Aeruginascin
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Formula | C13H20N2O4P |
Molar mass | 299.287 g·mol−1 |
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Aeruginascin or N,N,N-trimethyl-4-phosphoryloxytryptamine is an indoleamine derivative which occurs naturally within the mushroom Inocybe aeruginascens[1][2][3][4][5] and Pholiotina cyanopus. 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.[6][7] The first scientific literature about the pharmacological effects of aeruginascin is from a study published by Gartz in 1989.[8] Across 23 analyzed cases of accidental hallucinogenic mushroom poisonings, people who had ingested the mushroom Inocybe aeruginascens reported only euphoric experiences.[9] 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).
References[]
- ^ Gartz J (1995). "Inocybe aeruginascens Babos". Eleusis, Journal of Psychoactive Plants & Compounds. Museo Civico di Rovereto. 3: 31–4.
- ^ 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): 665–6. doi:10.1055/s-2006-931576. PMID 16673333. Archived from the original (PDF) on 2011-05-24.
- ^ 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.
- ^ 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): 9512–8. doi:10.1021/jf302767e. PMID 22957740.
- ^ 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). "Psychotria nuda (Cham. & Schltdl.) Wawra". Molecules. 24 (6): 1026. doi:10.3390/molecules24061026. PMC 6471101. PMID 30875889.
- ^ Chadeayne, Andrew R.; Pham, Duyen N. K.; Reid, Brian G.; Golen, James A.; Manke, David R. (2020-07-02). "Active Metabolite of Aeruginascin (4-Hydroxy-N,N,N-trimethyltryptamine): Synthesis, Structure, and Serotonergic Binding Affinity". ACS Omega. 5 (27): 16940–16943. doi:10.1021/acsomega.0c02208. ISSN 2470-1343. PMC 7365549. PMID 32685863.
- ^ Bauer, Barbara E. (2020-07-07). "Study Finds Aeruginascin Metabolite 4-HO-TMT is Active at the Serotonin 5-HT2A Receptor". Psychedelic Science Review. Archived from the original on 2020-08-05. Retrieved 2021-09-07.
- ^ Gartz J (January 1989). "Analysis of Aeruginascin in Fruit Bodies of the Mushroom Inocybe aeruginascens". International Journal of Crude Drug Research. 27 (3): 141–144. doi:10.3109/13880208909053954. ISSN 0167-7314.
- ^ "Aeruginascin". Psychedelic Science Review. 2018-11-19. Retrieved 2021-09-07.
- Drugs not assigned an ATC code
- Tryptamine alkaloids
- Psychedelic tryptamines
- Mycotoxins
- Organophosphates
- Amine stubs