Synthesis and binding studies of 2-arylapomorphines

Org Biomol Chem. 2005 Nov 21;3(22):4077-81. doi: 10.1039/b507195j. Epub 2005 Oct 13.


From codeine, four different 2-aryl substituted apomorphines were synthesised in 6 steps each. Oxidation of codeine with IBX followed by acid catalysed rearrangement gave morphothebaine, which was selectively triflylated at the 2-position and subsequently O-acetylated at the 11-position. The resulting triflate was coupled in a Suzuki-Miyaura type reaction with a series of 4-substituted arylboronic esters which, after deprotection, gave the desired 2-aryl apomorphines. The analogues were tested for affinity towards a range of dopaminergic, serotonergic and adrenergic receptors. 2-(4-Hydroxyphenyl)-apomorphine exhibited high affinity for the dopamine D2 receptor. A putative ligand-receptor interaction was put forward.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Apomorphine / chemical synthesis*
  • Apomorphine / chemistry
  • Apomorphine / metabolism*
  • Humans
  • Ligands
  • Male
  • Molecular Structure
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Biogenic Amine / metabolism*
  • Receptors, Dopamine D2 / metabolism


  • Ligands
  • Receptors, Biogenic Amine
  • Receptors, Dopamine D2
  • Apomorphine