Characterization of in vitro metabolites of JWH-018, JWH-073 and their 4-methyl derivatives, markers of the abuse of these synthetic cannabinoids

Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences

Volumn 957, Issue , 2014, Pages 68-76

  Gambaro, Veniero ^a   Arnoldi, Sebastiano ^a   Bellucci, Stefania ^a   Casagni, Eleonora ^a   Dell'Acqua, Lucia ^a   Fumagalli, Laura ^a   Pallavicini, Marco ^a   Roda, Gabriella ^a   Rusconi, Chiara ^a   Valoti, Ermanno ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

Alkylindole metabolites; GC FID; GC MS; JWH 018; JWH 073; JWH 122 ; 1 Butyl 3 (1 (4 methyl)naphthoyl)indole

Indexed keywords

BIOMOLECULES; BODY FLUIDS; EXTRACTION; NAPHTHALENE; POLYCYCLIC AROMATIC HYDROCARBONS;

ALKYLINDOLE; GC/FID; GC/MS; JWH-018; JWH-073; JWH-122 1-BUTYL-3-(1-(4-METHYL)NAPHTHOYL)INDOLE;

METABOLITES;

1 BUTYL 3 (1 NAPHTHOYL)INDOLE; 1 PENTYL 3 (4 METHYL 1 NAPHTHOYL)INDOLE; 3 (1 NAPHTHOYL) 1 PENTYLINDOLE; CANNABINOID; INDOLE; METHYL GROUP; NAPHTHALENE; UNCLASSIFIED DRUG;

ARTICLE; BODY FLUID; EXTRACTION; HUMAN; INCUBATION TIME; LIVER MICROSOME; MASS FRAGMENTOGRAPHY; METABOLITE; PLASMA; PRIORITY JOURNAL; RELIABILITY; SUBSTANCE ABUSE; URINALYSIS;

ALKYLINDOLE METABOLITES; GC/FID; GC/MS; JWH-018; JWH-073; JWH-122 ;1-BUTYL-3-(1-(4-METHYL)NAPHTHOYL)INDOLE;

CANNABINOIDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; INDOLES; MICROSOMES, LIVER; NAPHTHALENES; REPRODUCIBILITY OF RESULTS; STREET DRUGS;

EID: 84896496338     PISSN: 15700232     EISSN: 1873376X     Source Type: Journal    
DOI: 10.1016/j.jchromb.2014.03.001     Document Type: Article

References (34)

