Aeruginascin: Difference between revisions

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc}}

| verifiedrevid = 450944744

| IUPAC_name = [3-[2-(Trimethylazaniumyl)ethyl]-1''H''-indol-4-yl] hydrogen phosphate

| image = Aeruginascin.svg

| tradename =

| pregnancy_AU =

| pregnancy_US =

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| legal_AU =

| legal_CA =

| legal_DE = NpSG

| legal_UK = Class A

| legal_US =

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| routes_of_administration =

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| protein_bound =

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| CAS_number_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 7U9WQY1P7R

| ATC_suffix =

| PubChem = 60208479

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 26233970

| C=13 | H=20 | N=2 | O=4 | P=1

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| smiles = C[N+](C)(C)CCc1c[nH]c2c1c(ccc2)OP(=O)(O)[O-]

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = OIIPFLWAQQNCHA-UHFFFAOYSA-N

'''Aeruginascin''' or '''''N,N,N''-trimethyl-4-phosphoryloxytryptamine''' is an [[indoleamine]] derivative which occurs naturally within the mushrooms ''[[Inocybe aeruginascens]]'',<ref name="MCR">{{cite journal | vauthors = Gartz J | title = Inocybe aeruginascens Babos. | journal = Eleusis, Journal of Psychoactive Plants & Compounds. | date = 1995 | volume = 3 | pages = 31–4 |url=http://www.museocivico.rovereto.tn.it/context.jsp?ID_LINK=111258&area=279 |publisher = Museo Civico di Rovereto}}</ref><ref>{{cite journal | vauthors = Jensen N, Gartz J, Laatsch H | title = Aeruginascin, a trimethylammonium analogue of psilocybin from the hallucinogenic mushroom Inocybe aeruginascens | journal = Planta Medica | volume = 72 | issue = 7 | pages = 665–666 | date = June 2006 | pmid = 16673333 | doi = 10.1055/s-2006-931576 | s2cid = 260281286 | url = http://wwwuser.gwdg.de/~ucoc/laatsch/168_Aeruginascin_col.pdf | url-status = dead | archive-url = https://web.archive.org/web/20110524153555/http://wwwuser.gwdg.de/~ucoc/laatsch/168_Aeruginascin_col.pdf | archive-date = 2011-05-24 }}</ref><ref>{{cite journal | vauthors = Sherwood AM, Halberstadt AL, Klein AK, McCorvy JD, Kaylo KW, Kargbo RB, Meisenheimer P | title = Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin | journal = Journal of Natural Products | volume = 83 | issue = 2 | pages = 461–467 | date = February 2020 | pmid = 32077284 | doi = 10.1021/acs.jnatprod.9b01061 | s2cid = 211214973 }}</ref><ref>{{cite journal | vauthors = Servillo L, Giovane A, Balestrieri ML, Cautela D, Castaldo D | title = N-methylated tryptamine derivatives in citrus genus plants: identification of N,N,N-trimethyltryptamine in bergamot | journal = Journal of Agricultural and Food Chemistry | volume = 60 | issue = 37 | pages = 9512–9518 | date = September 2012 | pmid = 22957740 | doi = 10.1021/jf302767e }}</ref><ref>{{cite journal | vauthors = de Carvalho Junior AR, Oliveira Ferreira R, de Souza Passos M, da Silva Boeno SI, Glória das Virgens LL, Ventura TL, Calixto SD, Lassounskaia E, de Carvalho MG, Braz-Filho R, Curcino Vieira IJ | display-authors = 6 | title = Antimycobacterial and Nitric Oxide Production Inhibitory Activities of Triterpenes and Alkaloids from ''Psychotria nuda'' (Cham. & Schltdl.) Wawra | journal = Molecules | volume = 24 | issue = 6 | pages = 1026 | date = March 2019 | pmid = 30875889 | pmc = 6471101 | doi = 10.3390/molecules24061026 | doi-access = free }}</ref><ref name = "Gotvaldová_2022">{{cite journal | vauthors = Gotvaldová K, Borovička J, Hájková K, Cihlářová P, Rockefeller A, Kuchař M | title = Extensive Collection of Psychotropic Mushrooms with Determination of Their Tryptamine Alkaloids | journal = International Journal of Molecular Sciences | volume = 23 | issue = 22 | pages = 14068 | date = November 2022 | pmid = 36430546 | doi = 10.3390/ijms232214068 | pmc = 9693126 | doi-access = free }}</ref> ''[[Pholiotina cyanopus]]'',<ref name = "Gotvaldová_2022" /> and ''[[Psilocybe cubensis]]''.<ref>{{cite web|url=https://caam.tech/caamtech-publishes-fundamental-research-on-aeruginascin-derivatives/|title=CaaMTech Publishes Fundamental Research on Aeruginascin Derivatives|date=14 September 2022 }}</ref> Aeruginascin is the ''N''-tri[[methyl]] [[Analog (chemistry)|analogue]] of [[psilocybin]]. It is closely related to the frog skin toxin [[bufotenidine]] (5-HTQ), a potent [[5-HT3 receptor|5-HT₃ receptor]] agonist, but the aeruginascin metabolite [[4-HO-TMT]] shows strong binding at the [[5-HT receptor|5-HT2 receptors]] similar to [[psilocin]].<ref>{{cite journal | vauthors = Chadeayne AR, Pham DN, Reid BG, Golen JA, Manke DR | title = Active Metabolite of Aeruginascin (4-Hydroxy-N,N,N-trimethyltryptamine): Synthesis, Structure, and Serotonergic Binding Affinity | journal = ACS Omega | volume = 5 | issue = 27 | pages = 16940–16943 | date = July 2020 | pmid = 32685863 | pmc = 7365549 | doi = 10.1021/acsomega.0c02208 }}</ref><ref>{{Cite web| vauthors = Bauer BE |date=2020-07-07|title=Study Finds Aeruginascin Metabolite 4-HO-TMT is Active at the Serotonin 5-HT2A Receptor|url=https://psychedelicreview.com/study-finds-aeruginascin-metabolite-4-ho-tmt-is-active-at-the-serotonin-5-ht2a-receptor/|url-status=live|access-date=2021-09-07|website=Psychedelic Science Review |language=en-US |archive-url= https://web.archive.org/web/20200805013154/https://psychedelicreview.com/study-finds-aeruginascin-metabolite-4-ho-tmt-is-active-at-the-serotonin-5-ht2a-receptor/ |archive-date=2020-08-05 }}</ref> The first scientific literature about the pharmacological effects of aeruginascin is from a study published by Gartz in 1989.<ref>{{Cite journal| vauthors = Gartz J |date=January 1989|title=Analysis of Aeruginascin in Fruit Bodies of the Mushroom Inocybe aeruginascens|url=http://www.tandfonline.com/doi/full/10.3109/13880208909053954|journal=International Journal of Crude Drug Research|language=en|volume=27|issue=3|pages=141–144|doi=10.3109/13880208909053954|issn=0167-7314}}</ref> Across 23 analyzed cases of accidental hallucinogenic mushroom poisonings, people who had ingested the mushroom ''Inocybe aeruginascens'' reported only euphoric experiences.<ref>{{Cite web|date=2018-11-19|title=Aeruginascin|url=https://psychedelicreview.com/compound/aeruginascin/|access-date=2021-09-07|website=Psychedelic Science Review|language=en-US}}</ref> 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).

:[[Image:Inocybe aeruginascens.jpg|thumb|left|''[[Inocybe aeruginascens]]'']]{{clear-left}}

== References ==

{{reflist|30em}}

[[Category:Tryptamine alkaloids]]