Analytical characterization of some synthetic cannabinoids, derivatives of indole-3-carboxylic acid / Shevyrin V., Melkozerov V., Nevero A., Eltsov O., Shafran Y. // Forensic Science International. - 2013. - V. 37, l. . - P. 1-10.

ISSN:
03790738
Type:
Article
Abstract:
By means of gas chromatography with high resolution mass spectrometry (GC-HRMS), ultra-high performance liquid chromatography in combination with high resolution tandem mass spectrometry (UHPLC-HRMS), nuclear magnetic resonance spectroscopy (NMR) and Fourier transform infrared spectroscopy (FT-IR), structure of a series from a novel synthetic cannabinoids, derivatives of indole-3-carboxylic acid, was established. Methods for determination of the compounds in mixtures, involving chromatographic separation with mass-spectroscopic determination, were elaborated. Analytical data obtained in the paper will make reliable identification of synthetic cannabinoids of the new type during forensic examination possible. © 2013 Elsevier Ireland Ltd.
Author keywords:
Derivatives of indole-3-carboxylic acid; FT-IR; GC-HRMS; MS/MS; NMR; Synthetic cannabinoids; UHPLC-HRMS
Index keywords:
3 indolecarboxylic acid derivative; cannabinoid derivative; carboxylic acid derivative; unclassified drug; article; chemical analysis; chemical structure; forensic identification; gas chromatography;
DOI:
10.1016/j.forsciint.2013.06.01
Смотреть в Scopus:
https://www.scopus.com/inward/record.uri?eid=2-s2.0-84880657574&doi=10.1016%2fj.forsciint.2013.06.011&partnerID=40&md5=7bce4d613ad924e0a0d314997790b9ac
Соавторы в МНС:
Другие поля
Поле Значение
Link https://www.scopus.com/inward/record.uri?eid=2-s2.0-84880657574&doi=10.1016%2fj.forsciint.2013.06.011&partnerID=40&md5=7bce4d613ad924e0a0d314997790b9ac
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 Committee of Forensic Expertises of Republic of Belarus, 43 Kalvariyskaya Str., 220073 Minsk, Belarus; TOSLab. Ltd., Bldg. 1, 5 Initsiativnaia Str., 121357 Moscow, Russian Federation
Author Keywords Derivatives of indole-3-carboxylic acid; FT-IR; GC-HRMS; MS/MS; NMR; Synthetic cannabinoids; UHPLC-HRMS
References (2013) Synthetic Cannabinoids in Herbal Products, , www.unodc.org/documents/scientific/Synthetic_Cannabinoids.pdf, United Nation Office on Drugs and Crime (UNODC); Howlett, A.C., Barth, F., Bonner, T.I., Cabral, G., Casellas, P., Devane, W.A., Felder, C.C., Pertwee, R.G., International Union of Pharmacology. XXVII. Classification of cannabinoid receptors (2002) Pharmacol. Rev., 54 (2), pp. 161-202; 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; 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; 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; 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; Uchiyama, N., Kawamura, M., Kikura-Hanajiri, R., Goda, Y., Identification of two new-type synthetic cannabinoids, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide (APICA) and N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide (APINACA), and detection of five synthetic cannabinoids, AM-1220, AM-2233, AM-1241, CB-13 (CRA-13), and AM-1248, as designer drugs in illegal products (2012) Forensic Toxicol., 30, pp. 114-125; Shevyrin, V., Melkozerov, V., Morzherin, Y., Identification and analytical characteristics of two new-type synthetic cannabinoids of indazole (2012) Butlerov Commun., 30 (4), pp. 93-98. , (in Russian); Shevyrin, V., Melkozerov, V., Nevero, A., Eltsov, O., Morzherin, Y., Shafran, Y., Identification and analytical properties of new synthetic cannabimimetics bearing 2, 2,3,3-tetramethyl cyclopropanecarbonyl moiety (2013) Forensic Sci. Int., 226, pp. 62-73; 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; Bononi, M., Belgi, P., Tateo, F., Analytical data for identification of the cannabimimetic phenylacetylindole JWH-203 (2011) J. Anal. Toxicol., 35, pp. 360-363; Blaazer, A.R., Lange, J.H.M., van der Neut, M.A.W., Mulder, A., den Boon, F.S., Werkman, T.R., Kruse, C., Wadman, W.J., Novel indole and azaindole (pyrrolopyridine) cannabinoid (CB) receptor agonists: Design, synthesis, structure-activity relationships, physicochemical properties and biological activity, Eur (2011) J. Med. Chem., 46, pp. 5086-5098; Uchiyama, N., Matsuda, S., Kawamura, M., Kikura-Hanajiri, R., Goda, Y., Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products (2013) Forensic Toxicol., 31, pp. 223-240. , http://link.springer.com/article/10.1007%2Fs11419-013-0182-9; Stoliarov, B.V., Savinov, I.M., Vitenberg, 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); Pretsch, E., Bühlmann, P., Affolter, C., (2004) Structure Determination of Organic Compounds: Tables of Spectral Data, , Springer, Berlin
Correspondence Address Shevyrin, V.; Ural Federal University, Institute of Chemistry and Technology, 19 Mira Street, 620002 Ekaterinburg, Russian Federation; email: vadim.shevyrin@gmail.com
CODEN FSIND
Language of Original Document English
Abbreviated Source Title Forensic Sci. Int.
Source Scopus