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

Tsutsumi, Hiroe; Katagi, Munehiro; Miki, Akihiro; Shima, Noriaki; Kamata, Toshihide; Nishikawa, Mayumi; Nakajima, Kunio; Tsuchihashi, Hitoshi

doi:10.1016/j.jchromb.2005.02.016

Cited by 60 publications

(37 citation statements)

References 24 publications

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“…5) is also expected to be methylated to form 5-hydroxy-6-methoxy-diisopropyltryptamine, the positional isomer of 6-OH-5-MeO-DIPT, 6-OH-5-MeO-DIPT and 5-hydroxy-6-methoxy-diisopropyltryptamine should be distinguished by their retention times on GC/MS and LC/MS according to our previous studies. The positional isomers of Nbenzylpiperazine metabolites (Tsutsumi et al, 2005b) and methylenedioxymethamphetamine (Ecstasy) metabolites (unpublished data) had been well separated by GC/MS and LC/MS, and the urinary hydroxy-methoxy-diisopropyltryptamine detected in this study completely agreed with 6-OH-5-MeO-DIPT. We, therefore, concluded that the hydroxylated metabolite is 6-OH-5-MeO-DIPT.…”

Section: Discussionsupporting

confidence: 51%

METABOLISM OF THE PSYCHOTOMIMETIC TRYPTAMINE DERIVATIVE 5-METHOXY-N,N-DIISOPROPYLTRYPTAMINE IN HUMANS: IDENTIFICATION AND QUANTIFICATION OF ITS URINARY METABOLITES

Kamata¹,

Katagi²,

Kamata³

et al. 2005

Drug Metab Dispos

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ABSTRACT:The urinary metabolites of 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT) in humans have been investigated by analyzing urine specimens from its users. For the unequivocal identification and accurate quantification of its major metabolites, careful analyses were conducted by gas chromatography/mass spectrometry, liquid chromatography/mass spectrometry, and liquid chromatography-tandem mass spectrometry, using authentic standards of each metabolite synthesized. Three major metabolic pathways were revealed as follows: 1) side chain degradation by O-demethylation to form 5-hydroxy-N,N-diisopropyltryptamine (5-OH-DIPT), which would be partly conjugated to its sulfate and glucuronide; 2) direct hydroxylation on position 6 of the aromatic ring of 5-MeO-DIPT, and/or methylation of the hydroxyl group on position 5 after hydroxylation on position 6 of the aromatic ring of 5-OH-DIPT, to produce 6-hydroxy-5-methoxy-N,N-diisopropyltryptamine (6-OH-5-MeO-DIPT), followed by conjugation to its sulfate and glucuronide; and 3) side chain degradation by N-deisopropylation, to the corresponding secondary amine 5-methoxy-N-isopropyltryptamine (5-MeO-NIPT). Of these metabolites, which retain structural characteristics of the parent drug, 5-OH-DIPT and 6-OH-5-MeO-DIPT were found to be more abundant than 5-MeO-NIPT. Although the parent drug 5-MeO-DIPT was detectable even 35 h after dosing, no trace of its N-oxide was detected in any of the specimens examined.

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Section: Discussionsupporting

confidence: 51%

METABOLISM OF THE PSYCHOTOMIMETIC TRYPTAMINE DERIVATIVE 5-METHOXY-N,N-DIISOPROPYLTRYPTAMINE IN HUMANS: IDENTIFICATION AND QUANTIFICATION OF ITS URINARY METABOLITES

Kamata¹,

Katagi²,

Kamata³

et al. 2005

Drug Metab Dispos

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“…The published literature presents analytical data for various piperazines (in particular BZP, TFMPP, and CPP) relating to immunoassay, gas chromatography (GC)-MS (derivatized and underivatized), and GC with nitrogen-phosphorus detection (NPD) (1,5,7,(23)(24)(25)(26)(27). There have only been limited HPLC-UV (UV maxima only) and LC-MS data shown (1,(26)(27)(28).…”

