6-Hydroxylation: Effect on the Psychotropic Potency of Tryptamines

6-Hydroxy-5-methoxy-N,N dimethyltryptamine and 5-methoxy-N, N-dimnethyltryptamine were synthesized and their psychotropic effects compared on trained rats in a Skinner box. The nonhydroxylated form was the more po tent. The metabolism of 5-methoxytryp tophol acetate ester was also studied to determine whether hydroxylation might occur in other than the six position with exogenous indoles. One metabolite was formed, with properties of a hydroxy-5-methoxyindole-3-acetic acid, which proved on chromatography not to be the 6-hydroxy structural isomer. Phar macologic and metabolic studies suggest that psychotropic activity of trypt amines may result from metabolites other than the 6-hydroxylated forms.