugs recreationally. At the same time as psychedelic drugs were being used by the counterculture of the 1960s, they were also being used in experiments by governments, who saw them (apparently mistakenly) as useful agents for mind control; see MKULTRA for the CIA involvement in the use of psychedelic drugs.

External links

- [http://www.drugs-plaza.com/ Drugs-plaza] info about different Psychedelics and many Experiences reports
- Science & Consciousness Review, The Neurochemistry of Psychedelic Experience: http://www.sci-con.org/editorials/20030603.html
- [http://www.erowid.org/ Erowid]
- [http://www.spiritplants.org/ Spirit Plants]
- [http://www.futurehi.net/ Psychedelic Futurism]
- [http://www.phacelift.co.uk/psychedelic-books.html Psychedelic Books] Category:Psychedelics, dissociatives and deliriants Category:Psychedelia

Alkaloid

An alkaloid is a nitrogenous organic molecule that has a pharmacological effect on humans and animals. The name derives from the word alkaline; originally, the term was used to describe any nitrogen-containing base (an amine in modern terms). Alkaloids are found as secondary metabolites in plants (e.g., in potatoes and tomatoes), animals (e.g., in shellfish) and fungi, and can be extracted from their sources by treatment with acids (usually hydrochloric acid or sulfuric acid, though organic acids such as maleic acid and citric acid are sometimes used). Usually alkaloids are derivatives of amino acids. Even though many alkaloids are poisonous (such as strychnine or coniine), some are used in medicine as analgesics (pain relievers) or anaesthetics, particularly morphine and codeine. Most alkaloids have a very bitter taste. Although formally an alkaloid, the class of pyrazoles contain two nitrogen atoms in the aromatic ring structure and are not found in nature. They must be produced synthetically.

Alkaloid classifications

Alkaloids are usually classified by their common molecular precursors, based on the metabolic pathway used to construct the molecule. When not much was known about the biosynthesis of alkaloids, they were grouped under the names of known compounds, even some non-nitrogenous ones (since those molecules' structures appear in the finished product; the opium alkaloids are sometimes called "phenanthrenes", for example), or by the plants or animals they were isolated from. When more is learned about a certain alkaloid, the grouping is changed to reflect the new knowledge, usually taking the name of a biologically-important amine that stands out in the synthesis process.
- Pyrrolidine group: hygrine, cuscohygrine, nicotine.
- Tropane group: atropine, cocaine, ecgonine, scopolamine.
- Quinoline group: quinine, quinidine, dihydroquinine, dihydroquinidine, strychnine, brucine, veratrine, cevadine
- Isoquinoline group: The opium alkaloids (morphine, codeine, thebaine, heroin, papaverine, narcotine, narceine, hydrastine, berberine)
- Phenethylamine group: MDMA, methamphetamine, mescaline, ephedrine
- Indole group:
- Tryptamines: DMT, NMT, psilocybin, serotonin
- Ergolines: the ergot alkaloids (ergine, ergotamine, lysergic acid, etc.), LSD
- Beta-carbolines: harmine, yohimbine, reserpine, emetine
- Purine group:
- Xanthines: caffeine, theobromine, theophylline
- Terpenoid group:
- Aconite alkaloids: aconitine
- Steroids: solanine, samandarin
- Betaines (quaternary ammonium compounds): muscarine, choline, neurine
- Pyrazole group: pyrazole, fomepizole ? ja:アルカロイド

Tryptamine

Tryptamine
Chemical name	3-(2-Aminoethyl)indole
Chemical formula	C₁₀H₁₂N₂
Molecular mass	160.22 g/mol
SMILES	NCCC1=CNC2=C1C=CC=C2
Chemical structure of Tryptamine

External links

Fungi

Chytridiomycota
Deuteromycota
Zygomycota
Glomeromycota
Ascomycota
Basidiomycota Basidiomycota Basidiomycota] A fungus (plural fungi) is a eukaryotic organism that digests its food externally and absorbs the nutrient molecules into its cells. Fungi are very important economically: yeasts are responsible for fermentation of beer and bread and mushroom farming is a large industry in many countries. Fungi are the primary decomposers of dead plant and animal matter in many ecosystems, and are commonly seen on old bread as mold. However, the complex biology of fungi extends beyond this common knowlege and experience of them.

Phylogeny of fungus

Originally classified as plants, fungi are not true plants because they are heterotrophs (they do not fix their own carbon through photosynthesis but use the carbon fixed by other organisms.) Fungi are more closely related to animals, but unlike animals they are saprotrophic (they absorb their food rather than ingest it) and their cells have cell walls surrounding them. For these reasons, these organisms are now placed in their own kingdom, Fungi. The Fungi are a monophyletic group, meaning all varieties of fungi come from a common ancestor. Mycologists (scientists who study fungi) believe they are monophyletic because they have chitin in their cell walls and are saprotrophic, along with other shared characteristics.

