Norpsilocin

Last updated
Norpsilocin
Norpsilocin.svg
Clinical data
Other names
  • 4-HO-NMT
  • 4-Hydroxy-N-methyltryptamine
  • N-Desmethylpsilocin
  • AS-63499
  • PLZ-1017
Identifiers
  • 3-[2-(methylamino)ethyl]-1H-indol-4-ol
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H14N2O
Molar mass 190.246 g·mol−1
3D model (JSmol)
  • CNCCC1=CNC2=C1C(=CC=C2)O
  • InChI=1S/C11H14N2O/c1-12-6-5-8-7-13-9-3-2-4-10(14)11(8)9/h2-4,7,12-14H,5-6H2,1H3
  • Key:MTJOWJUQGYWRHT-UHFFFAOYSA-N

Norpsilocin, also known as 4-hydroxy-N-methyltryptamine (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 and was found to be more potent than psilocin. [3] [4] It also has affinity for other serotonin receptors. [5] Moreover, it has been found to cross the blood–brain barrier in animals and to have good metabolic stability similarly to psilocin. [5]

Surprisingly however, norpsilocin failed to induce the head-twitch response, a behavioral proxy of psychedelic effects, in animals. [5] Likewise, norbaeocystin and aeruginascin failed to induce the head-twitch response. [5] Only psilocybin was effective in this regard. [5] In any case, norbaeocystin showed antidepressant-like activity (forced swim test) similarly to psilocybin and fluoxetine in spite of its putative non-hallucinogenic nature. [5] Norpsilocin itself was not tested in this assay. [5]

Norpsilocin is being evaluated for the possible treatment of pervasive developmental disorders in children. [6]

See also

Related Research Articles

<span class="mw-page-title-main">Psilocybin</span> Chemical compound found in some species of mushrooms

Psilocybin, also known as 4-phosphoryloxy-N,N-dimethyltryptamine (4-PO-DMT), and formerly sold under the brand name Indocybin, is a naturally occurring psychedelic prodrug compound produced by more than 200 species of fungi. 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 other classical psychedelics. In general, the effects include euphoria, visual and mental hallucinations, changes in perception, a distorted sense of time, and perceived spiritual experiences. It can also cause adverse reactions such as nausea and panic attacks.

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

Psilocybe cubensis, commonly known as the magic mushroom, shroom, golden halo, golden teacher, 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.

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

Psilocybin mushrooms, commonly known as magic mushrooms,shrooms, or broadly as hallucinogenic mushrooms, are a polyphyletic informal group of fungi that contain psilocybin, which turns into psilocin upon ingestion. The most potent species are members of genus Psilocybe, such as P. azurescens, P. semilanceata, and P. cyanescens, but psilocybin has also been isolated from approximately a dozen other genera, including Panaeolus, Inocybe, Pluteus, Gymnopilus, and Pholiotina.

<i>Psilocybe</i> Genus of fungi

Psilocybe is a genus of gilled mushrooms, growing worldwide, in the family Hymenogastraceae. Many 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 en masse, ellipsoid in shape, and measure 10.5–15 by 6.5–8.5 micrometres.

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

Psilocin, also known as 4-hydroxy-N,N-dimethyltryptamine (4-OH-DMT), is a substituted tryptamine alkaloid and a serotonergic psychedelic. 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 serotonin 5-HT2A receptors, psilocin's psychedelic effects are directly correlated with the drug's occupancy at these receptor sites. The subjective mind-altering effects of psilocin are highly variable and are said to resemble those of lysergic acid diethylamide (LSD) and N,N-dimethyltryptamine (DMT).

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

Baeocystin, also known as norpsilocybin or 4-phosphoryloxy-N-methyltryptamine (4-PO-NMT), 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.

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

Norbaeocystin, also known as 4-phosphoryloxytryptamine (4-PO-T), 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.

<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.

<span class="mw-page-title-main">Serotonin receptor agonist</span> Neurotransmission-modulating substance

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.

<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.

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

Aeruginascin, also known as 4-phosphoryloxy-N,N,N-trimethyltryptamine (4-PO-TMT), is an indoleamine derivative which occurs naturally within the mushrooms Inocybe aeruginascens, Pholiotina cyanopus, and Psilocybe cubensis.

<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.

<span class="mw-page-title-main">5-MeO-NBpBrT</span> Chemical compound

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.

<small>L</small>-Tryptophan decarboxylase Enzyme

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

<span class="mw-page-title-main">4-HO-TMT</span> Serotonergic compound

4-HO-TMT, or 4-OH-TMT, also known as 4-hydroxy-N,N,N-trimethyltryptamine or as dephosphorylated aeruginascin, is a substituted tryptamine derivative and the active form of aeruginascin (4-PO-TMT), analogously to how psilocin (4-HO-DMT) is the active form of psilocybin (4-PO-DMT). 4-HO-TMT is closely related to bufotenidine, the N-trimethyl analogue of serotonin.

<span class="mw-page-title-main">4-Hydroxytryptamine</span> Serotonin receptor agonist

4-Hydroxytryptamine, also known as N,N-didesmethylpsilocin, is a naturally occurring tryptamine alkaloid. It is a positional isomer of serotonin and is the dephosphorylated form of norbaeocystin. The compound may serve as an alternative precursor of psilocybin in psilocybin mushrooms.

References

  1. Lenz C, Wick J, Hoffmeister D (October 2017). "Identification of ω-N-Methyl-4-hydroxytryptamine (Norpsilocin) as a Psilocybe Natural Product". Journal of Natural Products . 80 (10): 2835–2838. doi:10.1021/acs.jnatprod.7b00407. PMID   28929753.
  2. 1 2 "Two New Crystalline Forms of Norpsilocin".
  3. "Study Finds Norpsilocin is More Potent Than Psilocin at 5-HT2A".
  4. Sherwood AM, Halberstadt AL, Klein AK, McCorvy JD, Kaylo KW, Kargbo RB, Meisenheimer P (February 2020). "Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin". Journal of Natural Products . 83 (2): 461–467. doi:10.1021/acs.jnatprod.9b01061. PMID   32077284.
  5. 1 2 3 4 5 6 7 Rakoczy RJ, Runge GN, Sen AK, Sandoval O, Wells HG, Nguyen Q, Roberts BR, Sciortino JH, Gibbons WJ, Friedberg LM, Jones JA, McMurray MS (October 2024). "Pharmacological and behavioural effects of tryptamines present in psilocybin-containing mushrooms". Br J Pharmacol. 181 (19): 3627–3641. doi: 10.1111/bph.16466 . PMID   38825326.
  6. "Norpsilocin - Pilz Bioscience". AdisInsight. 19 January 2021. Retrieved 27 October 2024.