Sulfur analogs of psychotomimetic agents. 2. Analogs of (2,5-dimethoxy-4-methylphenyl)- and of (2,5-dimethoxy-4-ethylphenyl)isopropylamine
Journal of Medicinal Chemistry – May 01, 1983
Source: OpenAlex
Summary
The synthesized thio analogues of the psychotomimetic drugs DOM and DOET demonstrate intriguing potency differences. The 5-thio isomers were found to be significantly more potent than their 2-thio counterparts, yet both are notably less effective than the original compounds, showing a decrease in potency by an order of magnitude. Furthermore, the dithio analogue of DOM lacked central activity even at doses around 50 times higher than the mean effective dose of DOM, highlighting important distinctions in their pharmacological profiles.
Abstract
The two thio analogues of each of the well-known psychotomimetic drugs DOM [(2,5-dimethoxy-4-methylphenyl)isopropylamine] and DOET [(2,5-dimethoxy-4-ethylphenyl)isopropylamine] have been synthesized and pharmacologically evaluated in man. The 5-thio isomers are more potent as psychotomimetic agents than the 2-thio isomers but still represent a drop of an order of magnitude in potency from the sulfur-free counterparts. The dithio analogue of DOM was synthesized and found to be without central activity at a dosage of approximately 50 times the mean effective dose of DOM.