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.
Abbreviations
- CPP:
-
Chlorophenylpiperazine
- o:
-
Ortho
- m:
-
Meta
- p:
-
Para
- MDMA:
-
Methylendioxymethamphetamine
- QC:
-
Quality control
- LOD:
-
Limit of detection
- LOQ:
-
Limit of quantification
- RSD:
-
Relative standard deviation
- S/N ratio:
-
Signal-to-noise ratio
References
EMCDDA, Europol (2007) Active Monitoring Report on a new psychoactive substance: 1-(3-chlorophenyl)piperazine (mCPP)—Annex 1 Technical Information. http://www.emcdda.europa.eu/themes/new-drugs/early-warning. Accessed 28 February 2009
EMCDDA, Europol (2007) Joint report on a new psychoactive substance: 1-(3-chlorphenyl)piperazine (mCPP). http://www.emcdda.europa.eu/themes/new-drugs/early-warning. Accessed 28 February 2009
Hamik A, Peroutka SJ (1989) 1-(m-chlorophenyl)piperazine (mCPP) interactions with neurotransmitter receptors in the human brain. Biol Psychiatry 25:569–575
Eriksson E, Engberg G, Bing O, Nissbrandt H (1999) Effects of mCPP on the extracellular concentrations of serotonin and dopamine in rat brain. Neuropsychopharmacology 20:287–296
Tancer ME, Johanson CE (2001) The subjective effects of MDMA and mCPP in moderate MDMA users. Drug Alcohol Depend 65:97–101
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 26:127–131
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 81:27–36
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 79:207–212
Fineschi V, Masti A (1996) Fatal poisoning by MDMA (ecstasy) and MDEA: a case report. Int J Legal Med 108:272–275
Libiseller K, Pavlic M, Grubwieser P, Rabl W (2007) An announced suicide with ecstasy. Int J Legal Med 121:40–43
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 121:303–307
Bossong MG, Van Dijk JP, Niesink RJ (2005) Methylone and mCPP, two new drugs of abuse? Addict Biol 10:321–323
Bundesgesetzblatt Jahrgang 2007 Teil I Nr. 5, Zwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften—20. BtMÄndV vom 14.02.2007
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
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 121:47–56
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 27:560–568
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 38:659–676
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 113:229–235
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 50:326–335
Frost M, Kohler H, Blaschke G (1996) Analysis of “ecstasy” by capillary electrophoresis. Int J Legal Med 109:53–57
Nagai T, Kamiyama S, Nagai T (1988) Forensic toxicologic analysis of methamphetamine and amphetamine optical isomers by high performance liquid chromatography. Z Rechtsmed 101:151–159
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 1021:71–82
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
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 123:451–458
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 123:155–156
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Schürenkamp, J., Beike, J., Pfeiffer, H. et al. Separation of positional CPP isomers by chiral HPLC-DAD of seized tablets. Int J Legal Med 125, 95–99 (2011). https://doi.org/10.1007/s00414-010-0422-z
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DOI: https://doi.org/10.1007/s00414-010-0422-z