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The results of a study performed on samples of 'legal highs' seized in head shops by law enforcement and health services in Poland between mid-2008 and mid-2011 are presented. In total, 449 preparations which differed in labelling, net masses, forms of distribution, etc., were analyzed. A variety of sophisticated analytical methods, including gas chromatography-mass spectrometry (GC-MS), liquid chromatography-quadropole time-of-flight mass spectrometry (LC-QTOF-MS), high performance liquid chromatography (HPLC), and nuclear magnetic resonance (NMR) were applied for component identification and quantification. The most common ingredients of legal highs were (in descending order): MPDV, caffeine, butylone, TFMPP, lidocaine, 4-MEC, mephedrone, pFPP, BZP, and MDPBP. The scatter of substances changed over time, and piperazines were often ousted by cathinones. Most of the preparations were composed of two or more ingredients. Cathinones and piperazines were mixed mainly within the chemical classes (77.6% and 56.1% of dual links, respectively), caffeine was mixed both with piperazines (24 products) and cathinones (22 products), whereas lidocaine only with the latter class (47 products). A great inconsistency in the qualitative and quantitative composition of products with identical labelling was shown in an example of Coco products seized after August 2010; we found 10 different single component or mixture preparations, and the content of individual ingredients varied from several to hundreds of mgs. This paper summarizes potential dangers connected with the uncontrolled sale of psychoactive substances, and indicates important issues concerning the analysis of legal highs.

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This publication reports analytical properties of three new hallucinogenic substances identified in blotter papers seized from the drug market, namely 25D-NBOMe [2-(2,5-dimethoxy-4-methylphenyl)-N-(2-methoxybenzyl)ethanamine], 25E-NBOMe [2-(4-ethyl-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine] and 25G-NBOMe [2-(2,5-dimethoxy-3,4-dimethylphenyl)-N-(2-methoxybenzyl)ethanamine]. These substances are N-(2-methoxy)benzyl derivatives of the 2C-series of phenethylamine drugs. The applied procedure covered a variety of analytical methods, including gas chromatography with electron impact mass spectrometry (GC-EI-MS; without derivatization and after derivatization with trifluoroacetic anhydride (TFAA)), liquid chromatography-electrospray ionization-quadrupole time of flight mass spectrometry (LC-ESI-QTOF-MS), Fourier transform infrared spectroscopy (FTIR) and nuclear magnetic resonance (NMR), which made it possible to identify the active components unequivocally. The GC-MS spectra of analyzed compounds were very similar, with dominant ions observed at m/z = 150, 121, and 91. The remaining ions were analogous to those observed for parent substances, namely 2C-D, 2C-E, 2C-G, but their intensities were low. Derivatization allowed determination of molecular masses of the investigated substances. Their exact masses and chemical formulas were confirmed by LC-QTOF-MS experiments and the fragmentation patterns of these compounds following ESI were determined. The tandem mass spectrometry (MS/MS) experiments confirmed that the studied substances were N-(2-methoxy)benzyl derivatives of the 2C-series compounds. Final elucidation of the structures was performed by NMR spectroscopy. The substances were also characterized by FTIR spectroscopy to corroborate the identity of the compounds.