{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,27]],"date-time":"2026-06-27T05:26:19Z","timestamp":1782537979770,"version":"3.54.5"},"reference-count":51,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2021,7,1]],"date-time":"2021-07-01T00:00:00Z","timestamp":1625097600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Drug Testing and Analysis"],"published-print":{"date-parts":[[2022,3]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Amphetamine (<jats:italic>speed<\/jats:italic>), methamphetamine (<jats:italic>crystal meth<\/jats:italic>), and 3,4\u2010methylenedioxy\u2010N\u2010methylamphetamine (MDMA, <jats:italic>ecstasy<\/jats:italic>) represent the most frequently abused amphetamine\u2010type stimulants (ATS). Differences in pharmacological potency and metabolism have been shown for the enantiomers of all three stimulants. Legal consequences in cases of drug possession may also differ according to the German law depending on the enantiomeric composition of the seized drug. Therefore, enantioselective monitoring of seized specimens is crucial for legal and forensic casework.<\/jats:p><jats:p>Various kinds of samples of amphetamine (<jats:italic>n<\/jats:italic>\u2009=\u2009143), MDMA (<jats:italic>n<\/jats:italic>\u2009=\u200994), and methamphetamine (<jats:italic>n<\/jats:italic>\u2009=\u2009528) that were seized in southern Germany in 2019 and 2020 were analyzed for their chiral composition using different chromatographic methods.<\/jats:p><jats:p>Whereas all samples of amphetamine and MDMA were racemic mixtures, the chiral composition of the methamphetamine specimens was diverse. Although the vast majority (<jats:italic>n<\/jats:italic>\u2009=\u2009502) was present as (S)\u2010methamphetamine, also specimens containing pure (R)\u2010methamphetamine (<jats:italic>n<\/jats:italic>\u2009=\u20097) were found. Furthermore, few samples (<jats:italic>n<\/jats:italic>\u2009=\u20098) were of racemic nature or contained non\u2010racemic mixtures of both enantiomers (<jats:italic>n<\/jats:italic>\u2009=\u200910).<\/jats:p><jats:p>Because methamphetamine appears in varying enantiomeric compositions, any seizure should be analyzed using an enantioselective method. Amphetamine and MDMA, on the other hand, currently appear to be synthesized exclusively via racemic pathways and are not chirally purified. Nevertheless, regular monitoring of the chiral composition should be ensured.<\/jats:p>","DOI":"10.1002\/dta.3118","type":"journal-article","created":{"date-parts":[[2021,6,25]],"date-time":"2021-06-25T03:28:01Z","timestamp":1624591681000},"page":"557-566","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":26,"title":["Determination of the enantiomeric composition of amphetamine, methamphetamine and 3,4\u2010methylendioxy\u2010<i>N<\/i>\u2010methylamphetamine (MDMA) in seized street drug samples from southern Germany"],"prefix":"10.1002","volume":"14","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8880-1512","authenticated-orcid":false,"given":"Moritz","family":"Losacker","sequence":"first","affiliation":[{"name":"Department of Forensic Toxicology, Institute of Legal Medicine Johannes Gutenberg University Mainz  Mainz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Siegfried","family":"Z\u00f6rntlein","sequence":"additional","affiliation":[{"name":"Forensic Science Institute, Dez. 33 Chemistry\/Toxicology State Office of Criminal Investigation Rhineland\u2010Palatinate  Mainz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bernd","family":"Schwarze","sequence":"additional","affiliation":[{"name":"Department of Forensic Toxicology, Institute of Legal Medicine Friedrich\u2010Alexander University Erlangen\u2010N\u00fcrnberg  Erlangen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Svenja","family":"Staudt","sequence":"additional","affiliation":[{"name":"Department of Forensic Toxicology, Institute of Legal Medicine Friedrich\u2010Alexander University Erlangen\u2010N\u00fcrnberg  Erlangen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J\u00f6rg","family":"R\u00f6hrich","sequence":"additional","affiliation":[{"name":"Department of Forensic Toxicology, Institute of Legal Medicine Johannes Gutenberg University Mainz  Mainz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8405-4417","authenticated-orcid":false,"given":"Cornelius","family":"Hess","sequence":"additional","affiliation":[{"name":"Department of Forensic Toxicology, Institute of Legal Medicine Johannes Gutenberg University Mainz  Mainz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,7]]},"reference":[{"key":"e_1_2_7_2_1","unstructured":"United Nations Office on Drugs and Crime.World drug report 2020. UN;2020."