Synthesis and Pharmacological Activity of Fluorinated Tryptamine Derivatives

Abstract

The synthesis of several fluorinated tryptamine derivatives in which the fluorine atom occupies the 5- or 6-position is reported. The 5-fluoro and unsubstituted tryptamines are more active than the 6-substituted derivatives in inducing spontaneous locomotion when administered to reserpinized white mice. Both 6-fluoro-N,N-diethyltryptamine and N,N-diethyltryptamine exerted peripheral activity when tested in humans, but only the fluorine-free compound seemed to bear hallucinogenic properties. These results may be explained by change in the metabolic pathway of the tryptamines with substituted 6-position in the indole nucleus. © 1963, American Chemical Society. All rights reserved.