Serotonin transporter inhibitors: synthesis and binding potency of 2'-methyl- and 3'-methyl-6-nitroquipazine

Bioorg Med Chem Lett. 2000 Dec 4;10(23):2643-6. doi: 10.1016/s0960-894x(00)00546-1.

Abstract

Racemic 2'-methyl- and 3'-methyl-6-nitroquipazine ligands were selected as targets, synthesized and evaluated at the serotonin transporter employing an in vitro competitive inhibition assay with [3H]paroxetine and rat cortical membrane. The 2'-methyl-6-nitroquipazine was found to be 50 times more potent than the 3'-methyl-substituted counterpart and of comparable potency to the known high affinity agent 5-iodo-6-nitroquipazine.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Binding, Competitive
  • Carrier Proteins / antagonists & inhibitors*
  • Carrier Proteins / metabolism
  • Cerebral Cortex / metabolism
  • Membrane Glycoproteins / antagonists & inhibitors*
  • Membrane Glycoproteins / metabolism
  • Membrane Transport Proteins*
  • Nerve Tissue Proteins*
  • Paroxetine / metabolism
  • Quipazine / analogs & derivatives
  • Quipazine / chemical synthesis*
  • Quipazine / metabolism
  • Rats
  • Selective Serotonin Reuptake Inhibitors / metabolism
  • Serotonin Plasma Membrane Transport Proteins

Substances

  • 2'-methyl-6-nitroquipazine
  • 3'-methyl-6-nitroquipazine
  • Carrier Proteins
  • Membrane Glycoproteins
  • Membrane Transport Proteins
  • Nerve Tissue Proteins
  • Serotonin Plasma Membrane Transport Proteins
  • Serotonin Uptake Inhibitors
  • Slc6a4 protein, rat
  • Paroxetine
  • Quipazine