Advanced search
Publication Cover
Bioanalysis Volume 2, 2010 - Issue 5
Submit an article Journal homepage
482
Views
4
CrossRef citations to date
0
Altmetric
Review

Bioanalysis of New Designer Drugs

Ariane Wohlfarth1 Institute of Forensic Medicine, University Medical Centre Freiburg, Albertstraße 9, 79104Freiburg, Germany. [email protected]Correspondence[email protected]
&
Wolfgang Weinmann2 Institute of Forensic Medicine, Forensic Chemistry and Toxicology, Medical Faculty, University of Bern, Bühlstraße 20, 3012Bern, Switzerland
Pages 965-979 | Published online: 10 May 2010

>Bibliography

  • Campbell H , ClineW, EvansM, LloydJ, PeckAW. Comparison of the effects of dexamphetamine and 1-benzylpiperazine in former addicts. Eur. J. Clin. Pharmacol. 6, 170–176 (1973).
  • Howlett AC , BarthF, Bonner Tiet al. International union of pharmacology. Xxvii. Classification of cannabinoid receptors. Pharmacol. Rev. 54(2), 161–202 (2002).
  • United Nations Office on Drugs and Crime. World Drug Report 2008. United Nations Publication, NY, USA (2009).
  • Shulgin AT , ShulginA. Pihkal: A Chemical Love Story. Transform Press, CA, USA (1991).
  • Shulgin AT , ShulginA. Tihkal: The Continuation. Transform Press, CA, USA (1997).
  • De Boer D , EgbertsT, MaesRA. Para-methylthioamphetamine, a new amphetamine designer drug of abuse. Pharm. World Sci. 21(1), 47–48 (1999).
  • Felgate HE , FelgatePD, JamesRA, SimsDN, VozzoDC. Recent paramethoxyamphetamine deaths. J. Anal. Toxicol. 22(2), 169–172 (1998).
  • James RA , DinanA. Hyperpyrexia associated with fatal paramethoxyamphetamine (PMA) abuse. Med. Sci. Law38(1), 83–85 (1998).
  • Ling LH , MarchantC, BuckleyNA, PriorM, IrvineRJ. Poisoning with the recreational drug paramethoxyamphetamine (‘death‘). Med. J. Aust. 174(9), 453–455 (2001).
  • Kraner JC , McCoyDJ, EvansMA, EvansLE, SweeneyBJ. Fatalities caused by the mdma-related drug paramethoxyamphetamine (PMA). J. Anal. Toxicol. 25(7), 645–648 (2001).
  • Casale JF , HaysPA, SpratleyTK, SmithPR. The characterization of 4-methoxy-n-ethylamphetamine hydrochloride. Microgram J. 4, 42–45 (2006).
  • Zaitsu K , KatagiM, KamataTet al. Determination of a newly encountered designer drug ‘p-methoxyethylamphetamine’ and its metabolites in human urine and blood. Forensic Sci. Int. 177(1), 77–84 (2008).
  • Boatto G , NiedduM, DessiG, ManconiP, CerriR. Determination of four thiophenethylamine designer drugs (2c-t-series) in human plasma by capillary electrophoresis with mass spectrometry detection. J. Chromatogr. A1159(1–2), 198–202 (2007).
  • Boatto G , NiedduM, PirisiMA, DessiG. Simultaneous determination of new thioamphetamine designer drugs in plasma by capillary electrophoresis coupled with mass spectrometry. Rapid Commun. Mass Spectrom. 21(22), 3716–3720 (2007).
  • Habrdova V , PetersFT, TheobaldDS, MaurerHH. Screening for and validated quantification of phenethylamine-type designer drugs and mescaline in human blood plasma by gas chromatography/mass spectrometry. J. Mass Spectrom. 40(6), 785–795 (2005).
  • Bossong MG , Van DijkJP, NiesinkRJ. Methylone and MCPP, two new drugs of abuse? Addict. Biol. 10(4), 321–323 (2005).
  • Kamata HT , ShimaN, ZaitsuKet al. Metabolism of the recently encountered designer drug, methylone, in humans and rats. Xenobiotica36(8), 709–723 (2006).
