Identification and quantification of synthetic cannabinoids in “spice-like” herbal mixtures: Update of the German situation for the spring of 2016

The greatest challenge for European drug policies is how to effectively respond to the dynamic and constantly changing market for new psychoactive substances (NPS). Even small modifications in the chemical structure of substances often allow circumventing existing laws. Also in prison, the consumption of NPS is rising and there is growing evidence that NPS are responsible for a large share of drug‐related problems. Ion mobility spectrometry (IMS) is the technique of choice for trace analysis of illicit drugs or explosives at security points, for example airports. Currently, databases of the reduced mobility (K0) values are limited to classical drugs and should be completed with data of emerging NPS. In this article, K0 values, LODs (0.7–3.6 ng) and drift times of 25 synthetic cannabinoids were evaluated. The data were added to existing databases of IMS which were then applied for fast screening in prison. The detection capability of the portable IMS technique was evaluated by the determination of intra‐day (0.089%) and inter‐day precision (0.004% to 0.14%), systematic error (0.19%), and separation capability for structurally related NPS. The applicability of the methodology was demonstrated by the successful analysis of 12 different pieces of paper impregnated with synthetic cannabinoids, 7 different cosmetics, and 5 food samples (liquids), spiked with a mixture of narcotic drugs and a synthetic cannabinoid. In addition, 14 herbal mixtures and 36 different casework samples from prisons were analyzed provided by the State Office of Criminal Investigation Rhineland‐Palatinate (Germany).

Section: Introductionmentioning

confidence: 99%

Ion mobility spectrometry as a fast screening tool for synthetic cannabinoids to uncover drug trafficking in jail via herbal mixtures, paper, food, and cosmetics

Metternich

Zörntlein

Schönberger

et al. 2019

“…More than 230 synthetic cannabinoid receptor agonists (SCRAs) have been reported to the United Nations Office on Drugs and Crime (UNODC) as recreational drugs, representing the largest and most structurally diverse class of new psychoactive substances (NPS). The structural heterogeneity of SCRAs has increased since the first examples were identified in 2008, and novel chemotypes continue to emerge in an attempt to circumvent structure‐based prohibition . The earliest examples, such as 1‐alkyl‐3‐acylindole JWH‐018 ( 1 , Figure ), were repurposed from tool molecules described by John W. Huffman at Clemson University for studying cannabinoid receptors .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and pharmacology of new psychoactive substance 5F‐CUMYL‐P7AICA, a scaffold‐ hopping analog of synthetic cannabinoid receptor agonists 5F‐CUMYL‐PICA and 5F‐CUMYL‐PINACA

Banister

Adams

Kevin

et al. 2018

104

Synthetic cannabinoid receptor agonists (SCRAs) are a dynamic class of new psychoactive substances (NPS), with novel chemotypes emerging each year. Following the putative detection of 5F-CUMYL-P7AICA in Australia in 2016, the scaffold-hopping SCRAs 5F-CUMYL-PICA, 5F-CUMYL-PINACA, and 5F-CUMYL-P7AICA were synthesized and characterized by nuclear magnetic resonance (NMR) spectroscopy, gas chromatography-mass spectrometry (GC-MS), and liquid chromatography-quadrupole time-of-flight-MS (LC-QTOF-MS). Since little is known of the pharmacology of 7-azaindole SCRAs like 5F-CUMYL-P7AICA, the binding affinities and functional activities of all compounds at cannabinoid type 1 and type 2 receptors (CB and CB , respectively) were assessed using tritiated radioligand competition experiments and fluorescence-based plate reader membrane potential assays. Despite CB binding affinities differing by over two orders of magnitude (K = 2.95-174 nM), all compounds were potent and efficacious CB agonists (EC = 0.43-4.7 nM), with consistent rank order for binding and functional activity (5F-CUMYL-PINACA >5F-CUMYL-PICA >5F-CUMYL-P7AICA). Additionally, 5F-CUMYL-P7AICA was found to exert potent cannabimimetic effects in mice, inducing hypothermia (6°C, 3 mg/kg) through a CB -dependent mechanism.

“…[5][6][7] The earliest SC product, "Spice," was a herbal blend laced with psychoactive SCs CP 47,497-C8 (1, Figure 1) and JWH-018 (2). [9][10][11][12] Of particular concern are the seemingly greater toxicities and dependence liabilities of newer SCs. [9][10][11][12] Of particular concern are the seemingly greater toxicities and dependence liabilities of newer SCs.…”

Section: Introductionmentioning

confidence: 99%

The chemistry and pharmacology of synthetic cannabinoid SDB‐006 and its regioisomeric fluorinated and methoxylated analogs

Banister

Olson

Winchester

et al. 2018

Synthetic cannabinoids are the largest and most structurally diverse class of new psychoactive substances, with manufacturers often using isomerism to evade detection and circumvent legal restriction. The regioisomeric methoxy- and fluorine-substituted analogs of SDB-006 (N-benzyl-1-pentyl-1H-indole-3-carboxamide) were synthesized and could not be differentiated by gas chromatography-mass spectrometry (GC-MS), but were distinguishable by liquid chromatography-quadrupole time-of-flight-MS (LC-QTOF-MS). In a fluorescence-based plate reader membrane potential assay, SDB-006 acted as a potent agonist at human cannabinoid receptors (CB EC = 19 nM). All methoxy- and fluorine-substituted analogs showed reduced potency compared to SDB-006, although the 2-fluorinated analog (EC = 166 nM) was comparable to known synthetic cannabinoid RCS-4 (EC = 146 nM). Using biotelemetry in rats, SDB-006 and RCS-4 evoked comparable reduction in body temperature (~0.7°C at a dose of 10 mg/kg), suggesting lower potency than the recent synthetic cannabinoid AB-CHMINACA (>2°C, 3 mg/kg).