Gas and liquid chromatography-mass spectrometry detection of the urinary metabolites of ur-144 and its major pyrolysis product

Journal of Analytical Toxicology

Volumn 37, Issue 5, 2013, Pages 265-276

  Grigoryev, Andrej ^a   Kavanagh, Pierce ^b   Melnik, Alexandra ^a   Savchuk, Sergey ^c   Simonov, Anton ^d  

^a Bureau of Forensic Medical Expertise   (Russian Federation)

^b TRINITY COLLEGE DUBLIN   (Ireland)

^c National Research Center on Addictions   (Russian Federation)

^d Chemical Toxicology Laboratory   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

CANNABINOID RECEPTOR AGONIST; DRUG METABOLITE; UNCLASSIFIED DRUG; UR 144;

ARTICLE; DRUG URINE LEVEL; HUMAN; HYDROXYLATION; ISOMERIZATION; LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY MASS SPECTROMETRY; MASS FRAGMENTOGRAPHY; MASS SPECTROMETRY; PYROLYSIS; URINALYSIS;

CANNABINOIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CONTROLLED SUBSTANCES; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HOT TEMPERATURE; HUMANS; SMOKING; SUBSTANCE ABUSE DETECTION; TANDEM MASS SPECTROMETRY;

EID: 84882966506     PISSN: 01464760     EISSN: 19452403     Source Type: Journal    
DOI: 10.1093/jat/bkt028     Document Type: Article

References (45)