Section: Identification Of Piperazinesmentioning

confidence: 99%

“…There have only been limited HPLC-UV (UV maxima only) and LC-MS data shown (1,(26)(27)(28). The situation with TFMPP and CPP is complicated by the existence and availability of structural isomers such as 3-TFMPP, 4-TFMPP, 2-CPP, 3,CPP, and 4-CPP.…”

Section: Identification Of Piperazinesmentioning

confidence: 99%

Investigation of the First Deaths in the United Kingdom Involving the Detection and Quantitation of the Piperazines BZP and 3-TFMPP

Elliott

Smith

2008

Journal of Analytical Toxicology

116

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Abstract[Piperazines such as 1-benzylpiperazine (BZP), 1-(3-trifluromethylphenyl)piperazine (3-TFMPP), and 1-(3-chlorophenyl)piperazine (3-CPP) have become recent drugs of abuse. With stimulant effects comparable to amphetamines but with a lower potency and differential global scheduling status, they have been sold as a supposed legal alternative to "Ecstasy". A few non-fatal and fatal cases where BZP has been detected have been published and typically involve other drugs. However, toxicity involving BZP alone has also been reported. No case data currently exist for 3-TFMPP. The toxicological situation is complicated by the existence of positional isomers of TFMPP and CPP. This paper includes ultraviolet (UV) and liquid chromatography-mass spectrometry data for these isomers and indicates an advantage in using UV spectra to distinguish the structures. Consequently, the presence of BZP and 3-TFMPP has been confirmed in three fatalities (road traffic deaths and a fatal fall), with two cases involving both drugs. These are the first reported cases of 3-TFMPP in postmortem fluid. In all cases, other drugs and/or ethanol were found. BZP was found at concentrations of 0.71, < 0.50, and 1.39 mg/L and 3-TFMPP was found at concentrations of 0.05 and 0.15 mg/L in postmortem blood. Concentrations were also measured in urine. Although BZP and 3-TFMPP were not the direct cause of death, the toxicological findings presented in this paper may assist the interpretation of future cases involving these drugs where their significance may be more apparent.

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“…With regard to BZP, the analytical methods published are normally only used to detect and/or quantify BZP in combination to its main metabolites (14,15,96) or few other piperazines also used as designer drugs (89, 94,95,99). Nevertheless, some other methods also allow the identification of BZP in combination with other stimulant drugs being very useful in the rapid screening of biological samples with a forensic and for clinical purpose (16,97,98,(100)(101)(102).…”

Section: Methods Validationmentioning

confidence: 99%

“…The choice of the IS was one of the aspects that took into account its potential application as some of the published methods use as internal standard other piperazines also used as designer drugs and sometimes combined with BZP in the same preparations (14,96). Therefore, in the absence of a piperazine deuterated derivative it was selected a commercially available compound that is not a constituent of "party pills".…”

Section: Methods Validationmentioning

confidence: 99%

Development and validation of a gas chromatography/mass spectrometry method for simultaneous quantification of benzylpiperazine and its metabolites: Application to a pilot toxicokinetic study in mice

et al. 2013

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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

Cited by 60 publications

References 24 publications

METABOLISM OF THE PSYCHOTOMIMETIC TRYPTAMINE DERIVATIVE 5-METHOXY-N,N-DIISOPROPYLTRYPTAMINE IN HUMANS: IDENTIFICATION AND QUANTIFICATION OF ITS URINARY METABOLITES

METABOLISM OF THE PSYCHOTOMIMETIC TRYPTAMINE DERIVATIVE 5-METHOXY-N,N-DIISOPROPYLTRYPTAMINE IN HUMANS: IDENTIFICATION AND QUANTIFICATION OF ITS URINARY METABOLITES

Investigation of the First Deaths in the United Kingdom Involving the Detection and Quantitation of the Piperazines BZP and 3-TFMPP

Development and validation of a gas chromatography/mass spectrometry method for simultaneous quantification of benzylpiperazine and its metabolites: Application to a pilot toxicokinetic study in mice

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