Acute toxicity due to the confirmed consumption of synthetic cannabinoids: clinical and laboratory findings.

AIMS: Recently, several synthetic cannabinoids were identified in herbal mixtures consumed as recreational drugs alternative to cannabis products. The aim was to characterize the acute toxicity of synthetic cannabinoids as experienced by emergency patients. DESIGN: This was a retrospective study targeting patients seeking emergency treatment after recreational use of synthetic cannabinoids. SETTING AND PARTICIPANTS: Patients were selected from the database of the Poisons Information Center Freiburg between September 2008 and February 2011. The inclusion criteria were: hospitalization, available clinical reports and analytical verification of synthetic cannabinoid uptake. In total, 29 patients were included (age 14-30 years, median 19; 25 males, four females). MEASUREMENTS: Clinical reports were evaluated and synthetic cannabinoids and other drugs were determined analytically. FINDINGS: CP-47,497-C8 (one), JWH-015 (one), JWH-018 (eight), JWH-073 (one), JWH-081 (seven), JWH-122 (11), JWH-210 (11), JWH-250 (four) and AM 694 (one) were quantified in blood samples. JWH-018 was most common in 2008-9, JWH-122 in 2010, and JWH-210 in 2011. Tachycardia, agitation, hallucination, hypertension, minor elevation of blood glucose, hypokalaemia and vomiting were reported most frequently. Chest pain, seizures, myoclonia and acute psychosis were also noted. CONCLUSIONS: There appears to have been an increase in use of the extremely potent synthetic cannabinoids JWH-122 and JWH-210. Acute toxic symptoms associated with their use are also reported after intake of high doses of cannabis, but agitation, seizures, hypertension, emesis and hypokalaemia seem to be characteristic to the synthetic cannabinoids, which are high-affinity and high-efficacy agonists of the CB(1) receptor. Thus, these effects are due probably to a strong CB(1) receptor stimulation.

A fast and inexpensive procedure for the isolation of synthetic cannabinoids from 'Spice' products using a flash chromatography system.

In the age of the Internet, the variety of drugs offered online is constantly increasing, and new drugs emerge every month. One group of drugs showing such an enormous increase is that of synthetic cannabinoids. Since their first identification in 'herbal mixtures', new structural modifications continue to appear on the market. In order to keep up with this process, toxicological screening methods need to be up to date. This can become extremely difficult if no reference material is available. In this article, a fast and effective way to extract and purify synthetic cannabinoids from 'herbal mixtures' is presented. This method opens a new opportunity for a timely reaction by obtaining reference material straight out of the 'herbal mixtures' ordered via the Internet. Isolation was carried out on a flash chromatography system with gradient elution on a C18 column using methanol and 0.55 % formic acid as mobile phases. The obtained purity of all compounds exceeded 99 %. In addition to the isolation of single compounds, the method proved to be suitable for the separation of various synthetic cannabinoids in one mixture, including the diastereomers cis- and trans-CP-47,497-C8. This approach for obtaining pure standards of new drugs proved to be effective, inexpensive and much quicker than waiting for the substances to be commercially available as reference material.

Identification and structural characterization of the synthetic cannabinoid 3-(1-adamantoyl)-1-pentylindole as an additive in 'herbal incense'.

Since the end of 2010, more than 20 synthetic cannabimimetics have been identified in 'Spice' products, demonstrating the enormous dynamic in this field. In an effort to cope with the problem, many countries have already undertaken legal measures by putting some of these compounds under control. Nevertheless, once a number of compounds were scheduled, they were soon replaced by other synthetic cannabinoids. In this article, we report the identification of a new--and due to its substitution pattern rather uncommon--cannabimimetic found in several 'herbal incense' products. The GC-EI mass spectrum first led to misidentification as the alpha-methyl-derivative of JWH-250. However, since both substances show different retention indices, thin-layer chromatography was used to isolate the unknown compound. After application of nuclear magnetic resonance spectroscopy, high-resolution MS and GC-MS/MS techniques, the compound was identified as 3-(1-adamantoyl)-1-pentylindole, a derivative of JWH-018 carrying an adamantoyl moiety instead of a naphthoyl group. This finding supports that the listing of synthetic cannabinoids as prohibited substances triggers the appearance of compounds with uncommon substituents. Moreover, it emphasizes the necessity of being aware of the risk of misidentification when using techniques sometimes providing only limited structural information like GC-MS.