},{"key":"e_1_2_7_3_1","unstructured":"World Health Organization.Management of substance abuse: amphetamine\u2010type stimulants.https:\/\/www.who.int\/substance_abuse\/facts\/ATS\/en\/. Accessed October 8 2020."},{"key":"e_1_2_7_4_1","unstructured":"European Monitoring Centre for Drugs and Drug Addiction.Germany country drug report 2019. Luxembourg: Publications Office of the European Union;2019."},{"key":"e_1_2_7_5_1","unstructured":"European Monitoring Centre for Drugs and Drug Addiction.European drug report 2019: trends and developments. Luxembourg: Publications Office of the European Union;2019."},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00426687"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00702-017-1694-y"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.clpt.2006.06.013"},{"key":"e_1_2_7_9_1","first-page":"8","article-title":"Absolute configuration and psychotomimetic activity","volume":"22","author":"Anderson GM","year":"1978","journal-title":"NIDA Research Monograph, National Institute on Drug Abuse"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00212770"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1093\/clinchem\/45.7.1058"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/cpt1978235585"},{"issue":"9","key":"e_1_2_7_13_1","doi-asserted-by":"crossref","first-page":"1001","DOI":"10.1016\/S0090-9556(24)02984-2","article-title":"Stereochemical analysis of 3,4\u2010methylenedioxymethamphetamine and its main metabolites in human samples including the catechol\u2010type metabolite (3,4\u2010dihydroxymethamphetamine)","volume":"32","author":"Pizarro N","year":"2004","journal-title":"Drug Metab Dispos"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1124\/dmd.115.066340"},{"key":"e_1_2_7_15_1","first-page":"1","article-title":"Herleitung von Grenzwerten der \u201cnicht geringen Mengen\u201d im Sinne des BtMG [Derivation of threshold values of \u2018not insignificant quantities\u2019 in the sense of the BtMG]: Teil III Phenethylamine und Cathinone [Part III phenethylamines and cathinones]","volume":"86","author":"Bork WR","year":"2019","journal-title":"Toxichem Krimtech"},{"key":"e_1_2_7_16_1","unstructured":"Gesetz \u00fcber den Verkehr mit Bet\u00e4ubungsmitteln Bet\u00e4ubungsmittelgesetz (Act on the trade in narcotic drugs narcotic drugs act): BtMG;1981."},{"key":"e_1_2_7_17_1","unstructured":"United Nations: International Narcotics Control Board.Precursors and chemicals frequently used in the illicit manufacture of narcotic drugs and \u2026 psychotropic substances 2019. United Nations;2019."},{"key":"e_1_2_7_18_1","unstructured":"European Monitoring Centre for Drugs and Drug Addiction.Methamphetamine in Europe: EMCDDA\u2010Europol threat assessment 2019. Luxembourg: Publications Office of the European Union;2019."},{"key":"e_1_2_7_19_1","unstructured":"Gesellschaft f\u00fcr Toxikologische und Forensische Chemie GTFCh.Anhang A zur Richtlinie zur Qualit\u00e4tssicherung bei forensisch\u2010chemischen Untersuchungen von Bet\u00e4ubungsmitteln und Arzneimitteln [Annex A to the guideline for quality assurance in forensic\u2010chemical investigations of narcotics and pharmaceuticals]: Probennahme bei forensisch\u2010chemischen Untersuchungen von Bet\u00e4ubungsmitteln [Sampling for forensic\u2010chemical investigations of narcotics];2012."},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1093\/jat\/21.1.5"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1093\/jat\/24.3.223"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jksus.2020.05.003"},{"key":"e_1_2_7_23_1","unstructured":"MifsudM.The physical and chemical characterisation of 3 4\u2010methylenedioxymethamphetamine\/ecstasy tablets: implications for users. [Dissertation]. University of London King's College London Institute of Psychiatry;2013."