Skip to main content
Erschienen in: International Journal of Legal Medicine 1/2011

01.01.2011 | TECHNICAL NOTE

Separation of positional CPP isomers by chiral HPLC-DAD of seized tablets

verfasst von: Jennifer Schürenkamp, Justus Beike, Heidi Pfeiffer, Helga Köhler

Erschienen in: International Journal of Legal Medicine | Ausgabe 1/2011

Einloggen, um Zugang zu erhalten

Abstract

Meta-chlorophenylpiperazine, one of the synthetic piperazine-derived designer drugs, is to date controlled as an illicit substance in five European member states. Depending on the position of the chlorine atom, different positional isomers of CPP (ortho-, meta- and para-) are possible. Therefore, there is a need to develop an analytical method for the separation and identification of the three 1-chlorophenylpiperazines in tablets containing CPP. In this work, the position isomers o-, m- and p-CPP were separated by liquid chromatography (HPLC) on a reversed-phase chiral column. Different mobile phase compositions and pH ranges were systematically studied to find optimum chromatographic conditions. Best results were achieved with isocratic mobile phase of triethyl amine buffer and methanol (V/V = 70/30) at pH 9 with a flow rate of 0.8 ml/min. The method was validated in terms of selectivity, linearity, limit of detection and quantification and precision. At last, the developed method was successfully applied on seized ecstasy tablets.
Literatur
3.
Zurück zum Zitat Hamik A, Peroutka SJ (1989) 1-(m-chlorophenyl)piperazine (mCPP) interactions with neurotransmitter receptors in the human brain. Biol Psychiatry 25:569–575CrossRefPubMed Hamik A, Peroutka SJ (1989) 1-(m-chlorophenyl)piperazine (mCPP) interactions with neurotransmitter receptors in the human brain. Biol Psychiatry 25:569–575CrossRefPubMed
4.
Zurück zum Zitat Eriksson E, Engberg G, Bing O, Nissbrandt H (1999) Effects of mCPP on the extracellular concentrations of serotonin and dopamine in rat brain. Neuropsychopharmacology 20:287–296CrossRefPubMed Eriksson E, Engberg G, Bing O, Nissbrandt H (1999) Effects of mCPP on the extracellular concentrations of serotonin and dopamine in rat brain. Neuropsychopharmacology 20:287–296CrossRefPubMed
5.
Zurück zum Zitat Tancer ME, Johanson CE (2001) The subjective effects of MDMA and mCPP in moderate MDMA users. Drug Alcohol Depend 65:97–101CrossRefPubMed Tancer ME, Johanson CE (2001) The subjective effects of MDMA and mCPP in moderate MDMA users. Drug Alcohol Depend 65:97–101CrossRefPubMed
6.
Zurück zum Zitat Maurer HH, Kraemer T, Springer D, Staack RF (2004) Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (ecstasy), piperazine, and pyrrolidinophenone types: a synopsis. Ther Drug Monit 26:127–131CrossRefPubMed Maurer HH, Kraemer T, Springer D, Staack RF (2004) Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (ecstasy), piperazine, and pyrrolidinophenone types: a synopsis. Ther Drug Monit 26:127–131CrossRefPubMed
7.
Zurück zum Zitat Johanson CE, Kilbey M, Gatchalian K, Tancer M (2006) Discriminative stimulus effects of 3, 4-methylenedioxymethamphetamine (MDMA) in humans trained to discriminate among d-amphetamine, meta-chlorophenylpiperazine and placebo. Drug Alcohol Depend 81:27–36CrossRefPubMed Johanson CE, Kilbey M, Gatchalian K, Tancer M (2006) Discriminative stimulus effects of 3, 4-methylenedioxymethamphetamine (MDMA) in humans trained to discriminate among d-amphetamine, meta-chlorophenylpiperazine and placebo. Drug Alcohol Depend 81:27–36CrossRefPubMed
8.
Zurück zum Zitat Klaassen T, Ho Pian KL, Westenberg HG, den Boer JA, van Praag HM (1998) Serotonin syndrome after challenge with the 5-HT agonist meta-chlorophenylpiperazine. Psychiatry Res 79:207–212CrossRefPubMed Klaassen T, Ho Pian KL, Westenberg HG, den Boer JA, van Praag HM (1998) Serotonin syndrome after challenge with the 5-HT agonist meta-chlorophenylpiperazine. Psychiatry Res 79:207–212CrossRefPubMed
