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Invisiblemjshroomer
Sage
Registered: 07/22/99
Posts: 13,774
Loc: gone with my shrooms
The Isolation of Aeruginascine frm Inocybe aeruginascine
    #3840798 - 02/27/05 12:59 PM (12 years, 3 months ago)

Hm! Thought I already posted this here.

This is the dissertation of Neils Jansen sent to me by my colleague in Switzerland, Dr. Tjakko Stijve.

HEre is i his email to me about this substance and his comments and then the abstract and then the URL is in Tjakko's letter to me. Check it out.

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Hi John,

Thanks for the various pictures. Swami is a phantastic portrait !
The flowers and leaves are stunning, great photography!

Did Gartz tell you that the evasive compound aeruginascin in Inocybe aeruginascens has finally been
isolated and identified as 4-phosphoryloxy-N,N,N-trimethyltryptamine, the quaternary trimethylammonium analog of psilocybine. The work was subject of a doctoral thesis by Niels Jensen, and is accessible at

http://webdoc.sub.gwdg.de/diss/2004/jensen/

The thesis has more than 300 pages, so I only downloaded the abstract, and a few of the most interesting pages.
It seems that the compound is unstable, and unlikely to pass the brain barrier. Perhaps it still contributes a little to the psychoactivity of the 'shroom (by peripheral action?)

Best regards,

Tjakko


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ABSTRACT:

Elektronische Dissertationen an der SUB G?ttingen
Jensen, Niels: Tryptamines as Ligands and Modulators of the Serotonin 5‑HT2A Receptor and the Isolation of Aeruginascin from the Hallucinogenic Mushroom Inocybe aeruginascens

Tryptamine als Liganden und Modulatoren des 5‑HT2A Serotonin-Rezeptors und die Isolierung von Aeruginascin aus dem halluzinogenen Pilz Inocybe aeruginascens

Dissertation (PDF (.pdf), 2.215 KB)

Schl?sselw?rter
Aeruginascin, Psilocybin, Inocybe, Indol-Alkaloide, Halluzinogene, Tryptamine, 5-HT2A Serotonin Rezeptor
Aeruginascin, Psilocybin, Inocybe, Indole Alkaloids, Hallucinogens, Tryptamines, 5-HT2A Serotonin Receptor

Sachgruppe der DNB
540 Chemie
Basisklassifikation
44.38, 42.63, 35.50
G?ttinger Online Klassifikation
MED 351, SUU 400, SXE 000, SXY 100, WWG 000

Dissertation zur Erlangung des Doktortitels, angenommen von: Georg-August-Universit?t G?ttingen, Mathematisch-naturwissenschaftliche Fakult?ten, 2004-11-04

Abstract (ENG)

Aeruginascin is a natural product from the hallucinogenic mushroom Inocybe aeruginascens. This compound was isolated and identified as 4-phosphoryloxy-N,N,N-trimethyltryptamine. Aeruginascin is the quaternary trimethylammonium analog of the hallucinogenic compound psilocybin. Synthetic aeruginascin was identical in all aspects to the isolated sample. Additionally, the mushroom alkaloids norbaeocystin and baeocystin were synthesized and a new synthetic approach to 4‑hydroxy-tryptamines was investigated.

In a related project the influence of N-terminal substituents of tryptamines on serotonin receptor binding was studied. A series of tryptamines carrying a broad range of structurally diverse amino-substituents was synthesized. Most compounds had binding affinities in the nanomolar range for the 5‑HT1A, the 5‑HT2A, and the 5‑HT2C receptor. In functional 5‑HT2A IP accumulation assays most ligands acted as antagonists or partial agonists. Several compounds had biphasic dose-response curves. Sometimes the response at higher concentrations exceeded even that of the natural agonist serotonin. As shown by additional experiments, this effect was probably caused by non-competitive positive allosteric modulation of the 5‑HT2A receptor at higher concentrations. These results indicate a new independent regulatory binding site of the 5‑HT2A receptor. In contrast to a previous publication, in our hands the lead compound N‑(4‑bromobenzyl)-5‑methoxy?tryptamine was a low-affinity antagonist at the 5‑HT2A receptor.

Abstract (GER)

Aeruginascin ist ein Naturstoff aus dem halluzinogenen Pilz Inocybe aeruginascens. Die Substanz wurde isoliert und als 4-Phosphoryloxy-N,N,N-trimethyl-tryptamin identifiziert. Aeruginascin ist das quart?re Trimethylammonium-Analogon der halluzinogenen Substanz Psilocybin. Synthetisches Aeruginascin war in allen Aspekten identisch mit der isolierten Probe. Zus?tzlich wurden die Pilzalkaloide Norbaeocystin und Baeocystin synthetisiert und es wurde ein neuer synthetischer Zugang zu 4‑Hydroxy-tryptaminen untersucht.

Des weiteren wurde der Einfluss N-terminaler Substituenten von Tryptaminen auf die Bindung an Serotonin-Rezeptoren untersucht. Daf?r wurde eine Serie von Tryptaminen mit einer breiten Auswahl strukturell unterschiedlicher Substituenten an der Amino-Gruppe synthetisiert. Die meisten Substanzen hatten Bindungsaffinit?ten im nanomolaren Bereich f?r den 5‑HT1A-, den 5‑HT2A- und den 5‑HT2C-Rezeptor. In funktionellen 5‑HT2A IP-Akkumulations-Assays verhielten sich die meisten dieser Verbindungen als Antagonisten oder partielle Agonisten. Einige Verbindungen zeigten eine biphasische Dosis-Wirkungs-Beziehung. Teilweise ?bertraf die Wirkung bei h?heren Konzentrationen sogar die des nat?rlichen Agonisten Serotonin. Zus?tzliche Experimente zeigten, dass dieser Effekt vermutlich durch nicht-kompetitive, positiv allosterische Modulation des 5‑HT2A-Rezeptors bei h?heren Konzentrationen verursacht wurde. Diese Resultate deuten auf eine neue unabh?ngige regulatorische Bindungsstelle am 5‑HT2A-Rezeptor hin. Im Gegensatz zu einer fr?heren Ver?ffentlichung zeigte die Leitsubstanz N‑(4‑Brombenzyl)-5‑methoxy?tryptamin nur eine geringe Affinit?t f?r den 5‑HT2A-Rezeptor und verhielt sich als Antagonist.
Betreuer: Laatsch, Hartmut; Prof.Dr
Gutachter: Laatsch, Hartmut; Prof.Dr
Gutachter: Nichols,David E.; Prof.
URL der Dissertation: http://webdoc.sub.gwdg.de/diss/2004/jensen/jensen.pdf

Nieders?chsische Staats- und Universit?tsbibliothek G?ttingen
37070 G?ttingen

Urheberrecht

Copyright
Letztmalige

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mj


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OfflineKerr
Who else would I be

Registered: 02/05/05
Posts: 1,611
Loc: My roots in the Koots
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Re: The Isolation of Aeruginascine frm Inocybe aeruginascine [Re: mjshroomer]
    #3840928 - 02/27/05 01:36 PM (12 years, 3 months ago)

Good post mj :P


--------------------
"Easy going and organic thoughts bent on self experimentation and knowledge and growth for the betterment of self and those around us"
-Playdo the philosophiser


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