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Preclinical research indicates that\n                    <jats:italic>S<\/jats:italic>\n                    -MDMA releases monoamines and oxytocin more potently than\n                    <jats:italic>R<\/jats:italic>\n                    -MDMA, whereas\n                    <jats:italic>R<\/jats:italic>\n                    -MDMA more potently stimulates serotonin 5-hydroxytryptamine-2A receptors.\n                    <jats:italic>S<\/jats:italic>\n                    -MDMA may have more stimulant properties, and\n                    <jats:italic>R<\/jats:italic>\n                    -MDMA may be more psychedelic-like. However, acute effects of\n                    <jats:italic>S<\/jats:italic>\n                    - and\n                    <jats:italic>R<\/jats:italic>\n                    -MDMA have not been examined in a controlled human study. We used a double-blind, randomized, placebo-controlled, crossover design to compare acute effects of MDMA (125\u2009mg),\n                    <jats:italic>S<\/jats:italic>\n                    -MDMA (125\u2009mg),\n                    <jats:italic>R<\/jats:italic>\n                    -MDMA (125\u2009mg and 250\u2009mg), and placebo in 24 healthy participants. Outcome measures included subjective, autonomic, and adverse effects, pharmacokinetics, and plasma oxytocin, prolactin, and cortisol concentrations.\n                    <jats:italic>S<\/jats:italic>\n                    -MDMA (125\u2009mg) induced greater subjective effects (\u201cstimulation,\u201d \u201cdrug high,\u201d \u201chappy,\u201d \u201copen\u201d) and higher increases in blood pressure than\n                    <jats:italic>R<\/jats:italic>\n                    -MDMA (both 125 and 250\u2009mg) and MDMA (125\u2009mg). Unexpectedly,\n                    <jats:italic>R<\/jats:italic>\n                    -MDMA did not produce more psychedelic-like effects than\n                    <jats:italic>S<\/jats:italic>\n                    -MDMA.\n                    <jats:italic>S<\/jats:italic>\n                    -MDMA increased plasma prolactin more than MDMA, and\n                    <jats:italic>S<\/jats:italic>\n                    -MDMA increased plasma cortisol and oxytocin more than MDMA and\n                    <jats:italic>R<\/jats:italic>\n                    -MDMA. The plasma elimination half-life of\n                    <jats:italic>S<\/jats:italic>\n                    -MDMA was 4.1\u2009h after administration. The half-life of\n                    <jats:italic>R<\/jats:italic>\n                    -MDMA was 12 and 14\u2009h after the administration of 125 and 250\u2009mg, respectively. Half-lives for\n                    <jats:italic>S<\/jats:italic>\n                    -MDMA and\n                    <jats:italic>R<\/jats:italic>\n                    -MDMA were 5.1\u2009h and 11\u2009h, respectively, after racemic MDMA administration. Concentrations of the CYP2D6-formed MDMA-metabolite 4-hydroxy-3-methoxymethamphetamine were lower after\n                    <jats:italic>R<\/jats:italic>\n                    -MDMA administration compared with\n                    <jats:italic>S<\/jats:italic>\n                    -MDMA administration. The pharmacokinetic findings are consistent with the\n                    <jats:italic>R<\/jats:italic>\n                    -MDMA-mediated inhibition of CYP2D6. Stronger stimulant-like effects of\n                    <jats:italic>S<\/jats:italic>\n                    -MDMA in the present study may reflect the higher potency of\n                    <jats:italic>S<\/jats:italic>\n                    -MDMA rather than qualitative differences between\n                    <jats:italic>S<\/jats:italic>\n                    -MDMA and\n                    <jats:italic>R<\/jats:italic>\n                    -MDMA. Equivalent acute effects of\n                    <jats:italic>S<\/jats:italic>\n                    -MDMA, MDMA, and\n                    <jats:italic>R<\/jats:italic>\n                    -MDMA can be expected at doses of 100, 125, and 300\u2009mg, respectively, and need to be investigated.\n                  <\/jats:p>\n                  <jats:p>Trial registration: ClinicalTrials.gov identifier: NCT05277636<\/jats:p>","DOI":"10.1038\/s41386-024-01972-6","type":"journal-article","created":{"date-parts":[[2024,8,23]],"date-time":"2024-08-23T19:36:07Z","timestamp":1724441767000},"page":"362-371","update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["Acute effects of R-MDMA, S-MDMA, and racemic MDMA in a randomized double-blind cross-over trial in healthy participants"],"prefix":"10.1038","volume":"50","author":[{"given":"Isabelle","family":"Straumann","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Isidora","family":"Avedisian","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aaron","family":"Klaiber","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nimmy","family":"Varghese","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9341-3669","authenticated-orcid":false,"given":"Anne","family":"Eckert","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3069-9732","authenticated-orcid":false,"given":"Deborah","family":"Rudin","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0874-4875","authenticated-orcid":false,"given":"Dino","family":"Luethi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1765-9659","authenticated-orcid":false,"given":"Matthias E.","family":"Liechti","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2024,8,23]]},"reference":[{"key":"1972_CR1","doi-asserted-by":"crossref","first-page":"454","DOI":"10.1016\/S2213-8587(23)00120-1","volume":"11","author":"C Atila","year":"2023","unstructured":"Atila C, Holze F, Murugesu R, Rommers N, Hutter N, Varghese N, et al. 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