Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents

J Med Chem. 1985 Jul;28(7):892-6. doi: 10.1021/jm00145a007.


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.

Publication types

  • Comparative Study

MeSH terms

  • Adult
  • Chemical Phenomena
  • Chemistry
  • Hallucinations / chemically induced
  • Hallucinogens*
  • Humans
  • Kinetics
  • Middle Aged
  • Oxygen*
  • Structure-Activity Relationship
  • Tryptamines / pharmacology*


  • Hallucinogens
  • Tryptamines
  • Oxygen