  • Zaitsu K , KatagiM, KamataH, MikiA, TsuchihashiH. Discrimination and identification of regioisomeric β-keto analogues of 3,4-methylendioxyamphetamines by gas chromatography-mass spectrometry. Forensic Toxicol. 26, 45–51 (2008).
  • Zaitsu K , KatagiM, Kamata Htet al. Determination of the metabolites of the new designer drugs bk-mbdb and bk-mdea in human urine. Forensic Sci. Int. 188(1–3), 131–139 (2009).
  • Rosner P , QuednowB, GirreserU, JungeT. Isomeric fluoro-methoxy-phenylalkylamines: a new series of controlled-substance analogues (designer drugs). Forensic Sci. Int. 148(2–3), 143–156 (2005).
  • Carmo H , BrulportM, HermesMet al. Cyp2d6 increases toxicity of the designer drug 4-methylthioamphetamine (4-MTA). Toxicology229(3), 236–244 (2007).
  • Elliott SP . Fatal poisoning with a new phenylethylamine: 4-methylthioamphetamine (4-MTA). J. Anal. Toxicol. 24(2), 85–89 (2000).
  • Blachut D , WojtasiewiczK, CzarnockiZ, SzukalskiB. The analytical profile of some 4-methylthioamphetamine (4-MTA) homologues. Forensic Sci. Int. 192(1–3), 98–114 (2009).
  • Puchnarewicz M , DaviesS, ButtonJet al. Bromodragonfly – gives you wings? Ann. Toxicol. Anal . 21(S1), 57 (2009).
  • Wood DM , LookerJ, ShaikhLet al. Delayed onset of seizures and toxicity associated with recreational use of bromo-dragonfly. J. Med. Toxicol. 5(4), 226–229 (2009).
  • Alatrash G , MajhailNS, PileJC. Rhabdomyolysis after ingestion of ‘foxy’ a hallucinogenic tryptamine derivative. Mayo Clin. Proc. 81(4), 550–551 (2006).
  • Meatherall R , SharmaP. Foxy, a designer tryptamine hallucinogen. J. Anal. Toxicol. 27(5), 313–317 (2003).
  • Tanaka E , KamataT, KatagiM, TsuchihashiH, HondaK. A fatal poisoning with 5-methoxy-n,n-diisopropyltryptamine, foxy. Forensic Sci. Int. 163(1–2), 152–154 (2006).
  • Wilson JM , McGeorgeF, SmolinskeS, MeatherallR. A foxy intoxication. Forensic Sci. Int. 148(1), 31–36 (2005).
  • De Boer D , BosmanIJ, HidvegiEet al. Piperazine-like compounds: a new group of designer drugs-of-abuse on the European market. Forensic Sci. Int. 121(1–2), 47–56 (2001).
  • Drug Enforcement Administration (DEA), Department of Justice. Schedules of controlled substances: placement of α-methyltryptamine and 5-methoxy-N,N-diisopropyltryptamine into schedule I of the controlled substances act. Final rule. Fed. Regist. 69(188), 58950–58953 (2004).
  • Staack RF , MaurerHH. New designer drug 1-(3,4-methylenedioxybenzyl) piperazine (mdbp): studies on its metabolism and toxicological detection in rat urine using gas chromatography/mass spectrometry. J. Mass Spectrom. 39(3), 255–261 (2004).
  • Staack RF , MaurerHH. 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(8), 560–568 (2003).
  • Staack RF , MaurerHH. Toxicological detection of the new designer drug 1-(4-methoxyphenyl)piperazine and its metabolites in urine and differentiation from an intake of structurally related medicaments using gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 798(2), 333–342 (2003).
  • Westphal F , JungeT, GirreserU, StobbeS, PerezSB. Structure elucidation of a new designer benzylpiperazine: 4-bromo-2,5-dimethoxybenzylpiperazine. Forensic Sci. Int. 187(1–3), 87–96 (2009).
  • Maurer HH , KraemerT, SpringerD, StaackRF. Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (ecstasy), piperazine, and pyrrolidinophenone types: a synopsis. Ther. Drug Monit. 26(2), 127–131 (2004).
