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

Ludger Ernst; Kai Brandhorst; Uli Papke; Anna Altrogge; Simone Zodel; Nico Langer; Till Beuerle

doi:10.1016/j.forsciint.2017.05.019

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

Forensic Sci Int. 2017 Aug:277:51-58. doi: 10.1016/j.forsciint.2017.05.019. Epub 2017 May 26.

Authors

Ludger Ernst¹, Kai Brandhorst², Uli Papke³, Anna Altrogge⁴, Simone Zodel⁴, Nico Langer⁴, Till Beuerle⁵

Affiliations

¹ Chemistry Department, Central NMR Laboratory, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany.
² Chemistry Department, Institute of Inorganic and Analytical Chemistry, Hagenring 30, 38106 Braunschweig, Germany.
³ Chemistry Department, Central Mass Spectrometry Laboratory, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany.
⁴ Institute of Pharmaceutical Biology, Technische Universität Braunschweig, Mendelssohnstr. 1, 38106 Braunschweig, Germany.
⁵ Institute of Pharmaceutical Biology, Technische Universität Braunschweig, Mendelssohnstr. 1, 38106 Braunschweig, Germany. Electronic address: t.beuerle@tu-bs.de.

PMID: 28601726
DOI: 10.1016/j.forsciint.2017.05.019

Abstract

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.