9.
Zurück zum Zitat Fineschi V, Masti A (1996) Fatal poisoning by MDMA (ecstasy) and MDEA: a case report. Int J Legal Med 108:272–275CrossRefPubMed Fineschi V, Masti A (1996) Fatal poisoning by MDMA (ecstasy) and MDEA: a case report. Int J Legal Med 108:272–275CrossRefPubMed
10.
Zurück zum Zitat Libiseller K, Pavlic M, Grubwieser P, Rabl W (2007) An announced suicide with ecstasy. Int J Legal Med 121:40–43CrossRefPubMed Libiseller K, Pavlic M, Grubwieser P, Rabl W (2007) An announced suicide with ecstasy. Int J Legal Med 121:40–43CrossRefPubMed
11.
Zurück zum Zitat De Letter EA, Lambert WE, Bouche MP, Cordonnier JA, Van Bocxlaer JF, Piette MH (2007) Postmortem distribution of 3, 4-methylenedioxy-N, N-dimethyl-amphetamine (MDDM or MDDA) in a fatal MDMA overdose. Int J Legal Med 121:303–307CrossRefPubMed De Letter EA, Lambert WE, Bouche MP, Cordonnier JA, Van Bocxlaer JF, Piette MH (2007) Postmortem distribution of 3, 4-methylenedioxy-N, N-dimethyl-amphetamine (MDDM or MDDA) in a fatal MDMA overdose. Int J Legal Med 121:303–307CrossRefPubMed
12.
Zurück zum Zitat Bossong MG, Van Dijk JP, Niesink RJ (2005) Methylone and mCPP, two new drugs of abuse? Addict Biol 10:321–323CrossRefPubMed Bossong MG, Van Dijk JP, Niesink RJ (2005) Methylone and mCPP, two new drugs of abuse? Addict Biol 10:321–323CrossRefPubMed
13.
Zurück zum Zitat Bundesgesetzblatt Jahrgang 2007 Teil I Nr. 5, Zwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften—20. BtMÄndV vom 14.02.2007 Bundesgesetzblatt Jahrgang 2007 Teil I Nr. 5, Zwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften—20. BtMÄndV vom 14.02.2007
14.
Zurück zum Zitat Pütz M, Martin N (2008) Application of CE-ESI-MS in forensic toxicology: Identification of piperazine-derived designer drugs in Ecstasy tables and of food colorants in illicit drugs. In: Pragst F, Aderjan R (ed) XV. GTFCh-Symposium 2007 Aktuelle Beiträge zur Forensischen und Klinischen Toxikologie, Bad Vibel, pp. 487–501 Pütz M, Martin N (2008) Application of CE-ESI-MS in forensic toxicology: Identification of piperazine-derived designer drugs in Ecstasy tables and of food colorants in illicit drugs. In: Pragst F, Aderjan R (ed) XV. GTFCh-Symposium 2007 Aktuelle Beiträge zur Forensischen und Klinischen Toxikologie, Bad Vibel, pp. 487–501
15.
Zurück zum Zitat De Boer D, Bosman IJ, Hidvegi E, Manzoni C, Benko AA, dos Reys LJ, Maes RA (2001) Piperazine-like compounds: a new group of designer drugs-of-abuse on the European market. Forensic Sci Int 121:47–56CrossRefPubMed De Boer D, Bosman IJ, Hidvegi E, Manzoni C, Benko AA, dos Reys LJ, Maes RA (2001) Piperazine-like compounds: a new group of designer drugs-of-abuse on the European market. Forensic Sci Int 121:47–56CrossRefPubMed
16.
Zurück zum Zitat Staack RF, Maurer HH (2003) Piperazine-derived designer drug 1-(3-chlorophenyl)piperazine (mCPP): GC-MS studies on its metabolism and its toxicological detection in rat urine including analytical differentiation from its precursor drugs trazodone and nefazodone. J Anal Toxicol 27:560–568PubMed Staack RF, Maurer HH (2003) Piperazine-derived designer drug 1-(3-chlorophenyl)piperazine (mCPP): GC-MS studies on its metabolism and its toxicological detection in rat urine including analytical differentiation from its precursor drugs trazodone and nefazodone. J Anal Toxicol 27:560–568PubMed
17.
Zurück zum Zitat Peters FT, Schaefer S, Staack RF, Kraemer T, Maurer HH (2003) Screening for and validated quantification of amphetamines and of amphetamine- and piperazine-derived designer drugs in human blood plasma by gas chromatography/mass spectrometry. J Mass Spectrom 38:659–676CrossRefPubMed Peters FT, Schaefer S, Staack RF, Kraemer T, Maurer HH (2003) Screening for and validated quantification of amphetamines and of amphetamine- and piperazine-derived designer drugs in human blood plasma by gas chromatography/mass spectrometry. J Mass Spectrom 38:659–676CrossRefPubMed