  • Sauer C , PetersFT, HaasC, MeyerMR, FritschiG, MaurerHH. New designer drug α-pyrrolidinovalerophenone (PVP): studies on its metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques. J. Mass Spectrom. 44(6), 952–964 (2009).
  • Sauer C , PetersFT, StaackRF, FritschiG, MaurerHH. New designer drug n-(1-phenylcyclohexyl)-3-ethoxypropanamine (PCEPA): studies on its metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques. J. Mass Spectrom. 41(8), 1014–1029 (2006).
  • EMCDDA–Europol 2008 Annual Report on the Implementation of Council Decision 2005/387/JHA. Annex 2: new psychoactive substances reported to the EMCDDA and Europol for the first time in 2008 under the terms of council decision 2005/387/jha. Council of the European Union, Brussels, 20–21 (2009).
  • Lidder S , DarganP, SextonMet al. Cardiovascular toxicity associated with recreational use of diphenylprolinol (diphenyl-2-pyrrolidinemethanol [D2PM]). J. Med. Toxicol. 4(3), 167–169 (2008).
  • Wood D . Detection of the novel recreational drug diphenyl-2-pyrrolidinemethanol (d2pm) sold legally in combination with 1-benzylpiperzaine (BZP). Clin. Tox. 46, 393 (2008).
  • NIST/EPA/NIH Mass Spectral Library. Scientific instrument services, Inc., NJ, USA (2008).
  • Maurer HH , PflegerK, WeberAA. Mass Spectral Library of Drugs, Poisons, Pesticides, Pollutants and Their Metabolites. Wiley, Altenholz, Germany (2007).
  • McLafferty FW . Wiley Registry of Mass Spectral Data (9th Edition). Wiley, Altenholz, Germany (2009).
  • Mass Spectrometry Databse Committee. ‘Comprehensive’ Drug Mass Spectral Library. University of Alberta, Alberta, Canada (2009).
  • Rosner P , JungeT, WestphalF, FritschiG. Mass Spectra of Designer Drugs: Including Drugs, Chemical Warfare Agents, and Precursors. Wiley, Altenholz, Germany (2007).
  • Laks S , PelanderA, VuoriE, Ali-TolppaE, SippolaE, OjanperaI. Analysis of street drugs in seized material without primary reference standards. Anal. Chem. 76(24), 7375–7379 (2004).
  • Ojanpera S , PelanderA, PelzingM, KrebsI, VuoriE, OjanperaI. Isotopic pattern and accurate mass determination in urine drug screening by liquid chromatography/time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 20(7), 1161–1167 (2006).
  • Pelander A , TyrkkoE, OjanperaI. In silico methods for predicting metabolism and mass fragmentation applied to quetiapine in liquid chromatography/time-of-flight mass spectrometry urine drug screening. Rapid Commun. Mass Spectrom. 23(4), 506–514 (2009).
  • Ferreiros Bouzas N , DresenS, MunzB, WeinmannW. Determination of basic drugs of abuse in human serum by online extraction and LC–MS/MS. Anal. Bioanal. Chem. 395(8), 2499–507 (2009).
  • Boland DM , AndolloW, HimeGW, HearnWL. Fatality due to acute α-methyltryptamine intoxication. J. Anal. Toxicol. 29(5), 394–397 (2005).
  • Vorce SP , HollerJM, LevineB, PastMR. Detection of 1-benzylpiperazine and 1-(3-trifluoromethylphenyl)-piperazine in urine analysis specimens using GC–MS and LC–ESI–MS. J. Anal. Toxicol. 32(6), 444–450 (2008).
  • Miyajima M , MatsumotoT, ItoS. 2C-T-4 intoxication: acute psychosis caused by a designer drug. Psychiatry Clin. Neurosci. 62(2), 243 (2008).
  • Cody JT , SchwarzhoffR. Fluorescence polarization immunoassay detection of amphetamine, methamphetamine, and illicit amphetamine analogues. J. Anal. Toxicol. 17(1), 23–33 (1993).
  • Ishida T , KudoK, InoueH, TsujiA, KojimaT, IkedaN. Rapid screening for and simultaneous semiquantitative analysis of thirty abused drugs in human urine samples using gas chromatography–mass spectrometry. J. Anal. Toxicol. 30(7), 468–477 (2006).
