Psychotomimetic phenylisopropylamines. 5. 4-Alkyl-2,5-dimethoxyphenylisopropylamines
Journal of Medicinal Chemistry – December 01, 1975
Source: OpenAlex
Summary
The three-carbon homolog 6d of a series of 4-alkyl-2,5-dimethoxyphenylisopropylamines exhibited the highest potency as a serotonin agonist, surpassing mescaline in effectiveness. In a study involving sheep umbilical preparations, this compound demonstrated significant psychotomimetic properties. The series included compounds with alkyl groups ranging from hydrogen to pentyl and tertiary butyl, highlighting the importance of stereochemistry and chemical reaction mechanisms in their synthesis. Analytical chemistry techniques like chromatography were crucial for evaluating the asymmetric synthesis and catalysis involved in these compounds.
Abstract
A homologous series of 4-alkyl-2,5-dimethoxyphenylisopropylamines (alkyl = H through n-C5H11 and t-C4H9) was synthesized and compared with mescaline as serotonin agonists in a sheep umbilical preparation. The three-carbon homolog 6d was found to be the most potent of the straight-chain series in accordance with its observed psychotomimetic effectiveness in man.