Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety

Abstract

A series of N,N-dialkyltryptamines with methylthio or methylenedioxy substituents in the 4, 5 and 6 positions and methyl or isopropyl on the side-chain N were synthesized. The behavioral pharmacology of these compounds showed Bovet-Gatti profiles characteristic of hallucinogens [in rats], and the 5-methylthio congener was the most potent. Binding studies at [3H]LSD and [3H]5-HT [5-hydroxytryptamine] sites [in guinea pig cortex] demonstrated that no single structural feature correlated with binding or behavioral changes and suggest a complex mode of action for these potential hallucinogenic agents [6-(methylthio)-N,N-dimethyltryptamine and 4,5-(methylenedioxy)-N,N-dimethyltryptamine].