  • Nordgren HK , BeckO. Multicomponent screening for drugs of abuse: direct analysis of urine by LC–MS/MS. Ther. Drug Monit. 26(1), 90–97 (2004).
  • Peters FT , SchaeferS, StaackRF, KraemerT, MaurerHH. 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(6), 659–676 (2003).
  • Pichini S , PujadasM, MarcheiEet al. Liquid chromatography-atmospheric pressure ionization electrospray mass spectrometry determination of ‘hallucinogenic designer drugs’ in urine of consumers. J. Pharm. Biomed. Anal. 47(2), 335–342 (2008).
  • Vorce SP , SklerovJH. A general screening and confirmation approach to the analysis of designer tryptamines and phenethylamines in blood and urine using gc–ei–ms and hplc-electrospray-ms. J. Anal. Toxicol. 28(6), 407–410 (2004).
  • Wohlfarth A , WeinmannW, DresenS. LC–MS/MS screening method for designer amphetamines, tryptamines and piperazines in serum. Anal. Bioanal. Chem. (2010) (Epub ahead of print).
  • Boatto G , NiedduM, CartaAet al. Determination of amphetamine-derived designer drugs in human urine by spe extraction and capillary electrophoresis with mass spectrometry detection. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 814(1), 93–98 (2005).
  • Nieddu M , BoattoG, DessiG. Determination of 4-alkyl 2,5 dimethoxy-amphetamine derivatives by capillary electrophoresis with mass spectrometry detection from urine samples. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 852(1–2), 578–581 (2007).
  • Nieddu M , BoattoG, CartaA, SannaA, PisanoM. Simultaneous determination of ten amphetamine designer drugs in human whole blood by capillary electrophoresis with diode array detection. Biomed. Chromatogr. 19(10), 737–742 (2005).
  • Nieddu M , BoattoG, Pirisi Ma, Azara E, Marchetti M. LC–MS analysis of trimethoxyamphetamine designer drugs (TMA series) from urine samples. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 867(1), 126–130 (2008).
  • Carmo H , De Boer D, Remiao F, Carvalho F, Dos Reys LA, De Lourdes Bastos M. Metabolism of the designer drug 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in mice, after acute administration. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 811(2), 143–152 (2004).
  • Theobald DS , FritschiG, MaurerHH. Studies on the toxicological detection of the designer drug 4-bromo-2,5-dimethoxy-β-phenethylamine (2C-B) in rat urine using gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 846(1–2), 374–377 (2007).
  • De Boer D , BosmanI. A new trend in drugs-of-abuse; the 2c-series of phenethylamine designer drugs. Pharm. World Sci. 26(2), 110–113 (2004).
  • Takahashi M , NagashimaM, SuzukiJ, SetoT, YasudaI, YoshidaT. Analysis of phenylethylamines and tryptamines in designer drugs using gas chromatography–mass spectrometry. J. Health Sci. 54(1), 89–96 (2007).
  • Kanai K , TakekawaK, KumamotoT, IshikawaT, OhmoriT. Simultaneous analysis of six phenethylamine-type designer drugs by TLC, LC–MS, and GC–MS. Forensic Toxicol. 26, 6–12 (2008).
  • Nordgren HK , HolmgrenP, LiljebergP, ErikssonN, BeckO. Application of direct urine LC–MS–MS analysis for screening of novel substances in drug abusers. J. Anal. Toxicol. 29(4), 234–239 (2005).
  • Theobald DS , MaurerHH. Studies on the metabolism and toxicological detection of the designer drug 2,5-dimethoxy-4-methyl-β- phenethylamine (2C-D) in rat urine using gas chromatographic/mass spectrometric techniques. J. Mass Spectrom. 41(11), 1509–1519 (2006).
  • Theobald DS , MaurerHH. Studies on the metabolism and toxicological detection of the designer drug 4-ethyl-2,5-dimethoxy-β-phenethylamine (2C-E) in rat urine using gas chromatographic-mass spectrometric techniques. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 842(2), 76–90 (2006).
  • Theobald DS , MaurerHH. Identification of monoamine oxidase and cytochrome p450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series). Biochem. Pharmacol. 73(2), 287–297 (2007).
