[en] Since 2008, herbal mixtures with synthetic cannabinoid compounds have been sold as incense throughout the world. Although these new drugs are labeled as not for human consumption, these products are smoked for their cannabis-like effects. This study reports the structural and spectral elucidation of four cannabimimetic compounds seized in Belgium: (4-methoxyphenyl)-1-(pentyl-1H-indol-3-yl)methanone (RCS-4), 1-(5-fluoropentyl)-3-(1-naphtoyl)indole (AM-2201), 2-(2-chlorophenyl)-1-(1-pentylindol-3-yl)ethanone (JWH-203) and 4-ethylnaphthalen-1-yl-(1-pentylindol-3-yl)methanone (JWH-210). Laboratory investigations were conducted by liquid chromatography (LC)–ultraviolet spectroscopy, high-resolution accurate mass detection and nuclear magnetic resonance (NMR) analysis. This combined analytical approach allowed the detection of illicit compounds for which reference materials were not available. To facilitate identification and to complete existing databases, ultraviolet spectra and NMR data of all seized products are presented. Additionally, LC–quadrupole time-of-flight data were recorded to provide absolute identification.
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Denooz, Raphaël ; Université de Liège - ULiège > Département de pharmacie > Département de pharmacie
VAN HEUGEN, Jean-Claude ; Centre Hospitalier Universitaire de Liège - CHU > Diabétologie,nutrition, maladies métaboliques
Frederich, Michel ; Université de Liège - ULiège > Département de pharmacie > Pharmacognosie
De Tullio, Pascal ✱; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
Charlier, Corinne ✱; Université de Liège - ULiège > Département de pharmacie > Chimie toxicologique
✱ These authors have contributed equally to this work.
Language :
English
Title :
Identification and structure elucidation of four cannabimimetic compounds in seized products
Publication date :
March 2013
Journal title :
Journal of Analytical Toxicology
ISSN :
0146-4760
eISSN :
1945-2403
Publisher :
Preston Publications Inc, Niles, United States - Illinois
Theunis, L., De Backer, B., Charlier, C. (2010) Le cannabis: Historique, culture et modes d'utilisation. In Seutin, V., Scuvé e-Moreau, J., Quertemont, E. (eds.), Regards croisé s sur le cannabis. Mardaga, Wavre, Belgique, pp. 15-36.
De Backer, B., Debrus, B., Lebrun, P., Theunis, L., Dubois, N., Decock, L. et al. (2009) Innovative development and validation of an HPLC/DAD method for the qualitative and quantitative determination of major cannabinoids in cannabis plant material. Journal of Chromatography B, 877, 4115-4124.
Shire, D., Gouldson, P., Calandra, B., Portier, M., Bouaboula, M., Barth, F. et al. (2002) Cannabinoid receptors' interactions with synthetic cannabinoids agonists and antagonists. In Onaivi, E.S. (ed.), Biology of marijuana. Taylor and Francis, London.
Westphal, F., Sönnichsen, F D., Thiemt, S. (2012) Identification of 1-butyl-3-(1-(4-methyl)naphthoyl)indole in a herbal mixture. Forensic Science International, 215, 8-13.
Nakajima, J., Takahashi, M., Seto, T., Suzuki, J. (2010) Identifiation and quantification of cannabimimetic compound JWH-250 as an adulterant in products obtained via Internet. Forensic Toxicology, 29, 51-55.
Every-Palmer, S. (2011) Synthetic cannabinoid JWH-018 and psychosis: An exporative study. Drug and Alcohol Dependence, 117, 152-157.
Hudson, S., Ramsey, J. (2011) The emergence and analysis of synthetic cannabinoids. Drug Testing and Analysis, 3, 466-478.
Mechoulam, R., Feigenbaum, J.J., Lander, N. (1988) Enantiomeric cannabinoids: Stereospecificity of psychotropic activity. Experientia, 44, 762-763.
Davis, M., Maida, V., Daeninck, P., Pergolizzi, J. (2007) The emerging role of cannabinoid neuromodulators in symptom management. Support Care Cancer, 15, 63-71.
Weissman, A., Milne, G.M., Melvin, L.S. (1982) Cannabimimetic activity from CP-47,497, a derivative of 3-phenylcyclohexanol. The Journal of Pharmacology and Experimental Therapeutics, 223, 516-523.
Huffman, J.W., Dai, D., Martin, B.R., Compton, D.R. (1994) Design, synthesis and pharmacology of cannabimimetic indoles. Bioorganic and Medicinal Chemistry Letters, 4, 563-566.
Vardakou, I., Pistos, C., Spiliopoulou, C. (2010) Spice drugs as new trend: Mode of action, identification and legislation. Toxicology Letters, 197, 157-162.
