6-substituted 1,3,4,5-tetrahydrobenz[cd]indol-4-amines: potent serotonin agonists

J Med Chem. 1988 Sep;31(9):1746-53. doi: 10.1021/jm00117a013.

Abstract

A series of 6-substituted tricyclic ergoline partial structures has been synthesized and found to possess very strong serotonin agonist activity. A methoxy group at the 6-position greatly enhances activity, but at the expense of compound stability. Substituting the 6-position with protophyllic groups that are also electron-withdrawing in character enhances both activity and stability.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Brain / drug effects
  • Brain / metabolism
  • Chemical Phenomena
  • Chemistry
  • Corticosterone / blood
  • Hydroxyindoleacetic Acid / metabolism
  • Indoles / chemical synthesis
  • Indoles / metabolism
  • Indoles / pharmacology*
  • Male
  • Rats
  • Rats, Inbred Strains
  • Receptors, Serotonin / drug effects*
  • Receptors, Serotonin / metabolism
  • Serotonin / metabolism
  • Structure-Activity Relationship

Substances

  • Indoles
  • Receptors, Serotonin
  • Serotonin
  • Hydroxyindoleacetic Acid
  • Corticosterone