(+)-cis-N-ethyleneamino-N-normetazocine derivatives. Novel and selective sigma ligands with antagonist properties

J Med Chem. 1998 May 7;41(10):1574-80. doi: 10.1021/jm970333f.

Abstract

A series of (+)-cis-N-normetazocine derivatives has been described, and their affinities for sigma1, sigma2, and phencyclidine (PCP) sites and opioid, muscarinic (M2), dopamine (D2), and serotonin (5-HT2) receptors were evaluated. The effect of the N-substitution with a substituted ethylamino spacer was investigated. Compounds 8c-11c displayed high affinities for sigma1 sites and for opioid receptors. Substitution of the second basic nitrogen either with alkyl or cycloalkyl substituents give compounds (1a-6a) with high affinity and selectivity for sigma1 binding sites. Compounds 1a-5a were further characterized in vivo, and their agonist/antagonist activity was evaluated. In mouse, compound 1a and 2a as well as haloperidol suppressed in a dose-related manner the stereotyped behavior induced by (+)-SKF 10,047. Compounds 3a-5a and (+)-pentazocine do not affect the stereotyped behavior induced by ip injection of (+)-SKF 10,047. Therefore, from this series of compounds we identified potent and selective sigma1 ligands which might prove useful to unveil the functional role of sigma1 sites.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Benzomorphans / chemical synthesis
  • Benzomorphans / chemistry
  • Benzomorphans / metabolism
  • Benzomorphans / pharmacology*
  • Brain / metabolism
  • Guinea Pigs
  • Ligands
  • Male
  • Mice
  • Radioligand Assay
  • Rats
  • Receptor, Muscarinic M2
  • Receptors, Dopamine D2 / metabolism
  • Receptors, Muscarinic / metabolism
  • Receptors, Opioid / metabolism
  • Receptors, Serotonin / metabolism
  • Receptors, sigma / agonists
  • Receptors, sigma / antagonists & inhibitors*
  • Receptors, sigma / metabolism
  • Stereoisomerism
  • Stereotyped Behavior / drug effects
  • Structure-Activity Relationship

Substances

  • Benzomorphans
  • Ligands
  • Receptor, Muscarinic M2
  • Receptors, Dopamine D2
  • Receptors, Muscarinic
  • Receptors, Opioid
  • Receptors, Serotonin
  • Receptors, sigma