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A Review of Aeruginascin and Potential Entourage Effect in Hallucinogenic Mushrooms

Published online by Cambridge University Press:  01 September 2022

P. Chue ,
A. Andreiev ,
E. Bucuci ,
C. Els  and
J. Chue
P. Chue*
Affiliation:
UNIVERSITY OF ALBERTA, Psychiatry, EDMONTON, Canada
A. Andreiev
Affiliation:
UNIVERSITY OF OTTAWA, Psychiatry, OTTAWA, Canada
E. Bucuci
Affiliation:
UNIVERSITY OF ALBERTA, Clinical Trials And Research Program, EDMONTON, Canada
C. Els
Affiliation:
UNIVERSITY OF ALBERTA, Psychiatry, EDMONTON, Canada
J. Chue
Affiliation:
UNIVERSITY OF ALBERTA, Clinical Trials And Research Program, EDMONTON, Canada
*
*Corresponding author.

Abstract

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Introduction

The 5-HT2A agonist classic psychedelic, psilocybin (O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine) is a tryptophan, indole-based alkaloid present in up to 2% of certain hallucinogenic “magic” mushroom species; typically Psilocybe azurescens, semilanceata, and cyanescens,. In addition, mushrooms may contain psilocin (4-hydroxy-N,N-dimethyltryptamine). Both are indolylalkylamines (tryptamines); other naturally occurring tryptamine compounds include norbaeocystin, baeocystin, norpsilocin, and aeruginascin. A putative synergistic contribution of these compounds has been referred to as the “entourage” effect. Aeruginascin (N,N,N-trimethyl-4-phosphoryloxytryptamine) is found naturally in Inocybe aeruginascens and Pholiotina cyanopus mushroom species and ingestion reportedly invokes elevation in mood without accompanying hallucinogenic effects:

Objectives

To review the pharmacology of aeruginascin and putative entourage effect.

Methods

The extant literature on aeruginascin was reviewed and discussed.

Results

Methylation of aeruginascin results in an active metabolite, 4-hydroxy-N,N,N-trimethyltryptamine (4-HO-TMT) which has been shown to bind at 5-HT1A, 5-HT2A, and 5-HT2B receptors with Inhibition Constants (Ki) of 4400, 670, and 120 nM respectively; compared with psilocybin’s binding of 567.4, 107.2 and 4.6 nM respectively. Further, 4-HO-TMT does not bind at the 5-HT3 receptor, and as a quaternary trimethylammonium compound it is less likely to be able to cross the blood-brain-barrier (BBB).

Conclusions

There are very limited data with respect to the pharmacology of aeruginascin. Its activity at serotonin receptors is less by several orders of magnitude than psilocybin and it has potentially less brain penetrance. Given that it is found in different mushrooms species the data would suggest that its direct contribution to any entourage effect is limited. Further research in needed into other naturally occurring tryptamine compounds.

Disclosure

PC is a member of the Scientific Advisory Board of Zylorion. AA, EB, JC, CE have no disclosures to report.

Keywords

ENTOURAGE EFFECTPsilocybinAeruginascin
Type
Abstract
Information
European Psychiatry , Volume 65 , Special Issue S1: Abstracts of the 30th European Congress of Psychiatry , June 2022 , pp. S885
Creative Commons
Creative Common License - CCCreative Common License - BY
This is an Open Access article, distributed under the terms of the Creative Commons Attribution licence (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted re-use, distribution, and reproduction in any medium, provided the original work is properly cited.
Copyright
© The Author(s), 2022. Published by Cambridge University Press on behalf of the European Psychiatric Association
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