C1-Methylated 5-hydroxy-2-(dipropylamino)tetralins: central dopamine-receptor stimulating activity

J Med Chem. 1984 Aug;27(8):1003-7. doi: 10.1021/jm00374a012.

Abstract

C1-Methylated derivatives of the potent dopaminergic agonist 5-hydroxy-2-(di-n-propylamino)tetralin (6) have been synthesized and tested for central dopamine (DA) receptor stimulating activity, by using biochemical and behavioral tests in rats. Both cis- and trans-5-hydroxy-1-methyl-2-(di-n-propylamino) tetralin (4 and 3) may be classified as central DA-receptor agonists, albeit of lower potency than 6. The results obtained indicate that both 4 and 3 display DA-autoreceptor stimulation capacity. However, only one of the isomers, trans-3, is able to elicit clear-cut postsynaptic DA receptor agonist actions at larger doses. 5-Hydroxy-1,1-dimethyl-2-(n-propylamino) tetralin (5) was found to be inactive.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Dihydroxyphenylalanine / biosynthesis
  • Isomerism
  • Male
  • Methylation
  • Methyltyrosines / pharmacology
  • Motor Activity / drug effects
  • Naphthalenes / chemical synthesis*
  • Rats
  • Rats, Inbred Strains
  • Receptors, Dopamine / drug effects*
  • Reserpine / pharmacology
  • Tetrahydronaphthalenes / chemical synthesis*
  • Tetrahydronaphthalenes / pharmacology
  • alpha-Methyltyrosine

Substances

  • Methyltyrosines
  • Naphthalenes
  • Receptors, Dopamine
  • Tetrahydronaphthalenes
  • Dihydroxyphenylalanine
  • alpha-Methyltyrosine
  • Reserpine