  • Theobald DS , PutzM, SchneiderE, MaurerHH. New designer drug 4-iodo-2,5-dimethoxy-β-phenethylamine (2c-i): studies on its metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric and capillary electrophoretic/mass spectrometric techniques. J. Mass Spectrom. 41(7), 872–886 (2006).
  • Nieddu M , BoattoG, PirisiMA, BarallaE. Multi-residue analysis of eight thioamphetamine designer drugs in human urine by liquid chromatography/tandem mass spectrometry. Rapid Commun. Mass Spectrom. 23(19), 3051–3056 (2009).
  • Theobald DS , StaackRF, PuetzM, MaurerHH. New designer drug 2,5-dimethoxy-4-ethylthio-β-phenethylamine (2C-T-2): studies on its metabolism and toxicological detection in rat urine using gas chromatography/mass spectrometry. J. Mass Spectrom. 40(9), 1157–1172 (2005).
  • Theobald DS , FehnS, MaurerHH. New designer drug, 2,5-dimethoxy-4-propylthio-β-phenethylamine (2C-T-7): studies on its metabolism and toxicological detection in rat urine using gas chromatography/mass spectrometry. J. Mass Spectrom. 40(1), 105–116 (2005).
  • Curtis B , KempP, HartyL, ChoiC, ChristensenD. Postmortem identification and quantitation of 2,5-dimethoxy-4-N-propylthiophenethylamine using GC–MSD and GC–NPD. J. Anal. Toxicol. 27(7), 493–498 (2003).
  • Ewald AH , PetersFT, WeiseM, MaurerHH. Studies on the metabolism and toxicological detection of the designer drug 4-methylthioamphetamine (4-mta) in human urine using gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 824(1–2), 123–131 (2005).
  • Uchiyama N , Kikura-HanajiriR, KawaharaN, GodaY. [Analysis of designer drugs detected in the products purchased in fiscal year 2006]. Yakugaku Zasshi128(10), 1499–1505 (2008).
  • Archer RP . Fluoromethcathinone, a new substance of abuse. Forensic Sci. Int. 185(1–3), 10–20 (2009).
  • Kamata H , ShimaN, ZaitsuKet al. Simultaneous analysis of new designer drug, methylone, and its metabolites in urine by gas chromatography-mass spectrometry and liquid chromatography- electrospray ionization mass spectrometry. Jpn J. Forensic Science Technol. 12(1), 97–106 (2007).
  • Shimizu E , WatanabeH, KojimaTet al. Combined intoxication with methylone and 5-MEO-MIPT. Prog. Neuropsychopharmacol. Biol. Psychiatry31(1), 288–291 (2007).
  • Ewald AH , FritschiG, BorkWR, MaurerHH. Designer drugs 2,5-dimethoxy-4-bromo-amphetamine (DOB) and 2,5-dimethoxy-4-bromo-methamphetamine (mdob): studies on their metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques. J. Mass Spectrom. 41(4), 487–498 (2006).
  • Balikova M . Nonfatal and fatal DOB (2,5-dimethoxy-4-bromoamphetamine) overdose. Forensic Sci. Int. 153(1), 85–91 (2005).
  • Ewald AH , EhlersD, MaurerHH. Metabolism and toxicological detection of the designer drug 4-chloro-2,5-dimethoxyamphetamine in rat urine using gas chromatography-mass spectrometry. Anal. BioAnal. Chem. 390(7), 1837–1842 (2008).
  • Ovaska H , ViljoenA, PuchnarewiczMet al. First case report of recreational use of 2,5-dimethoxy-4-chloroamphetamine confirmed by toxicolgical screening. Eur. J. Emerg. Med. 15, 354–356 (2008).
  • Ewald AH , FritschiG, MaurerHH. Metabolism and toxicological detection of the designer drug 4-iodo-2,5-dimethoxy-amphetamine (DOI) in rat urine using gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 857(1), 170–174 (2007).
  • Staack RF , FehnJ, MaurerHH. New designer drug p-methoxymethamphetamine: studies on its metabolism and toxicological detection in urine using gas chromatography–mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 789(1), 27–41 (2003).
