Planta Med 2006; 72(7): 665-666
DOI: 10.1055/s-2006-931576
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Aeruginascin, a Trimethylammonium Analogue of Psilocybin from the Hallucinogenic Mushroom Inocybe aeruginascens

Niels Jensen1 , Jochen Gartz2 , Hartmut Laatsch1
  • 1Institute of Organic and Biomolecular Chemistry, Georg-August University Göttingen, Göttingen, Germany
  • 2Fungal Biotransformations, Leipzig, Germany
Dedicated to Dr. Albert Hofmann in honour of his 100th birthday
Further Information

Publication History

Received: November 10, 2005

Accepted: February 3, 2006

Publication Date:
28 April 2006 (online)

Abstract

The hallucinogenic mushroom Inocybe aeruginascens contains several typical Psilocybe alkaloids including psilocybin. We have now elucidated the structure of a further indole derivative named aeruginascin as the quaternary ammonium compound N,N,N-trimethyl-4-phosphoryloxytryptamine. Aeruginascin is closely related to the frog skin toxin bufotenidine (5-HTQ), a potent 5-HT3 receptor agonist, and has been found exclusively in Inocybe aeruginascens so far.

References

  • 1 Gartz J, Drewitz G. Der grünlichverfärbende Rißpilz - eine Inocybe-Art mit halluzinogener Wirkung.  Z Ärztl Fortbild (Jena). 1986;  80 551-3
  • 2 Drewitz G. Eine halluzinogene Rißpilzart, der grünlichverfärbende Rißpilz - Inocybe aeruginascens .  Mykol Mitteilungsblatt (Halle). 1983;  26 11-7
  • 3 Hofmann A, Heim R, Brack A, Kobel H, Frey A, Ott H. Psilocybin and Psilocin, zwei psychotrope Wirkstoffe aus mexikanischen Rauschpilzen.  Helv Chim Acta. 1959;  52 1557
  • 4 Gartz J. Vergleichende dünnschichtchromatographische Untersuchung zweier Psilocybe- und einer halluzinogenen Inocybe-Art.  Pharmazie. 1985;  40 134
  • 5 Gartz J. Nachweis von Tryptaminderivaten in Pilzen der Gattungen Gerronema, Hygrocybe, Psathyrella und Inocybe .  Biochem Physiol Pflanzen. 1986;  181 275-8
  • 6 Semerdžieva M, Wurst M, Koza T, Gartz J. Psilocybin in Fruchtkörpern von Inocybe aeruginascens .  Planta Med. 1986;  47 83-5
  • 7 Gartz J. Untersuchungen zum Vorkommen des Muscarins in Inocybe aeruginascens Babos.  Z Mykol. 1986;  52 359-61
  • 8 Gartz J. Variation der Alkaloidmenge in Fruchtkörpern von Inocybe aeruginascens .  Planta Med. 1987;  53 539-41
  • 9 Leung A L, Paul A G. Baeocystin and norbaeocystin, new analogs of psilocybin from Psilocybe baeocystis .  J Pharm Sci. 1968;  57 1667
  • 10 Jensen N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens . Dissertation University of Göttingen; 2004
  • 11 McClean S, Robinson R C, Shaw C, Smyth W F. Characterisation and determination of indole alkaloids in frog-skin secretions by electrospray ionisation ion trap mass spectrometry.  Rapid Commun Mass Spectrom. 2002;  16 346-54
  • 12 Glennon R A, Peroutka S J, Dukat M. Binding characteristics of a quaternary amine analog of serotonin: 5-HTQ. In: Fozard JR, Saxena PR, editors Serotonin: molecular biology, receptors and functional effects. Basel; Birkhäuser-Verlag 1991: p 186-91

Prof. Dr. Hartmut Laatsch

Institute of Organic and Biomolecular Chemistry

Georg-August University Göttingen

Tammannstrasse 2

37077 Göttingen

Germany

Phone: +49-551-39-3211

Fax: +49-551-39-9660

Email: hlaatsc@gwdg.de