{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,9]],"date-time":"2026-08-09T11:11:46Z","timestamp":1786273906055,"version":"build-2736575974"},"reference-count":28,"publisher":"Springer Science and Business Media LLC","issue":"1","license":[{"start":{"date-parts":[[2021,9,14]],"date-time":"2021-09-14T00:00:00Z","timestamp":1631577600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2021,9,14]],"date-time":"2021-09-14T00:00:00Z","timestamp":1631577600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"funder":[{"DOI":"10.13039\/501100004569","name":"Ministerstwo Nauki i Szkolnictwa Wy\u017cszego","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004569","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["Forensic Toxicol"],"published-print":{"date-parts":[[2022,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:sec>\n                <jats:title>Purpose<\/jats:title>\n                <jats:p>New psychoactive substances (NPSs) still appear on the market, mainly due to their legal status. This situation indicates and alarms that permanent recognition of the designer drug scene should be conducted. In this paper, we describe the detection of three psychoactive substances in samples collected from drug users.<\/jats:p>\n              <\/jats:sec><jats:sec>\n                <jats:title>Methods<\/jats:title>\n                <jats:p>Qualitative characterization was performed using liquid chromatography\u2013high-resolution tandem mass spectrometry with a quadrupole time-of-flight analyzer, gas chromatography with mass spectrometry and nuclear magnetic resonance spectroscopy.<\/jats:p>\n              <\/jats:sec><jats:sec>\n                <jats:title>Results<\/jats:title>\n                <jats:p>In this study, we reported the detection and structural elucidation of three psychoactive substances: 1-(4-bromophenyl)piperazine (<jats:italic>p<\/jats:italic>BPP), 1-(3-chloro-4-fluorophenyl)piperazine (3,4-CFPP) and methyl 8-methyl-3-phenyl-8-azabicyclo[3.2.1]octane-4-carboxylate (troparil).<\/jats:p>\n              <\/jats:sec><jats:sec>\n                <jats:title>Conclusions<\/jats:title>\n                <jats:p>To the best of our knowledge, this is the first report that presents an identification methodology for these substances found in illegal products. Comprehensive characterization of the NPSs presented in this paper facilitates their detection and identification by forensic and clinical laboratories.<\/jats:p>\n              <\/jats:sec>","DOI":"10.1007\/s11419-021-00597-4","type":"journal-article","created":{"date-parts":[[2021,9,14]],"date-time":"2021-09-14T09:02:57Z","timestamp":1631610177000},"page":"132-143","update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Identification and structural characterization of three psychoactive substances, phenylpiperazines (pBPP and 3,4-CFPP) and a cocaine analogue (troparil), in collected samples"],"prefix":"10.1007","volume":"40","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0042-9088","authenticated-orcid":false,"given":"Magdalena","family":"Pop\u0142awska","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"El\u017cbieta","family":"Bednarek","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Beata","family":"Naumczuk","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Agata","family":"B\u0142a\u017cewicz","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2021,9,14]]},"reference":[{"key":"597_CR1","doi-asserted-by":"publisher","DOI":"10.2810\/18539","volume-title":"European drug report 2021: trends and developments","author":"European Monitoring Centre for Drugs and Drug Addiction","year":"2021","unstructured":"European Monitoring Centre for Drugs and Drug Addiction (2021) European drug report 2021: trends and