{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,11]],"date-time":"2026-09-11T00:28:32Z","timestamp":1789086512268,"version":"build-2803163510"},"reference-count":30,"publisher":"Wiley","issue":"7","license":[{"start":{"date-parts":[[2014,10,20]],"date-time":"2014-10-20T00:00:00Z","timestamp":1413763200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Drug Testing and Analysis"],"published-print":{"date-parts":[[2015,7]]},"abstract":"<jats:p>The recent occurrence of deaths associated with the psychostimulant <jats:italic>cis<\/jats:italic>\u20104,4\u2032\u2010dimethylaminorex (4,4\u2032\u2010DMAR) in Europe indicated the presence of a newly emerged psychoactive substance on the market. Subsequently, the existence of 3,4\u2010methylenedioxy\u20104\u2010methylaminorex (MDMAR) has come to the authors' attention and this study describes the synthesis of <jats:italic>cis<\/jats:italic>\u2010 and <jats:italic>trans<\/jats:italic>\u2010MDMAR followed by extensive characterization by chromatographic, spectroscopic, mass spectrometric platforms and crystal structure analysis. MDMAR obtained from an online vendor was subsequently identified as predominantly the <jats:italic>cis<\/jats:italic>\u2010isomer (90%). Exposure of the <jats:italic>cis<\/jats:italic>\u2010isomer to the mobile phase conditions (acetonitrile\/water 1:1 with 0.1% formic acid) employed for high performance liquid chromatography analysis showed an artificially induced conversion to the <jats:italic>trans<\/jats:italic>\u2010isomer, which was not observed when characterized by gas chromatography. Monoamine release activities of both MDMAR isomers were compared with the non\u2010selective monoamine releasing agent (+)\u20103,4\u2010methylenedioxymethamphetamine (MDMA) as a standard reference compound. For additional comparison, both <jats:italic>cis<\/jats:italic>\u2010 and <jats:italic>trans<\/jats:italic>\u20104,4\u2032\u2010DMAR, were assessed under identical conditions. <jats:italic>cis<\/jats:italic>\u2010MDMAR, <jats:italic>trans<\/jats:italic>\u2010MDMAR, <jats:italic>cis<\/jats:italic>\u20104,4\u2032\u2010DMAR and <jats:italic>trans<\/jats:italic>\u20104,4\u2032\u2010DMAR were more potent than MDMA in their ability to function as efficacious substrate\u2010type releasers at the dopamine (DAT) and norepinephrine (NET) transporters in rat brain tissue. While <jats:italic>cis<\/jats:italic>\u20104,4\u2032\u2010DMAR, <jats:italic>cis<\/jats:italic>\u2010MDMAR and <jats:italic>trans<\/jats:italic>\u2010MDMAR were fully efficacious releasing agents at the serotonin transporter (SERT), <jats:italic>trans<\/jats:italic>\u20104,4\u2032\u2010DMAR acted as a fully efficacious uptake blocker. Currently, little information is available about the presence of MDMAR on the market but the high potency of ring\u2010substituted methylaminorex analogues at all three monoamine transporters investigated here might be relevant when assessing the potential for serious side\u2010effects after high dose exposure. Copyright \u00a9 2014 John Wiley &amp; Sons, Ltd.<\/jats:p>","DOI":"10.1002\/dta.1732","type":"journal-article","created":{"date-parts":[[2014,10,20]],"date-time":"2014-10-20T10:29:39Z","timestamp":1413800979000},"page":"555-564","source":"Crossref","is-referenced-by-count":19,"title":["Synthesis, characterization, and monoamine transporter activity of the new psychoactive substance 3\u2032,4\u2032\u2010methylenedioxy\u20104\u2010methylaminorex (MDMAR)"],"prefix":"10.1002","volume":"7","author":[{"given":"Gavin","family":"McLaughlin","sequence":"first","affiliation":[{"name":"Department of Life and Physical Sciences, School of Science Athlone Institute of Technology  Dublin Road, Athlone Co. 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