Concise Synthesis of N,N -Dimethyltryptamine and 5-Methoxy- N,N -dimethyltryptamine Starting with Bufotenine from Brazilian Anadenanthera ssp

Bufotenine, a compound found in seeds of the Anadenanthera tree native to the Brazilian cerrado, was extracted using an acid-base method. The researchers developed a new, short process to convert bufotenine into N,N-dimethyltryptamine and 5-methoxy-N,N-dimethyltryptamine, involving a novel bufotenine-aminoborane complex. They also established a straightforward method to produce 5-hydroxy-N,N,N-trimethyltryptamine from bufotenine. This work presents bufotenine as a source for producing N,N-dimethyltryptamines for pharmacological, toxicological, or synthetic use.

Study at a glance

Abstract

Bufotenine (1, 5-hydroxy- N,N-dimethyltryptamine) was isolated from seeds of Anadenanthera spp., a tree widespread in the Brazilian cerrado, using an efficient acid-base shakeout protocol. The conversion of bufotenine into N,N-dimethyltryptamine (4) and 5-methoxy- N,N-dimethyltryptamine (5) was accomplished through an innovative and short approach featuring the use of novel bufotenine-aminoborane complex (7). Furthermore, an easy methodology for conversion of bufotenine into 5-hydroxy -N,N,N-trimethyltryptamine (6) was well-established. This is the first study that highlights bufotenine as a resource for the production of N, N-dimethyltryptamines for either pharmacological and toxicological investigations or for synthetic purposes.