Aeruginascin

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).

Inocybe aeruginascens
Aeruginascin
Clinical data
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) Y
  • Key:OIIPFLWAQQNCHA-UHFFFAOYSA-N Y
  (verify)

References
  1. Gartz J (1995). "Inocybe aeruginascens Babos". Eleusis, Journal of Psychoactive Plants & Compounds. Museo Civico di Rovereto. 3: 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): 665–6. doi:10.1055/s-2006-931576. PMID 16673333. 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): 9512–8. 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). "Psychotria nuda (Cham. & Schltdl.) Wawra". Molecules. 24 (6): 1026. doi:10.3390/molecules24061026. PMC 6471101. PMID 30875889.
  6. 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.
  7. 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.
  8. 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.
  9. "Aeruginascin". Psychedelic Science Review. 2018-11-19. Retrieved 2021-09-07.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.