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2008 | 6 | 4 | 526-534
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The Henry reaction: spectroscopic studies of nitrile and hydroxylamine by-products formed during synthesis of psychoactive phenylalkylamines

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A clandestine two-step route to psychoactive racemic phenylalkylamines utilises the Henry reaction. In the first step an aromatic aldehyde reacts with a nitroalkane to give the nitrostyrene intermediate. In the second step the nitrostyrene is reduced to the phenylalkylamine. An impurity profile of both steps was evaluated through the synthesis and analysis of common street derivatives. The formation of nitrile impurities in the nitroaldol reaction and hydroxylamine impurities in the reduction step were shown by NMR spectroscopy and GC-MS. A selection of reducing agents has been used to give the phenylalkylamines, together with variable quantities of the partially reduced hydroxylamine product. GC-MS analysis of the hydroxylamines showed heat-induced disproportionation which led to the detection of the corresponding oximes. [...]
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  • School of Pharmacy and Pharmaceutical Sciences, The University of Manchester, Oxford Road, M13 9PT, Manchester, UK
  • School of Pharmacy and Pharmaceutical Sciences, The University of Manchester, Oxford Road, M13 9PT, Manchester, UK
  • Centre for Instrumentation and Analytical Science, The University of Manchester, M60 1QD, Manchester, UK
  • Institute for Health Research, School of Pharmacy and Chemistry, Liverpool John Moores University, Byrom Street, L3 3AF, Liverpool, UK,
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