18.
Zurück zum Zitat Weinmann W, Renz M, Vogt S, Pollak S (2000) Automated solid-phase extraction and two-step derivatisation for simultaneous analysis of basic illicit drugs in serum by GC/MS. Int J Legal Med 113:229–235CrossRefPubMed Weinmann W, Renz M, Vogt S, Pollak S (2000) Automated solid-phase extraction and two-step derivatisation for simultaneous analysis of basic illicit drugs in serum by GC/MS. Int J Legal Med 113:229–235CrossRefPubMed
19.
Zurück zum Zitat Bishop SC, McCord BR, Gratz SR, Loeliger JR, Witkowski MR (2005) Simultaneous separation of different types of amphetamine and piperazine designer drugs by capillary electrophoresis with a chiral selector. J Forensic Sci 50:326–335CrossRefPubMed Bishop SC, McCord BR, Gratz SR, Loeliger JR, Witkowski MR (2005) Simultaneous separation of different types of amphetamine and piperazine designer drugs by capillary electrophoresis with a chiral selector. J Forensic Sci 50:326–335CrossRefPubMed
20.
Zurück zum Zitat Frost M, Kohler H, Blaschke G (1996) Analysis of “ecstasy” by capillary electrophoresis. Int J Legal Med 109:53–57CrossRefPubMed Frost M, Kohler H, Blaschke G (1996) Analysis of “ecstasy” by capillary electrophoresis. Int J Legal Med 109:53–57CrossRefPubMed
21.
Zurück zum Zitat Nagai T, Kamiyama S, Nagai T (1988) Forensic toxicologic analysis of methamphetamine and amphetamine optical isomers by high performance liquid chromatography. Z Rechtsmed 101:151–159CrossRefPubMed Nagai T, Kamiyama S, Nagai T (1988) Forensic toxicologic analysis of methamphetamine and amphetamine optical isomers by high performance liquid chromatography. Z Rechtsmed 101:151–159CrossRefPubMed
22.
Zurück zum Zitat Sokoliess T, Schönherr J, Menyes U, Roth U, Jira T (2003) Characterization of calixarene- and resorcinarene-bonded stationary phases. I. Hydrophobic interactions. J Chromatogr A 1021:71–82CrossRefPubMed Sokoliess T, Schönherr J, Menyes U, Roth U, Jira T (2003) Characterization of calixarene- and resorcinarene-bonded stationary phases. I. Hydrophobic interactions. J Chromatogr A 1021:71–82CrossRefPubMed
23.
Zurück zum Zitat Nirogi RVS, Kota S, Peruri BG, Kandikere VN, Mudigonda K (2006) Chiral high-performance liquid chromatographic method for enantioselective analysis of zaltoprofen. Acta Chromatogr 17:202–209 Nirogi RVS, Kota S, Peruri BG, Kandikere VN, Mudigonda K (2006) Chiral high-performance liquid chromatographic method for enantioselective analysis of zaltoprofen. Acta Chromatogr 17:202–209
24.
Zurück zum Zitat Wille SM, De Letter EA, Piette MH, Van Overschelde LK, Van Peteghem CH, Lambert WE (2009) Determination of antidepressants in human postmortem blood, brain tissue, and hair using gas chromatography-mass spectrometry. Int J Legal Med 123:451–458CrossRefPubMed Wille SM, De Letter EA, Piette MH, Van Overschelde LK, Van Peteghem CH, Lambert WE (2009) Determination of antidepressants in human postmortem blood, brain tissue, and hair using gas chromatography-mass spectrometry. Int J Legal Med 123:451–458CrossRefPubMed
25.
Zurück zum Zitat Abondo M, Bouvet R, Baert A, Morel I, Le Gueut M (2009) Sexual assault and MDMA: the distinction between consciousness and awareness when it comes to consent. Int J Legal Med 123:155–156CrossRefPubMed Abondo M, Bouvet R, Baert A, Morel I, Le Gueut M (2009) Sexual assault and MDMA: the distinction between consciousness and awareness when it comes to consent. Int J Legal Med 123:155–156CrossRefPubMed
Metadaten
Titel
Separation of positional CPP isomers by chiral HPLC-DAD of seized tablets
verfasst von
Jennifer Schürenkamp
Justus Beike
Heidi Pfeiffer
Helga Köhler
Publikationsdatum
01.01.2011
Verlag
Springer-Verlag
Erschienen in
International Journal of Legal Medicine / Ausgabe 1/2011
Print ISSN: 0937-9827
Elektronische ISSN: 1437-1596
DOI
https://doi.org/10.1007/s00414-010-0422-z

