Synthesis of Baeocystin, a natural Psilocybin Analogue

✍ Scribed by Rudolf Brenneisen; Stefan Borner; Nelly Peter-Oesch; Urs P. Schlunegger

• Publisher: John Wiley and Sons
• Year: 1988
• Tongue: English
• Weight: 273 KB
• Volume: 321
• Category: Article
• ISSN: 0365-6233
• DOI: 10.1002/ardp.19883210812

✦ Synopsis

Baeocystin (7) (4-phosphoryloxy-N-methyltryptamine) has been synthe-Synthese von Baeocystin, einem naturlichen Psilocybin-Analogen lichem 7 , isoliert aus Psilocybe semilanceata, iiberein. Baeocystin (7) (4-phosphoryloxy-N-methyltryptamine) is the naturally occuring monomethyl analogue of psilocybin (8) (4-phosphoryloxy-N,Ndimethyltryptamine). It was first isolated from Psilocybe baeocystis (Strophariaceae)'.2). Later on it was found in other species of the genus Psilo-~y b e 3 -~) as well as of Znocybe (Cortinariaceaey. 9% lo), Conocybe (Bolbitiaceae)3), Panaeolus (Coprinaceae)3.6), and Pluteus (Pluteaceae)6. I 12). 7 is possibly the direct biochemical precursor of 83. 7,9.11), and mostly detected together with 8. Until now it is not known whether 7 produces psilocybin-like psychotropic effects. It was shown, however, that 4-hydroxy-N-methyltryptamine (6), the dephosphorylation product of 7, has a CNSactivity qualitatively similar to that of psilocin (4-hydroxy-N,N-dimethyltryptamine), the dephosphorylation product and active metabolite of 8'3).