9-(Aminomethyl)-9,10-dihydroanthracene is a novel and unlikely 5-HT2A receptor antagonist

Eur J Pharmacol. 1999 Sep 3;380(1):R5-7. doi: 10.1016/s0014-2999(99)00525-7.

Abstract

Structural elaboration of phenylethylamine to 9-(aminomethyl)-9,10-dihydroanthracene (AMDA) produces an agent with high affinity (Ki = 9.5-21 nM) at 5-HT2A receptors. It was shown that AMDA acts as a 5-HT2A receptor antagonist. The structure and molecular geometry of AMDA are not consistent with existing pharmacophore models for 5-HT2A receptor antagonist activity. Thus, AMDA may be a structurally novel parent of a new class of 5-HT2A receptor antagonists that binds to the receptor in a unique fashion that is distinct from the binding topology of existing 5-HT2A receptor antagonists.

Publication types

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

MeSH terms

  • 3T3 Cells
  • Animals
  • Anthracenes / chemistry
  • Anthracenes / metabolism*
  • Binding, Competitive
  • Ketanserin / metabolism
  • Mice
  • Phenols / metabolism
  • Phosphatidylinositols / metabolism
  • Propane / analogs & derivatives
  • Propane / metabolism
  • Radioligand Assay
  • Receptor, Serotonin, 5-HT2A
  • Receptors, Serotonin / metabolism*
  • Serotonin Antagonists / chemistry
  • Serotonin Antagonists / metabolism*
  • Structure-Activity Relationship
  • Tritium

Substances

  • 1,2,5-dimethoxy-4-bromophenol-2-aminopropane
  • 9-(aminomethyl)-9,10-dihydroanthracene
  • Anthracenes
  • Phenols
  • Phosphatidylinositols
  • Receptor, Serotonin, 5-HT2A
  • Receptors, Serotonin
  • Serotonin Antagonists
  • Tritium
  • Ketanserin
  • Propane