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MDMA is a psychoactive drug, typically regarded as an empathogen or entactogen, which leads to transporter\u2010mediated monoamine release. Despite its therapeutic potential, MDMA can induce dose\u2010, individual\u2010, and context\u2010dependent untoward effects outside safe settings. In this study, we investigated whether three new methylenedioxy bioisosteres of MDMA improve its off\u2010target profile. In\u00a0vitro methods included radiotracer assays, transporter electrophysiology, bioluminescence resonance energy transfer and fluorescence\u2010based assays, pooled human liver microsome\/S9 fraction incubations, metabolic stability studies, isozyme mapping, and liquid chromatography coupled to high\u2010resolution mass spectrometry. In silico methods included molecular docking. Compared with MDMA, all three MDMA bioisosteres (ODMA, TDMA, and SeDMA) showed similar pharmacological activity at human serotonin, dopamine, and norepinephrine transporters (hSERT, hDAT, and hNET, respectively) but decreased agonist activity at 5\u2010HT\n                    <jats:sub>2A\/2B\/2C<\/jats:sub>\n                    receptors. Regarding their hepatic metabolism, they differed from MDMA, with\n                    <jats:italic>N<\/jats:italic>\n                    \u2010demethylation being the only metabolic route shared, and without forming phase II metabolites. In addition, TDMA showed an enhanced intrinsic clearance in comparison to its congeners. Additional screening for their interaction with human organic cation transporters (hOCTs) and plasma membrane monoamine transporter (hPMAT) revealed a weaker interaction of the MDMA analogs with hOCT1, hOCT2, and hPMAT. Our findings suggest that these new MDMA bioisosteres might constitute appealing therapeutic alternatives to MDMA, sparing the primary pharmacological activity at hSERT, hDAT, and hNET, but displaying a reduced activity at 5\u2010HT\n                    <jats:sub>2A\/2B\/2C<\/jats:sub>\n                    receptors and alternative hepatic metabolism. Whether these MDMA bioisosteres may pose lower risk alternatives to the clinically re\u2010emerging MDMA warrants further studies.\n                    <jats:boxed-text content-type=\"graphic\" position=\"anchor\">\n                      <jats:graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" mimetype=\"image\/png\" position=\"anchor\" specific-use=\"enlarged-web-image\" xlink:href=\"graphic\/jnc16149-fig-0007-m.png\">\n                        <jats:alt-text>image<\/jats:alt-text>\n                      <\/jats:graphic>\n                    <\/jats:boxed-text>\n                  <\/jats:p>","DOI":"10.1111\/jnc.16149","type":"journal-article","created":{"date-parts":[[2024,6,20]],"date-time":"2024-06-20T02:06:16Z","timestamp":1718849176000},"page":"2022-2042","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Bioisosteric analogs of\n                    <scp>MDMA<\/scp>\n                    : Improving the pharmacological profile?"],"prefix":"10.1111","volume":"168","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5662-0581","authenticated-orcid":false,"given":"Ana Sofia","family":"Alberto\u2010Silva","sequence":"first","affiliation":[{"name":"Center for Physiology and Pharmacology Institute of Pharmacology, Medical University of Vienna  Vienna Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-5534-0612","authenticated-orcid":false,"given":"Selina","family":"Hemmer","sequence":"additional","affiliation":[{"name":"Department of Experimental and Clinical Toxicology Institute of Experimental and Clinical Pharmacology and Toxicology, Center for Molecular Signaling (PZMS), Saarland University  Homburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3457-9319","authenticated-orcid":false,"given":"Hailey A.","family":"Bock","sequence":"additional","affiliation":[{"name":"Department of 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