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Research ArticleArticle

Mass Spectrometric Evaluation of Mephedrone In Vivo Human Metabolism: Identification of Phase I and Phase II Metabolites, Including a Novel Succinyl Conjugate

Óscar J. Pozo, María Ibáñez, Juan V. Sancho, Julio Lahoz-Beneytez, Magí Farré, Esther Papaseit, Rafael de la Torre and Félix Hernández
Drug Metabolism and Disposition February 2015, 43 (2) 248-257; DOI: https://doi.org/10.1124/dmd.114.061416
Óscar J. Pozo
Bioanalysis Research Group, Institut Hospital del Mar d'Investigacions Mèdiques, Hospital del Mar Medical Research Institute, Barcelona, Spain (O.J.P.); Research Institute for Pesticides and Water, University Jaume I, Castellón, Spain (M.I., J.V.S., F.H.); Human Pharmacology and Clinical Neurosciences Research Group, Institut Hospital del Mar d'Investigacions Mèdiques, Hospital del Mar Medical Research Institute, Universitat Autònoma de Barcelona and Universitat Pompeu Fabra, Barcelona, Spain (J.L.-B., M.F., E.P., R.d.l.T.); and Warwick Systems Biology Centre, University of Warwick, Coventry, United Kingdom (J.L.-B.)
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María Ibáñez
Bioanalysis Research Group, Institut Hospital del Mar d'Investigacions Mèdiques, Hospital del Mar Medical Research Institute, Barcelona, Spain (O.J.P.); Research Institute for Pesticides and Water, University Jaume I, Castellón, Spain (M.I., J.V.S., F.H.); Human Pharmacology and Clinical Neurosciences Research Group, Institut Hospital del Mar d'Investigacions Mèdiques, Hospital del Mar Medical Research Institute, Universitat Autònoma de Barcelona and Universitat Pompeu Fabra, Barcelona, Spain (J.L.-B., M.F., E.P., R.d.l.T.); and Warwick Systems Biology Centre, University of Warwick, Coventry, United Kingdom (J.L.-B.)
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Juan V. Sancho
Bioanalysis Research Group, Institut Hospital del Mar d'Investigacions Mèdiques, Hospital del Mar Medical Research Institute, Barcelona, Spain (O.J.P.); Research Institute for Pesticides and Water, University Jaume I, Castellón, Spain (M.I., J.V.S., F.H.); Human Pharmacology and Clinical Neurosciences Research Group, Institut Hospital del Mar d'Investigacions Mèdiques, Hospital del Mar Medical Research Institute, Universitat Autònoma de Barcelona and Universitat Pompeu Fabra, Barcelona, Spain (J.L.-B., M.F., E.P., R.d.l.T.); and Warwick Systems Biology Centre, University of Warwick, Coventry, United Kingdom (J.L.-B.)
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Julio Lahoz-Beneytez
Bioanalysis Research Group, Institut Hospital del Mar d'Investigacions Mèdiques, Hospital del Mar Medical Research Institute, Barcelona, Spain (O.J.P.); Research Institute for Pesticides and Water, University Jaume I, Castellón, Spain (M.I., J.V.S., F.H.); Human Pharmacology and Clinical Neurosciences Research Group, Institut Hospital del Mar d'Investigacions Mèdiques, Hospital del Mar Medical Research Institute, Universitat Autònoma de Barcelona and Universitat Pompeu Fabra, Barcelona, Spain (J.L.-B., M.F., E.P., R.d.l.T.); and Warwick Systems Biology Centre, University of Warwick, Coventry, United Kingdom (J.L.-B.)
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Magí Farré
Bioanalysis Research Group, Institut Hospital del Mar d'Investigacions Mèdiques, Hospital del Mar Medical Research Institute, Barcelona, Spain (O.J.P.); Research Institute for Pesticides and Water, University Jaume I, Castellón, Spain (M.I., J.V.S., F.H.); Human Pharmacology and Clinical Neurosciences Research Group, Institut Hospital del Mar d'Investigacions Mèdiques, Hospital del Mar Medical Research Institute, Universitat Autònoma de Barcelona and Universitat Pompeu Fabra, Barcelona, Spain (J.L.-B., M.F., E.P., R.d.l.T.); and Warwick Systems Biology Centre, University of Warwick, Coventry, United Kingdom (J.L.-B.)
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Esther Papaseit
Bioanalysis Research Group, Institut Hospital del Mar d'Investigacions Mèdiques, Hospital del Mar Medical Research Institute, Barcelona, Spain (O.J.P.); Research Institute for Pesticides and Water, University Jaume I, Castellón, Spain (M.I., J.V.S., F.H.); Human Pharmacology and Clinical Neurosciences Research Group, Institut Hospital del Mar d'Investigacions Mèdiques, Hospital del Mar Medical Research Institute, Universitat Autònoma de Barcelona and Universitat Pompeu Fabra, Barcelona, Spain (J.L.-B., M.F., E.P., R.d.l.T.); and Warwick Systems Biology Centre, University of Warwick, Coventry, United Kingdom (J.L.-B.)
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Rafael de la Torre
Bioanalysis Research Group, Institut Hospital del Mar d'Investigacions Mèdiques, Hospital del Mar Medical Research Institute, Barcelona, Spain (O.J.P.); Research Institute for Pesticides and Water, University Jaume I, Castellón, Spain (M.I., J.V.S., F.H.); Human Pharmacology and Clinical Neurosciences Research Group, Institut Hospital del Mar d'Investigacions Mèdiques, Hospital del Mar Medical Research Institute, Universitat Autònoma de Barcelona and Universitat Pompeu Fabra, Barcelona, Spain (J.L.-B., M.F., E.P., R.d.l.T.); and Warwick Systems Biology Centre, University of Warwick, Coventry, United Kingdom (J.L.-B.)
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Félix Hernández
Bioanalysis Research Group, Institut Hospital del Mar d'Investigacions Mèdiques, Hospital del Mar Medical Research Institute, Barcelona, Spain (O.J.P.); Research Institute for Pesticides and Water, University Jaume I, Castellón, Spain (M.I., J.V.S., F.H.); Human Pharmacology and Clinical Neurosciences Research Group, Institut Hospital del Mar d'Investigacions Mèdiques, Hospital del Mar Medical Research Institute, Universitat Autònoma de Barcelona and Universitat Pompeu Fabra, Barcelona, Spain (J.L.-B., M.F., E.P., R.d.l.T.); and Warwick Systems Biology Centre, University of Warwick, Coventry, United Kingdom (J.L.-B.)
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Abstract

