Chemistry:Aeruginascin

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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,[1][2][3][4][5][6] Pholiotina cyanopus,[6] and Psilocybe cubensis.[7] It was discovered by Jochen Gartz.[8][9][10][11][12]

Use and effects

Inocybe aeruginascens.

The first report about the possible effects of aeruginascin is from a study published by Jochen Gartz in 1989.[13] Across 23 analyzed cases of accidental hallucinogenic mushroom poisonings, people who had ingested the mushroom Inocybe aeruginascens reported only euphoric experiences.[14][15] 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).[15] However, these findings are anecdotal and preliminary.[15]

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.[16][17] 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.[18] Unlike psilocybin, but similarly to 4-HO-TMT, aeruginascin does not produce the head-twitch response in rodents.[19][20] It lacks affinity or activation of the mouse 5-HT2A and 5-HT1A receptors.[20]

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.

See also

References

  1. ↑ "Inocybe aeruginascens Babos.". Eleusis, Journal of Psychoactive Plants & Compounds. (Museo Civico di Rovereto) 3: 31–4. 1995. http://www.museocivico.rovereto.tn.it/context.jsp?ID_LINK=111258&area=279. 
  2. ↑ "Aeruginascin, a trimethylammonium analogue of psilocybin from the hallucinogenic mushroom Inocybe aeruginascens". Planta Medica 72 (7): 665–666. June 2006. doi:10.1055/s-2006-931576. PMID 16673333. Bibcode: 2006PlMed..72..665J. http://wwwuser.gwdg.de/~ucoc/laatsch/168_Aeruginascin_col.pdf. 
  3. ↑ "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. doi:10.1021/acs.jnatprod.9b01061. PMID 32077284. Bibcode: 2020JNAtP..83..461S. 
  4. ↑ "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. doi:10.1021/jf302767e. PMID 22957740. Bibcode: 2012JAFC...60.9512S. 
  5. ↑ "Antimycobacterial and Nitric Oxide Production Inhibitory Activities of Triterpenes and Alkaloids from Psychotria nuda (Cham. & Schltdl.) Wawra". Molecules 24 (6): 1026. March 2019. doi:10.3390/molecules24061026. PMID 30875889. 
  6. ↑ 6.0 6.1 "Extensive Collection of Psychotropic Mushrooms with Determination of Their Tryptamine Alkaloids". International Journal of Molecular Sciences 23 (22). November 2022. doi:10.3390/ijms232214068. PMID 36430546. 
  7. ↑ "CaaMTech Publishes Fundamental Research on Aeruginascin Derivatives". CaaMTech. 14 September 2022. https://caam.tech/caamtech-publishes-fundamental-research-on-aeruginascin-derivatives/. 
  8. ↑ "Indole Alkaloids from Psychoactive Mushrooms: Chemical and Pharmacological Potential as Psychotherapeutic Agents". Biomedicines 11 (2): 461. February 2023. doi:10.3390/biomedicines11020461. PMID 36830997. "Some magic mushrooms, such as those belonging to the Inocybe genus, do not have reports of traditional uses and instead were discovered by accidental hallucinogenic poisonings. For example, I. aeruginascens (Table 1) was described as psychoactive in the 1980s from unintentional intoxication in Germany and Hungary because of its similarity to the edible mushroom Marasmius oreades. Despite the unintentional consumption of I. aeruginascens, the user reported an extremely pleasant experience, described as a "good trip". This feature caught the attention of the German chemist Jochen Gartz, who discovered a new alkaloid structurally related to those found in other species of magic mushrooms, although in turn, has different pharmacological properties [30].". 
  9. ↑ "Aeruginascin, a trimethylammonium analogue of psilocybin from the hallucinogenic mushroom Inocybe aeruginascens". Planta Med 72 (7): 665–666. June 2006. doi:10.1055/s-2006-931576. PMID 16673333. Bibcode: 2006PlMed..72..665J. 
  10. ↑ Butler, Gavin (31 March 2020). "Scientists are Trying to Redesign Magic Mushrooms so You Never Have a Bad Trip". https://www.vice.com/en/article/scientists-redesign-magic-mushrooms-so-you-never-have-a-bad-trip/. 
  11. ↑ Bauer, Barbara E. (13 November 2020). "Aeruginascin Identified in Psilocybe cubensis Magic Mushrooms". https://psychedelicreview.com/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". https://doubleblindmag.com/mushrooms/about-magic-mushrooms/psilocybin-magic-mushrooms-compounds/. "On the timeline of mushroom alkaloid discovery, aeruginascin sits somewhere in the middle. It was first discovered by Jochen Gartz in 1989 in Inocybe aeruginascens [...] though recent research in late 2020 by Klára Gotvaldová and colleagues at University of Chemistry and Technology, Czech Republic discovered the presence of this alkaloid in Psilocybe cubensis, suggesting it may be more common than was once thought. [...] As well as being chemically similar to other mushroom alkaloids, aeruginascin also shares a similar structure to bufotenidine, a chemical found in the venom of some toads. In the same paper from 1989, Jochen Gartz analysed 23 cases of accidental ingestion of Inocybe aeruginascens and found that the effects always resulted in euphoria, however as with other alkaloids described here, little is known about the effects of pure formulations of aeruginascin." 
  13. ↑ "Analysis of Aeruginascin in Fruit Bodies of the Mushroom Inocybe aeruginascens" (in en). International Journal of Crude Drug Research 27 (3): 141–144. January 1989. doi:10.3109/13880208909053954. ISSN 0167-7314. http://www.tandfonline.com/doi/full/10.3109/13880208909053954. 
  14. ↑ "Aeruginascin" (in en-US). 2018-11-19. https://psychedelicreview.com/compound/aeruginascin/. 
  15. ↑ 15.0 15.1 15.2 "A journey with psychedelic mushrooms: From historical relevance to biology, cultivation, medicinal uses, biotechnology, and beyond". Biotechnol Adv 69. December 2023. doi:10.1016/j.biotechadv.2023.108247. PMID 37659744. 
  16. ↑ "Active Metabolite of Aeruginascin (4-Hydroxy-N,N,N-trimethyltryptamine): Synthesis, Structure, and Serotonergic Binding Affinity". ACS Omega 5 (27): 16940–16943. July 2020. doi:10.1021/acsomega.0c02208. PMID 32685863. 
  17. ↑ "Study Finds Aeruginascin Metabolite 4-HO-TMT is Active at the Serotonin 5-HT2A Receptor" (in en-US). 2020-07-07. https://psychedelicreview.com/study-finds-aeruginascin-metabolite-4-ho-tmt-is-active-at-the-serotonin-5-ht2a-receptor/. 
  18. ↑ "Active Metabolite of Aeruginascin (4-Hydroxy-N,N,N-trimethyltryptamine): Synthesis, Structure, and Serotonergic Binding Affinity". ACS Omega 5 (27): 16940–16943. July 2020. doi:10.1021/acsomega.0c02208. PMID 32685863. 
  19. ↑ "Pharmacological and behavioural effects of tryptamines present in psilocybin-containing mushrooms". Br J Pharmacol 181 (19): 3627–3641. October 2024. doi:10.1111/bph.16466. PMID 38825326. 
  20. ↑ 20.0 20.1 "Structure-Activity Relationships for Psilocybin, Baeocystin, Aeruginascin, and Related Analogues to Produce Pharmacological Effects in Mice". ACS Pharmacol Transl Sci 5 (11): 1181–1196. November 2022. doi:10.1021/acsptsci.2c00177. PMID 36407948. 



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