Movatterモバイル変換


[0]ホーム

URL:


Jump to content
WikipediaThe Free Encyclopedia
Search

Aeruginascin

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
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
Identifiers
  • [3-[2-(Trimethylazaniumyl)ethyl]-1H-indol-4-yl] hydrogen phosphate
CAS Number
PubChemCID
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 as4-phosphoryloxy-N,N,N-trimethyltryptamine (4-PO-TMT), is anindoleamine derivative which occurs naturally within the mushroomsInocybe aeruginascens,[1][2][3][4][5][6]Pholiotina cyanopus,[6] andPsilocybe cubensis.[7] It was discovered byJochen Gartz.[8][9][10][11][12]

Use and effects

[edit]
Inocybe aeruginascens.

The first report about the possible effects of aeruginascin is from a study published byJochen Gartz in 1989.[13] Across 23 analyzed cases of accidental hallucinogenic mushroom poisonings, people who had ingested the mushroomInocybe aeruginascens reported onlyeuphoric experiences.[14][15] This is in contrast to the slight and in some cases extremelydysphoric experiences reported from the accidental ingestion of non-aeruginascin-containing mushrooms (containing solely psilocybin and psilocin).[15] However, these findings areanecdotal and preliminary.[15]

Pharmacology

[edit]

Aeruginascin is theN-trimethylanalogue ofpsilocybin. It is closely related to the frog skin toxinbufotenidine (5-HTQ), a potentserotonin5-HT3 receptor agonist, but the aeruginascinmetabolite4-HO-TMT (thought to be its active form) shows strong binding at the serotonin5-HT2 receptors similar topsilocin.[16][17] Aeruginascin itself has been found to have highaffinity for the serotonin5-HT1A,5-HT2A, and5-HT2B receptors, but does not bind to the 5-HT3 receptor.[18] Unlike psilocybin, but similarly to 4-HO-TMT, aeruginascin does not produce thehead-twitch response in rodents.[19][20] It lacks affinity or activation of the mouse 5-HT2A and 5-HT1A receptors.[20]

Chemistry

[edit]

Analogues

[edit]

Analogues of aerguinascin include4-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), andethocybin (4-PO-DET), among others.

See also

[edit]

References

[edit]
  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.Bibcode:2006PlMed..72..665J.doi:10.1055/s-2006-931576.PMID 16673333.S2CID 260281286. Archived fromthe 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.Bibcode:2020JNAtP..83..461S.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 fromPsychotria nuda (Cham. & Schltdl.) Wawra".Molecules.24 (6): 1026.doi:10.3390/molecules24061026.PMC 6471101.PMID 30875889.
  6. ^abGotvaldová 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".CaaMTech. 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.Bibcode:2006PlMed..72..665J.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. Retrieved27 January 2025.
  11. ^Bauer BE (13 November 2020)."Aeruginascin Identified in Psilocybe cubensis Magic Mushrooms".Psychedelic Science Review. Retrieved27 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. Retrieved27 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.
  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. Retrieved2021-09-07.
  15. ^abcPepe 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.
  16. ^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.
  17. ^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. Retrieved2021-09-07.
  18. ^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.
  19. ^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.
  20. ^abGlatfelter 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.

External links

[edit]
Tryptamines
No ring subs.
4-Hydroxytryptamines
5-Hydroxytryptamines
5-Methoxytryptamines
Other ring subs.
α-Alkyltryptamines
Others
Cyclized
Bioisosteres
Phenethylamines
Scalines
2C-x
3C-x
DOx
4C-x
Ψ-PEA
MDxx
FLY
25x-NB (NBOMes)
Others
Cyclized
Lysergamides
  • Bioisosteres:JRT
Others
Natural sources
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT37
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Tryptamines
4-Hydroxytryptamines
andesters/ethers
5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
Cyclized tryptamines
Isotryptamines
Related compounds
Retrieved from "https://en.wikipedia.org/w/index.php?title=Aeruginascin&oldid=1323751779"
Categories:
Hidden categories:

[8]ページ先頭

©2009-2025 Movatter.jp