Chemical characterization of "legal highs" containing 4-fluoroamphetamine and synthetic cathinones

Rodriguez Zancajo, Victor Manuel

http://hdl.handle.net/10400.26/19075

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Authors

Rodriguez Zancajo, Victor Manuel

Advisor(s)

Lopes, Álvaro Teixeira

Abstract(s)

The number of “Smart Shops” and online distributors of “Legal highs” have proliferated in the last years, they are becoming a thread to public health and an international motive of concern. Unfortunately, there is very little chemical or toxicological literature on these substances. This study presents the results of the analysis of fourteen “legal highs” that were purchased in “Smart Shops” in Portugal in February 2013. These substances were analysed by a wide variety of sophisticated analytical methods including Fourier transform infrared (FTIR), Gas chromatography couple with mass spectrometry (GCMS), Proton nuclear magnetic resonance (1H NMR) and Wave-length dispersive X-ray fluorescence (WD-XRF). The next synthetic cathinones were detected: flephedrone, buphedrone, ethcathinone, 4-methylethcathinone, dimethylmethcathinone and methedrone. 4-fluoroamphetamine was also identified and all were confirmed by at least one different technique. Analytical data of these substances are presented. Methedrone, which was present in three products, is a cathinone derivative responsible for some fatalities. A particularly high toxicity and narrow therapeutic window linked with the methoxy group have been attributed to methedrone. Data obtained indicate products of high purity with small amounts of caffeine. Active ingredients were found on its own or in mixtures in the different products, and great inconsistencies and erroneous information were observed after evaluation of the packages of products. Legal status of these substances is changing continuously, and most of the chemicals that have been detected in this study were banned in Portugal some weeks after the acquisition of the products. Thus, they belong now to the illegal market of stimulants of abuse. Elemental composition of the products is also presented, obtained by XRF analysis. X-ray irradiation resulted in an unanticipated change in colour at different degree on the products. It was demonstrated that this change in colour did not chemically altered the compounds present in the samples, making XRF a suitable technique for producing inorganic profiles of samples containing cathinones.