C1- and C3-methyl-substituted derivatives of 7-hydroxy-2-(di-n-propylamino)tetralin: activities at central dopamine receptors

J Med Chem. 1987 Oct;30(10):1827-37. doi: 10.1021/jm00393a025.


C1- and C3-methyl-substituted derivatives of the potent dopamine (DA) receptor agonist 7-hydroxy-2-(di-n-propylamino)tetralin (7-OH-DPAT) have been synthesized, and their conformational preferences have been studied by use of NMR spectroscopy, X-ray crystallography, and molecular mechanics (MMP2) calculations. The compounds were tested for activity at central DA receptors, by use of biochemical and behavioral tests in rats. (1S,2R)-7-Hydroxy-1-methyl-2-(di-n-propylamino)tetralin [(+)-10] was demonstrated to be sevenfold less potent than (2R)-7-OH-DPAT as a DA receptor agonist. The other new compounds were of lower potency or inactive.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Apomorphine / metabolism
  • Magnetic Resonance Spectroscopy
  • Methylation
  • Models, Molecular
  • Motor Activity / drug effects
  • Naphthalenes / pharmacology*
  • Rats
  • Receptors, Dopamine / metabolism*
  • Structure-Activity Relationship
  • Tetrahydronaphthalenes / pharmacology*
  • X-Ray Diffraction


  • Naphthalenes
  • Receptors, Dopamine
  • Tetrahydronaphthalenes
  • Apomorphine