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Aeruginascin

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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]

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.[8][9] 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.[10] Unlike psilocybin, but similarly to 4-HO-TMT, aeruginascin does not produce the head-twitch response in rodents.[11][12] It lacks affinity or activation of the mouse 5-HT2A and 5-HT1A receptors.[12]

The first scientific literature about the pharmacological effects of aeruginascin is from a study published by 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]

Inocybe aeruginascens

See also

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References

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  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. ^ Chadeayne AR, Pham DN, Reid BG, Golen JA, Manke DR (July 2020). "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. PMC 7365549. PMID 32685863.
  9. ^ Bauer BE (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.
  10. ^ Chadeayne AR, Pham DN, Reid BG, Golen JA, Manke DR (July 2020). "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. PMC 7365549. PMID 32685863.
  11. ^ Rakoczy RJ, Runge GN, Sen AK, Sandoval O, Wells HG, Nguyen Q, Roberts BR, Sciortino JH, Gibbons WJ, Friedberg LM, Jones JA, McMurray MS (October 2024). "Pharmacological and behavioural effects of tryptamines present in psilocybin-containing mushrooms". Br J Pharmacol. 181 (19): 3627–3641. doi:10.1111/bph.16466. PMID 38825326.
  12. ^ a b Glatfelter GC, Pottie E, Partilla JS, Sherwood AM, Kaylo K, Pham DN, Naeem M, Sammeta VR, DeBoer S, Golen JA, Hulley EB, Stove CP, Chadeayne AR, Manke DR, Baumann MH (November 2022). "Structure-Activity Relationships for Psilocybin, Baeocystin, Aeruginascin, and Related Analogues to Produce Pharmacological Effects in Mice". ACS Pharmacol Transl Sci. 5 (11): 1181–1196. doi:10.1021/acsptsci.2c00177. PMC 9667540. PMID 36407948.
  13. ^ 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.
  14. ^ "Aeruginascin". Psychedelic Science Review. 2018-11-19. Retrieved 2021-09-07.
  15. ^ a b c Pepe M, Hesami M, de la Cerda KA, Perreault ML, Hsiang T, Jones AM (December 2023). "A journey with psychedelic mushrooms: From historical relevance to biology, cultivation, medicinal uses, biotechnology, and beyond". Biotechnol Adv. 69: 108247. doi:10.1016/j.biotechadv.2023.108247. PMID 37659744.
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