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    J Med Chem. 1985 Jul;28(7):892-6.

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

    Repke DB, Grotjahn DB, Shulgin AT.

    Abstract

    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.

    PMID:
    4009612
    [PubMed - indexed for MEDLINE]

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