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| Formula | C11H14N2O |
| Molar mass | 190.246 g·mol−1 |
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Norpsilocin (4-HO-NMT) is a tryptamine alkaloid recently discovered in 2017 in the psychedelic mushroom Psilocybe cubensis . [1] [2] It is hypothesized to be a dephosphorylated metabolite of baeocystin. [2] Norpsilocin was found to be a near full agonist of the 5-HT2A receptor. It is also more potent than psilocin. [3] [4]
Psilocybin is a naturally occurring psychedelic prodrug compound produced by more than 200 species of fungi. The most potent are members of genus Psilocybe, such as P. azurescens, P. semilanceata, and P. cyanescens, but psilocybin has also been isolated from about a dozen other genera. Psilocybin is itself biologically inactive but is quickly converted by the body to psilocin, which has mind-altering effects similar, in some aspects, to those of lysergic acid diethylamide (LSD), mescaline, and dimethyltryptamine (DMT). In general, the effects include euphoria, visual and mental hallucinations, changes in perception, distorted sense of time, and perceived spiritual experiences. It can also cause adverse reactions such as nausea and panic attacks.
Psilocybe cubensis, commonly known as the magic mushroom, shroom, golden halo, cube, or gold cap, is a species of psilocybin mushroom of moderate potency whose principal active compounds are psilocybin and psilocin. It belongs to the fungus family Hymenogastraceae and was previously known as Stropharia cubensis. It is the best-known psilocybin mushroom due to its wide distribution and ease of cultivation. This mushroom being optimal for home cultivation specifically, as was suggested in the 1970s, is primarily what led to P. cubensis being the psilocybin mushroom species most common on the black market as a street drug.
Psilocybin mushrooms, commonly known as magic mushrooms, are a polyphyletic informal group of fungi that contain psilocybin, which turns into psilocin upon ingestion. Biological genera containing psilocybin mushrooms include Psilocybe, Panaeolus, Inocybe, Pluteus, Gymnopilus, and Pholiotina.
Psilocybe is a genus of gilled mushrooms, growing worldwide, in the family Hymenogastraceae. Most or nearly all species contain the psychedelic compounds psilocybin and psilocin.
Psilocybe semilanceata, commonly known as the liberty cap, is a species of fungus which produces the psychoactive compounds psilocybin, psilocin and baeocystin. It is both one of the most widely distributed psilocybin mushrooms in nature, and one of the most potent. The mushrooms have a distinctive conical to bell-shaped cap, up to 2.5 cm (1 in) in diameter, with a small nipple-like protrusion on the top. They are yellow to brown, covered with radial grooves when moist, and fade to a lighter color as they mature. Their stipes tend to be slender and long, and the same color or slightly lighter than the cap. The gill attachment to the stipe is adnexed, and they are initially cream-colored before tinting purple to black as the spores mature. The spores are dark purplish-brown in mass, ellipsoid in shape, and measure 10.5–15 by 6.5–8.5 micrometres.
Psilocybe cyanescens, commonly known as the wavy cap or potent psilocybe, is a species of potent psychedelic mushroom. The main compounds responsible for its psychedelic effects are psilocybin and psilocin. It belongs to the family Hymenogastraceae. A formal description of the species was published by Elsie Wakefield in 1946 in the Transactions of the British Mycological Society, based on a specimen she had recently collected at Kew Gardens. She had begun collecting the species as early as 1910. The mushroom is not generally regarded as being physically dangerous to adults. Since all the psychoactive compounds in P. cyanescens are water-soluble, the fruiting bodies can be rendered non-psychoactive through parboiling, allowing their culinary use. However, since most people find them overly bitter and they are too small to have great nutritive value, this is not frequently done.
Psilocin is a substituted tryptamine alkaloid and a serotonergic psychedelic substance. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. Acting on the 5-HT2A receptors, psilocin modulates the production and reuptake of serotonin. The mind-altering effects of psilocin are highly variable and subjective and resemble those of LSD and DMT.
Baeocystin is a zwitterionic alkaloid and analog of psilocybin. It is found as a minor compound in most psilocybin mushrooms together with psilocybin, norbaeocystin, aeruginascin, and psilocin. Baeocystin is an N-demethylated derivative of psilocybin, and a phosphorylated derivative of 4-HO-NMT (4-hydroxy-N-methyltryptamine). The structures at right illustrate baeocystin in its zwitterionic form.
Norbaeocystin is a psilocybin mushroom alkaloid and analog of psilocybin. It is found as a minor compound in most psilocybin mushrooms together with psilocin, psilocybin, aeruginascin, and baeocystin, from which it is a derivative.