Overview

Although often inconspicuous, fungi occur in every environment on earth and play very important roles in most ecosystems. Some fungi are major decomposers of dead plant and animal matter in forests and many other environments. Some types of fungi are parasites on plants and animals, including humans. They are responsible for numerous diseases, such as athlete’s foot and ringworm in humans and Dutch elm disease in plants. Other fungi are partners in symbiotic relationships with other organisms. For example, lichens are formed by a symbiotic relationship between algae or cyanobacteria and fungi. Most vascular plants benefit from a symbiosis between their roots and fungi. Fungi have a long history of use by humans. Many types of mushrooms and other fungi are eaten, including button mushrooms, shiitake mushrooms, and oyster mushrooms. Of course, many species of mushrooms are poisonous and are responsible for a numerous cases of sickness and death every year. A type of fungus called yeast is used in baking bread and fermenting alcoholic beverages. Fungi are also used to produce industrial chemicals like lactic acid, and even to make stonewashed jeans. Some types of fungi are ingested for their hallucinogenic properties, both recreationally and religiously (as entheogens).

Types of Fungi

The major groups of fungi are mainly classified based on their reproductive structures, such as the types of spores they produce. Currently, there are five divisions (or phyla) recognized by mycologists (scientists who study fungi):
- The Chytridiomycota are commonly known as chytrids. These fungi produce zoospores that are capable of moving on their own through the use of flagella.
- The Zygomycota are known as zygomycetes and produce sexual spores called zygospores. Black bread mold is a common species that belongs to this group.
- Members of the Glomeromycota are also known as the arbuscular mycorrhizal fungi. Only one species has been observed forming zygospores, but all other species only reproduce asexually.
- The Ascomycota, commonly known as sac fungi or ascomycetes, produce spores called ascospores, which are enclosed in a special sac-like structure called an ascus. This division includes morels, mushrooms and truffles, as well as single-celled yeasts and many species that have only been observed undergoing asexual reproduction.
- Members of the Basidiomycota, commonly known as the club fungi or basidiomycetes, produce spores called basidiospores on club-like stalks called basidia. Most mushrooms belong to this group. Although the water molds and slime molds have traditionally been placed in kingdom Fungi and are still studied by mycologists, they are not true fungi. Unlike true fungi, the water molds and slime molds do not have cell walls made of chitin. They are currently placed in kingdom Protista.

Structure

Fungi may be single-celled or multicellular. Multicellular fungi are composed networks of long hollow tubes called hyphae. The hyphae often aggregate in a dense network known as mycelium. The mycelium grows through the substrate on which the fungus feeds. Because fungi are imbedded in the medium in which they grow, they are often not visible to the naked eye. Although fungi lack true organs, the mycelia of ascomycetes and basidiomycetes may become organized into more complex reproductive structures called fruiting bodies, or sporocarps, when conditions are right. "Mushroom" is the common name given to the above-ground fruiting bodies of many fungal species. Although these above-ground structures are the most conspicuous to humans, they make up only a small portion of the entire fungal body. The largest organism in the world is purported to be a single Armillaria ostoyae individual growing in a forest in eastern Oregon, USA. The underground mycelial network may cover as much as 890 ha (2200 acres).

Reproduction

Fungi may reproduce sexually or asexually. In asexual reproduction, the offspring are genetically identical to the “parent” organism. During sexual reproduction, a mixing of genetic material occurs so that the offspring exhibit traits of both parents. Many species can use both strategies at different times, while others are apparently strictly sexual or strictly asexual. Sexual reproduction has not been observed in the Glomeromycota or in ascomycetes commonly referred to as Fungi imperfecti or Deuteromycota. Yeasts and other unicellular fungi can reproduce simply by budding, or “pinching off” a new cell. Many multicellular species produce a variety of different asexual spores that are easily dispersed and resistant to harsh environmental conditions. When the conditions are right, these spores will germinate and colonize new habitats. Sexual reproduction in fungi is somewhat different from that of animals or plants, and each fungal division reproduces using different strategies. Fungi that are known to reproduce sexually all have a haploid stage and a diploid stage in their life cycles. Ascomycetes and basidiomycetes also go through a dikaryotic stage, in which the nuclei inherited by the two parents do not fuse right away, but remain separate in the hyphal cells. In zygomycetes, the haploid hyphae of two compatible individuals fuse, forming a zygote, which becomes a resistant zygospore. When this zygospore germinates, it quickly undergoes meiosis, generating new haploid hyphae and asexual sporangiospores. These sporangiospores may then be distributed and germinate into new genetically-identical individuals, each producing their own haploid hyphae. When the hyphae of two compatible individuals come into contact with one another, they will fuse and generate new zygospores, thus completing the cycle. In ascomycetes, when compatible haploid hyphae fuse with one another, their nuclei do not immediately fuse. The dikaryotic hyphae form structures called asci (sing. ascus), in which karyogamy (nuclear fusion) occurs. These asci are embedded in an ascocarp, or fruiting body, of the fungus. Karyogamy in the asci is followed immediately by meiosis and the production of ascospores. The ascospores are disseminated and germinate to form new haploid mycelium. Asexual conidia may be produced by the haploid mycelium. Many ascomycetes appear to have lost the ability to reproduce sexually and only reproduce via conidia. Sexual reproduction in basidiomycetes is similar to that of ascomycetes. Sexually compatible haploid hyphae fuse to produce a dikaryotic mycelium. This leads to the production of a basidiocarp. The most commonly-known basidiocarps are mushrooms, but they may also take many other forms. Club-like structures known as basidia generate haploid basidiospores following karyogamy and meiosis. These basidiospores then germinate to produce new haploid mycelia.

