The Preparation of Potentially Psychoactive β-Alkoxyphenethylamines

Abstract

The preparation of β-alkoxyphenethylamines 3 is described. As part of our interest in structure-activity relationships of psychotomimetic phenethylamines ¹ and their interactions with serotoninergic receptors ², we describe in the present communication the preparation of a series of substituted β-alkoxyphenylethylamines. A few of these compounds had been prepared before 3,4 and their psychotropic properties described with human volunteers. However, no pharmacological studies on these new compounds have been carried out since then, aside from the few instances in which a β-methoxylated derivative has shown a potency similar to or slightly greater than that of the parent compound. Little is known about the effects of substitution at the β-position of the side chain of hallucinogenic phenethylamines, although it was speculated that their activity might be mediated in part by mteractions with adrenergic receptors.