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The Naphyrone Story: The Alpha or Beta-naphthyl Isomer? (2010)

The Naphyrone Story: The Alpha or Beta-naphthyl Isomer? (2010)

  1. catseye
    Drug Test Anal 2010 Oct;2(10):496-502

    Brandt SD, Wootton RC, De Paoli G, Freeman S

    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 (β-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 (α-naphyrone). Analyses of both α- and β-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 α-naphyrone in the scientific literature and the ability to differentiate it from the β-isomer should be of interest to forensic and clinical communities.