},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02466533"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/elps.200390128"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.watres.2017.11.051"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00213-003-1712-7"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1136\/jcp.49.2.149"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1081\/ja-100000227"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0379-0738(96)02101-9"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1136\/emj.16.3.194"},{"key":"e_1_2_7_32_1","first-page":"137","article-title":"Impurities in illicit drug preparation: 3,4\u2010(methylenedioxy) amphetamine and 3,4\u2010(methylenedioxy)methamphetamine","volume":"4","author":"Verweij AM","year":"1992","journal-title":"Forensic Sci Rev"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.forsciint.2006.10.013"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1093\/jat\/bkv060"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.scitotenv.2017.05.045"},{"issue":"4","key":"e_1_2_7_36_1","first-page":"426","article-title":"Monitoring precursor chemicals through enantiomer profiling of methamphetamine","volume":"38","author":"Zhang J","year":"2009","journal-title":"Wei Sheng Yan Jiu"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.forsciint.2012.08.036"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11419-011-0119-0"},{"issue":"1","key":"e_1_2_7_39_1","first-page":"20","article-title":"Characterisation of seized clandestine methamphetamine in Malaysia","volume":"6","author":"Hamdan R","year":"2015","journal-title":"Malaysian Journal of Forensic Sciences"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.drugalcdep.2012.10.001"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.yrtph.2020.104747"},{"key":"e_1_2_7_42_1","unstructured":"European Monitoring Centre for Drugs and Drug Addiction.European drug report 2020: trends and developments. Luxembourg: Publications Office of the European Union;2020."},{"key":"e_1_2_7_43_1","unstructured":"Bundesministerium f\u00fcr Gesundheit Die Drogenbeauftragte. Drogen\u2010 und Suchtbericht der Bundesregierung 2017 [Drug and addiction report of the German federal government 2017].2017."},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00414-018-1979-1"},{"key":"e_1_2_7_45_1","unstructured":"European Monitoring Centre for Drugs and Drug Addiction.Amphetamine drug profile.https:\/\/www.emcdda.europa.eu\/publications\/drug-profiles\/amphetamine_en. Accessed October 13 2020."},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.forsciint.2018.08.013"},{"key":"e_1_2_7_47_1","unstructured":"Bundesministerium f\u00fcr Gesundheit Die Drogenbeauftragte. Drogen\u2010 und Suchtbericht der Bundesregierung 2020 [Drug and addiction report of the German federal government 2017].2020."},{"key":"e_1_2_7_48_1","unstructured":"Reuters.Mexico seizes over 800 tonnes of meth chemicals.https:\/\/www.reuters.com\/article\/us-mexico-drugs-meth\/mexico-seizes-over-800-tonnes-of-meth-chemicals-idUSTRE76K45I20110721. Accessed October 7 2020."},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(00)86170-4"},{"key":"e_1_2_7_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo061033l"},{"key":"e_1_2_7_51_1","first-page":"737","volume-title":"International Tables for Crystallography: Online MRW","author":"Rendle DF","year":"2010"},{"key":"e_1_2_7_52_1","unstructured":"Bundesministerium f\u00fcr Gesundheit und Frauen.Suchtgift\u2010Grenzmengenverordnung [Narcotic drugs limit ordinance]: SGV;1998."}],"container-title":["Drug Testing and Analysis"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/dta.3118","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/dta.3118","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/dta.3118","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T09:43:43Z","timestamp":1760348623000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/dta.3118"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,7]]},"references-count":51,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2022,3]]}},"alternative-id":["10.1002\/dta.3118"],"URL":"https:\/\/doi.org\/10.1002\/dta.3118","archive":["Portico"],"relation":{},"ISSN":["1942-7603","1942-7611"],"issn-type":[{"value":"1942-7603","type":"print"},{"value":"1942-7611","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,7]]},"assertion":[{"value":"2021-04-13","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-06-21","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-07-01","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}