Recently, carboxamide-type synthetic cannabinoids have been distributed globally as new psychoactive substances (NPS). Some of these compounds possess asymmetric carbon, which is derived from an amide moiety composed of amino acid derivatives (i.e., amides or esters of amino acids). In this study, we synthesized both enantiomers of synthetic cannabinoids, N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(2-fluorobenzyl)-1H-indazole-3-carboxamide (AB-FUBINACA 2-fluorobenzyl isomer), N-(1-amino-1-oxo-3-phenylpropan-2-yl)-1-(cyclohexylmethyl)-1H-indazole-3-carboxamide (APP-CHMINACA), ethyl [1-(5-fluoropentyl)-1H-indazole-3-carbonyl]valinate (5F-EMB-PINACA), ethyl [1-(4-fluorobenzyl)-1H-indazole-3-carbonyl]valinate (EMB-FUBINACA), and methyl 2-[1-(4-fluorobenzyl)-1H-indole-3-carboxamido]-3,3-dimethylbutanoate (MDMB-FUBICA), which were reported as NPS found in Europe from 2014 to 2015, to evaluate their activities as CB1/CB2 receptor agonists. With the exception of (R) MDMB-FUBICA, all of the tested enantiomers were assumed to be agonists of both CB1 and CB2 receptors, and the EC50 values of the (S)-enantiomers for the CB1 receptors were about five times lower than those of (R)-enantiomers. (R) MDMB-FUBICA was shown to function as an agonist of the CB2 receptor, but lacks CB1 receptor activity. To the best of our knowledge, this is the first report to show that the (R)-enantiomers of the carboxamide-type synthetic cannabinoids have the potency to activate CB1 and CB2 receptors. The findings presented here shed light on the pharmacological properties of these carboxamide-type synthetic cannabinoids in forensic cases.
A rapid and simple method to determine taurine in energy drinks by pre-column high-performance liquid chromatography was developed using a derivative of 4-fluoro-7-nitrobenzofurazan (NBD-F) without the need for an exclusive instrument. The reaction of taurine with NBD-F finished in 10 min at 60• C. The derivative was measured on a UV-Visible detector (470 nm) by HPLC using a conventional Octadecyl silane (ODS) column. A mixture of disodium hydrogenphosphate-citric acid buffer solution (pH 5.4) containing 10 mmol/l tetrabutylammonium bromide and acetonitrile (7:3) was used as the mobile phase. The recoveries were in the range of 98.2-99.9%, the precision as standard deviation was in the range of 0.3-0.5%, the linearity as a coefficient of correlation value was 0.999 and the specification was confirmed for taurine added to three commercial energy drinks. The content of taurine measured compared to the labeled amount in five commercial energy drinks containing taurine was 92.9-105.1%.
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