  • Mortier KA , DamsR, LambertWE, De Letter EA, Van Calenbergh S, De Leenheer AP. Determination of paramethoxyamphetamine and other amphetamine-related designer drugs by liquid chromatography/sonic spray ionization mass spectrometry. Rapid Commun. Mass Spectrom. 16(9), 865–870 (2002).
  • Zaitsu K , KatagiM, KamataHet al. Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography–mass spectrometry (GC–MS). J. Mass Spectrom. 43(4), 528–534 (2008).
  • Ewald AH , FritschiG, MaurerHH. Designer drug 2,4,5-trimethoxyamphetamine (TMA-2): studies on its metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques. J. Mass Spectrom. 41(9), 1140–1148 (2006).
  • Sauer C , PetersFT, StaackRF, FritschiG, MaurerHH. New designer drugs N-(1-phenylcyclohexyl)-2-ethoxyethanamine (PCEEA) and N-(1-phenylcyclohexyl)-2-methoxyethanamine (pcmea): studies on their metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques. J. Mass Spectrom. 43(3), 305–316 (2008).
  • Sauer C , PetersFT, StaackRF, FritschiG, MaurerHH. Metabolism and toxicological detection of the designer drug N-(1-phenylcyclohexyl)-3-methoxypropanamine (PCMPA) in rat urine using gas chromatography–mass spectrometry. Forensic Sci. Int. 181(1), 47–51 (2008).
  • Sauer C , PetersFT, StaackRF, FritschiG, MaurerHH. Metabolism and toxicological detection of a new designer drug, N-(1-phenylcyclohexyl)propanamine, in rat urine using gas chromatography-mass spectrometry. J. Chromatogr. A1186(1–2), 380–390 (2008).
  • Staack RF , FritschiG, MaurerHH. Studies on the metabolism and toxicological detection of the new designer drug N-benzylpiperazine in urine using gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 773(1), 35–46 (2002).
  • Tsutsumi H , KatagiM, MikiAet al. Development of simultaneous gas chromatography-mass spectrometric and liquid chromatography-electrospray ionization mass spectrometric determination method for the new designer drugs, N-benzylpiperazine (BZP), 1-(3-trifluoromethylphenyl)piperazine (TFMPP) and their main metabolites in urine. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 819(2), 315–322 (2005).
  • Tsutsumi H , KatagiM, MikiAet al. Metabolism and the urinary excretion profile of the recently scheduled designer drug N-benzylpiperazine (BZP) in the rat. J. Anal. Toxicol. 30(1), 38–43 (2006).
  • Wikstrom M , HolmgrenP, AhlnerJ. A2 (N-benzylpiperazine) a new drug of abuse in Sweden. J. Anal. Toxicol. 28(1), 67–70 (2004).
  • Elliott S , SmithC. Investigation of the first deaths in the United Kingdom involving the detection and quantitation of the piperazines BZP and 3-TFMPP. J. Anal. Toxicol. 32(2), 172–177 (2008).
  • Wood DM , DarganPI, ButtonJet al. Collapse, reported seizure – and an unexpected pill. Lancet369(9571), 1490 (2007).
  • Bishop SC , MccordBR, GratzSR, LoeligerJR, WitkowskiMR. Simultaneous separation of different types of amphetamine and piperazine designer drugs by capillary electrophoresis with a chiral selector. J. Forensic Sci. 50(2), 326–335 (2005).
  • Staack RF , PaulLD, SchmidD, RoiderG, RolfB. Proof of a 1-(3-chlorophenyl)piperazine (MCPP) intake: use as adulterant of cocaine resulting in drug-drug interactions? J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 855(2), 127–133 (2007).
  • Kovaleva J , DevuystE, De Paepe P, Verstraete A. Acute chlorophenylpiperazine overdose: a case report and review of the literature. Ther. Drug Monit. 30(3), 394–398 (2008).
  • Staack RF , FritschiG, MaurerHH. New designer drug 1-(3-trifluoromethylphenyl) piperazine (TFMPP): gas chromatography/mass spectrometry and liquid chromatography/mass spectrometry studies on its phase I and II metabolism and on its toxicological detection in rat urine. J. Mass Spectrom. 38(9), 971–981 (2003).