developments. Publications Office of the European Union, Luxembourg. Available at: https:\/\/www.emcdda.europa.eu\/system\/files\/publications\/13838\/TDAT21001ENN.pdf. https:\/\/doi.org\/10.2810\/18539"},{"key":"597_CR2","unstructured":"European Monitoring Centre for Drugs and Drug Addiction. European Database on New Drugs. Accessed 6 Feb 2021"},{"key":"597_CR3","doi-asserted-by":"publisher","unstructured":"European Monitoring Centre for Drugs and Drug Addiction and Europol (2019) EU Drug markets report 2019. Publications Office of the European Union, Luxembourg, Available at: http:\/\/www.emcdda.europa.eu\/system\/files\/publications\/12078\/20192630_TD0319332ENN_PDF.pdf. https:\/\/doi.org\/10.2810\/796253. Accessed 6 Feb 2021","DOI":"10.2810\/796253"},{"key":"597_CR4","doi-asserted-by":"publisher","DOI":"10.1016\/j.forsciint.2019.110107","volume":"307","author":"CS Johnson","year":"2020","unstructured":"Johnson CS, Stansfield CR, Hassan VR, Kolbe E, Partington HK, Kappatos DC, Somerville RF (2020) The phenomenon of para-fluorophenylpiperazine (pFPP) in combination with the synthetic cannabinoid AMB-FUBINACA in seized plant material in New Zealand. Forensic Sci Int 307:110107. https:\/\/doi.org\/10.1016\/j.forsciint.2019.110107","journal-title":"Forensic Sci Int"},{"key":"597_CR5","unstructured":"European Monitoring Centre for Drugs and Drug Addiction (2016) Dichloropane, RTI-111. EU early warning system formal notification EU-EWS-RCS-FN-2016 0065. European database on new drugs (EDND)"},{"key":"597_CR6","unstructured":"European Monitoring Centre for Drugs and Drug Addiction (2018) WIN 35428. EU early warning system formal notification EU-EWS-RCS-FN-2018-0041. European database on new drugs (EDND)"},{"issue":"1","key":"597_CR7","first-page":"3","volume":"8","author":"JF Casale","year":"2011","unstructured":"Casale JF, Hays PA (2011) Characterization of 2\u03b2-(1,2,4-oxadiazol-5-methyl)-3\u03b2-phenyltropane (\u201cRTI-126\u201d). Microgram J 8(1):3\u201311 (Open access article)","journal-title":"Microgram J"},{"issue":"3","key":"597_CR8","doi-asserted-by":"publisher","first-page":"203","DOI":"10.1002\/jms.4053","volume":"53","author":"HJ Dias","year":"2018","unstructured":"Dias HJ, Bento MVB, da Silva \u00c9H, Saturnino-J\u00fanior A, de Oliveira MF, Vessecchi R, Parreira RLT, Crotti AEM (2018) Gas-phase fragmentation reactions of protonated cocaine: new details to an old story. J Mass Spectrom 53(3):203\u2013213. https:\/\/doi.org\/10.1002\/jms.4053","journal-title":"J Mass Spectrom"},{"issue":"10","key":"597_CR9","doi-asserted-by":"publisher","first-page":"1169","DOI":"10.1517\/13543776.2012.719878","volume":"22","author":"RC Maia","year":"2012","unstructured":"Maia RC, Tesch R, Manssour Fraga CA (2012) Phenylpiperazine derivatives: a patent review (2006\u2013present). Expert Opin Ther Pat 22(10):1169\u20131178. https:\/\/doi.org\/10.1517\/13543776.2012.719878","journal-title":"Expert Opin Ther Pat"},{"key":"597_CR10","unstructured":"http:\/\/www.emcdda.europa.eu\/publications\/drug-profiles\/bzp. Accessed 5 Feb 2020"},{"key":"597_CR11","doi-asserted-by":"publisher","first-page":"335","DOI":"10.1080\/09595230701255791","volume":"26","author":"J Sheridan","year":"2007","unstructured":"Sheridan J, Butler R, Wilkins C, Russell B (2007) Legal piperazine-containing party pills\u2014a new trend in substance misuse. Drug Alcohol Rev 26:335\u2013343. https:\/\/doi.org\/10.1080\/09595230701255791","journal-title":"Drug Alcohol Rev"},{"key":"597_CR12","doi-asserted-by":"publisher","first-page":"550","DOI":"10.1038\/sj.npp.1300585","volume":"30","author":"MH Baumann","year":"2005","unstructured":"Baumann MH, Clark RD, Budzynski AG, Partilla JS, Blough BE, Rothman RB (2005) N-substituted piperazines abused by humans mimic the