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.

中文翻译：

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1-（1,3-苯并二恶唑-5-基）-2-丁胺的衍生物：新型治疗剂的代表。

制备α-乙基苯乙胺衍生物1-（1，3-苯并二恶唑-5-基）-2-丁胺。不对称合成用于制备该化合物和相关的α-甲基同系物（MDA）的对映异构体。在训练以从0.08 mg / kg的LSD酒石酸盐中区分出盐水的大鼠中，在双杠杆药物歧视试验中评估了这两种化合物的外消旋物和对映体。外消旋物和α-甲基同系物的R-（-）对映异构体以及α-乙基伯胺的S-（+）对映异构体引起刺激泛化。其他对映异构体或任一系列的N-甲基衍生物均未发生泛化。人类心理药理学研究表明，标题化合物的N-甲基衍生物具有非hallucinogenic的作用，并且具有新型的新型精神活性。