  • Tsutsumi H , KatagiM, MikiAet al. Isolation, identification and excretion profile of the principal urinary metabolite of the recently banned designer drug 1-(3-trifluoromethylphenyl)piperazine (TFMPP) in rats. Xenobiotica35(1), 107–116 (2005).
  • Springer D , FritschiG, MaurerHH. Metabolism and toxicological detection of the new designer drug 3´,4´-methylenedioxy-α-pyrrolidinopropiophenone studied in urine using gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 793(2), 377–388 (2003).
  • Springer D , FritschiG, MaurerHH. Metabolism and toxicological detection of the new designer drug 4´-methoxy-α-pyrrolidinopropiophenone studied in rat urine using gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 793(2), 331–342 (2003).
  • Peters FT , MeyerMR, FritschiG, MaurerHH. Studies on the metabolism and toxicological detection of the new designer drug 4´-methyl-α-pyrrolidinobutyrophenone (MPBP) in rat urine using gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 824(1–2), 81–91 (2005).
  • Westphal F , JungeT, RosnerP, FritschiG, KleinB, GirreserU. Mass spectral and NMR spectral data of two new designer drugs with an α-aminophenone structure: 4´-methyl-α-pyrrolidinohexanophenone and 4´-methyl-α-pyrrolidinobutyrophenone. Forensic Sci. Int. 169(1), 32–42 (2007).
  • Springer D , PetersFT, FritschiG, MaurerHH. New designer drug 4´-methyl-α-pyrrolidinohexanophenone: studies on its metabolism and toxicological detection in urine using gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 789(1), 79–91 (2003).
  • Springer D , PaulLD, StaackRF, KraemerT, MaurerHH. Identification of cytochrome p450 enzymes involved in the metabolism of 4´-methyl-α-pyrrolidinopropiophenone, a novel scheduled designer drug, in human liver microsomes. Drug Metab. Dispos. 31(8), 979–982 (2003).
  • Springer D , FritschiG, MaurerHH. Metabolism of the new designer drug α-pyrrolidinopropiophenone (PPP) and the toxicological detection of PPP and 4´-methyl-α-pyrrolidinopropiophenone (mPPP) studied in rat urine using gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 796(2), 253–266 (2003).
  • Westphal F , JungeT, RosnerP, SonnichsenF, SchusterF. Mass and NMR spectroscopic characterization of 3,4-methylenedioxypyrovalerone: a designer drug with α-pyrrolidinophenone structure. Forensic Sci. Int. 190(1–3), 1–8 (2009).
  • Spratley TK , HaysPA, GeerLC, CooperSD, McKibbenTD. Analytical profiles of five ‘designer’ tryptamines. Microgram J. 3, 54–68 (2005).
  • Chen BH , LiuJT, ChenWX, ChenHM, LinCH. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta74(4), 512–517 (2008).
  • Kamata T , KatagiM, Kamata Htet al. Metabolism of the psychotomimetic tryptamine derivative 5-methoxy-N,N-diisopropyltryptamine in humans: identification and quantification of its urinary metabolites. Drug Metab. Dispos. 34(2), 281–287 (2006).
  • Sklerov J , LevineB, MooreKA, KingT, FowlerD. A fatal intoxication following the ingestion of 5-methoxy-N,N-dimethyltryptamine in an ayahuasca preparation. J. Anal. Toxicol. 29(8), 838–841 (2005).
  • Auwarter V , DresenS, WeinmannW, MullerM, PutzM, FerreirosN. ’spice’ and other herbal blends: harmless incense or cannabinoid designer drugs? J. Mass Spectrom. 44(5), 832–837 (2009).
  • Lindigkeit R , BoehmeA, EiserlohIet al. Spice: a never ending story? Forensic Sci. Int . 191(1–3), 58–63 (2009).
  • Action on New Drugs Briefing Paper: Understanding The “Spice” Phenomenon. Presented at: EMCDDA Expert Meeting. Lisbon, Portugal, 6 March, 2009.
  • “Spice” – Plant Material(S) Laced with Synthetic Cannabinoids or Cannabinoid Mimicking Compounds. Drug Enforcement Administration Office of Forensic Sciences, DC, USA, 2009.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.