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Aeruginascin

Aeruginascin
Clinical data
Other names4-Phosphoryloxy-N,N,N-trimethyltryptamine; 4-PO-TMT; 4-PO-N,N,N-TMT; 4-Hydroxy-N,N,N-trimethyltryptamine 4-phosphate
ATC code
  • None
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
Identifiers
  • [3-[2-(Trimethylazaniumyl)ethyl]-1H-indol-4-yl] hydrogen phosphate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H20N2O4P
Molar mass299.287 g·mol−1
3D model (JSmol)
  • C[N+](C)(C)CCc1c[nH]c2c1c(ccc2)OP(=O)(O)[O-]
  • InChI=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) checkY
  • Key:OIIPFLWAQQNCHA-UHFFFAOYSA-N checkY
  (verify)

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]

  1. ^ Gartz J (1995). "Inocybe aeruginascens Babos". Eleusis, Journal of Psychoactive Plants & Compounds. 3. Museo Civico di Rovereto: 31–4.
  2. ^ Jensen N, Gartz J, Laatsch H (June 2006). "Aeruginascin, a trimethylammonium analogue of psilocybin from the hallucinogenic mushroom Inocybe aeruginascens" (PDF). Planta Medica. 72 (7): 665–666. doi:10.1055/s-2006-931576. PMID 16673333. S2CID 260281286. Archived from the original (PDF) on 2011-05-24.
  3. ^ 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. S2CID 211214973.
  4. ^ Servillo L, Giovane A, Balestrieri ML, Cautela D, Castaldo D (September 2012). "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. Bibcode:2012JAFC...60.9512S. doi:10.1021/jf302767e. PMID 22957740.
  5. ^ de Carvalho Junior AR, Oliveira Ferreira R, de Souza Passos M, da Silva Boeno SI, Glória das Virgens LL, Ventura TL, et al. (March 2019). "Antimycobacterial and Nitric Oxide Production Inhibitory Activities of Triterpenes and Alkaloids from Psychotria nuda (Cham. & Schltdl.) Wawra". Molecules. 24 (6): 1026. doi:10.3390/molecules24061026. PMC 6471101. PMID 30875889.
  6. ^ a b Gotvaldová K, Borovička J, Hájková K, Cihlářová P, Rockefeller A, Kuchař M (November 2022). "Extensive Collection of Psychotropic Mushrooms with Determination of Their Tryptamine Alkaloids". International Journal of Molecular Sciences. 23 (22): 14068. doi:10.3390/ijms232214068. PMC 9693126. PMID 36430546.
  7. ^ "CaaMTech Publishes Fundamental Research on Aeruginascin Derivatives". 14 September 2022.
  8. ^ Plazas E, Faraone N (February 2023). "Indole Alkaloids from Psychoactive Mushrooms: Chemical and Pharmacological Potential as Psychotherapeutic Agents". Biomedicines. 11 (2): 461. doi:10.3390/biomedicines11020461. PMC 9953455. 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. ^ Jensen N, Gartz J, Laatsch H (June 2006). "Aeruginascin, a trimethylammonium analogue of psilocybin from the hallucinogenic mushroom Inocybe aeruginascens". Planta Med. 72 (7): 665–666. doi:10.1055/s-2006-931576. PMID 16673333.
  10. ^ Butler G (31 March 2020). "Scientists are Trying to Redesign Magic Mushrooms so You Never Have a Bad Trip". VICE. Retrieved 27 January 2025.
  11. ^ Bauer BE (13 November 2020). "Aeruginascin Identified in Psilocybe cubensis Magic Mushrooms". Psychedelic Science Review. Retrieved 27 January 2025.
  12. ^ K. Mandrake (1 March 2021). "Psilocybin Isn't the Only Compound in Magic Mushrooms—Here's What Else There Is". doubleblindmag.com. Retrieved 27 January 2025. 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.
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