Edible and poisonous fungi

Some of the most well-known types of fungi are the edible and poisonous mushrooms. Many species are commercially raised, but others must be harvested from the wild. Button mushrooms (Agaricus bisporus) are the most commonly eaten species, used in salads, soups, and many other dishes. Portobello mushrooms are also members of this species, but grow to a much larger size. Other commercially-grown mushrooms that have gained in popularity in the West and are often available fresh in grocery stores include oyster mushrooms, shiitakes, and enoki mushrooms. There are many more mushroom species that are harvested from the wild for personal consumption or commercial sale. Morels, chanterelles, truffles, black trumpets, and porcini mushrooms (also known as king boletes) all command a high price on the market. They are often used in gourmet dishes. Hundreds of mushroom species are toxic to humans, causing anything from upset stomachs to hallucinations to death. Some of the most deadly belong to the genus Amanita, including A. virosa (the "Destroying Angel") and A. phalloides (the "Death Cap"). Stomach cramps, vomiting, and diarrhea usually occur within 6-24 hours after ingestion of these mushrooms, followed by a brief period of remission (usually 1-2 days). Patients often fail to present themselves for treatment at this time, assuming that they have recovered. However, within 2-4 weeks liver and kidney failure leads to death if untreated. There is no antidote for the toxins in these mushrooms, but kidney dialysis and administration of corticosteroids may help. In severe cases, a liver transplant may be necessary (Kaminstein 2002). Fly agaric mushrooms (A. muscaria) are also responsible for a large number of poisonings, but these cases rarely result in death. The most common symptoms are nausea and vomiting, drowsiness, and hallucinations. In fact, this species is used ritually and recreationally for its hallucinogenic properties. However, if it is taken in over a long period of time (regularly over more than six months), this species might cause a temporary loss of sight, which can last from several minutes until up to an hour.

References

- [http://www.healthatoz.com/healthatoz/Atoz/ency/mushroom_poisoning.jsp Kaminstein, D. 2002. "Mushroom poisoning".] Last accessed 9 November 2005.

External links

- [http://www.britmycolsoc.org.uk/ British Mycological Society]
- [http://www.mycolog.com/fifthtoc.html The Fifth Kingdom]
- [http://www.msafungi.org/ Mycological Society of America]
- [http://www.mykoweb.com/ MykoWeb]
- [http://www.namyco.org/ North American Mycological Society]
- Category:Mycology Category:Cryptogams ja:菌類 ko:균류 th:เห็ดรา

Psilocybe

See text. Psilocybe is a genus of fungi that is best known for its hallucinogenic species—the so-called "magic mushrooms" or teonanacatl ("divine flesh").

Biological Aspects

Psilocybe fruiting bodies are typically small, undistinguished mushrooms with a typical "little brown mushroom" morphology. Macroscopically, they are characterized by their small to occasionally medium size, brown to orange-white coloration, hygrophanous pileus, and a spore print-color that ranges from medium gray-brown to dark purple-brown (though rusty-brown colored varieties are known in at least one species). Hallucinogenic species typically have a blue-staining reaction when the fruiting body is bruised. Microscopically, they are characterized by cutis-type pileipellis, lack of chrysocystidia, and spores that are smooth, ellipsoid to rhomboid to subhexagonal in shape, with a distinct apical germ pore. Ecologically, all species of Psilocybe are saprotrophs, growing on various kinds of decaying organic matter. A recent study of the molecular phylogeny of the agarics by Moncalvo, et al. (2002)[http://www.botany.utoronto.ca/faculty/moncalvo/117clade.pdf] indicates that the genus Psilocybe as presently defined is polyphyletic, falling into two distinct clades that are not directly related to each other. The blue-staining hallucinogenic species constitute one clade and the non-bluing species constitute the other. If this finding is supported by other studies, it will result in a new genus being split off from Psilocybe. Since the type species (Psilocybe montana) is a non-bluing species, the non-bluing clade will retain the name Psilocybe, while the bluing clade will be renamed as a separate genus. Psilocybe is placed taxonomically in the agaric family Strophariaceae based upon its spore and pileipellis morphology. However, molecular studies indicate that the Strophariaceae may be a polyphyletic grouping of several clades that are fairly close to each other, but not necessarily sister taxa, hence, the precise relationship of Psilocybe to other agaric genera awaits further study. The phylogenetic study by Moncalvo, et al. (2002)[http://www.botany.utoronto.ca/faculty/moncalvo/117clade.pdf] has confirmed that the agaric genus Melanotus is simply a subgroup of the non-bluing Psilocybe, and also points to a close relationship between the latter group and the genera Kuehneromyces and Phaeogalera. Geographically, species in this genus are found throughout the world in most biomes, with the exception of high deserts. For the bluing Psilocybe, the greatest species diversity seems to be in the neotropics, from Mesoamerica through Brazil and Chile (Guzman 1983). Psilocybe are found in a variety of habitats and substrates. Many of the bluing species found in temperate regions, such as P. cyanescens, seem to have an affinity for landscaped areas mulched with woodchips and are actually rather rare in natural settings removed from human habitation. Contrary to popular belief, only a minority of Psilocybe species, such as P. coprophila and P. cubensis, grow directly on dung. Many other species are found in habitats such as mossy, grassy, or forest humus soils.

