Mass and NMR spectroscopic characterization of 3,4-methylenedioxypyrovalerone: A designer drug with α-pyrrolidinophenone structure

Westphal, Folker; Junge, Thomas; Rösner, Peter; Sönnichsen, Frank D.; Schuster, Frank

doi:10.1016/j.forsciint.2009.05.001

Cited by 73 publications

(54 citation statements)

References 19 publications

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“…Over the past decade, MDPV has gained popularity as a designer drug, or "legal high," across Europe. The first designer drug containing MDPV was identified in Germany in 2007 [4]. In Japan, MDPV was retrospectively identified in designer drugs confiscated in the year 2006 [5].…”

Section: Introductionmentioning

confidence: 99%

Death Following Recreational Use of Designer Drug “Bath Salts” Containing 3,4-Methylenedioxypyrovalerone (MDPV)

Murray

Murphy

Beuhler³

2012

J. Med. Toxicol.

245

122

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Introduction 3,4-Methylenedioxypyrovalerone (MDPV) is a designer stimulant drug that has gained popularity in the USA. Although adverse effects of MDPV have been described, to our knowledge, this is the first reported death. Case Report We report the case of a 40-year-old male who injected and snorted "bath salts" containing MDPV and subsequently became agitated, aggressive, and experienced a cardiac arrest. He was resuscitated after his initial arrest; however, he developed hyperthermia, rhabdomyolysis, coagulopathy, acidosis, anoxic brain injury, and subsequently died. Discussion This is the first case in the medical literature to report death due to isolated confirmed MDPV intoxication. The manner of death is also consistent with excited delirium syndrome.

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Section: Introductionmentioning

confidence: 99%

Death Following Recreational Use of Designer Drug “Bath Salts” Containing 3,4-Methylenedioxypyrovalerone (MDPV)

Murray

Murphy

Beuhler³

2012

J. Med. Toxicol.

245

122

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“…It can therefore be freely commercialized in many parts of the world. MDPV has been characterized by NMR and mass spectrometry in samples obtained from confiscation 6,7 and the metabolism of drugs with similar structures has been studied in rats. [8][9][10][11][12][13][14] Because of regulations and Italian law, it was not possible to assess the metabolism and excretion of MDPV in humans.…”

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confidence: 99%

Toxicological determination and in vitro metabolism of the designer drug methylenedioxypyrovalerone (MPDV) by gas chromatography/mass spectrometry and liquid chromatography/quadrupole time‐of‐flight mass spectrometry

Rossi

Cadwallader

Torre

et al. 2010

Rapid Comm Mass Spectrometry

100

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A method for the toxicological screening of the new designer drug methylenedioxypyrovalerone (MDPV) is described; with an emphasis on its application for anti-doping analysis. The metabolism of MDPV was evaluated in vitro using human liver microsomes and S9 cellular fractions for CYP450 phase I and uridine 5'-diphosphoglucuronosyltransferase (UGT) and sulfotransferase (SULT) phase II metabolism studies. The resulting metabolites were subsequently liquid/liquid extracted and analyzed using gas chromatography/mass spectrometry (GC/MS) as trimethylsilyl (TMS) derivatives. The structures of the metabolites were further confirmed by accurate mass measurement using a liquid chromatography/quadrupole time-of-flight (LC/QTOF) mass spectrometer. The studies demonstrated that the main metabolites of MDPV are catechol and methyl catechol pyrovalerone, which are in turn sulfated and glucuronated. The method for the determination of MDPV in urine has been fully validated by assessing the limits of detection and quantification, linearity, repeatability, and accuracy. This validation demonstrates the suitability for screening of this stimulant substance for anti-doping and forensic toxicology purposes.

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“…Several analytical techniques like GC ion trap or quadruple MS with electron ionization (EI) or chemical ionization (CI) [2][3][4][5][6], and high performance liquid chromatography (HPLC) MS [7] as well as nuclear magnetic resonance (NMR) spectroscopy [2,5] have been used to identify such compounds. However, NMR spectroscopy is expensive because it may require not only onedimensional but two-dimensional 1 H-and 13 C-spectroscopy [5], furthermore it requires microgram quantities of the analyte for identification.…”

Section: Identification Of Pyrrolidinophenone-type Designer Drugs By mentioning

confidence: 99%

“…When using GC-MS with EI, the unpaired electron on the N atom induces an α-cleavage of the benzyl bond leading to the formation of an abundant immonium ion at m/z 126 for MDPV [2][3][4]6], and m/z 112 for MDPBP [5]. The EI mass spectra of a series of homologs and regioisomers of MDVP also yield only the immonium ion [6].…”

Section: Issn: 2348-9804mentioning

confidence: 99%

“…Although CI provides information on the molecular ion, it does not provide enough information on the functional groups on the phenyl ring or the alkyl moiety attached to the Cα atom. However, product ion mass spectrometry of the immonium ions was used successfully to identify the alkyl-amino moiety [2]. This study focused on the identification of pyrrolidinophenone-type designer drugs using GC-TOFMS with soft ionization, only to discover that even despite the softest ionization with Xe plasma at 8.44 eV, there were no molecular ions in the spectra and the only ions were the immonium ions.…”

Section: Issn: 2348-9804mentioning

confidence: 99%

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Identification of Pyrrolidinophenone-type Designer Drugs by Gas Chromatography/Time-of-Flight Mass Spectrometry

Lopez-Avila¹

2014

Journal of Forensic Science & Criminology

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Use of gas chromatography (GC) combined with time-of -flight mass spectrometry (TOFMS) with soft ionization generated with three different plasma gases (i.e., Xe, Kr, Ar) was evaluated for the identification of several pyrrolidinophenone-type designer drugs that are commercially available. Surprisingly, the mass spectra obtained with soft ionization exhibited only the immonium ions and lacked the molecular ions just like with 70 eV electron ionization. However, use of derivatization with 1-methyl-1-phenylhydrazine and soft ionization of the hydrazones with Ar plasma at 11.61/11.82 eV provides information that is helpful in structure elucidation. This paper focuses on the soft ionization of the hydrazones of 2,3-methylenedioxypyrovalerone (MDPV) and its deuterated analog containing eight deuterium atoms on the pyrrolidine ring, to establish a fragmentation pathway for the soft ionization of such compounds when using GC-TOFMS.

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Mass and NMR spectroscopic characterization of 3,4-methylenedioxypyrovalerone: A designer drug with α-pyrrolidinophenone structure

Cited by 73 publications

References 19 publications

Death Following Recreational Use of Designer Drug “Bath Salts” Containing 3,4-Methylenedioxypyrovalerone (MDPV)

Death Following Recreational Use of Designer Drug “Bath Salts” Containing 3,4-Methylenedioxypyrovalerone (MDPV)

Toxicological determination and in vitro metabolism of the designer drug methylenedioxypyrovalerone (MPDV) by gas chromatography/mass spectrometry and liquid chromatography/quadrupole time‐of‐flight mass spectrometry

Identification of Pyrrolidinophenone-type Designer Drugs by Gas Chromatography/Time-of-Flight Mass Spectrometry

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