Positional isomer differentiation of synthetic cannabinoid JWH-081 by GC-MS/MS

Journal of Mass Spectrometry

Volumn 50, Issue 3, 2015, Pages 586-591

  Kusano, Maiko ^a   Zaitsu, Kei ^a   Nakayama, Hiroshi ^a   Nakajima, Junichi ^b   Hisatsune, Kazuaki ^c   Moriyasu, Takako ^b   Matsuta, Shuntaro ^d   Katagi, Munehiro ^d   Tsuchihashi, Hitoshi ^a,e   Ishii, Akira ^a  

^a NAGOYA UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

^b TOKYO METROPOLITAN INSTITUTE OF PUBLIC HEALTH   (Japan)

^c Forensic Science Laboratory   (Japan)

^d Chuo ward   (Japan)

^e OSAKA MEDICAL COLLEGE   (Japan)

Author keywords

GC MS MS; JWH 081; positional isomers; synthetic cannabinoids

Indexed keywords

DRUG PRODUCTS; GAS CHROMATOGRAPHY; IONIZATION OF GASES; IONS; MASS SPECTROMETRY; MEDICINE; PLANTS (BOTANY); SPECTROMETRY; TOXICITY;

ELECTRON IONIZATION MASS SPECTROMETRY; GC-MS/MS; ISOMER DIFFERENTIATIONS; JWH-081; POSITIONAL ISOMERS; SYNTHETIC CANNABINOID; SYNTHETIC CANNABINOIDS; TANDEM MASS SPECTROMETRY;

ISOMERS;

(4 METHOXYNAPHTHALEN 1 YL)(1 PENTYL 1H INDOL 3 YL)METHANONE; CANNABINOID DERIVATIVE; UNCLASSIFIED DRUG; (4-METHOXY-1-NAPHTHALENYL)(1-PENTYL-1H-INDOL-3-YL)METHANONE; DESIGNER DRUG; INDOLE DERIVATIVE; NAPHTHALENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; ISOMER; MASS FRAGMENTOGRAPHY; PRIORITY JOURNAL; REPRODUCIBILITY; STATISTICAL SIGNIFICANCE; STEREOISOMERISM; CHEMISTRY; ISOLATION AND PURIFICATION; ISOMERISM; PROCEDURES; TANDEM MASS SPECTROMETRY;

DESIGNER DRUGS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; INDOLES; ISOMERISM; NAPHTHALENES; TANDEM MASS SPECTROMETRY;

EID: 84925437972     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.3565     Document Type: Article

References (27)

