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All synthetic cathinones exist as chiral molecules; the biological and\/or toxicological properties of cathinones generally differ according to the enantiomers in human body. In this study, a chiral liquid chromatography method was developed to separate and determine the enantiomeric ratio of synthetic cathinones present in \u201clegal highs\u201d acquired in old smart shops or over the Internet. All the synthetic cathinones were efficiently enantio-separated with \u03b1 and Rs ranging from 1.24 to 3.62 and from 1.24 to 10.52, respectively, using polysaccharide-based chiral stationary phases. All synthetic cathinones, with the exception of 4-methylethcathinone (4-MEC), were present in the commercialized \u201clegal highs\u201d in an enantiomeric proportion of 50:50. One of the studied chiral compounds was 3,4-methylenedioxypyrovalerone (MDPV), one of the most consumed cathinone derivative worldwide. Our research group has recently reported its hepatotoxicity in the racemic form. Thus, the analytical enantioresolution of the MDPV was scaled up to multi-milligram using a semi-preparative amylose <jats:italic>tris<\/jats:italic>-3,5-dimethylphenylcarbamate column (20\u00a0cm\u00a0\u00d7\u00a07.0\u00a0mm ID, 7\u00a0\u00b5m particle size). Both enantiomers were isolated with high enantiomeric purity (enantiomeric excess\u00a0&gt;\u00a099\u00a0%). The toxicity of <jats:italic>S<\/jats:italic>-(\u2212)-MDPV and <jats:italic>R<\/jats:italic>-(+)-MDPV was evaluated, for the first time, using primary cultures of rat hepatocytes. It was also possible to verify that MDPV enantiomers showed hepatotoxicity in a concentration-dependent manner, but displayed no enantioselective toxicity in this cell culture model.<\/jats:p>","DOI":"10.1007\/s11419-016-0324-y","type":"journal-article","created":{"date-parts":[[2016,6,13]],"date-time":"2016-06-13T09:35:22Z","timestamp":1465810522000},"page":"372-385","update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":52,"title":["Chiral enantioresolution of cathinone derivatives present in \u201clegal highs\u201d, and enantioselectivity evaluation on cytotoxicity of 3,4-methylenedioxypyrovalerone (MDPV)"],"prefix":"10.1007","volume":"34","author":[{"given":"B\u00e1rbara","family":"Silva","sequence":"first","affiliation":[]},{"given":"Carla","family":"Fernandes","sequence":"additional","affiliation":[]},{"given":"Maria Elizabeth","family":"Tiritan","sequence":"additional","affiliation":[]},{"given":"Madalena M.M.","family":"Pinto","sequence":"additional","affiliation":[]},{"given":"Maria Jo\u00e3o","family":"Valente","sequence":"additional","affiliation":[]},{"given":"M\u00e1rcia","family":"Carvalho","sequence":"additional","affiliation":[]},{"given":"Paula Guedes","family":"de Pinho","sequence":"additional","affiliation":[]},{"given":"Fernando","family":"Remi\u00e3o","sequence":"additional","affiliation":[]}],"member":"297","published-online":{"date-parts":[[2016,6,13]]},"reference":[{"key":"324_CR1","unstructured":"EMCDDA-Europol (2014) Annual report on the implementation of council decision 2005\/387\/JHA.http:\/\/www.emcdda.europa.eu\/attachements.cfm\/att_212366_EN_EMCDDA-Europol%202012%20Annual%20Report_final.pdf. 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