Chemistry and Pharmacology

The blue-staining species of Psilocybe are characterized by the presence of psilocin and psilocybin. The blue-staining reaction, while not completely understood, is thought to be a caused by a degradation reaction of psilocin, hence the degree of bluing in a Psilocybe fruiting body correlates directly with the concentration of psilocin in the mushroom. Psilocybin is chemically far more stable than psilocin, the latter compound being largely lost when the mushroom is heated or dried. Psilocin and psilocybin are hallucinogenic compounds and are responsible for the psychoactive effects of these mushrooms. (See Psilocybin for a more in-depth discussion of the pharmacology of psilocybin and psilocin.) Some psychoactive species contain baeocystin and norbaeocystin in addition to psilocin and psilocybin.

History and Ethnography

Hallucinogenic species of Psilocybe have a long history of use among the native peoples of Mesoamerica for religious communion, divination, and healing, from pre-Columbian times up to the present day. Mushroom-shaped statuettes found at archaeological sites seem to indicate that ritual use of hallucinogenic mushrooms is quite ancient. Mushroom stones have been found in pre-Classic sites from Guatemala to El Salvador, though there is considerable controversy whether these objects are associated with the use of hallucinogenic mushrooms or whether the objects had some other significance and the mushroom shape is simply coincidence. More concretely, a statuette dating from ca. 200 CE and depicting a mushroom strongly resembling Psilocybe mexicana was found in a west Mexican shaft and chamber tomb in Colima state. Hallucinogenic Psilocybe were known to the Aztecs as teonanacatl and were reportedly served at the coronation of Moctezuma II in 1502. After the Spanish conquest, the use of hallucinogenic plants and mushrooms, like other pre-Christian traditions, was forcibly suppressed and driven underground. By the 20th century, hallucinogenic mushroom use was thought by non-Indians to have disappeared entirely. Some authors even held that Mesoamerican cultures did not use mushrooms as hallucinogens at all and that the Spanish had simply mistaken peyote for a mushroom. Later investigations by Blas Reko, Richard Evans Schultes, and R. Gordon Wasson demonstrated that hallucinogenic mushrooms were still widely used by several indigenous Mesoamerican peoples, particularly the Mazatecs of Oaxaca. At present, hallucinogenic mushroom use has been reported among a number of groups spanning from central Mexico to Oaxaca, including groups of Nahua, Mixtecs, Mixe, Mazatecs, Zapotecs, and others. There has not, however, been any confirmed observations of hallucinogenic mushroom use among the Maya peoples, either in the pre-Columbian or post-Contact eras.

Medical and Psychiatric Aspects

Social and Legal Aspects

Notable Species

- Psilocybe cubensis, (= Stropharia cubensis); the most commonly grown and consumed Psilocybe, due to ease of cultivation and large size of carpophores; nicknamed the commercial Psilocybe.
- Psilocybe semilanceata, found in northern temperate climates; nicknamed the Liberty Cap.
- Psilocybe cyanescens, native to northwestern North America; nicknamed wavy-capped Psilocybe. See "List of Psilocybe species" for a more complete list of psychoactive species.

References and Further Reading

- Furst, Peter T. 1976. Hallucinogens and Culture. San Francisco: Chandler and Sharp Publishers. Chapter Seven, The sacred mushrooms: Rediscovery in Mexico; pp 75-88. Available from: [http://www.sunrisedancer.com/radicalreader/library/hallucogensandculture/hallucogensandculture07.asp http://www.sunrisedancer.com/radicalreader/library/hallucogensandculture/hallucogensandculture07.asp]
- Guzman, Gaston. 1983. The Genus Psilocybe: A Systematic Revision of the Known Species Including the History, Distribution and Chemistry of the Hallucinogenic Species. (Beihefte zur Nova Hedwigia 74.) Vaduz, LI: J. Cramer. [out of print]
- Metzner, Ralph (ed). 2005. Sacred Mushroom of Visions: Teonanácatl [2nd ed]. Rochester, VT: Park Street Press. 304 pp. [http://www.amazon.com/exec/obidos/ASIN/1594770441/]
- Moncalvo JM, et al. 2002. One hundred and seventeen clades of euagarics. Molecular Phylogenetics and Evolution 23:357-400. Available from: [http://www.botany.utoronto.ca/faculty/moncalvo/117clade.pdf http://www.botany.utoronto.ca/faculty/moncalvo/117clade.pdf]
- Stamets, Paul. 1996. Psilocybin Mushrooms of the World. Berkeley: Ten Speed Press. 245 pp. [http://www.amazon.com/exec/obidos/ASIN/0898158397/]