Weitere Artikel der Ausgabe 1/2011

International Journal of Legal Medicine 1/2011 Zur Ausgabe

Neu im Fachgebiet Rechtsmedizin

Assistierter Suizid durch Infusion von Thiopental

Thiopental Originalie

Als Folge des Urteils des Bundesverfassungsgerichts zur Sterbehilfe im Jahr 2020 wurde in den Jahren 2021–2023 eine Reihe (n = 23) von assistierten Suiziden im Landesinstitut für gerichtliche und soziale Medizin Berlin mit jeweils identischen …

Molekularpathologische Untersuchungen im Wandel der Zeit

Open Access Biomarker Leitthema

Um auch an kleinen Gewebeproben zuverlässige und reproduzierbare Ergebnisse zu gewährleisten ist eine strenge Qualitätskontrolle in jedem Schritt des Arbeitsablaufs erforderlich. Eine nicht ordnungsgemäße Prüfung oder Behandlung des …

Vergleichende Pathologie in der onkologischen Forschung

Pathologie Leitthema

Die vergleichende experimentelle Pathologie („comparative experimental pathology“) ist ein Fachbereich an der Schnittstelle von Human- und Veterinärmedizin. Sie widmet sich der vergleichenden Erforschung von Gemeinsamkeiten und Unterschieden von …

Gastrointestinale Stromatumoren

Open Access GIST CME-Artikel

Gastrointestinale Stromatumoren (GIST) stellen seit über 20 Jahren ein Paradigma für die zielgerichtete Therapie mit Tyrosinkinaseinhibitoren dar. Eine elementare Voraussetzung für eine mögliche neoadjuvante oder adjuvante Behandlung bei …