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. 2016 Mar 11;11(3):e0150955. doi: 10.1371/journal.pone.0150955

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© 2016 Steuer et al

This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

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Fig 1 — MDMA is mainly metabolized by CYP2D6-mediated O-demethylenation to 3,4-dihydroxymethamphetamine (DHMA), followed by catechol-O-methyltransferase (COMT) O-methylation mainly to 4-hydroxy-3-methoxymethamphetamine (HMMA). DHMA is further sulfated mainly by sulfotransferases (SULTs) to DHMA 3-sulfate (DHMA 3S) and DHMA 4-sulfate (DHMA 4S). HMMA can be further conjugated by UDP-glucuronyltransferases to HMMA glucuronide (HMMA G) or sulfotransferases to HMMA sulfate (HMMA S). Bold arrows indicate preferences in depicted metabolic reaction for R- or S-stereoisomer, respectively. Only sulfation of HMMA revealed no enantiomeric preferences.