External links

- [http://www.erowid.org/plants/mushrooms/mushrooms.shtml Erowid - Psilocybin Mushrooms]
- [http://www.erowid.org/plants/mushrooms/mushrooms_faq.shtml Erowid Psilocybe Mushroom FAQ]
- [http://www.inchem.org/documents/pims/fungi/pimg027.htm INCHEM - Psilocybe and others] - Toxicology of psilocybian mushrooms.
- [http://www.lifeline.org.uk/new_sitefiles/articles/20050421_2.html Lifeline.org.uk - Psilocybe Made a Class A Drug] - Legal status of Psilocybe in the UK.
- [http://www.entoloma.nl/html/psilocybeeng.html Machiel E. Noordeloos: Psilocybe] - taxonomy and characteristics of non-bluing Psilocybe.
- [http://www.magic-mushrooms.net MagicMushrooms.net]
- [http://www.mushroomexpert.com/strophariaceae.html MushroomExpert.com Taxonomy in Transition: The Strophariaceae] - Taxonomic issues of Psilocybe and other stropharioid fungi.
- [http://www.stainblue.com/ The Ones that Stain Blue]
- [http://www.maui.net/~jms/chapter6.html The Sacred Mushroom Teonanacatl] - Chapter from "LSD: My Problem Child" by Albert Hofmann
- [http://www.shroomery.org/ The Shroomery] Detailed information about psilocybe mushrooms including identification, cultivation and spores, psychedelic images, trip reports, a dosage calculator and an active community. See also: Psychedelic mushrooms Category:Fungi Category:Herbal & fungal hallucinogens Category:Entheogens Category:Psychedelic tryptamine carriers

Psilocybe cubensis

Psilocybe cubensis is a species of psychedelic mushroom whose primary, pharmacologically active constituents are psilocybin and psilocin. They belong to the Strophariaceae family, are grey to violet-gray in color, and bruise bluish/purplish when crushed or dried. Their caps are planar when fully mature, and their gills are adnate (horizontally attached to the stem) to adnexed (slightly indented at the attachment point) depending on the subspecies. The gills are closely spaced and drop dark purple spores. Psilocybe cubensae are coprophilic, and colonize the dung of large herbivores, most notably cows and other grazing mammals. They prefer humid grasslands and have been found in tropical and subtropical environments in the Americas, Asia and Australia. In the US, they are sometimes found growing wild in the south, generally below the 35th parallel. They have been found in the highlands and river valleys of Colombia, Ecuador and Peru in South America. Psilocybe cubensis is used in spiritual and or healing rituals in Mesoamerica, notably by the Chol and the Lacandon Maya people in southern Mexico. This species was identified as Stropharia cubensis by F.S. Earle in Cuba in 1904 (hence the specific name). It was later identified independently as Naematoloma caerulescens in Tonkin in 1907 by N. Patouillard and as Stropharia cyanescens by W.A. Murrill in 1941 in Florida novelty. These synonyms were later assigned to the species P. cubensis. It was later found throughout U.S. Gulf Coast, Mexico, Central America, South America, West Indies, Thailand, Cambodia, India, and Australia. Its psychoactive compounds are:
- Psilocybin (4-Phosphoryloxy-N,N-dimethyltryptamine)
- Psilocin (4-hydroxy-N,N-dimethyltryptamine)
- Baeocystin (4-Phosphoryloxy-N-methyltryptamine)
- Norbaeocystin (4-Phosphoryloxytryptamine) Psilocin and psilocybin are substances isolated by Albert Hofmann in 1958 in a related and less potent species, P. mexicana. All four compounds are presumed hallucinogenic, though it is suspected that baeocystin and norbaeocystin are less psychoactive than psilocybin and psilocin. Psychedelic mushrooms have rich and varied spiritual significance -- they have been used in religious ceremonies for centuries. The Aztecs reserved them for their holiest ceremonies and called them Teonancatl ("divine flesh"). Lacandón priests take them in seclusion with "god pots". Aztec Please note that individual brain chemistry plays a significant role in determining appropriate doses. For a modest psychedelic effect, a minimum of one gram of dried cubensis mushrooms is ingested orally. 0.25-1 gram is usually sufficient to produce a mild effect, 1-2.5 grams usually provides a moderate effect. 2.5 grams and higher usually produces strong effects. For most people, 3.5 dried grams (1/8 oz) would be considered a high dose and likely to produce a very intense experience. Above this, the mushroom experience rapidly becomes overwhelming. For a few rare people, doses as small as 0.25 grams can produce full-blown effects normally associated with very high doses. For most people, however, that dose level would result in virtually no effects. People taking MAOIs need to be very careful, as psilocybin and psilocin are metabolized by the enzyme monoamine oxidase. An MAOI reduces the body's ability to handle the mushrooms (roughly doubling their potency), and can lead to an unpleasant, prolonged, or dangerously strong experience. While it's nearly impossible to overdose on magic mushrooms (one would have to consume nearly their entire body weight in fresh mushrooms), the effects of very high doses can be completely and dangerously overwhelming. Depending on the particular strain, growth method, and age at harvest, psilocybe cubensis mushrooms can come in rather different sizes. It is recommended that one weighs the actual mushrooms, as opposed to simply counting them. Fresh mushrooms have an average water content of about 90%, so doses with dried mushrooms are thus ten times larger than for fresh mushrooms. Effects usually start after approximately 20-60 minutes (depending on method of ingestion and what else is in the stomach) and last from four to five hours. Hallucinatory effects often 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 intense and spiritual in nature. Although it is illegal in many nations to possess psilocybin containing mushrooms or mycelium (both of which contain psychoactive substances), it is legal in several places to own and sell spores. In the United States only the psychoactive compounds (see above) are scheduled under federal law. The spores do not contain either (but possession is prohibited by state law in Ohio, Georgia, California, and Utah). Home cultivation of psilocybin mushrooms is not very difficult (in small quantities), and a number of books and online guides have been written that discuss various techniques. Extreme caution is suggested if one is seeking to find psilocybin mushrooms in the wild; there are many mushrooms that look similar to Psilocybe cubensis that are actually poisonous.

