Concise large-scale synthesis of psilocin and psilocybin, principal hallucinogenic constituents of "magic mushroom"

Osamu Shirota; Wataru Hakamata; Yukihiro Goda

doi:10.1021/np030059u

Concise large-scale synthesis of psilocin and psilocybin, principal hallucinogenic constituents of "magic mushroom"

J Nat Prod. 2003 Jun;66(6):885-7. doi: 10.1021/np030059u.

Authors

Osamu Shirota¹, Wataru Hakamata, Yukihiro Goda

Affiliation

¹ Division of Pharmacognosy, Phytochemistry and Narcotics, and Division of Organic Chemistry, National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo 158-8501, Japan. shirota@nihs.go.jp

PMID: 12828485
DOI: 10.1021/np030059u

Abstract

The concise large-scale syntheses of psilocin (1) and psilocybin (2), the principal hallucinogenic constituents of "magic mushroom", were achieved without chromatographic purification. The key step in the synthesis of 2 was the isolation of the dibenzyl-protected intermediate (7) as a zwitterionic derivative (8), which was completely identified by means of 2D NMR analyses.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Agaricales / chemistry*
Combinatorial Chemistry Techniques*
Hallucinogens / chemical synthesis*
Hallucinogens / chemistry
Hallucinogens / pharmacology
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Psilocybin / analogs & derivatives*
Psilocybin / chemical synthesis*
Psilocybin / chemistry
Psilocybin / pharmacology

Substances

Hallucinogens
Psilocybin
psilocin