molecular mechanism of 3,4-methylenedioxymethamphetamine (MDMA or \u2018Ecstasy\u2019). Neuropsychopharmacol 30:550\u2013560. https:\/\/doi.org\/10.1038\/sj.npp.1300585","journal-title":"Neuropsychopharmacol"},{"key":"597_CR13","unstructured":"European Monitoring Centre for Drugs and Drug Addiction (2018) Troparil. EU early warning system formal notification EU-EWS-RCS-FN-2018-0022. European database on new drugs (EDND)"},{"key":"597_CR14","unstructured":"European Monitoring Centre for Drugs and Drug Addiction (2019) pBPP. EU early warning system formal notification EU-EWS-RCS-FN-2019-0034. European database on new drugs (EDND)"},{"key":"597_CR15","unstructured":"European Monitoring Centre for Drugs and Drug Addiction (2019) 3,4-CFP. EU early warning system formal notification EU-EWS-RCS-FN-2019-0033. European database on new drugs (EDND)"},{"issue":"3","key":"597_CR16","doi-asserted-by":"publisher","first-page":"915","DOI":"10.1007\/s00213-018-5063-9","volume":"236","author":"BE Blough","year":"2019","unstructured":"Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, Rothman RB (2019) The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes. Psychopharmacology 236(3):915\u2013924. https:\/\/doi.org\/10.1007\/s00213-018-5063-9","journal-title":"Psychopharmacology"},{"key":"597_CR17","unstructured":"European Monitoring Centre for Drugs and Drug Addiction (2015) EU early warning system case report RF 04.08.2015 ES 1-(2,3-dichlorophenyl)-piperazine (2,3-XP) EDND-CR-2019-2729. European database on new drugs (EDND)"},{"key":"597_CR18","unstructured":"Horrom BW, Wright HB (1972) Anorexigenic N-3,4-dihalophenylpiperazines. Patent US 3637705."},{"issue":"3","key":"597_CR19","doi-asserted-by":"publisher","first-page":"174","DOI":"10.1016\/j.drugalcdep.2011.10.007","volume":"122","author":"MD Arbo","year":"2012","unstructured":"Arbo MD, Bastos ML, Carmo HF (2012) Piperazine compounds as drugs of abuse. Drug Alcohol Depend 122(3):174\u2013185. https:\/\/doi.org\/10.1016\/j.drugalcdep.2011.10.007","journal-title":"Drug Alcohol Depend"},{"key":"597_CR20","unstructured":"ANALYTICAL REPORT Kleferein, National Forensic Laboratory https:\/\/www.policija.si\/apps\/nfl_response_web\/0_Analytical_Reports_final\/kleferein-ID-2150-19-report.pdf. Accessed 10 Feb 2021"},{"key":"597_CR21","unstructured":"ANALYTICAL REPORT 2Cl-3-FPP, National Forensic Laboratory https:\/\/www.policija.si\/apps\/nfl_response_web\/0_Analytical_Reports_final\/2Cl-3-FPP-ID-2167-20_report.pdf. Accessed 10 Feb 2021"},{"issue":"11","key":"597_CR22","doi-asserted-by":"publisher","first-page":"1260","DOI":"10.1021\/jm00269a600","volume":"16","author":"RL Clarke","year":"1973","unstructured":"Clarke RL, Daum SJ, Gambino AJ, Aceto MD, Pearl J, Levitt M, Cumiskey WR, Bogado EF (1973) Compounds affecting the central nervous system. 4. 3 Beta-phenyltropane-2-carboxylic esters and analogs. J Med Chem 16(11):1260\u20131267. https:\/\/doi.org\/10.1021\/jm00269a600","journal-title":"J Med Chem"},{"issue":"9","key":"597_CR23","doi-asserted-by":"publisher","first-page":"2719","DOI":"10.1021\/jm00113a008","volume":"34","author":"FI Carroll","year":"1991","unstructured":"Carroll FI, Gao YG, Rahman MA, Abraham P, Parham K, Lewin AH, Boja JW, Kuhar MJ (1991) Synthesis, ligand binding, QSAR, and CoMFA study of 3 beta-(p-substituted phenyl)tropane-2 beta-carboxylic acid methyl esters. J Med Chem 34(9):2719\u20132725. https:\/\/doi.org\/10.1021\/jm00113a008","journal-title":"J Med Chem"},{"issue":"20","key":"597_CR24","doi-asserted-by":"publisher","first-page":"2886","DOI":"10.1021\/jm00072a007","volume":"36","author":"FI Carroll","year":"1993","unstructured":"Carroll FI, Gray JL, Abraham P, Kuzemko MA, Lewin AH, Boja JW, Kuhar MJ (1993) 3-Aryl-2-(3\u2019-substituted-1\u2019,2\u2019,4\u2019-oxadiazol-5\u2019-yl)tropane