Synthesis and action on the central nervous system of mescaline analogues containing piperazine or homopiperazine rings.
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.
D000818:Animals; D002490:Central Nervous System / Q000187:drug effects*; D055598:Chemical Phenomena; D002621:Chemistry; D006591:Hexobarbital / Q000494:pharmacology; D006801:Humans; D008297:Male; D008635:Mescaline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D051379:Mice; D009043:Motor Activity / Q000187:drug effects; D010879:Piperazines / Q000138:chemical synthesis / Q000494:pharmacology; D051381:Rats; D011919:Rats, Inbred Strains; D012890:Sleep / Q000187:drug effects; D013239:Stereotyped Behavior / Q000187:drug effects; D013997:Time Factors
D010879:Piperazines; D006591:Hexobarbital; D008635:Mescaline