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.
D000818:Animals; D001522:Behavior, Animal / Q000187:drug effects*; D002625:Chemistry, Organic; D002855:Chromatography, Thin Layer; D003216:Conditioning, Operant; D008297:Male; D055601:Organic Chemistry Phenomena; D051381:Rats; D014363:Tryptamines / Q000378:metabolism* / Q000494:pharmacology*
D014363:Tryptamines