Bufotenine can be efficiently converted into N,N-dimethyltryptamine and 5-methoxy-N,N-dimethyltryptamine via a novel bufotenine-aminoborane complex.
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.