Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class
David E. Nichols, Andrew J. Hoffman, Robert Oberlender, Peyton Jacob, Alexander T. Shulgin
Journal of Medicinal Chemistry October 1, 1986 DOI: 10.1021/jm00160a035 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Preclinical and human psychopharmacology study Peer reviewed |
|---|---|
| Population | Rats and humans |
| Interventions | 1-(1 3-benzodioxol-5-yl)-2-butanamine MDA N-methyl derivatives |
| Keywords | Enantiomer Phenethylamine Stereochemistry |
| Citations | 189 |
| Key points | The S-(+) enantiomer of the alpha-ethyl primary amine and the R-(-) enantiomer of the alpha-methyl homologue generalized to LSD in rats, while the N-methyl derivative was nonhallucinogenic in humans and produced a novel psychoactive effect, suggesting a new class of entactogens. |
Abstract
The alpha-ethyl phenethylamine derivative 1-(1,3-benzodioxol-5-yl)-2-butanamine was prepared. An asymmetric synthesis was used to prepare the enantiomers of this compound and the related alpha-methyl homologue (MDA). The racemates and enantiomers of both compounds were evaluated in the two-lever drug discrimination assay in rats trained to discriminate saline from 0.08 mg/kg of LSD tartrate. Stimulus generalization occurred with the racemate and the R-(-) enantiomer of the alpha-methyl homologue and the S-(+) enantiomer of the alpha-ethyl primary amine. No generalization occurred with the other enantiomers or with the N-methyl derivatives of either series. Human psychopharmacology studies revealed that the N-methyl derivative of the title compound was nonhallucinogenic and that it had a new, novel psychoactive effect. It is suggested that this compound is the prototype of a new pharmacologic class that may have value in facilitating psychotherapy and that this class be designated as entactogens.