Psilocybe azurescens is a species of psychedelic mushroom whose main active compounds are psilocybin and psilocin. It is among the most potent of the tryptamine-bearing mushrooms, containing up to 1.8% psilocybin, 0.5% psilocin, and 0.4% baeocystin by dry weight, averaging to about 1.1% psilocybin and 0.15% psilocin. It belongs to the family Hymenogastraceae in the order Agaricales.
4-Hydroxy-5-methoxydimethyltryptamine, also known as 4-HO-5-MeO-DMT or psilomethoxin, is a hypothetical novel psychedelic drug. It is the 4-hydroxy counterpart of 5-MeO-DMT, or the 5-methoxy counterpart of psilocin.
Ethocybin is a homologue of the mushroom alkaloid psilocybin, and a semi-synthetic psychedelic alkaloid of the tryptamine family. Effects of ethocybin are comparable to those of a shorter LSD or psilocybin trip, although intensity and duration vary depending on dosage, individual physiology, and set and setting.
A serotonin receptor agonist is an agonist of one or more serotonin receptors. They activate serotonin receptors in a manner similar to that of serotonin, a neurotransmitter and hormone and the endogenous ligand of the serotonin receptors.
Psilocybe baeocystis is a psilocybin mushroom of the family Hymenogastraceae. It contains the hallucinogenic compounds psilocybin, psilocin and baeocystin. The species is commonly known by various names such as bottle caps, knobby tops, blue bells, olive caps.
Pholiotina cyanopus is a species of fungus that contains psychoactive compounds including psilocybin and the uncommon aeruginascin. Originally described as Galerula cyanopus by American mycologist George Francis Atkinson in 1918. It was transferred to Conocybe by Robert Kühner in 1935 before being transferred to Pholiotina by Rolf Singer in 1950. A 2013 molecular phylogenetics study found it to belong to a group of species currently assigned to Pholiotina that are more closely related to Galerella nigeriensis than to Pholiotina or Conocybe. It is likely that it will be moved to a different genus in the future, but this has not happened yet.
Aeruginascin or N,N,N-trimethyl-4-phosphoryloxytryptamine is an indoleamine derivative which occurs naturally within the mushrooms Inocybe aeruginascens and Pholiotina cyanopus, and Psilocybe cubensis. Aeruginascin is the N-trimethyl analogue of psilocybin. It is closely related to the frog skin toxin bufotenidine (5-HTQ), a potent 5-HT3 receptor agonist, but the aeruginascin metabolite 4-HO-TMT shows strong binding at the 5-HT2 receptors similar to psilocin. The first scientific literature about the pharmacological effects of aeruginascin is from a study published by Gartz in 1989. Across 23 analyzed cases of accidental hallucinogenic mushroom poisonings, people who had ingested the mushroom Inocybe aeruginascens reported only euphoric experiences. This is in contrast to the slight and in some cases extremely dysphoric experiences reported from the accidental ingestion of non aeruginascin containing mushrooms (containing solely psilocybin and psilocin).
Psilocybe serbica is a species of mushroom in the family Hymenogastraceae. The mushroom contains the psychotropic compounds psilocybin and psilocin, and also related tryptamine alkaloids baeocystin, norbaeocystin, and aeruginascin. It is closely related to Psilocybe aztecorum. It was reported as new to science by Meinhard Moser and Egon Horak in 1969. Molecular analysis published in 2010 has shown that P. serbica is the same species as Psilocybe bohemica described by Šebek in 1983, Psilocybe arcana described by Borovička and Hlaváček in 2001, and Psilocybe moravica by Borovička in 2003. Psilocybe serbica is common in Central Europe.
Substituted tryptamines, or serotonin analogues, are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all tryptamines contain an indole ring, joined to an amino (NH2) group via an ethyl (−CH2–CH2−) sidechain. In substituted tryptamines, the indole ring, sidechain, and/or amino group are modified by substituting another group for one of the hydrogen (H) atoms.
5-MeO-NBpBrT is a N-substituted member of the methoxytryptamine family of compounds. Like other such compounds it acts as an antagonist for the 5-HT2A receptor, with a claimed 100x selectivity over the closely related 5-HT2C receptor. While N-benzyl substitution of psychedelic phenethylamines often results in potent 5-HT2A agonists, it had been thought that N-benzyl tryptamines show much lower efficacy and are either very weak partial agonists or antagonists at 5-HT2A, though more recent research has shown stronger agonist activity for 3-substituted benzyl derivatives. Extending the benzyl group to a substituted phenethyl can also recover agonist activity in certain cases.
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