Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety

J Med Chem. 1982 Aug;25(8):908-13. doi: 10.1021/jm00350a005.


A series of N,N-dialkyltryptamines with methylthio or methylenedioxy substituents in the 4, 5, and 6 positions and methyl or isopropyl on the side-chain nitrogen has been synthesized. The behavioral pharmacology of these compounds showed them to possess Bovet-Gatti profiles characteristic of hallucinogens, and the 5-methylthio congener was the most potent. Binding studies at [3H]LSD and [3H]5-HT sites demonstrated that no single structural feature correlated with binding or behavioral changes and suggest a complex mode of action for these potential hallucinogenic agents.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Behavior, Animal / drug effects
  • Chemical Phenomena
  • Chemistry
  • Hallucinogens / chemical synthesis*
  • Lysergic Acid Diethylamide / pharmacology
  • Male
  • Rats
  • Receptors, Serotonin / drug effects
  • Structure-Activity Relationship
  • Tryptamines / chemical synthesis*
  • Tryptamines / pharmacology


  • Hallucinogens
  • LSD receptor
  • Receptors, Serotonin
  • Tryptamines
  • Lysergic Acid Diethylamide