Identification and analytical properties of new synthetic cannabimimetics bearing 2,2,3,3-tetramethylcyclopropanecarbonyl moiety / Shevyrin V., Melkozerov V., Nevero A., Eltsov O., Morzherin Y., Shafran Y. // Forensic Science International. - 2013. - V. 226, l. 1-3. - P. 62-73.

ISSN:
03790738
Type:
Article
Abstract:
By means of gas chromatography with mass spectrometry detector (GC-MS), liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance spectroscopy (NMR), structure of a series from a novel class of synthetic cannabimimetics bearing 2,2,3,3-tetramethylcyclopropanecarbonyl moiety was established. It was found that this fragment could undergo thermal ring-opening into isomeric structures. The title compounds under action of hydrochloric acid can transform into new compounds which structure is discussed in the paper. The compounds identified could be referred to a new class of 'designer drugs' and are in illegal turnover in Russia and Belarus since the summer of 2011. Analytical data obtained in the paper will make possible reliable identification of such new 'designer drugs' during forensic examination. © 2012 Elsevier Ireland Ltd.
Author keywords:
(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone derivatives; A-836,339; Cannabimimetics; Designer drugs; GC-MS; LC-MS; NMR
Index keywords:
(2,2,3,3 tetramethylcyclopropyl)methanone derivative; cannabimimetic agent; designer drug; unclassified drug; article; chemical structure; forensic science; gas chromatography; isomer; liquid chromato
DOI:
10.1016/j.forsciint.2012.12.00
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Affiliations Ural Federal University, Institute of Chemistry and Technology, 19 Mira Str., 620002 Ekaterinburg, Russian Federation; Expert and Criminalistic Center, Main Agency of the Ministry of the Interior of the Russian Federation, Sverdlovsk Region Branch, 17 Lenina Avenue, 620014 Ekaterinburg, Russian Federation; State Expert and Criminalistic Center, Ministry of the Internal Affairs of Republic of Belarus, 2A Volodarskogo Str., 220030 Minsk, Belarus
Author Keywords (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone derivatives; A-836,339; Cannabimimetics; Designer drugs; GC-MS; LC-MS; NMR
References Auwarter, V., Dresen, S., Weinmann, W., Muller, M., Putz, M., Ferreiros, N., 'Spice' and other herbal blends: harmless incense or cannabinoid designer drugs? (2009) J. Mass Spectrom., 44, pp. 832-837; Lindigkeit, R., Boehme, A., Eiserloh, I., Luebbecke, M., Wiggermann, M., Ernst, L., Beuerle, T., Spice: a never ending story? (2009) Forensic Sci. Int., 191, pp. 58-63; Uchiyama, N., Kikura-Hanajiri, R., Kawahara, N., Goda, Y., Identification of a cannabimimetic indole as a designer drug in a herbal product (2009) Forensic Toxicol., 27, pp. 61-66; Uchiyama, N., Kawamura, M., Kikura-Hanajiri, R., Goda, Y., Identification and quantitation of two cannabimimetic phenylacetylindoles JWH-251 and JWH-250, and four cannabimimetic naphthoylindoles JWH-081, JWH-015, JWH-200, and JWH-073 as designer drugs in illegal products (2011) Forensic Toxicol., 29, pp. 25-37; Uchiyama, N., Kikura-Hanajiri, R., Kawahara, N., Haishima, Y., Goda, Y., Identification of a cannabinoid analog as a new type of designer drug in a herbal product (2009) Chem. Pharm. Bull., 57, pp. 439-441; Nakajima, J., Takahashi, M., Seto, T., Kanai, C., Suzuki, J., Yoshida, M., Hamano, T., Identification and quantitation of two benzoylindoles AM-694 and (4-methoxyphenyl)(1-pentyl-1H-indol-3-yl)methanone, and three cannabimimetic naphthoylindoles JWH-210, JWH-122, and JWH-019 as adulterants in illegal products obtained via the Internet (2011) Forensic Toxicol., 29, pp. 95-110; Kneisel, S., Westphal, F., Rosner, P., Brecht, V., Ewald, A., Klein, B., Putz, M., Auwarter, V., Cannabimimetics: mass spectra and IR-ATR spectra of new compounds from the years 2009 and 2010 (2011) TIAFT Bull., 41 (1), pp. 38-48; Kneisel, S., Westphal, F., Moosmann, B., Brecht, V., Bisel, P., Vidal, C., Jacobsen-Bauer, A., Auwarter, V., Cannabimimetics II: mass spectra and ATR-IR spectra of new compounds between the end of 2010 and late 2011 (2011) TIAFT Bull., 41 (3), pp. 