External links

- [http://www.shroomery.org/ The Shroomery] Detailed information about magic mushrooms including identification, cultivation and spores, psychedelic images, trip reports and an active community.
- [http://www.stainblue.com/cubensis.html Drawings and chemical structures]
- [http://www.erowid.org/plants/mushrooms/mushrooms.shtml Erowid Psilocybin Vault]
- [http://www.fungifun.org/fanaticus/ PF TEK - Psilocybe Cubensis growing techniques]
- [http://sulcus.berkeley.edu/mcb/165_001/papers/manuscripts/_471.html Psilocybin Awareness] Molecular Neurobiology Student Manuscript Category:Entheogens Category:Herbal & fungal hallucinogens Category:Mushrooms Category:Mycology Category:Psychedelics, dissociatives and deliriants Category:Psychedelic tryptamine carriers

Psilocybe semilanceata

The liberty cap (Psilocybe semilanceata) is a hallucinogenic mushroom, a so called magic mushroom, that contains the psychoactive compound psilocybin (Phosophorylated 4-hydroxydimethyltryptamine). It grows on grassy meadows and similar; particularly in wet, South facing fields and other habitats well fertilised by sheep and other cattle dung (although unlike Psilocybe cubensis it does not grow directly on dung). It grows in various places throughout the world, but is known primarily as a native of Europe, growing throughout continental Europe, the UK and Ireland. It can begin to flower as early as July at high altitudes if the year has been wet enough. Gradually, as the season begins to wetten and cool from August onwards the mushroom will spread to the lowlands. Generally, by the first frost (later October/early November) growth will dissipate unless the Autumn is particularly mild. The mushroom takes its name from an actual cap, the Phrygian cap, also known as the liberty cap, which it resembles.

Traditional use

Traditional uses of entheogenic mushrooms are recorded across the globe, yet there are no certain instances of the particular use of psilocybe semilanceata. It is widely considered that the druids of ancient Ireland ingested the liberty cap ritualistically and it is almost certain that Celtic warriors consumed a psychedelic potion before entering into battle. Celt However, it is more probable that Celtic use involved the fungi 'Fly Agaric' (Amanita Muscaria), which contains the deleriant psychotropic compound muscimol.

