Concise synthesis of N,N-dimethyltryptamine and 5-methoxy-N,N-dimethyltryptamine starting with bufotenine from Brazilian Anadenanthera ssp

Nat Prod Commun. 2015 Apr;10(4):581-4.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Brazil
  • Bufotenin / chemistry*
  • Fabaceae / chemistry*
  • Methoxydimethyltryptamines / chemical synthesis*
  • Methoxydimethyltryptamines / chemistry
  • Models, Molecular
  • Molecular Structure
  • N,N-Dimethyltryptamine / chemical synthesis*
  • N,N-Dimethyltryptamine / chemistry
  • Seeds / chemistry

Substances

  • Methoxydimethyltryptamines
  • Bufotenin
  • N,N-Dimethyltryptamine