Synthesis of Phenethylamine Derivatives as Hallucinogen.

Abstract

In Japan, several phenethylamine derivatives such as mescaline and 3, 4-methylenedioxyamphetamine, which are hallucinogens were appointed to narcotics in 1989 and 1990. Reference standards of phenethylamine derivatives are required for their forensic chemical analyses. Present study was intended to synthesize phenethylamine derivatives from benzaldehyde derivatives by a novel route improving the yield. Five narcotic phenethylamine derivatives, mescaline hydrochloride, p-methoxyamphetamine hydrochloride (PMA), 3, 4-methylenedioxyamphetamine hydrochloride (MDA), 2, 5-dimethoxyamphetamine hydrochloride (DMA), 3, 4, 5-trimethoxyamphetamine hydrochloride (TMA) and their β-hydroxy derivatives that can be their raw materials were obtained. The methods were as follows 1) Nitroalcohols were obtained by a condensation of nitroalkane and benzaldehydes using sodium methoxide as a catalyst. 2) The nitroalcohols were acetylated with acetic anhydride. 3) The acetyl derivatives were converted into nitro-olefins by elimination of acetic acid. 4) Phenethylamine derivatives were synthesized from nitro-olefins by catalytic reduction using palladium on carbon in an autoclave. 5) In the same way, β-hydroxyphenethylamine derivatives were synthesized from nitroalcohols.