Concise Synthesis of N,N -Dimethyltryptamine and 5-Methoxy- N,N -dimethyltryptamine Starting with Bufotenine from Brazilian Anadenanthera ssp
Leandro A. Moreira, Maria M. Murta, Claudia C. Gatto, Christopher W. Fagg, Maria L. Dos Santos
Natural Product Communications April 1, 2015 Peer reviewed DOI: 10.1177/1934578x1501000411
Summary
Bufotenine was isolated from Anadenanthera spp. seeds using an efficient method, and it can be converted into N,N-dimethyltryptamine and 5-methoxy-N,N-dimethyltryptamine through a novel bufotenine-aminoborane complex. Additionally, a straightforward method for converting bufotenine into 5-hydroxy-N,N,N-trimethyltryptamine was established. This study emphasizes bufotenine's potential as a source for producing N,N-dimethyltryptamines for pharmacological, toxicological, or synthetic applications.
Study at a glance
| Key finding | Bufotenine is highlighted as a resource for the production of N,N-dimethyltryptamines for pharmacological and toxicological investigations. |
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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.