Identification and quantification of synthetic cannabinoids in ‘spice-like’ herbal mixtures: Update of the German situation in early 2017

• Published in: Forensic science international Vol. 277; pp. 51 - 58
• Main Authors: Ernst, Ludger, Brandhorst, Kai, Papke, Uli, Altrogge, Anna, Zodel, Simone, Langer, Nico, Beuerle, Till
• Format: Journal Article
• Language: English
• Published: Ireland Elsevier B.V 01.08.2017; Elsevier Limited
• Subjects: active ingredients; Cannabinoids; Chemicals; Chromatography; Drugs; electrospray ionization mass spectrometry; Forensic sciences; gas chromatography-mass spectrometry; Identification; Internet; Legislation; Marijuana; Mass spectrometry; NMR; Nuclear magnetic resonance; nuclear magnetic resonance spectroscopy; Pathology; Scientific imaging; ultraviolet-visible spectroscopy; Germany
• ISSN: 0379-0738; 1872-6283; 1872-6283
• DOI: 10.1016/j.forsciint.2017.05.019

[Display omitted] •Identification and quantification of MDMB-CHMICA, 5F-Cumyl-P7AICA and Cumyl-PeGACLONE in herbal smoking mixtures.•Full physico-chemical characterization of the new 5F-Cumyl-P7AICA and Cumyl-PeGACLONE.•Global minima calculation comparison for Cumyl-PeGACLONE and JWH-018.•GC–MS quantification of all synthetic cannabinoids using JWH-018 as internal standard. In February 2017, eleven “Spice-like” products (14 individual packages including replicates) from German language internet shops were analyzed. In total, three different synthetic cannabinoids (SCs) were identified by gas-chromatography–mass spectrometry (GC–MS), namely MDMB-CHMICA and two, so far only partially described compounds, 5F-Cumyl-P7AICA and Cumyl-PeGACLONE. All analyzed products contained only one synthetic cannabinoid as active ingredient. 5F-Cumyl-P7AICA and Cumyl-PeGACLONE were subject to an in-depth characterization by nuclear magnetic resonance spectroscopy (NMR), electron ionization mass spectrometry (EI-MS), electrospray ionization tandem mass spectrometry (ESI-MS/MS), infrared and ultraviolet-visible spectroscopy (IR and UV/Vis). Cumyl-PeGACLONE shows a rather unexpected structure compared to conventional SCs of the past. Hence a global minima calculation was conducted to demonstrate structural similarity of Cumyl-PeGACLONE to JWH-018, a classical SC. In addition, all SCs were quantified by a GC–MS method using JWH-018 as internal standard and corresponding response factors. While MDMB-CHMICA was detected in six out of 14 tested products (ranging from 6 to 20mg/g; average 10mg/g), 5F-Cumyl-P7AICA and Cumyl-PeGACLONE were detected in three (109–153mg/g; average 131mg/g) and five products (15–74mg/g; average 39mg/g), respectively.