title: Identification and structural characterization of the synthetic cannabinoid 3-(1-adamantoyl)-1-pentylindole as an additive in 'herbal incense'.
abstract: 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.
authors.affiliation: Institute of Forensic Medicine, Department of Forensic Toxicology, University Medical Center Freiburg, Albertstr. 9, 79104 Freiburg, Germany.
authors.forename: Stefan
authors.initials: S
authors.lastname: Kneisel
authors.forename: Folker
authors.initials: F
authors.lastname: Westphal
authors.forename: Philippe
authors.initials: P
authors.lastname: Bisel
authors.forename: Volker
authors.initials: V
authors.lastname: Brecht
authors.forename: Sebastian
authors.initials: S
authors.lastname: Broecker
authors.forename: Volker
authors.initials: V
authors.lastname: Auwärter
mesh_terms: D002186:Cannabinoids / Q000737:chemistry*; D015198:Designer Drugs; D008401:Gas Chromatography-Mass Spectrometry; D007211:Indoles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009281:Naphthalenes / Q000737:chemistry*; D028321:Plant Preparations / Q000737:chemistry*; D053719:Tandem Mass Spectrometry
chemical_list: D002186:Cannabinoids; D015198:Designer Drugs; D007211:Indoles; D009281:Naphthalenes; D028321:Plant Preparations; C552597:1-pentyl-3-(1-naphthoyl)indole