Synthesis of hydroxy- and methoxy-substituted octahydrobenzo[g]isoquinolines as potential ligands for serotonin receptors†

In 7 steps, 6- or 9-hydroxylated or -methoxylated trans-octahydrobenzo [g] isoquinolines were efficiently synthesized starting from dimethoxynaphthalenes, as potential new selective ligands for serotonin receptors. The 6-substituted compounds had very little affinity to common neurotransmitter receptors, with the exception of adrenergic α 2 . The 9-substituted compounds, while showing interesting affinity for 5HT 1a receptors, had comparable affinities for adrenergic α 1 and α 2 , and in one case for dopamine D2 receptors