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

doi:10.1002/CHIN.198544156

Paper

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

Published Nov 5, 1985 · D. B. Repke, D. Grotjahn, A. Shulgin

Journal of medicinal chemistry

Q1 SJR score

17

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1

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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.

In Vitro Study

Study Snapshot

Aromatic oxygen substituents in N-methyl-N-isopropyltryptamines can increase their potency and oral activity, with 4-hydroxy-N-methyl-N-isopropyltryptamine producing a classic hallucinogenic profile.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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

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