Analysis of synthetic cannabinoids in “spice-like” herbal highs: snapshot of the German market in summer 2011

Abstract

In this study, seven commercial "spice-like" products available on the German market were analyzed. They all contained significant amounts of synthetic cannabinoids and had distinctly different compositions of these adulterants. All synthetic cannabinoids were extracted and purified by different chromatographic techniques from the respective product. The structures of all compounds were elucidated by nuclear magnetic resonance spectroscopy and further characterized by mass spectrometry (MS) and ultraviolet and infrared spectroscopy to generate a full data set of each compound. Altogether, eight compounds were identified, and one deuterium-labeled cannabinoid was used as internal standard. Four products contained only one individual compound, while three products contained mixtures of two compounds. Among the eight isolated compounds, six were already known from recent publications (JWH-081, JWH-210, JWH-122, AM2201, RCS-4, and JWH-203), but the published data were not always complete. In addition, two unknown compounds (AM2201-pMe, RCS-4-(N-Me)) were isolated. Overall, compounds from three distinct classes of synthetic cannabinoids could be identified, characterized, and compared. The MS data of the different subclasses allowed the postulation of some general key fragmentations to distinguish between these subclasses. In addition, we established a general method using an isotopically labeled internal standard (JWH-018-D(3)) to quantify synthetic cannabinoids in herbal mixtures. The total content of the synthetic cannabinoids ranged from 77.5 to 202 mg/g, while individual compounds were detected from 19.3 to 202 mg/g in these products. The spectroscopic data for all compounds mentioned here were collected and added en bloc as Electronic supplementary material to this manuscript.

Structure–activity relationships of synthetic cannabinoid designer drug RCS-4 and its regioisomers and C4 homologues

“…In 2011, RCS-4 was the third most common substance identified in ''herbal highs'' products obtained in Poland [20]. A survey of SC products in Germany in 2011 found RCS-4 in a herbal blend at a concentration of 157 mg/g, one of the highest SC contents of all samples tested in that study [21]. However, various products from Japan contained RCS-4 at concentrations of 18 and 1.7 mg/g herbal matter, suggesting limited knowledge about the potency of this compound by manufacturers [14].…”

Identification and quantification of synthetic cannabinoids in “spice-like” herbal mixtures: update of the German situation for the spring of 2015

“…The total contents of [25] Quantification was achieved by ESI-MS/MS applying MRM and 3-(3-(1-naphthoyl)-1H-indol-1-yl)propionate as an IS (9). Binding affinities (K i ) for cannabinoid receptor type 1 (CB 1 ) are listed when available a Samples were fluffy greenish plant material; except for sample 5B which was a brown hashish like resin b Mean of two individual extractions and measurements (n = 2) c Numbers reflect the source, letters reflect different products d Diluted in 90 % methanol, 10 % water, 1 % formic acid and 0.1 % ammonium formate Forensic Toxicol synthetic cannabinoids found in the analyzed products ranged from 66 to 446 mg/g, reflecting the ''normal'' range frequently found for such products [13,33,34]. The calculation of the concentration of the synthetic cannabinoids in commercial products depends to a great extent on the RFs.…”

“…This established protocol was facilitated by the fact that the concentration of synthetic cannabinoids is usually of the order of 50-300 mg/g [13,33,34], allowing the use of a single protocol for all samples analyzed, here, using 10 mg of each commercial product. This sample amount requires a final dilution by a factor of 100-200 to meet the dynamic range requirements of our instrumentation.…”

Bioanalytical methods for the determination of synthetic cannabinoids and metabolites in biological specimens

“…MS detector is mostly carried out for SCs detection. Other types in use are nitrogen phosphorus detector (NPD) [4] which is suitable for most types of aminoalkylindoles, and flame ionization detector (FID) [106,107].…”