1. United Nations Office on Drugs and Crime (UNODC). Synthetic cannabinoids in herbal products. http://www.unodc.org/documents/ scientific/Synthetic_Cannabinoids.pdf (10 July 2011, date last accessed).
2. European Monitoring Centre for Drug and Drug Addiction. EMCCDA-Europol 2011 Annual Report on the implementation of Council Decision 2005/387/JHA. http://www.emcdda.europa.eu/ attachements.cfm/att_155113_EN_EMCDDA-Europol%20Annual% 20Report%202011_2012_final.pdf (25 April 2012, date last accessed).
3. Frost, J.M., Dart, M.J., Tietje, K.R., Garrison, T.R., Grayson, G.K., Daza, A.V. et al. (2010) Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity. Journal of Medicinal Chemistry, 53, 295-315.
4. Hammond, B. United Nation Office on Drugs and Crime (UNODC). New and emerging psychoactive substances - the global perspective. http://www.unodc.org/documents/eastasiaandpacific//2012/ 07/smart-workshop/06_New_and_emerging_psychoactive_substances_ The_global_perspective.pdf (15 September 2012, date last accessed).
5. Choi, H., Heo, S., Kim, E., Hwang, B.Y., Lee, C., Lee, J. (2012) Identification of (1-pentylindol-3-yl)-(2,2,3,3-tetramethylcyclo propyl)methanone and its 5-pentyl fluorinated analog in herbal incense seized for drug trafficking. Forensic Toxicology. DOI:10.1007/s11419-012-0170-5.
6. New Zealand Ministry of Health, Temporary Class Drug Notice. http:// www.dia.govt.nz/MSOS118/On-Line/NZGazette.nsf/6cee7698a9bbc7 cfcc256d510059ed0b/ba1ce64512c56083cc257ac5005db54e!Open Document (29 March 2012, date last accessed); Resolution of the Government of the Russian Federation. http://www.rg.ru/2012/03/06/ izmeneniya-dok.html (6 March 2012, date last accessed).
7. Teske, J., Weller, J.-P, Fieguth, A., Rothämel, T., Schulz, Y., Trö ger, H.D. (2010) Sensitive and rapid quantification of the cannabinoid receptor agonist naphthalen-1-yl-(1-pentylindol-3-yl)methanone (JWH-018) in human serum by liquid chromatography-tandem mass spectrometry. Journal of Chromatography B, 878, 2659-2993.
8. Ammann, J., McLaren, J.M., Gerostamoulos, D., Beyer, J. (2012) Detection and quantification of new designer drugs in human blood: Part 1 - synthetic cannabinoids. Journal of Analytical Toxicology, 36, 372-380.
9. Dresen, S., Kneisel, S., Weinmann, W., Zimmermann, R., Auwä rter, V. (2011) Development and validation of a liquid chromatography- tandem mass spectrometry method for the quantitation of synthetic cannabinoids of the aminoalkylindole type and methanandamide in serum and its application to forensic samples. Journal of Mass Spectrometry, 46, 163-171.
10. Kacinko, S.L., Xu, A., Homan, J.W., McMullin, M.M., Warrington, D.M., Logan, B.K. (2011) Development and validation of a liquid chromatography-tandem mass spectrometry method for the identification and quantification of JWH-018, JWH-073, JWH-019 and JWH-250 in human whole blood. Journal of Analytical Toxicology, 35, 386-393.
11. Kneisel, S., Auwä rter, V. (2012) Analysis of 30 synthetic cannabinoids in serum by liquid chromatography-electrospray ionization tandem mass spectrometry after liquid-liquid extraction. Journal of Mass Spectrometry, 47, 825-835.
12. Shanks, K.G., Dahn, T., Terrell, A.R. (2012) Detection of JWH-018 and JWH-073 by UPLC-MS-MS in postmortem whole blood casework. Journal of Analytical Toxicology, 36, 145-152.
13. Coulter, C., Garnier, M., Moore, C. (2011) Synthetic cannabinoids in oral fluid. Journal of Analytical Toxicology, 35, 424-430.
14. Kneisel, S., Auwä rter, V., Kempf, J. (2012) Analysis of 30 synthetic cannabinoids in oral fluid using liquid chromatography-electrospray ionization tandem mass spectrometry. Drug Testing and Analysis. DOI:10.1002/dta.1429.
15. Hutter, M., Kneisel, S., Auwä rter, V., Neukamm, M.A. (2012) Determination of 22 synthetic cannabinoids in human hair by liquid chromatography-tandem mass spectrometry. Journal of Chromatography B, 903, 95-101.
16. Salomone, A., Gerace, E., D'Urso, F., Di Corcia, D., Vincenti, M. (2012) Simultaneous analysis of several synthetic cannabinoids, THC, CBD and CBN, in hair by ultra-high performance liquid chromatography tandem mass spectrometry. Method validation and application to real samples. Journal of Mass Spectrometry, 47, 604-610.
17. Poklis, J.L., Amira, D., Wisea, L.E., Wiebelhausa, J.M., Haggertyc, B.J., Poklis, A. (2012) Detection and disposition of JWH-018 and JWH-073 in mice after exposure to "Magic Gold" smoke. Forensic Science International. DOI:10.1016/j.forsciint.2012.02.003.
18. Zhang, Q., Ma, P., Cole, R.B., Wang, G. (2006) Identification of in vitro metabolites of JWH-015, an aminoalkylindole agonist for the peripheral cannabinoid receptor (CB2) by HPLC-MS-MS. Analytical Bioanalytical Chemistry, 386, 1345-1355.
19. Kraemer, T., Rust, K.Y., Meyer, M.R., Wissenbach, D.K., Bregel, D., Hopf, M., Maurer, H.H., Wilske, J. (2009) Studies on the metabolism of JWH-018 and of a homologue of CP 47,497, pharmacologically active ingredients of different misused incense ("Spice") using GC-MS and LCMSn techniques. Annales de Toxicologue Analytique, 21, 21-22.
20. Sobolevsky, T., Prasolov, I., Rodchenkov, G. (2010) Detection of JWH-018 metabolites in smoking mixture post-administration urine. Forensic Science International, 200, 141-147.
21. Mö ller, I., Wintermeyer, A., Bender, K., Jü bner, M., Thomas, A., Krug, O., Schänzer, W., Thevis, M. (2011) Screening for the synthetic cannabinoid JWH-018 and its major metabolites in human doping controls. Drug Testing and Analysis, 3, 609-620.
22. Wintermeyer, A., Mö ller, I., Thevis, M., Jü bner, M., Beike, J., Rothschild, M.A., Bender, K. (2010) In vitro phase I metabolism of the synthetic cannabimimetic JWH-018. Analytical Bioanalytical Chemistry, 398, 2141-2153.
