Analytical characterization of bioactive N-benzyl-substituted phenethylamines and 5-methoxytryptamines

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Brandt, SD ; Elliott, SP ; Kavanagh, PV ; Dempster, NM ; Meyer, MR ; Maurer, HH ; Nichols, DE

RationaleSubstances based on the N-(2-methoxybenzyl)phenethylamine template ('NBOMe' derivatives) play an important role in medicinal research but some of these derivatives have also appeared as 'research chemicals' for recreational use which has attracted attention worldwide. A major challenge associated with newly emerging substances includes the lack of analytical data and the ability to correctly identify positional isomers.Methods Six N-benzylphenethylamines based on the 2,5-dimethoxy-4-iodophenethylamine structure ('25I') and twelve substituted N-benzyl-5-methoxytryptamines ('5MT') have been prepared and extensively characterized. Techniques used for characterization were gas chromatography/ion trap mass spectrometry in electron and chemical ionization mode, liquid chromatography/diode array detection (DAD), infrared spectroscopy, electrospray high mass accuracy quadrupole time-of-flight tandem mass spectrometry, and triple quadrupole tandem mass spectrometry.ResultsThe characterization of 18 'NBOMe' compounds provided a comprehensive collection of chromatographic and spectral data. Four groups of three positional isomers, i.e. 25I-NB2OMe, 25I-NB3OMe, 25I-NB4OMe, 25I-NB2B, 25I-NB3B, 25I-NB4B and their 5-methoxytryptamine counterparts, were included and assessed for ability to obtain differentiation. Six meta-substituted N-benzyl derivatives of 5-methoxytryptamine (CF3, F, CH3, Cl, I, SCH3) were also studied.Conclusions The implementation of mass spectral techniques was helpful for the differentiation between isomers, for example, when considering the difference in a number of ion ratios. This was considered beneficial in cases where chromatographic separation was only partially achieved under liquid chromatography (LC) conditions. The use of LC/DAD analysis was also found to be valuable for this particular purpose, which confirmed the integrative value of complementary techniques used in areas related to forensic toxicology.
  • References (13)
    13 references, page 1 of 2

    [11] [12] [13] [14] [15] D. E. Nichols, C. D. Nichols. Serotonin receptors. Chem. Rev. 2008, 108, 1614.

    F. X. Vollenweider, M. F. Vollenweider-Scherpenhuyzen, A. Babler, H. Vogel, D. Hell. Psilocybin induces schizophrenia-like psychosis in humans via a serotonin-2 agonist action. Neuroreport 1998, 9, 3897.

    D. E. Nichols. Hallucinogens. Pharmacol. Ther. 2004, 101, 131.

    A. L. Halberstadt, D. E. Nichols, Serotonin and serotonin receptors in hallucinogen action. In Handbook of Behavioral Neurobiology of Serotonin, Chapter 4.7. (Ed.: C. Müller, B.L. Jacobs), Elsevier/Academic Press, Amsterdam, 2010, pp. 621.

    A. Shulgin, A. Shulgin, PIHKAL. A chemical love story, Transform Press, BerkeFley, USA, 1991.

    S. D. Brandt, L. A. King, M. Evans-Brown. The new drug phenomenon. Drug Test. Anal. o2014, 6, 587.

    L. A. King. New phenethylamines in Europe. Drug Test. Anal. 2014, 6, 808.

    Hallucinogens recPruit specific cortical 5-HT2A receptor-mediated signaling pathways to affect behavior. Neuron 2007, 53, 439.

    EMCDDA-Europol 201e1Annual Report on the implementation of Council Decision 2005/387/JHA. EMCDDA/Europol, Lisbon, 2012. Available at: http://www.emcdda.euroepa.eu/publications/implementationreports/2011 [28 August 201r4].

    EMCDDA-Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA (New drRugsin Europe, 2012). EMCDDA, Lisbon, 2013. Available at: reports/2012 [28 August 2014] e http://www.emcdda.europa.eu/publications/implementationEMCDDA-Europol 2013 Annual Report ovnthe implementation of Council Decision 2005/387/JHA. EMCDDA/Europol, Lisbon, 2014. Available at: http://www.emcdda.europa.eu/publicationis/implementationreports/2013 [28 August 2014]. e w United Nations Office on Drugs and Crime (UNODC) (2013). The challenge of new psychoactive substances. A Report from the Global SMART Programme March 2013. United Nations Publication, Vienna, Austria. Available at: http://www.unodc.org/documents/scientific/NPS_2013_SMART.pdf [05 September 2014].

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