Studies on Theoretical Psychotogens. Synthesis of O-Methylated Analogs of Catecholamine Neurotransmitters and Metabolic Precursors

Abstract

The catecholamine analogs (±)-1-(3,4-dimethoxyphenyl)-2-alanine (1), β-(3,4-dimethoxyphenyl)ethylamine (2), (±)-1-(3,4-dimethoxyphenyl)-2-amino propane (3), (±)-erythro, threo-α-aminomethyl-3,4-dimethoxybenzyl alcohol (4), and (±)-erythro, threo-α-methylaminomethyl-3,4-dimethoxybenzyl alcohol (5) have been synthesized and optimized yields are reported. The availability of certain carbon-14 compounds has dictated logical starting points in the synthesis of 14C-tagged analogs. These syntheses were designed for metabolic and disposition work in connection with a pilot project concerned with the aetiology of schizophrenia with particular reference to the Osmond–Smythies – Harley-Mason hypothesis (2) of 1952.