Modern use

Widespread use of the psilocybin mushroom began, as with many 20th Century substances, in scientific circles with the development of synthetic psilocybin and its use as a psychotherapeutic tool in the mid-1950s. The widespread growth of psychoactive mushrooms across the Americas and Europe proved to be influential in their emergence as a popular recreational drug. In England, a 'loophole' in UK law allowed the consumption of fresh, unprepared psychoactive mushrooms. Consequently, the early 21st Century has seen a movement away from the 'club drugs' (such as ecstasy, ketamine and amphetamines) of the 90s and a return to the 'psychedelica' of the drug culture's forefathers in the 1960s. thumb Integration of the psychoactive mushroom into British culture culminated in the retail exchange of easily cultivated strains of psychedelic mushrooms such as Psilocybe cubensis and Psilocybe cyanescens. The consumption of 'shrooms' was popularised by the media, magazines such as NME featuring staggering statistics of the use of the drug during festivals and declaring a new 'Summer of Love'. The legal status of this psychedelic resurgence remained ambiguous. Though fresh mushrooms were generally sold and ingested openly (pioneered by the stalls in Camden Markets) policial interjection was not unheard of, some outlets being charged under drug laws and the possession of a Class A substance (which is what psilocybe containing mushrooms effectively were). After much indecision (or unwillingness to legislate) governmental forces closed the loop hole. On the 18th of July 2005 all retail transactions involving psychoactive mushrooms had to have ceased and possession of the mushroom was fully illegalised under the Drugs Act of 2005. Any transgression was treatable as a criminal offence involving a Class A substance. In the weeks following the new legislature police raids were widespread and the initial stages of a 'shroom black market' akin to the rest of illegalised substances was halted by massive seizures of the substance. Somewhat unsurprisingly the comprehensive curtailing of 'shroom culture' so suddenly has resulted in a tremendous increase in the use of the liberty cap by people who can no longer obtain their substance of choice by retail. Consequently many ancient sites of liberty cap 'nexuses' across the UK have been destroyed due to inexpert harvesting. Removal of the root of a sufficient number of individual organisms results in the death of the mycelium and the loss of mushroom growth over a widespread area. This is averted by the severance of the mushroom at the base of the stem as oppossed to simple 'plucking'. It is now illegal in the UK to pick or prepare any strain of psilocybe mushrooms in any form. The disturbance of psilocybe semilanceata from their natural state, the drying or preparation thereof or the possession of any psilocybin containing mushroom in any state is prohibited under that country's law and can lead to prosecution, a fine and/or imprisonment. A certain amount of ambiguity remains around the cultivation of psilocybe mushrooms for scientific/mycological purposes, but it is not recommended without the previous consultation of appropriate authorites. Category:Entheogens Category:Psychedelics, dissociatives and deliriants Category:Psychedelic tryptamine carriers Category:Herbal & fungal hallucinogens Category:Mycology

Psychedelic mushroom

Psychedelic mushrooms are also known as magic mushrooms, shrooms, sacred mushrooms, and, more generally, hallucinogenic mushrooms. They are also known simply as mushrooms. See the section below on nomenclature for further discussion. Psychedelic mushrooms are fungi which have psychedelic, i.e., "mind manifesting", properties when ingested and can be roughly divided into two groups: psilocybin/psilocin containing mushrooms found mainly in the genus Psilocybe (though there are also psilocybin containing species belonging to the genera Conocybe, Copelandia, Gymnopilus, Inocybe and Panaeolus) and the muscimol containing mushroom Amanita muscaria. Both groups belong to the Agaricaceae family of fungi. A third group of ergoline alkaloid containing psychoactive fungi like ergot, which is a precursor to LSD, could be defined in connection with the Kykeon. The principal actives in the psilocybin mushrooms are the tryptamines psilocybin and psilocin, which are closely related to DMT, serotonin and LSD. Several psilocybe species also contain the alkaloids baeocystin and norbaeocystin, which are also suspected of being psychoactive. The fly-agaric Amanita muscaria contains the principal active muscimol which, however, is both chemically and symptomatically unrelated to psilocybin. Examples of common psilocybin containing "magic mushroom" species are Psilocybe cubensis, Psilocybe cyanescens, and Psilocybe semilanceata.

History

Various cultures throughout the ages have used psychedelic fungi for shamanistic and other purposes. Mesoamerican mushroom stones of the pre-classic Mayans representing deified mushrooms date back to approximately 500 BC, while rock paintings in the Sahara of mushroom effigies date back to 7000 BC. Some scholars believe that Soma, the drink mentioned in Vedic literature, was derived from psychedelic mushrooms (R. Gordon Wasson suggests that this was amanita muscaria), while Albert Hofmann and Carl Ruck contend that the Eleusinian Mysteries made use of the psychedelic fungus ergot in the Kykeon. Amanita muscaria is known to have been used in Siberian shamanism. S. Odman first suggested in 1784 that Nordic Vikings used fly-agaric (Amanita muscaria) to produce their berserker rages. Supposedly, the Norse took these mushrooms so that the effect came on during the heat of battle or while at work. During the berserker rage they performed deeds which otherwise would have been impossible. The rage started with shivering, chattering of the teeth and a chill. Their faces became swollen and changed color. A great rage developed in which they howled like wild animals and violently killed anyone in their way, friend or foe alike. Afterward their mind became dulled and feeble for several days. The potency of North-American fly agarics has been confirmed by Siberian shamans, but the methodology of effective use has eluded modern experimenters. Psilocybin mushrooms were a revered tradition in native Central American cultures at the time of the European invasion and have been in continuous use up to the present. Named teonanacatl in Nahuatl, ("flesh of the gods"), they may have been employed for healing, divination and for intercession with spirits. Since the beginning of colonial times, their use has been hidden due to persecution by the Christian church, which branded all native religious practices and especially those employing entheogenic sacraments as "Devil worship". According to the BBC, the first documented use of psychedelic mushrooms was in the Medical and Physical Journal: in 1799, a man who had been picking mushrooms for breakfast in London's Green Park included them in his harvest, accidentally sending his entire family on a trip. The doctor who treated them later described how the youngest child "was attacked with fits of immoderate laughter, nor could the threats of his father or mother refrain him". Around the middle of the twentieth century, two amateur western mycologists, R. Gordon Wasson and his wife, Valentina Pavlovna, were admitted to these secrets rites and became the first westerners to experience the agape of this sacrament. The ceremony, known as a velada, Spanish for "vigil", took place in a Mazatec mountain village named Huautla de Jimenez and the shamaness who introduced the Wassons and a few of their friends to the secret rites was later to become the famous Maria Sabina. Later, as the village was overrun with westerners seeking either God or just sensation, she was to rue her action, declaring, "from the moment the foreigners arrived, the 'holy children' [Mazatec euphemism for the mushrooms, which are otherwise not named directly] lost their purity. They lost their force, they ruined them. Henceforth they will no longer work. There is no remedy for it". Subsequently the Wassons wrote about their experiences, first in an article for Life magazine, followed by various books. Their accounts triggered a wave of experimentation with these mushrooms which resulted in their eventual classification in the United States as a Schedule I drug under the Controlled Substances Act. Magic Mushrooms are also used anally.