1. V. Shevyrin, V. Melkozerov, A. Nevero, O. Eltsov, A. Baranovsky, Y. Shafran,. Synthetic cannabinoids as designer drugs: New representatives of indol-3-carboxylates series and indazole-3-carboxylates as novel group of cannabinoids. Identification and analytical data. Forensic Sci. Int. 2014, 244, 263.
2. C. L. German, A. E. Fleckenstein, G. R. Hanson,. Bath salts and synthetic cathinones: An emerging designer drug phenomenon. Life Sci. 2014, 97, 2.
3. A. H. Lewin, H. H. Seltzman, F. I. Carroll, S. W. Mascarella, P. A. Reddy,. Emergence and properties of spice and bath salts: A medicinal chemistry perspective. Life Sci. 2014, 97, 9.
4. K. A. Seely, A. L. Patton, C. L. Moran, M. L. Womack, P. L. Prather, W. E. Fantegrossi, A. Radominska-Pandya, G. W. Endres, K. B. Channell, N. H. Smith, K. R. McCain, L. P. James, J. H. Moran,. Forensic investigation of K2, Spice, and "bath salt" commercial preparations: A three-year study of new designer drug products containing synthetic cannabinoid, stimulant, and hallucinogenic compounds. Forensic Sci. Int. 2013, 233, 416.
5. R. Lindigkeit, A. Boehme, I. Eiserloh, M. Luebbecke, M. Wiggermann, L. Ernst, T. Beuerle,. Spice: A never ending story?. Forensic Sci. Int. 2009, 191, 58.
6. V. Auwärter, S. Dresen, W. Weinmann, M. Müller, M. Pütz, N. Ferreirõs,. 'Spice' and other herbal blends: harmless incense or cannabinoid designer drugs?. J. Mass Spectrom. 2009, 44, 832.
7. U. S. D. o. J. D. E. Administration. Schedules of Controlled Substances: Placement of Five Synthetic Cannabinoids Into Schedule I. Fed. Regist. 2012, 77, 7.
8. U. N. O. o. D. a. Crime, UNODC, Synthetic Cannabinoids in Herbal Products 2011.
9. R. Kikura-Hanajiri, N. U. M. Kawamura, Y. Goda,. Changes in the prevalence of new psychoactive substances before and after the introduction of the generic scheduling of synthetic cannabinoids in Japan. Drug Test. Anal. 2014, 6, 832.
10. A. C. o. t. M. o. Drugs, in ACMD drug-specific reports, Consideration of the major cannabinoid agonists, London, 2009.
11. K. Zaitsu, M. Katagi, H. Kamata, T. Kamata, N. Shima, A. Miki, T. Iwamura, H. Tsuchihashi,. Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS). J. Mass Spectrom. 2008, 43, 528.
12. K. Zaitsu, M. Katagi, H. Kamata, A. Miki, H. Tsuchihashi,. Discrimination and identification of regioisomeric β-keto analogues of 3,4-methylenedioxyamphetamines by gas chromatography-mass spectrometry. Forensic Toxicol. 2008, 26, 45.
13. L. Aalberg, J. DeRuiter, F. T. Noggle, E. Sippola, C. R. Clark,. Chromatographic and Spectroscopic Methods of Identification for the Side-Chain Regioisomers of 3,4-Methylenedioxyphenethylamines Related to MDEA, MDMMA, and MBDB. J. Chromatogr. Sci. 2003, 41, 227.
14. C. R. Clark, J. DeRuiter,. Chromatographic and Mass Spectrometry Methods for the Differentiation of N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine from Regioisomeric Derivatives. J. Chromatogr. Sci. 1996, 34, 230.
15. K. Zaitsu, M. Katagi, T. Kamata, H. Kamata, N. Shima, H. Tsuchihashi, T. Hayashi, H. Kuroki, R. Matoba,. Determination of a newly encountered designer drug "p-methoxyethylamphetamine" and its metabolites in human urine and blood. Forensic Sci. Int. 2008, 177, 77.
16. M. Mazzarino, X. d. l. Torre, F. Botrè,. A liquid chromatography-mass spectrometry method based on class characteristic fragmentation pathways to detect the class of indole-derivative synthetic cannabinoids in biological samples. Anal. Chim. Acta 2014, 837, 70.
17. R. Kikura-Hanajiri, M. Kawamura, N. Uchiyama, J. Ogata, H. Kamakura, K. Saisho, Y. Goda,. Analytical Data of Designated Substances (Shitei-Yakubutsu) Controlled by the Pharmaceutical Affairs Law in Japan, Part I: GC-MS and LC-MS. Yakugaku Zasshi 2008, 128, 971.
18. N. Uchiyama, M. Kawamura, R. Kikura-Hanajiri, Y. Goda,. 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. Forensic Toxicol. 2011, 29, 25.
19. N. Uchiyama, R. Kikura-Hanajiri, J. Ogata, Y. Goda,. Chemical analysis of synthetic cannabinoids as designer drugs in herbal products. Forensic Sci. Int. 2010, 198, 31.
20. B. Moosmann, S. Kneisel, U. Girreser, V. Brecht, F. Westphal, V. Auwärter,. Separation and structural characterization of the synthetic cannabinoids JWH-412 and 1-[(5-fluoropentyl)-1H-indol-3yl]-(4-methylnaphthalen-1-yl)methanone using GC-MS, NMR analysis and a flash chromatography system. Forensic Sci. Int. 2012, 220, e17.
21. D. N. Harris, S. Hokanson, V. Miller, G. P. Jackson,. Fragmentation differences in the EI spectra of three synthetic cannabinoid positional isomers: JWH-250, JWH-302, and JWH-201. Int. J. Mass Spectrom. 2014, 368, 23.
22. F. Westphal, P. Rösner, T. Junge,. Differentiation of regioisomeric ring-substituted fluorophenethylamines with product ion spectrometry. Forensic Sci. Int. 2010, 194, 53.
23. S. Borth, W. Hänsel, P. Rösner, T. Junge,. Regioisomeric differentiation of 2,3- and 3,4-methylenedioxy ring-substituted phenylalkylamines by gas chromatography/tandem mass spectrometry. J. Mass Spectrom. 2000, 35, 705.
24. S. Borth, W. Hänsel, P. Rösner, T. Junge,. Synthesis of 2,3- and 3,4-methylenedioxyphenylalkylamines and their regioisomeric differentiation by mass spectral analysis using GC-MS-MS. Forensic Sci. Int. 2000, 114, 139.
25. K. Zaitsu, H. Miyagawa, Y. Sakamoto, S. Matsuta, K. Tsuboi, H. Nishioka, M. Katagi, T. Sato, M. Tatsuno, H. Tsuchihashi, K. Suzuki, A. Ishii,. Mass spectrometric differentiation of the isomers of mono-methoxyethylamphetamines and mono-methoxydimethylamphetamines by GC-EI-MS-MS. Forensic Toxicol. 2013, 31, 292.
26. M. Karni, A. Mandelbaum,. The 'Even-Electron Rule'. Org. Mass Spectrom. 1980, 15, 53.
27. S. Hammerum,. Distonic radical cations in gaseous and condensed phase. Mass Spectrom. Rev. 1988, 7, 123.