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Norbaeocystin zwitterion 3D spacefill.png
Clinical data
Routes of
ATC code
  • none
Legal status
Legal status
  • 3-(2-ammonioethyl)-1H-indol-4-yl hydrogen phosphate
CAS Number
PubChem CID
Chemical and physical data
Formula C10H13N2O4P
Molar mass 256.198 g·mol−1
3D model (JSmol)
  • NCCc1c[nH]c2cccc(OP(=O)(O)O)c12
  • InChI=1S/C10H13N2O4P/c11-5-4-7-6-12-8-2-1-3-9(10(7)8)16-17(13,14)15/h1-3,6,12H,4-5,11H2,(H2,13,14,15)

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. [1] [2]

Norbaeocystin is a N-demethylated derivative of baeocystin (itself a N-demethylated derivative of psilocybin), and a phosphorylated derivative of 4-hydroxytryptamine. The latter is notable as a positional isomer of serotonin, which is 5-hydroxytryptamine.

See also

Related Research Articles

<i>Psilocybe cubensis</i> Species of fungus

Psilocybe cubensis is a species of psilocybin mushroom of moderate potency whose principal active compounds are psilocybin and psilocin. Commonly called shrooms, magic mushrooms, golden halos, cubes, or gold caps, 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 cubensis being the psilocybin mushroom species most common on the black market as a street drug.

<span class="mw-page-title-main">Psilocybin mushroom</span> Mushrooms containing psychoactive indole alkaloids

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. Psilocybin mushrooms have been and continue to be used in indigenous New World cultures in religious, divinatory, or spiritual contexts. Psilocybin mushrooms are also used as recreational drugs. They may be depicted in Stone Age rock art in Africa and Europe but are most famously represented in the Pre-Columbian sculptures and glyphs seen throughout North, Central, and South America.

<i>Psilocybe</i> Genus of fungi

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.

<i>Psilocybe semilanceata</i> Species of fungus in the family Hymenogastraceae, native to Europe

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.

<span class="mw-page-title-main">Psilocin</span> Psychedelic substance

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.

<span class="mw-page-title-main">Baeocystin</span> Chemical compound

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.

<i>Panaeolus cinctulus</i> Species of fungus

Panaeolus cinctulus, syn. Panaeolus subbalteatus, commonly known as the banded mottlegill, weed Panaeolus or subbs is a very common, widely distributed psilocybin mushroom. According to American naturalist and mycologist David Arora, Panaeolus cinctulus is the most common psilocybin mushroom in California.

<span class="mw-page-title-main">4-HO-MiPT</span> Chemical compound

4-HO-MiPT is a synthetic substituted aromatic compound and a lesser-known psychedelic tryptamine. It is thought to be a serotonergic psychedelic, similar to magic mushrooms, LSD and mescaline. Its molecular structure and pharmacological effects somewhat resemble those of the tryptamine psilocin, which is the primary psychoactive chemical in magic mushrooms.

<span class="mw-page-title-main">Indole alkaloid</span> Class of alkaloids

Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.

<span class="mw-page-title-main">Ethocybin</span> Chemical compound

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.

<i>Psilocybe baeocystis</i> Species of fungus

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.

<i>Inocybe aeruginascens</i> Species of fungus

Inocybe aeruginascens is a member of the genus Inocybe which is widely distributed in Europe. The species was first documented by I. Ferencz in Ócsa, Hungary on June 15, 1965.

<i>Pholiotina cyanopus</i> Species of fungus

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.

<span class="mw-page-title-main">Aeruginascin</span> Chemical compound

Aeruginascin or N,N,N-trimethyl-4-phosphoryloxytryptamine is an indoleamine derivative which occurs naturally within the mushroom Inocybe aeruginascens and Pholiotina cyanopus. 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).

<i>Psilocybe serbica</i> Species of fungus

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.

<span class="mw-page-title-main">Substituted tryptamine</span> Class of indoles

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.

<i>N</i>-Methylserotonin Chemical compound

N-Methylserotonin is a tryptamine alkaloid. Chemically, it is a derivative of serotonin in which a methyl group resides at its alkyl amine. It is also called Nω-methylserotonin (Nω-methyl-5-hydroxytryptamine) to distinguish it from tryptamine-derived compounds in which a methyl group is bonded to the nitrogen atom of the indole group.

<span class="mw-page-title-main">Norpsilocin</span> Chemical compound

Norpsilocin (4-HO-NMT) is tryptamine alkaloid recently discovered in 2017 in the psychedelic mushroom Psilocybe cubensis. It is hypothesized to be a dephosphorylated metabolite of baeocystin. Norpsilocin was found to be a full agonist of 5-HT2A receptor. It is also more potent than psilocin.

<small>L</small>-Tryptophan decarboxylase

L-Tryptophan decarboxylase is an enzyme distinguished by the substrate L-tryptophan.


  1. Leung AY, Paul AG (October 1968). "Baeocystin and norbaeocystin: new analogs of psilocybin from Psilocybe baeocystis". Journal of Pharmaceutical Sciences. 57 (10): 1667–71. doi:10.1002/jps.2600571007. PMID   5684732.
  2. Gotvaldova, Klara; Borovicka, Jan; Hajkova, Katerina; Cihlarova, Petra; Rockefeller, Alan; Kuchar, Martin (2022). "Extensive Collection of Psychotropic Mushrooms with Determination of Their Tryptamine Alkaloids". International Journal of Molecular Sciences. 23 (22): 14068. doi: 10.3390/ijms232214068 . ISSN   1422-0067.