(+)-cis-8-Hydroxy-1-methyl-2-(di-n-propylamino)tetralin: a potent and highly stereoselective 5-hydroxytryptamine receptor agonist

J Med Chem. 1987 Nov;30(11):2105-9. doi: 10.1021/jm00394a029.

Abstract

C1-Methylated derivatives of the potent 5-hydroxytryptamine (5-HT) receptor agonist 8-hydroxy-2-(di-n-propylamino)tetralin (8-OH-DPAT, 1) were synthesized and tested for central 5-HT and dopamine receptor activity by use of a biochemical test method in rats. cis-8-Hydroxy-1-methyl-2-(di-n-propylamino)tetralin (8) was found to be a 5-HT receptor agonist. The (+)-enantiomer of 8 had a potency equal to that of 1, whereas (-)-8 and the trans isomer (+/-)-9 were inactive.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 8-Hydroxy-2-(di-n-propylamino)tetralin
  • Animals
  • Male
  • Molecular Conformation
  • Naphthalenes / chemical synthesis*
  • Rats
  • Rats, Inbred Strains
  • Receptors, Dopamine / drug effects
  • Receptors, Serotonin / drug effects*
  • Serotonin / biosynthesis
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tetrahydronaphthalenes / chemical synthesis*
  • Tetrahydronaphthalenes / pharmacology

Substances

  • Naphthalenes
  • Receptors, Dopamine
  • Receptors, Serotonin
  • Tetrahydronaphthalenes
  • 8-hydroxy-1-methyl-2-(di-n-propylamino)tetralin
  • Serotonin
  • 8-Hydroxy-2-(di-n-propylamino)tetralin