Effects

Psychedelic mushrooms can elicit a range of bodily and mental effects, such as:
- Physical
- Torpor
- Chills
- Sensory
- Closed-eye visuals
- Open-eye visual effects
- Auditory effects
- Emotional
- Euphoric states
- Beatific states
- Paranoia and/or anxiety, even panic
- Intellectual
- Looped or confused thinking
- Introspective thinking
- Mental "clarity"
- Transcendent insight As with many psychoactive substances, the effects of any mushrooms consumed are unpredictable and strongly dependent upon set and setting. Generally speaking, the experience of psilocybin containing mushrooms lasts four to six hours or more, is inwardly oriented and there can be strong visual and auditory components. Visions and revelations may be experienced and the effect can range from exhilarating to terrifying. There can be also a total absence of effects, even when under the influence of large doses. Non-western native practice suggests that the effects are also affected by the user's preparation. The Mazatecs purify themselves before a velada, abstaining from meat, eggs, alcohol and sex for four days prior to a velada. The veladas are always done in the dark, in a protected and sealed space which no one may enter or leave until all have regained their composure. Modern psychonauts often speak of "packing" for the "trip," by which is meant a loading of information into the brain prior to "departure," for example, by reading a philosophical writing or watching natural history or science documentaries in the days immediately prior to a planned experience. Regular or experienced users find that there are ways of adjusting their environment to enhance their trip. In addition, there have been calls for the medical investigation of psychedelic mushrooms in regards to the treatment of chronic cluster headaches following numerous anecdotal reports of benefits.

Dosage

Dosage of psychedelic mushrooms depends on the total psilocybin and psilocin content of the mushrooms, which varies significantly between species and can also vary significantly within the same species, but is typically around 0.5-2% of the dried weight of the mushroom. A light dose of P. cubensis is usually cited to be about 1g dried material, corresponding to approximately 10mg of psilocybin/psilocin. A common or average dose is approximately 1-3g, corresponding to 10-30mg psilocybin/psilocin and a heavy dose is about 3-5g dried material or 30-50mg of psilocybin/psilocin. Mushrooms are approximately 90% water and accordingly dosages for fresh mushrooms will be about 10 times higher, i.e. 5-50g fresh material. Contempory western users rarely consume them raw, instead prefering to prepare them with a meal - usually a soup/stew or a noodle-based dish - or as a specially brewed tea.

Legal Status

The fly-agaric is not a controlled substance in most countries. Access to ergot and ergoline alkaloids is usually restricted since these substances are precursors to LSD. In most western countries, possession and use of psilocybin mushrooms is illegal. An exception to that rule is The Netherlands, where fresh mushrooms can be obtained in so-called "smart shops" which specialize in ethnobotanicals. Dried mushrooms however are considered a "preparation" and thus remain illegal, even in Holland, the same law is currently in place in Ireland. Nonetheless there is an active international trade both in mushrooms and in spores, which can be grown in sterile medium. (See Drug policy of the Netherlands). As of 18 July 2005, both dried and 'prepared' (made into a tea, et cetera) psilocybian mushrooms were made illegal in the United Kingdom. Prior to this date, fresh mushrooms were widely available, but Clause 21 of the Drugs Bill 2005 made fresh psychedelic mushrooms, ('fungi containing psilocin'), a Class A drug. In the United States, possession of psilocybin-containing mushrooms is largely illegal. Fresh or unprepared psilocybian mushrooms that grow wild in the state of Florida are legal to possess; however, those caught would be hard-pressed not to be hassled by authorities for having them. Psychedelic mushrooms are usually sold on the black market dried, but are sometimes incorporated into chocolate or baked into brownies, cakes or muffins.

Psilocybin

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Methyl

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Psychedelic

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Fungi

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Psilocybe

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Psilocybe cubensis

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Psilocybe semilanceata

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Psychedelic mushroom

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