The naphyrone story: the alpha or beta-naphthyl isomer?

Simon D. Brandt, Robert C. R. Wootton, Giorgia De Paoli, Sally Freeman

    Research output: Contribution to journalArticlepeer-review

    31 Citations (Scopus)


    Naphyrone (naphthylpyrovalerone, O-2482) has been recently advertised for purchase on a number of websites. This compound has been viewed as a so-called 'legal high' and was classified as a controlled drug under the UK Misuse of Drugs Act 1971 in mid-July 2010. So far, naphyrone is commonly equated with 1-naphthalen-2-yl-2-pyrrolidin-1-yl-pentan-1-one (beta-naphyrone) but analytical characterization of two naphyrone samples revealed the existence of a novel isomer consistent with 1-naphthalen-1-yl-2-pyrrolidin-1-yl-pentan-1-one (alpha-naphyrone). Analyses of both alpha- and beta-naphyrone were carried out using gas chromatography ion trap (EI/CI) mass spectrometry and 1D/2D nuclear magnetic resonance spectroscopy. This provides the first report of alpha-naphyrone in the scientific literature and the ability to differentiate it from the beta-isomer should be of interest to forensic and clinical communities. Copyright (C) 2010 John Wiley & Sons, Ltd.

    Original languageEnglish
    Pages (from-to)496-502
    Number of pages7
    JournalDrug Testing and Analysis
    Issue number10
    Publication statusPublished - Oct 2010


    • Naphyrone
    • Legal highs
    • NRG-1
    • Nuclear magnetic resonance spectroscopy
    • Mass spectrometry
    • Forensic
    • Clinical


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