23. Beuck, S., Mö ller, I., Thomas, A., Klose, A., Schlö rer, N., Schänzer, W., Thevis, M. (2011) Structure characterisation of urinary metabolites of the cannabimimetic JWH-018 using chemically synthesised reference material for the support of LC-MS-MS-based drug testing. Analytical Bioanalytical Chemistry, 401, 493-505.
24. Grigoryev, A., Savchuk, S., Melnik, A., Moskaleva, N., Dzhurko, J., Ershov, M. et al. (2011) Chromatography-mass spectrometry studies on the metabolism of synthetic cannabinoids JWH-018 and JWH-073, psychoactive components of smoking mixtures. Journal of Chromatography B, 879, 1126-1136.
25. Chimalakonda, K.C., Bratton, S.M., Le, V.-H., Yiew, K.H., Dineva, A., Moran, C.L. et al. (2011) Conjugation of synthetic cannabinoids JWH-018 and JWH-073, metabolites by human UDP-glucuronosyltransferases. Drug Metabolism and Disposition: the Biological Fate of Chemicals, 39, 1967-1976.
26. Chimalakonda, K.C., Moran, C.L., Kennedy, P.D., Endres, G.W., Uzieblo, A., Dobrowolski, P.J. et al. (2011) Solid-phase extraction and quantitative measurement of omega and omega-1 metabolites of JWH-018 and JWH-073 in human urine. Analytical Chemistry, 83, 6381-6388.
27. ElSohly, M.A., Gul,W., ElSohly, K.M., Murphy, T.P., Madgula, V.L., Khan, S.I. (2011) Liquid chromatography-tandem mass spectrometry analysis of urine specimens for K2 (JWH-018) metabolites. Journal of Analytical Toxicology, 35, 487-495.
28. Moran, C.L., Le, V.-H., Chimalakonda, K.C., Smedley, A.L., Lackey, F.D., Owen, S.N. et al. (2011) Quantitative measurement of JWH-018 and JWH-073 metabolites excreted in human urine. Analytical Chemistry, 83, 4228-4236.
29. Yanes, E.G., Lovett, D.P. (2012) High-throughput bioanalytical method for analysis of synthetic cannabinoid metabolites in urine using salting-out sample preparation and LC-MS-MS. Journal of Chromatography B, 909, 42-50.
30. Grigoryev, A., Melnik, A., Savchuk, S., Simonov, A., Rozhanets, V. (2011) Gas and liquid chromatography-mass spectrometry studies on the metabolism of synthetic phenylacetylindole cannabimimetic JWH-250, psychoactive components of smoking mixtures. Journal of Chromatography B, 879, 2519-2526.
31. Hutter, M., Broecker, S., Kneisel, S., Auwä rter, V. (2012) Identification of the major urinary metabolites in man of seven synthetic cannabinoids of the aminoalkylindole type present as adulterants in 'herbal mixtures' using LC-MS-MS techniques. Journal of Mass Spectrometry, 47, 54-65.
32. Grigoryev, A., Kavanagh, P., Melnik, A. (2012) The detection of the urinary metabolites of 3-[(adamantan-1-yl)carbonyl]-1-pentylindole (AB-001), a novel cannabimimetic, by gas chromatography-mass spectrometry. Drug Testing and Analysis, 4, 519-524.
33. Grigoryev, A., Kavanagh, P., Melnik, A. (2012) The detection of the urinary metabolites of 1-[(5-fluoropentyl)-1H-indol-3-yl]-(2-iodophenyl) methanone (AM-694), a high affinity cannabimimetic, by gas chromatography- mass spectrometry. Drug Testing and Analysis. DOI:10.1002/ dta.1336.
34. Kavanagh, P., Grigoryev, A., Melnik, A., Simonov, A. (2012) The identification of the urinary metabolites of 3-(4-methoxybenzoyl)-1- pentylindole (RCS-4), a novel cannabimimetic, by gas chromatography- mass spectrometry. Journal of Analytical Toxicology, 36, 303-311.
35. Chimalakonda, K.C., Seely, K.A., Bratton, S.M., Brents, L.K., Moran, C.L., Endres, G.W. et al. (2012) Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in "K2/Spice": identification of novel cannabinoid receptor ligands. Drug Metabolism and Disposition, 40, 2174-2184.
36. de Jager, A.D., Warner, J.V., Henman, M., Ferguson, W., Hall, A. (2012) LC-MS-MS method for the quantitation of metabolites of eight commonly-used synthetic cannabinoids in human urine - an Australian perspective. Journal of Chromatography B, 897, 22-31.
37. Sobolevsky, T., Prasolov, I., Rodchenkov, G. (2012) Detection of urinary metabolites of AM-2201 and UR-144, two novel synthetic cannabinoids. Drug Testing and Analysis, 4, 745-753.
38. Falconer, W.E., Hunter, T.F., Trotman-Dickenson, A.F. (1961) The thermal isomerization of cyclopropane. Journal of Chemical Society (Resumed), 609-611.
39. Frey, H.M. (1966) The gas phase pyrolyses of some small ring hydrocarbons. Advances in Physical Organic Chemistry, 4, 147-193.
40. Bradley, J.N., Frend, M.A. (1971) Single-pulse shock tube stidues of hydrocarbon pyrolysis. Part 1. - Pyrolysis of cyclopropane. Transactions of the Faraday Society, 67, 72-79.
41. Wong, H.N.C., Hon, M.-Y., Tse, C.-W., Yip, Y.-C., Tanko, J., Hudlicky, T. (1989) Use of cyclopropanes and their derivatives in organic synthesis. Chemical Reviews, 89, 165-198.
42. Kavanagh, P., Grigoryev, A., Savchuk, S., Mikhura, I., Formanovsky, A. (2013) UR-144 in products sold via the Internet: identification of related compounds and characterization of pyrolysis products. Drug Testing and Analysis. DOI:10.1002/dta.1456.
43. Uchiyama, N., Kawamura, M., Kikura-Hanajiri, R., Goda, Y. (2012) 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. Forensic Toxicology, 30, 114-125.
44. Kim, U., Jin, M.J., Lee, J., Han, S.B., In, M.K., Yoo, H.H. (2012) Tentative identification of phase I metabolites of HU-210, a classical synthetic cannabinoid, by LC-MS-MS. Journal of Pharmaceutical and Biomedical Analysis, 64, 26-34.
45. Meyer, M.R., Peters, F.T., Maurer, H.H. (2010) Automated mass spectral deconvolution and identification system for GC-MS screening for drugs, poisons, and metabolites in urine. Clinical Chemistry, 56, 575-584.