In recent years, many new designer drugs have emerged, including the group of cathinone derivatives. One frequently occurring drug is mephedrone; although mephedrone was originally considered as a “legal high” product, it is currently banned in most Western countries. Despite the banning, abuse of the drug and seizures are continuously reported. Although the metabolism of mephedrone has been studied in rats or in vitro using human liver microsomes, to the best of our knowledge, no dedicated study with human volunteers has been performed for studying the in vivo metabolism of mephedrone in humans. Therefore, the aim of this study was to establish the actual human metabolism of mephedrone and to compare it with other models. For this purpose, urine samples of two healthy volunteers, who ingested 200 mg mephedrone orally, were taken before administration and 4 hours after substance intake. The discovery and identification of the phase I and phase II metabolites of mephedrone were based on ultra-high-performance liquid chromatography coupled to hybrid quadrupole time-of-flight mass spectrometry, operating in the so-called MSE mode. Six phase I metabolites and four phase II metabolites were identified, four of them not previously reported in the literature. The structure of four of the detected metabolites was confirmed by synthesis of the suggested compounds. Remarkably, a mephedrone metabolite conjugated with succinic acid has been identified and confirmed by synthesis. According to the reviewed literature, this is the first time that this type of conjugate is reported for human metabolism.

Footnotes

    • Received September 29, 2014.
    • Accepted December 2, 2014.
  • This research was supported by the Spanish Ministry of Economy and Competitiveness [Grant Ciencias y Tecnologías Químicas (CTQ) 2012-36189], the Ministry of Health [Grant Instituto de Salud Carlos III (ISC-III) Proyecto de Investigación (PI) 11/01961], Departament d'Innovació, Universitats i Empresa (DIUE) de la Generalitat de Catalunya [Grant 2014 Grup de recerca Reconegut de la Generalitat (SGR) 680], and Generalitat Valenciana [Research Group of Excellence Grants PROMETEO II/2014/023 and Institutos Superiores de Investigación Cooperativa (ISIC) 2012/016]. This research was also supported in part by Instituto de Salud Carlos III-Fondo Europeo de Desarrollo Regional (FEDER) [Grants Fondo de Investigación Sanitaria (FIS) PI11/0196 and Red trastornos adictivos (RTA) RD12/0028/0009 and Rio Hortega Fellowship ISC-III-CM13/00016].

  • dx.doi.org/10.1124/dmd.114.061416.

  • ↵Embedded ImageThis article has supplemental material available at dmd.aspetjournals.org.

  • Copyright © 2014 by The American Society for Pharmacology and Experimental Therapeutics
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Drug Metabolism and Disposition: 43 (2)
Drug Metabolism and Disposition
Vol. 43, Issue 2
1 Feb 2015
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Research ArticleArticle

Mephedrone Metabolism in Humans

Óscar J. Pozo, María Ibáñez, Juan V. Sancho, Julio Lahoz-Beneytez, Magí Farré, Esther Papaseit, Rafael de la Torre and Félix Hernández
Drug Metabolism and Disposition February 1, 2015, 43 (2) 248-257; DOI: https://doi.org/10.1124/dmd.114.061416

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Research ArticleArticle

Mephedrone Metabolism in Humans

Óscar J. Pozo, María Ibáñez, Juan V. Sancho, Julio Lahoz-Beneytez, Magí Farré, Esther Papaseit, Rafael de la Torre and Félix Hernández
Drug Metabolism and Disposition February 1, 2015, 43 (2) 248-257; DOI: https://doi.org/10.1124/dmd.114.061416
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