Aeruginascin

Quality 0.50 · 1 view · Updated 2 months ago

Chemical compound

title: "Aeruginascin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["mycotoxins", "non-hallucinogenic-5-ht2a-receptor-agonists", "peripherally-selective-drugs", "4-phosphoryloxytryptamines", "prodrugs", "psychedelic-tryptamines", "quaternary-ammonium-compounds", "serotonin-receptor-agonists", "n,n,n-trialkyltryptamines"] description: "Chemical compound" topic_path: "general/mycotoxins" source: "https://en.wikipedia.org/wiki/Aeruginascin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| verifiedrevid = 450944744 | image = Aeruginascin.svg | image_class = skin-invert-image | width = 200px | image2 = 4-PO-TMT 3D.png | image_class2 = bg-transparent | width2 = 200px

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | routes_of_administration = | class = | ATC_prefix = None | ATC_suffix =

| legal_AU = | legal_CA = | legal_DE = NpSG | legal_UK = Class A | legal_US = | legal_US_comment = | legal_status =

| bioavailability = | protein_bound = | metabolism = | onset = | elimination_half-life = | duration_of_action = | excretion =

| CAS_number_Ref = | CAS_number = 114264-95-8 | UNII_Ref = | UNII = 7U9WQY1P7R | PubChem = 60208479 | ChemSpiderID_Ref = | ChemSpiderID = 26233970 | synonyms = 4-Phosphoryloxy-N,N,N-trimethyltryptamine; 4-PO-TMT; 4-PO-N,N,N-TMT; 4-Hydroxy-N,N,N-trimethyltryptamine 4-phosphate

| IUPAC_name = [3-[2-(Trimethylazaniumyl)ethyl]-1H-indol-4-yl] hydrogen phosphate | C=13 | H=20 | N=2 | O=4 | P=1 | SMILES = CN+(C)CCc1c[nH]c2c1c(ccc2)OP(=O)(O)[O-] | StdInChI_Ref = | StdInChI = 1S/C13H19N2O4P/c1-15(2,3)8-7-10-9-14-11-5-4-6-12(13(10)11)19-20(16,17)18/h4-6,9,14H,7-8H2,1-3H3,(H-,16,17,18) | StdInChIKey_Ref = | StdInChIKey = OIIPFLWAQQNCHA-UHFFFAOYSA-N

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. It was discovered by Jochen Gartz.

Use and effects

::figure[src="https://upload.wikimedia.org/wikipedia/commons/c/cb/Inocybe_aeruginascens.jpg" caption="''[[Inocybe aeruginascens]]''."] ::

The first report about the possible effects of aeruginascin is from a study published by Jochen 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). However, these findings are anecdotal and preliminary.

Pharmacology

Aeruginascin is the N-trimethyl analogue of psilocybin. It is closely related to the frog skin toxin bufotenidine (5-HTQ), a potent serotonin 5-HT3 receptor agonist, but the aeruginascin metabolite 4-HO-TMT (thought to be its active form) shows strong binding at the serotonin 5-HT2 receptors similar to psilocin. Aeruginascin itself has been found to have high affinity for the serotonin 5-HT1A, 5-HT2A, and 5-HT2B receptors, but does not bind to the 5-HT3 receptor. Unlike psilocybin, but similarly to 4-HO-TMT, aeruginascin does not produce the head-twitch response in rodents. It lacks affinity or activation of the mouse 5-HT2A and 5-HT1A receptors.

Chemistry

Analogues

Analogues of aerguinascin include 4-HO-TMT, norbaeocystin (4-PO-T), 4-hydroxytryptamine (4-HT or 4-HO-T), baeocystin (4-PO-NMT), norpsilocin (4-HO-NMT), psilocybin (4-PO-DMT), psilocin (4-HO-DMT), and ethocybin (4-PO-DET), among others.

References

References

  1. (1995). "Inocybe aeruginascens Babos.". Museo Civico di Rovereto.
  2. (June 2006). "Aeruginascin, a trimethylammonium analogue of psilocybin from the hallucinogenic mushroom Inocybe aeruginascens". Planta Medica.
  3. (February 2020). "Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin". Journal of Natural Products.
  4. (September 2012). "N-methylated tryptamine derivatives in citrus genus plants: identification of N,N,N-trimethyltryptamine in bergamot". Journal of Agricultural and Food Chemistry.
  5. (March 2019). "Antimycobacterial and Nitric Oxide Production Inhibitory Activities of Triterpenes and Alkaloids from ''Psychotria nuda'' (Cham. & Schltdl.) Wawra". Molecules.
  6. (November 2022). "Extensive Collection of Psychotropic Mushrooms with Determination of Their Tryptamine Alkaloids". International Journal of Molecular Sciences.
  7. (14 September 2022). "CaaMTech Publishes Fundamental Research on Aeruginascin Derivatives". CaaMTech.
  8. (February 2023). "Indole Alkaloids from Psychoactive Mushrooms: Chemical and Pharmacological Potential as Psychotherapeutic Agents". Biomedicines.
  9. (June 2006). "Aeruginascin, a trimethylammonium analogue of psilocybin from the hallucinogenic mushroom Inocybe aeruginascens". Planta Med.
  10. Butler, Gavin. (31 March 2020). "Scientists are Trying to Redesign Magic Mushrooms so You Never Have a Bad Trip".
  11. Bauer, Barbara E.. (13 November 2020). "Aeruginascin Identified in Psilocybe cubensis Magic Mushrooms".
  12. K. Mandrake. (1 March 2021). "Psilocybin Isn't the Only Compound in Magic Mushrooms—Here's What Else There Is".
  13. (January 1989). "Analysis of Aeruginascin in Fruit Bodies of the Mushroom Inocybe aeruginascens". International Journal of Crude Drug Research.
  14. (2018-11-19). "Aeruginascin".
  15. (December 2023). "A journey with psychedelic mushrooms: From historical relevance to biology, cultivation, medicinal uses, biotechnology, and beyond". Biotechnol Adv.
  16. (July 2020). "Active Metabolite of Aeruginascin (4-Hydroxy-N,N,N-trimethyltryptamine): Synthesis, Structure, and Serotonergic Binding Affinity". ACS Omega.
  17. (2020-07-07). "Study Finds Aeruginascin Metabolite 4-HO-TMT is Active at the Serotonin 5-HT2A Receptor".
  18. (July 2020). "Active Metabolite of Aeruginascin (4-Hydroxy-N,N,N-trimethyltryptamine): Synthesis, Structure, and Serotonergic Binding Affinity". ACS Omega.
  19. (October 2024). "Pharmacological and behavioural effects of tryptamines present in psilocybin-containing mushrooms". Br J Pharmacol.
  20. (November 2022). "Structure-Activity Relationships for Psilocybin, Baeocystin, Aeruginascin, and Related Analogues to Produce Pharmacological Effects in Mice". ACS Pharmacol Transl Sci.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

mycotoxinsnon-hallucinogenic-5-ht2a-receptor-agonistsperipherally-selective-drugs4-phosphoryloxytryptaminesprodrugspsychedelic-tryptaminesquaternary-ammonium-compoundsserotonin-receptor-agonistsn,n,n-trialkyltryptamines