3,4-Methylenedioxymethamphetamine (MDMA) is researched in clinical trials as possible complementary treatment to psychotherapy in depression and posttraumatic stress disorder. It received break-through status after clinical evidence showed its potential, although questions regarding its abuse potential and cytotoxicity persist. There has been interest in exploring similar alternative substances that may retain therapeutic benefits while reducing adverse events. In this study, we characterized MDMA analogue 1,3-benzodioxolylbutanamine (BDB) and its structural analogue N-methyl-1,3-benzodioxolylbutanamine (MBDB) and compared them to the well-established 3,4-methylenedioxyamphetamine (MDA) and MDMA. The compounds differ in the addition of a methyl substituent on the terminal amine group and/or increased carbon chain length the alpha-carbon. To evaluate interactions with monoamine transporters, we performed in vitro radiotracer flux experiments in HEK293 cells stably expressing human isoforms of monoamine transporters. We show that that the interaction profile of BDB compares very well to MBDB and MDA at serotonin (SERT) and dopamine (DAT), but slightly differs at noradrenaline (NET) transporters. Additionally, due to higher selectivity for DAT than for SERT of BDB, MBDB and MDA may be associated with higher abuse liability than MDMA. However, MDA and MDMA evoke substrate release at DAT, which is linked to abuse, in contrast to BDB and MBDB. To further characterize these substances, we plan to examine potential interactions with 5-HT-receptors, which are known to contribute to the effects of MDA and MDMA. Further, we will perform in vivo behavioral assays to investigate changes in locomotion, anxiolytic effects, reward and motivational aspects.