Aeruginascin Explained

Aeruginascin or N,N,N-trimethyl-4-phosphoryloxytryptamine is an indoleamine derivative which occurs naturally within the mushrooms Inocybe aeruginascens,[1] [2] [3] [4] [5] [6] Pholiotina cyanopus, and Psilocybe cubensis.[7] 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.[8] [9] The first scientific literature about the pharmacological effects of aeruginascin is from a study published by Gartz in 1989.[10] Across 23 analyzed cases of accidental hallucinogenic mushroom poisonings, people who had ingested the mushroom Inocybe aeruginascens reported only euphoric experiences.[11] 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).

Notes and References

  1. Gartz J . Inocybe aeruginascens Babos. . Eleusis, Journal of Psychoactive Plants & Compounds. . 1995 . 3 . 31–4 . Museo Civico di Rovereto.
  2. Jensen N, Gartz J, Laatsch H . Aeruginascin, a trimethylammonium analogue of psilocybin from the hallucinogenic mushroom Inocybe aeruginascens . Planta Medica . 72 . 7 . 665–666 . June 2006 . 16673333 . 10.1055/s-2006-931576 . 260281286 . dead . https://web.archive.org/web/20110524153555/http://wwwuser.gwdg.de/~ucoc/laatsch/168_Aeruginascin_col.pdf . 2011-05-24 .
  3. Sherwood AM, Halberstadt AL, Klein AK, McCorvy JD, Kaylo KW, Kargbo RB, Meisenheimer P . Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin . Journal of Natural Products . 83 . 2 . 461–467 . February 2020 . 32077284 . 10.1021/acs.jnatprod.9b01061 . 211214973 .
  4. Servillo L, Giovane A, Balestrieri ML, Cautela D, Castaldo D . N-methylated tryptamine derivatives in citrus genus plants: identification of N,N,N-trimethyltryptamine in bergamot . Journal of Agricultural and Food Chemistry . 60 . 37 . 9512–9518 . September 2012 . 22957740 . 10.1021/jf302767e .
  5. de Carvalho Junior AR, Oliveira Ferreira R, de Souza Passos M, da Silva Boeno SI, Glória das Virgens LL, Ventura TL, Calixto SD, Lassounskaia E, de Carvalho MG, Braz-Filho R, Curcino Vieira IJ . 6 . Antimycobacterial and Nitric Oxide Production Inhibitory Activities of Triterpenes and Alkaloids from Psychotria nuda (Cham. & Schltdl.) Wawra . Molecules . 24 . 6 . 1026 . March 2019 . 30875889 . 6471101 . 10.3390/molecules24061026 . free .
  6. Gotvaldová K, Borovička J, Hájková K, Cihlářová P, Rockefeller A, Kuchař M . Extensive Collection of Psychotropic Mushrooms with Determination of Their Tryptamine Alkaloids . International Journal of Molecular Sciences . 23 . 22 . 14068 . November 2022 . 36430546 . 10.3390/ijms232214068 . 9693126 . free .
  7. Web site: CaaMTech Publishes Fundamental Research on Aeruginascin Derivatives. 14 September 2022 .
  8. Chadeayne AR, Pham DN, Reid BG, Golen JA, Manke DR . Active Metabolite of Aeruginascin (4-Hydroxy-N,N,N-trimethyltryptamine): Synthesis, Structure, and Serotonergic Binding Affinity . ACS Omega . 5 . 27 . 16940–16943 . July 2020 . 32685863 . 7365549 . 10.1021/acsomega.0c02208 .
  9. Web site: Bauer BE . 2020-07-07. Study Finds Aeruginascin Metabolite 4-HO-TMT is Active at the Serotonin 5-HT2A Receptor. live. 2021-09-07. Psychedelic Science Review . en-US . https://web.archive.org/web/20200805013154/https://psychedelicreview.com/study-finds-aeruginascin-metabolite-4-ho-tmt-is-active-at-the-serotonin-5-ht2a-receptor/ . 2020-08-05 .
  10. Gartz J . January 1989. Analysis of Aeruginascin in Fruit Bodies of the Mushroom Inocybe aeruginascens. International Journal of Crude Drug Research. en. 27. 3. 141–144. 10.3109/13880208909053954. 0167-7314.
  11. Web site: 2018-11-19. Aeruginascin. 2021-09-07. Psychedelic Science Review. en-US.

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