29-38; Jankovics, P., Varadi, A., Tolgyesi, L., Lohner, S., Nemeth-Palotas, J., Balla, J., Detection and identification of the new potential synthetic cannabinoids 1-pentyl-3-(2-iodobenzoyl)indole and 1-pentyl-3-(1-adamantoyl)indole in seized bulk powders in Hungary (2012) Forensic Sci. Int., 214, pp. 27-32; Shevyrin, V.A., Melkozerov, V.P., Nevero, A.S., Toricin, A.V., Chevtchouk, T.A., Chemical structure and identification of new synthetic drugs the components of herbal smoking mixtures (2012) Sudeb. Expert., 1, pp. 107-120. , (in Russian); Kneisel, S., Bisel, P., Brecht, V., Broecker, S., Muller, M., Auwarter, V., Identification of the cannabimimetic AM-1220 and its azepane isomer (N-methylazepan-3-yl)-3-(1-naphthoyl)indole in a research chemical and several herbal mixtures (2012) Forensic Toxicol., 30, pp. 126-134; Uchiyama, N., Kikura-Hanajiri, R., Ogata, J., Goda, Y., Chemical analysis of synthetic cannabinoids as designer drugs in herbal products (2010) Forensic Sci. Int., 198, pp. 31-38; Nakajima, J., Takahashi, M., Seto, T., Suzuki, J., Identification and quantitation of cannabimimetic compound JWH-250 as an adulterant in products obtained via the Internet (2011) Forensic Toxicol., 29, pp. 51-55; Dresen, S., Ferreiros, N., Putz, M., Westphal, F., Zimmermann, R., Auwarter, V., Monitoring of herbal mixtures potentially containing synthetic cannabinoids as psychoactive compounds (2010) J. Mass Spectrom., 45, pp. 1186-1194; Nakajima, J., Takahashi, M., Nonaka, R., Seto, T., Suzuki, J., Yoshida, M., Kanai, C., Hamano, T., Identification and quantitation of a benzoylindole (2-methoxyphenyl)(1-pentyl-1H-indol-3-yl)methanone and a naphthoylindole 1-(5-fluoropentyl-1H-indol-3-yl)-(naphthalene-1-yl)methanone (AM-2201) found in illegal products obtained via the Internet and their cannabimimetic effects evaluated by in vitro [35S]GTPγS binding assays (2011) Forensic Toxicol., 29, pp. 132-141; Ernst, L., Schiebel, H.-M., Theuring, C., Lindigkeit, R., Beuerle, T., Identification and characterization of JWH-122 used as new ingredient in "Spice-like" herbal incenses (2011) Forensic Sci. Int., 208, pp. e31-e35; Westphal, F., Sönnichsen, F.D., Thiemt, S., Identification of 1-butyl-3-(1-(4-methyl)naphthoyl)indole in a herbal mixture (2012) Forensic Sci. Int., 215, pp. 8-13; Hudson, S., Ramsey, J., The emergence and analysis of synthetic cannabinoids (2011) Drug Test. Anal., 3, pp. 466-478; Shevyrin, V.A., 1-Pentyl-3-(4-methoxybenzoyl)indole - new synthetic component as a part of herbal smoking mixes (2010) Sudeb. Expertiza, 3, pp. 49-55. , (in Russian); Frost, J.M., Dart, M.J., Tietje, K.R., Garrison, T.R., Grayson, G.K., Daza, A.V., El-Kouhen, O.F., Meyer, M.D., Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB2 cannabinoid receptor activity (2010) J. Med. Chem., 53, pp. 295-315; Pace, J.M., Tietje, K., Dart, M.J., Meyer, M.D., (2006), 3-Cycloalcylcarbonyl indoles as cannabinoid receptor ligands, WO Patent 069196 A1; Frost, J.M., Tietje, K., Dart, M.J., Meyer, M.D., (2010), Indoles a cannabinoid receptor ligands, US Patent 7750039 B2; Frost, J.M., Tietje, K., Dart, M.J., Meyer, M.D., (2011), Novel indoles are cannabinoid receptor ligands, US Patent 0065685 A1; Ochiai, M., Sumi, K., Fujita, E., Silicon-assisted ring opening of cyclopropyl ketones with boron trifluoride-acetic acid complex (1983) Chem. Pharm. Bull., 31 (11), pp. 3931-3938; Stoliarov, B.V., Savinov, I.M., Vittenberg, A.G., Kartsova, L.A., Zenkevich, I.G., Kalmanovsky, V.I., Kalambet, Y., (2002) Practical Gas and Liquid Chromatography, pp. 249-252. , St. Petersburg University, St. Petersburg (in Russian); Byers, J.H., Zhang, Y., Syntheses of 3-acylindoles via the alkylation of the dianion of 3-acetylindole (2002) Heterocycles, 57 (7), pp. 1293-1297; Guchait, S.K., Kashyap, M., Kamble, H., ZrCl4-mediated regio- and chemoselective Friedel-Crafts acylation of indole (2011) J. Org. Chem., 76 (11), pp. 4753-4758
Correspondence Address Shafran, Y.; Ural Federal University, Institute of Chemistry and Technology, 19 Mira Str., 620002 Ekaterinburg, Russian Federation; email: yu.m.shafran@ustu.ru
CODEN FSIND
Language of Original Document English
Abbreviated Source Title Forensic Sci. Int.
Source Scopus