title: Concise synthesis of N,N-dimethyltryptamine and 5-methoxy-N,N-dimethyltryptamine starting with bufotenine from Brazilian Anadenanthera ssp..
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.
authors.forename: Leandro A
authors.initials: LA
authors.lastname: Moreira
authors.forename: Maria M
authors.initials: MM
authors.lastname: Murta
authors.forename: Claudia C
authors.initials: CC
authors.lastname: Gatto
authors.forename: Christopher W
authors.initials: CW
authors.lastname: Fagg
authors.forename: Maria L
authors.initials: ML
authors.lastname: dos Santos
mesh_terms: D001938:Brazil; D002027:Bufotenin / Q000737:chemistry*; D007887:Fabaceae / Q000737:chemistry*; D008732:Methoxydimethyltryptamines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D004130:N,N-Dimethyltryptamine / Q000138:chemical synthesis* / Q000737:chemistry; D012639:Seeds / Q000737:chemistry
chemical_list: D008732:Methoxydimethyltryptamines; D002027:Bufotenin; D004130:N,N-Dimethyltryptamine