Psychotomimetic phenylisopropylamines. 5. 4-Alkyl-2,5-dimethoxyphenylisopropylamines
Alexander T. Shulgin, Donald C. Dyer
Journal of Medicinal Chemistry December 1, 1975 DOI: 10.1021/jm00246a006 via OpenAlex
Summary
AI-generated from the abstractA series of chemically related compounds, 4-alkyl-2,5-dimethoxyphenylisopropylamines with alkyl groups ranging from hydrogen to five-carbon straight chains and a branched four-carbon chain, was synthesized and tested for their ability to mimic serotonin in a sheep umbilical tissue preparation. Among the straight-chain variants, the compound with a three-carbon alkyl group was the most potent, matching its known mind-altering effects in humans.
Study at a glance
| Characteristics | Laboratory experiment Peer reviewed |
|---|---|
| Topics | Mescaline |
| Keywords | Psychotomimetic Homologous series Alkyl Stereochemistry |
| Citations | 37 |
| Key finding | The three-carbon homolog was the most potent serotonin agonist among the straight-chain series, consistent with its psychotomimetic potency in humans. |
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.