Synthesis, characterisation and quantification of the new psychoactive substance 1-(1,3-benzodioxol-5-yl)-2-(propylamino)butan-1-one (bk-PBDB, putylone)

Baumann, 2018, Neuropharmacology of synthetic cathinones, vol. 252 Zawilska, J.B. (2018) Synthetic Cathinones. Novel Addictive and Stimulatory Psychoactive Substances, Current Topics in Neurotoxicity. Springer, Cham. doi: 10.1007/978-3-319-78707-7. Stevens, 2018, DARK classics in chemical neuroscience: cathinone-derived psychostimulants, ACS Chem. Neurosci., 9, 2379, 10.1021/acschemneuro.8b00147 Soares, 2021, An updated review on synthetic cathinones, Arch. Toxicol., 95, 2895, 10.1007/s00204-021-03083-3 UNODC EMCDDA (2021) European drug report 2021: trends and developments. doi: 10.2810/18539. Accessed 11 June 2023. Dal Cason, 1997, Cathinone: an investigation of several N-alkyl and methylenedioxy-substituted analogs, Pharmacol. Biochem. Behav., 58, 1109, 10.1016/S0091-3057(97)00323-7 Miner, 2017, The combined effects of 3,4-methylenedioxymethamphetamine (MDMA) and selected substituted methcathinones on measures of neurotoxicity, Neurotoxicol. Teratol., 61, 74, 10.1016/j.ntt.2017.02.003 López-Arnau, 2012, Comparative neuropharmacology of three psychostimulant cathinone derivatives: butylone, mephedrone and methylone, Br. J. Pharmacol., 167, 407, 10.1111/j.1476-5381.2012.01998.x Karila, 2015, Synthetic cathinones: A new public health problem, Curr. Neuropharmacol., 13, 12, 10.2174/1570159X13666141210224137 Schifano, 2020, The clinical challenges of synthetic cathinones, Br. J. Clin. Pharmacol., 86, 410, 10.1111/bcp.14132 Riley, A.L., Nelson, K.H., To, P., López-Arnau, R., Peng, X., Wang, D., Wang, Y., Shen, H-W., Kuhn, D.M., Angoa-Perez, M., Anneken, J.H., Muskiewicz, D., Hall, F.S. (2020), Abuse potential and toxicity of the synthetic cathinones (i.e., “Bath salts”), 110, 150-173. doi: 10.1016/j.neubiorev.2018.07.015. CND (2015) Decision 58/13. Inclusion of methylone (beta-keto-MDMA) in Schedule II of the Convention on Psychotropic Substances of 1971. https://www.unodc.org/documents/commissions/CND/CND_Sessions/CND_58/2015_Desicions/Desicion_58_13.pdf. Accessed 11 June 2023. CND (2017) Decision 60/5. Inclusion of ethylone in Schedule II of the Convention on Psychotropic Substances of 1971. https://www.unodc.org/documents/commissions/CND/CND_Sessions/CND_60/CNDdec_2017/Decision_60_5_60CND.pdf. Accessed 11 June 2023. CND (2019) Decision 62/9. Inclusion of N-ethylnorpentylone (ephylone) in Schedule II of the Convention on Psychotropic Substances of 1971. https://www.unodc.org/documents/commissions/CND/Drug_Resolutions/2010-2019/2019/Decisions/CND_Decision_62_9.pdf. Accessed 11 June 2023. CND (2022) Decision 62/9 Inclusion of eutylone in Schedule II of the Convention on Psychotropic Substances of 1971. https://www.unodc.org/documents/commissions/CND/Drug_Resolutions/2010-2019/2019/Decisions/CND_Decision_62_9.pdf. Accessed 11 June 2023. Kuropka, 2023, A review of synthetic cathinones emerging in recent years (2019–2022), Foren. Toxicol., 41, 25, 10.1007/s11419-022-00639-5 Krotulski, A.J., Shellman F.V., Fogarty, M.F., Walton, S.E., Logan, B.K. (2022) N-Propylbutylone. Pennsylvania: Center for Forensic Science Research & Education. https://www.cfsre.org/images/monographs/N-Propyl-Butylone-072122-CFSRE-Chemistry-Report.pdf. Accessed 11 June 2023. Bradley, 2010, Drying of organic solvents: quantitative evaluation of the efficiency of several desiccants, J. Org. Chem., 75, 8351, 10.1021/jo101589h Santali, 2011, Synthesis, full chemical characterisation and development of validated methods for the quantification of (±)-4′-methylmethcathinone (mephedrone): A new “legal high”, J. Pharm. Biomed. Anal., 56, 246, 10.1016/j.jpba.2011.05.022 Ogawa, 1992, Purines. LII. Synthesis and biological evaluation of 8-methylguanine 7-oxide and its 9-arylmethyl derivatives, Chem. Pharm. Bull., 40, 1315, 10.1248/cpb.40.1315 Fulmer, 2010, NMR chemical shifts of trace impurities: common laboratory solvents, organics, and gases in deuterated solvents relevant to the organometallic chemist, Organometallics, 29, 2176, 10.1021/om100106e Ammann, 1982, A simple multi-nuclear NMR thermometer, J. Magn. Reason., 46, 319 Antonides, 2019, Rapid identification of novel psychoactive and other controlled substances using low-field 1H NMR spectroscopy, ACS Omega, 4, 7103, 10.1021/acsomega.9b00302 Dixon, 2022, Comparative study of the analysis of seized samples by GC-MS, 1H NMR and FT-IR spectroscopy within a Night-Time Economy (NTE) setting, J. Pharm. Biomed. Anal., 219, 10.1016/j.jpba.2022.114950 International Council for Harmonisation of Technical Requirements for Pharmaceuticals for Human Use (2005), Validation of Analytical Procedures: Text and Methodology, http://www.ich.org/products/guidelines/quality/quality-single/article/validation-of-analytical-procedures-text-and-methodology.html. Accessed 11 June 2023. Pauli, 2014, Importance of purity evaluation and the potential of quantitative 1H NMR as a purity assay, J. Med. Chem., 57, 9220, 10.1021/jm500734a Maheux, 2015, Identification of polymorphism in ethylone hydrochloride: synthesis and characterization, Drug Test. Anal., 8, 847, 10.1002/dta.1859 Hussain, 2020, Quantification of MDMA in seized tablets using benchtop 1H NMR spectroscopy in the absence of internal standards, Foren. Chem.., 20 Davidson, 2020, Fragmentation pathways of odd- and even-electron N-alkylated synthetic cathinones, Int. J. Mass Spectrom., 453, 10.1016/j.ijms.2020.116354