title: Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class.
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.
mesh_terms: D000328:Adult; D000818:Animals; D002082:Butylamines / Q000138:chemical synthesis* / Q000494:pharmacology; D004149:Dioxoles / Q000138:chemical synthesis* / Q000494:pharmacology; D004193:Discrimination Learning / Q000187:drug effects; D005260:Female; D005795:Generalization, Stimulus / Q000187:drug effects; D006213:Hallucinogens / Q000494:pharmacology; D006801:Humans; D008238:Lysergic Acid Diethylamide / Q000494:pharmacology; D008297:Male; D008875:Middle Aged; D011619:Psychotropic Drugs / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D011919:Rats, Inbred Strains; D013329:Structure-Activity Relationship
chemical_list: D002082:Butylamines; D004149:Dioxoles; D006213:Hallucinogens; D011619:Psychotropic Drugs; D008238:Lysergic Acid Diethylamide