Synthesis and Action on the Central Nervous System of Mescaline Analogues Containing Piperazine or Homopiperazine Rings

A series of mescaline analogues were synthesized by attaching a piperazine or homopiperazine ring to the 3,4,5-trimethoxyphenyl group. Pharmacological tests of central nervous system action showed that replacing the amino group in mescaline with these heterocycles significantly alters biological activity. Both the piperazine and homopiperazine derivatives displayed sedative activity to about the same extent. The study compared six-membered piperazine and seven-membered homopiperazine rings to determine whether the larger ring conferred special properties.

Study at a glance

Abstract

Structural juxtaposition of the 3,4,5-trimethoxyphenyl group in the same molecule with a piperazine or homopiperazine ring has been realized in a series of mescaline analogues (I-IV) as part of an investigation into the pharmacological properties of the seven-membered perhydro-1,4-diazepines (homopiperazines). The analogous six-membered piperazines were synthesized and tested as reference substances to determine whether the seven-membered ring conveyed special properties. A variety of pharmacological tests of action on the CNS showed that replacement of the amino group in mescaline by the heterocycles significantly alters the biological activity. In particular, both the piperazine and the homopiperazine derivatives displayed sedative activity to about the same extent.