Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents.
Eight N-methyl-N-isopropyltryptamines (MIPTs) possessing various aromatic oxygen substituents were prepared, characterized, and evaluated for hallucinogenic activity in man. In at least two instances (the Ar H and the Ar 5-OCH3, 1 and 4) the unsymmetrical nitrogen substitution led to a substantial increase in potency as well as oral activity when compared to the symmetrical dimethyl homologues. Qualitatively, 4-hydroxy-N-methyl-N-isopropyltryptamine (2) was the most interesting in overall effect, producing a classic hallucinogenic profile. The 5-methoxy congener 4 resulted in a state characterized by heightened conceptual stimulation lacking in visual phenomena. Other members of the series exhibited diminished effects.
D000328:Adult; D055598:Chemical Phenomena; D002621:Chemistry; D006212:Hallucinations / Q000139:chemically induced; D006213:Hallucinogens; D006801:Humans; D007700:Kinetics; D008875:Middle Aged; D010100:Oxygen; D013329:Structure-Activity Relationship; D014363:Tryptamines / Q000494:pharmacology*
D006213:Hallucinogens; D014363:Tryptamines; D010100:Oxygen