1. Valoti E., Casagni E., Dell'Acqua L., Pallavicini M., Roda G., Rusconi C., Straniero V., Gambaro V. Forensic Sci. Int. 2012, 223(1-3):e42-e46.
2. Pacher P., Batkai S., Kunos G. Pharmacol. Rev. 2006, 58:389-462.
3. Lindigkeit R., Boehme A., Einserloh I., Luebbecke M., Wiggermann M., Ernst L., Beuerle T. Forensic Sci. Int. 2009, 191:58-63.
4. EMCDDA EMCDDA 2009 Thematic paper: Understanding the "Spice" phenomenon, Office for Official Publications of the European Communities 2009, EMCDDA, 〈http://www.emcdda.europa.eu/publications/thematic-papers/spice〉 (accessed January 2010).
5. Auwärter V., Dresen S., Weinmann W., Muller M., Putz M., Ferreiros N. J. Mass Spectrom. 2009, 44:832-837.
6. Uchiyama N., Kikura-Hanajiri R., Kawahara N., Goda Y. Forensic Toxicol. 2009, 27:61-66.
7. Uchiyama N., Kikura-Hanajiri R., Kawahara N., Haishima Y., Goda Y. Chem. Pharm. Bull. 2009, 57:439-441.
8. Mustata C., Torrens M., Pardo R., Perez C. Addition 2009, 21:181-186.
9. Vardakou I., Pistos C., Spiliopoulou C. Toxicol. Lett. 2010, 197:157-162.
10. Emanuel C.E.J., Ellison B., Banks C.E. Anal. Meth. 2010, 2:614-616.
11. Uchiyama N., Kikura-Hanajiri R., Ogata J., Goda Y. Forensic Sci. Int. 2010, 198:31-38.
12. Zuba D., Byrska B., Maciow M. Anal. Bioanal. Chem. 2011, 400:119-126.
13. Chin C., Murphy J.W., Huffman J.W., Kendall D.A. J Pharmacol. Exp. Ther. 1999, 291:837-844.
14. Atwood B.K., Huffman J., Straiker A., Mackie K. Pharmacology 2010, 160:585-593.
15. Zimmermann U.S., Winkelmann P.R., Pilhatsch M., Nees J.A., Spanagel R. Deut. Äerzt. Int. 2009, 106:464-467.
16. Yanes E.G., Lovett D.P. J. Chromatogr. B 2012, 909:42-50.
17. Pallavicini M., Valoti E., Villa L., Lianza E. Tetrahedron: Asimmetry 1994, 5:111-116.
18. Pallavicini M., Valoti E., Villa L., Resta I. Tetrahedron: Asimmetry 1994, 5:363-370.
19. Fumagalli L., Pallavicini M., Budriesi R., Bolchi C., Canovi M., Chiarini A., Chiodini G., Gobbi M., Laurino P., Micucci M., Straniero V., Valoti E. J. Med. Chem. 2013, 56:6402-6412.
20. F A.M., Grigor'Ev S.A., Savchuk A.A., Mel'Nik M.B., Ershov Y.A., Dzhurko A.N., Vedenin A.E., Nosyrev B.N., Izotov V.V., Rozhanets J. Anal. Chem. 2012, 67:895-903.
21. Sobolevskii T.G., Prasolov I.S., Rodchenkov G.M. J. Anal. Chem. 2011, 66:1314-1323.
22. Brents L.K., Reichard E.E., Zimmerman S.M., Moran J.H., Fantegrossi W.E., Prather P.L. PloS One 2011, 6:1-9.
23. Brents L.K., Gallus-Zawada A., Radominska-Pandya A., Vasiljenk T., Prisinzano T.E., Fantegrossi W.E., Moran J.H., Prather P.L. Biochem. Pharmacol. 2012, 83:952-961.
24. Emerson B., Durham B., Gidden J., Lay J.O. Forensic Sci. Int. 2013, 229:1-6.
25. Grigoryev A., Savchuk S., Melnik A., Moskaleva N., Dzhurko J., Ershov M., Nosyrev A., Vedenin A., Izotov B., Zabirova I., Rozhanets V. J. Chromatogr. B 2011, 879:1126-1136.
26. Beuck S., Möller I., Thomas A., Klose A., Schlörer N., Schänzer W., Thevis M. Anal. Bioanal. Chem. 2011, 401:493-505.
27. Jang M., Yang W., Choi H., Chang H., Lee S., Kim E., Chung H. Forensic Sci. Int. 2013, 231:13-19.
28. Wohlfarth A., Scheidweiler K.B., Chen X., Liu H., Huestis M.A. Anal. Chem. 2013, 85:3730-3738.
29. Chimalakonda K.C., Moran C.L., Kennedy P.D., Endres G.W., Uzieblo A., Dobrowolski P.J., Fifer E.K., Lapoint J., Nelson L.S., Hoffman R.S., James L.P., Radominska-Pandya A., Moran J.H. Anal. Chem. 2011, 83:6381-6388.
30. Moran C.L., Le V.-H., Chimalakonda K.C., Smedley A.L., Lackey F.D., Owen S.N., Kennedy P.D., Endres G.W., Ciske F.L., Kramer J.B., Kornilov A.M., Bratton L.D., Dobrowolski P.J., Wessinger W.D., Fantegrossi W.E., Prather P.L., James L.P., Radominska-Pandya A., Moran J.H. Anal. Chem. 2011, 83:4228-4236.
31. De Brabanter N., Esposito S., Geldof L., Lootens L., Meuleman P., Leroux-Roels G., Deventer K., Van Eeno P. Forensic Toxicol. 2013, 31:212-222.
32. Mammalian Liver Microsomes, Guidelines for Use, BD;https://w.w.w.bdbiosciences.com/eu/documents/tissue_fraction_brochure_EUR.pdf.2010 BD Biosciences .
33. Laboratory and Scientific Section United Nations Office on Drugs and Crime Vienna Recommended methods for the Identification and analysis of synthetic cannabinoid receptor agonists in seized materials. Manual for use by National Drug Analysis Laboratories 2013, United Nations, New York, NY.
34. Hutter M., Broecker S., Kneisel S., Auwaerter V. J. Mass Spectrom. 2012, 47:54-65.