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

TY - JOUR

T1 - The naphyrone story

T2 - the alpha or beta-naphthyl isomer?

AU - Brandt, Simon D.

AU - Wootton, Robert C. R.

AU - De Paoli, Giorgia

AU - Freeman, Sally

PY - 2010/10

Y1 - 2010/10

N2 - 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.

AB - 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.

KW - Naphyrone

KW - Legal highs

KW - NRG-1

KW - Nuclear magnetic resonance spectroscopy

KW - Mass spectrometry

KW - Forensic

KW - Clinical

U2 - 10.1002/dta.185

DO - 10.1002/dta.185

M3 - Article

C2 - 20886463

SN - 1942-7603

VL - 2

SP - 496

EP - 502

JO - Drug Testing and Analysis

JF - Drug Testing and Analysis

IS - 10

ER -