analogues of cocaine: affinities at the cocaine binding site at the dopamine, serotonin, and norepinephrine transporters. J Med Chem 36(20):2886\u20132890. https:\/\/doi.org\/10.1021\/jm00072a007","journal-title":"J Med Chem"},{"issue":"3","key":"597_CR25","doi-asserted-by":"publisher","first-page":"327","DOI":"10.1016\/0163-7258(87)90079-9","volume":"32","author":"VV Zakusov","year":"1987","unstructured":"Zakusov VV, Kozhechkin SN, Naumova VI (1987) Pharmacology of new tropan derivatives. Pharmacol Ther 32(3):327\u2013337. https:\/\/doi.org\/10.1016\/0163-7258(87)90079-9","journal-title":"Pharmacol Ther"},{"issue":"49","key":"597_CR26","doi-asserted-by":"publisher","first-page":"19257","DOI":"10.1021\/jacs.9b11208","volume":"141","author":"LR Mills","year":"2019","unstructured":"Mills LR, Graham JM, Patel P, Rousseaux SAL (2019) Ni-catalyzed reductive cyanation of aryl halides and phenol derivatives via transnitrilation. J Am Chem Soc 141(49):19257\u201319262. https:\/\/doi.org\/10.1021\/jacs.9b11208","journal-title":"J Am Chem Soc"},{"issue":"5","key":"597_CR27","doi-asserted-by":"publisher","first-page":"393","DOI":"10.1002\/(sici)1097-458x(199605)34:5<393::aid-omr891>3.0.co;2-9","volume":"34","author":"A Petri\u010d","year":"1996","unstructured":"Petri\u010d A (1996) 13C and 1H NMR Assignments for (1R)-3\u03b2-Phenyl-8-methyl-8-azabicyclo[3.2.1]octane-2\u03b2-carboxylic Acid Methyl Ester. Magn Reson Chem 34(5):393\u2013394. https:\/\/doi.org\/10.1002\/(sici)1097-458x(199605)34:5%3c393::aid-omr891%3e3.0.co;2-9","journal-title":"Magn Reson Chem"},{"issue":"34","key":"597_CR28","doi-asserted-by":"publisher","first-page":"10537","DOI":"10.1016\/s0040-4020(99)00577-3","volume":"55","author":"AJ Airaksinen","year":"1999","unstructured":"Airaksinen AJ, Tuppurainen KA, L\u00f6tj\u00f6nen SE, Nieitz M, Yu M, Veps\u00e4l\u00e4inen JJ, Laatikainen R, Hiltunen J, Bergstr\u00f6m KA (1999) Nuclear magnetic resonance and molecular orbital study of some cocaine analogues. Tetrahedron 55(34):10537\u201310546. https:\/\/doi.org\/10.1016\/s0040-4020(99)00577-3","journal-title":"Tetrahedron"}],"container-title":["Forensic Toxicology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1007\/s11419-021-00597-4.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/article\/10.1007\/s11419-021-00597-4\/fulltext.html","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1007\/s11419-021-00597-4.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,1,7]],"date-time":"2022-01-07T18:27:03Z","timestamp":1641580023000},"score":1,"resource":{"primary":{"URL":"https:\/\/link.springer.com\/10.1007\/s11419-021-00597-4"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,9,14]]},"references-count":28,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2022,1]]}},"alternative-id":["597"],"URL":"https:\/\/doi.org\/10.1007\/s11419-021-00597-4","relation":{},"ISSN":["1860-8965","1860-8973"],"issn-type":[{"value":"1860-8965","type":"print"},{"value":"1860-8973","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,9,14]]},"assertion":[{"value":"27 March 2021","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"10 August 2021","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"14 September 2021","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}},{"order":1,"name":"Ethics","group":{"name":"EthicsHeading","label":"Declarations"}},{"value":"The authors declare that they have no conflict of interest.","order":2,"name":"Ethics","group":{"name":"EthicsHeading","label":"Conflict of interest"}},{"value":"This article does not contain any studies with human participants or animals performed by any of the authors.","order":3,"name":"Ethics","group":{"name":"EthicsHeading","label":"Ethical approval"}}]}}