111635-19-9Relevant articles and documents
R-(-)-N-alkyl-11-hydroxy-10-hydroxymethyl- and 10-methyl-aporphines as 5-HT1A receptor ligands
Si, Yu-Gui,Gardner, Matthew P.,Tarazi, Frank I.,Baldessarini, Ross J.,Neumeyer, John L.
, p. 4128 - 4130 (2007)
Several N-substituted-11-hydroxy-10-hydroxymethyl- and 11-hydroxy-10-methylaporphines were synthesized and their binding affinities at dopamine D1 and D2 receptors and serotonin 5-HT1A and 5-HT2A receptors in rat forebrain tissue were evaluated. Tested compounds displayed moderate to high affinity to 5-HT1A receptors but low affinity to D1 and D2 receptors. The most potent novel 5-HT1A agent was R-(-)-N-methyl-10-hydroxymethyl-11-hydroxyaporphine.
(R)-11-Hydroxy- and (R)-11-Hydroxy-10-methylaporphine: Synthesis, Pharmacology, and Modelling of D2A and 5-HT1A Receptor Interactions
Hedberg, Martin H.,Johansson, Anette M.,Nordvall, Gunnar,Yliniemelae, Ari,Li, Hong Bing,et al.
, p. 647 - 658 (1995)
(R)-11-Hydroxyaporphine (2) and (R)-11-hydroxy-10-methylaporphine (3) were synthesized from natural morphine by using new, short, and efficent synthetic sequences.The dopaminergic and serotonergic effects of 2 and 3 were evaluated by use of in vitro and in vivo test systems.The results indicate that 3 is a potent, selective, and efficacious 5-HT1A receptor agonist.In contrast, 2 is a partial 5-HT1A receptor agonist of low potency which has affinity also for central D1 and D2A receptors.The differences in pharmacological profiles were rationalized by modeling of ligand-receptor interactions using homology-based receptor models of the 5-HT1A and D2A receptor binding site.The selective and pronounced serotonergic effects of 3 appear to be due to the C10-methyl group, which is accommodated by a lipophilic pocket in the 5-HT1A receptor.In contrast, the C10-methyl group of 3 is not accommodated by the binding site model of the D2A receptor.
