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Journal
2008 | 6 | 4 | 526-534
Article title

The Henry reaction: spectroscopic studies of nitrile and hydroxylamine by-products formed during synthesis of psychoactive phenylalkylamines

Content
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Languages of publication
EN
Abstracts
EN
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. [...]
Keywords
Publisher

Journal
Year
Volume
6
Issue
4
Pages
526-534
Physical description
Dates
published
1 - 12 - 2008
online
28 - 10 - 2008
Contributors
author
  • School of Pharmacy and Pharmaceutical Sciences, The University of Manchester, Oxford Road, M13 9PT, Manchester, UK
author
  • School of Pharmacy and Pharmaceutical Sciences, The University of Manchester, Oxford Road, M13 9PT, Manchester, UK
author
  • Centre for Instrumentation and Analytical Science, The University of Manchester, M60 1QD, Manchester, UK
author
  • Institute for Health Research, School of Pharmacy and Chemistry, Liverpool John Moores University, Byrom Street, L3 3AF, Liverpool, UK, s.brandt@ljmu.ac.uk
References
  • [1] F.A. Luzzio, Tetrahedron 57, 915 (2001) http://dx.doi.org/10.1016/S0040-4020(00)00965-0[Crossref]
  • [2] N. Milhazes, R. Calheiros, M.P.M. Marques, J. Garrido, M. Cordeiro, C. Rodrigues, S. Quinteira, C. Novais, L. Peixe, F. Borges, Bioorganic & Medicinal Chemistry 14, 4078 (2006) http://dx.doi.org/10.1016/j.bmc.2006.02.006[Crossref]
  • [3] W.Y. Wang, P.W. Hsieh, Y.C. Wu, C.C. Wu, Biochemical Pharmacology 74, 601 (2007) http://dx.doi.org/10.1016/j.bcp.2007.06.001[Crossref]
  • [4] A.T. Shulgin, in R.R. Laing (Editor), Hallucinogens. A Forensic Drug Handbook (Elsevier Science Ltd., London, 2003) 67
  • [5] D.E. Nichols, Journal of Psychoactive Drugs 18, 305 (1986) [Crossref]
  • [6] D.E. Nichols, Pharmacology & Therapeutics 101, 131 (2004) http://dx.doi.org/10.1016/j.pharmthera.2003.11.002[Crossref]
  • [7] A.T. Shulgin, A. Shulgin, PIHKAL. A Chemical Love Story (Transform Press, Berkeley, 1991)
  • [8] S. Freeman, J.F. Alder, European Journal of Medicinal Chemistry 37, 527 (2002) http://dx.doi.org/10.1016/S0223-5234(02)01382-X[Crossref]
  • [9] K. Andersson, K. Jalava, E. Lock, Y. Finnon, H. Huizer, E. Kaa, A. Lopes, A. Poortman-Van Der Meer, M.D. Cole, J. Dahlen, E. Sippola, Forensic Science International 169, 50 (2007) http://dx.doi.org/10.1016/j.forsciint.2006.10.018[Crossref]
  • [10] W.D. Barker, U. Antia, Forensic Science International 166, 102 (2007) http://dx.doi.org/10.1016/j.forsciint.2006.04.005[Crossref]
  • [11] R.J.H. Waddell-Smith, Journal of Forensic Sciences 52, 1297 (2007)
  • [12] W.C. Still, M. Kahn, A. Mitra, Journal of Organic Chemistry 43, 2923 (1978) http://dx.doi.org/10.1021/jo00408a041[Crossref]
  • [13] S.N. Karmarkar, S.L. Kelkar, M.S. Wadia, Synthesis-Stuttgart 510 (1985) [Crossref]
  • [14] M.J. Miller, G.M. Loudon, Journal of Organic Chemistry 40, 126 (1975) http://dx.doi.org/10.1021/jo00889a034[Crossref]
  • [15] K. Srinivas, I. Mahender, B. Das, Chemistry Letters 32, 738 (2003) http://dx.doi.org/10.1246/cl.2003.738[Crossref]
  • [16] R.S. Varma, G.W. Kabalka, Synthetic Communications 15, 843 (1985) http://dx.doi.org/10.1080/00397918508063880[Crossref]
  • [17] U. Braun, A.T. Shulgin, G. Braun, Journal of Pharmaceutical Sciences 69, 192 (1980) http://dx.doi.org/10.1002/jps.2600690220[Crossref]
  • [18] J.R. Butterick, A.M. Unrau, Journal of the Chemical Society, Chemical Communications 88, 307 (1974) http://dx.doi.org/10.1039/c39740000307[Crossref]
  • [19] Anonymous, United Nations Report, United Nations Office on Drugs and Crime (Laboratory and Scientific Section, 2006)
  • [20] R.O. Hutchins, D. Rotstein, N. Natale, J. Fanelli, D. Dimmel, Journal of Organic Chemistry 41, 3328 (1976) http://dx.doi.org/10.1021/jo00882a029[Crossref]
  • [21] G.W. Kabalka, L.H.M. Guindi, R.S. Varma, Tetrahedron 46, 7443 (1990) http://dx.doi.org/10.1016/S0040-4020(01)89059-1[Crossref]
  • [22] D.H. Williams, I. Fleming, Spectroscopic Methods in Organic Chemistry, 5th edition (McGraw-Hill, London, 1995)
  • [23] N. Kornblum, R.A. Brown, Journal of the American Chemical Society 87, 1742 (1965) http://dx.doi.org/10.1021/ja01086a023[Crossref]
  • [24] J.M. Khurana, G. Kukreja, Synthetic Communications 32, 1265 (2002) http://dx.doi.org/10.1081/SCC-120003619[Crossref]
  • [25] Y.G. Suh et al., Journal of Medicinal Chemistry 48, 5823 (2005) http://dx.doi.org/10.1021/jm0502790[Crossref]
  • [26] H. Shechter, D.E. Ley, E.B. Roberson, Journal of the American Chemical Society 78, 4984 (1956) http://dx.doi.org/10.1021/ja01600a049[Crossref]
  • [27] R.T. Gilsdorf, F.F. Nord, Journal of the American Chemical Society 74, 1837 (1952) http://dx.doi.org/10.1021/ja01127a064[Crossref]
  • [28] T.A. Dal Cason, Journal of Forensic Sciences 34, 928 (1989)
  • [29] A.H. Beckett, R.T. Coutts, F.A. Ogunbona, Journal of Pharmacy and Pharmacology 25, 708 (1973) [Crossref]
  • [30] C.R. Clark, J. Deruiter, A. Valaer, F.T. Noggle, Journal of Chromatographic Science 33, 328 (1995) [Crossref]
Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_s11532-008-0054-z
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