Quantitative urine confirmatory testing for synthetic cannabinoids in randomly collected urine specimens

Drug Testing and Analysis

Volumn 7, Issue 6, 2015, Pages 483-493

  Castaneto, Marisol S ^a,b   Scheidweiler, Karl B ^a   Gandhi, Adarsh ^a,d   Wohlfarth, Ariane ^a   Klette, Kevin L ^c   Martin, Thomas M ^c   Huestis, Marilyn A ^a  

^a NATIONAL INSTITUTE ON DRUG ABUSE   (United States)

^b UNIVERSITY OF MARYLAND   (United States)

^c Office of the under Secretary of Defense for Personnel and Readiness   (United States)

^d LUNDBECK RESEARCH USA   (United States)

Author keywords

Immunoassay; LC MS MS; Synthetic cannabinoids; Urine drug testing

Indexed keywords

BIOMOLECULES; BODY FLUIDS; IMMUNOLOGY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; STATISTICAL TESTS;

DRUG TESTING; HEALTH ISSUES; IMMUNOASSAY; LC-MS-MS; LC.MS/MS; MATRIX; METABOLITE CONCENTRATIONS; SYNTHETIC CANNABINOID; URINE DRUG TESTING; US MILITARY;

METABOLITES;

1 (5 FLUOROPENTYL) 3 (1 NAPHTHOYL)INDOLE; 1 BUTYL 3 (1 NAPHTHOYL)INDOLE; 3 (1 NAPHTHOYL) 1 PENTYLINDOLE; CANNABINOID DERIVATIVE; JWH 122; JWH 210; JWH 250; JWH 398; MAM 2201; RCS 8; UNCLASSIFIED DRUG; UR 144; CANNABINOID;

ARTICLE; CONCENTRATION (PARAMETERS); DRUG SCREENING; HUMAN; IMMUNOASSAY; LIMIT OF DETECTION; LIMIT OF QUANTITATION; LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; SOLDIER; TANDEM MASS SPECTROMETRY; UNITED STATES; URINALYSIS; URINE LEVEL; METABOLISM; PROCEDURES; SUBSTANCE ABUSE; SYNTHESIS; URINE;

CANNABINOIDS; CHROMATOGRAPHY, LIQUID; HUMANS; IMMUNOASSAY; LIMIT OF DETECTION; SUBSTANCE ABUSE DETECTION; TANDEM MASS SPECTROMETRY;

EID: 84930276072     PISSN: 19427603     EISSN: 19427611     Source Type: Journal    
DOI: 10.1002/dta.1709     Document Type: Article

References (57)

1. I. Buchler, M. Hayes, S. Hedge, S. Hockerman, D.E. Jones, S. Kortum, J. Rico, R. Tenbrink, K. Wu. Indazole Derivatives. International Patent PCT/IB2009/000432, 2009.
2. A. Makriyannis, H. Deng. Cannabimimetic Indole Derivatives. US Patent 6, 900, 236 B1, 2001.
3. A. Makriyannis, H. Deng. Receptor selective cannabimimetic aminoalkylindoles. US Patent 20070243134, 2007.
4. R.G. Pertwee. Receptors and channels targeted by synthetic cannabinoid receptor agonists and antagonists. Curr. Med. Chem. 2010, 17, 1360.
5. J.L. Wiley, J.A. Marusich, J.W. Huffman. Moving around the molecule: Relationship between chemical structure and in vivo activity of synthetic cannabinoids. Life Sci. 2014, 97, 55.
6. United Nations Office on Drugs and Crime. Synthetic Cannabinoids in Herbal Products. Available at: http://www.unodc.org/unodc/en/scientists/synthetic-cannabinoids-in-herbal-products.html [1 May 2014].
7. S.M.R. Gurney, K.S. Scott, S.L. Kacinko, B.C. Presley, B.K. Logan. Pharmacology, toxicology, and adverse effects of synthetic cannabinoid drugs. Forensic Sci. Rev. 2014, 26, 53.
8. American Association of Poison Control Centers. Synthetic Marijuana Data. Available at: http://www.aapcc.org/alerts/synthetic-marijuana [1 May 2014].
9. US Drug Enforcement Administration. Establishment of drug codes for 26 substances. Final rule. Fed. Regist. 2013, 78, 664.
10. European Monitoring Centre for Drugs and Drug Addiction. Perspective on Drugs: Synthetic cannabinoids in Europe. Available at: http://www.emcdda.europa.eu/attachements.cfm/att_212361_EN_EMCDDA_POD_2013_Synthetic%20cannabinoids.pdf [Accessed 25 August 2014].
11. N. Uchiyama, Y. Shimokawa, S. Matsuda, M. Kawamura, R. Kikura-Hanajiri, Y. Goda. Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3, 4, 5-trimethyoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products. Forensic Toxicol. 2014, 32, 105.
12. A.D. de Jager, J.V. Warner, M. Henman, W. Ferguson, A. Hall. LC-MS/MS method for the quantitation of metabolites of eight commonly-used synthetic cannabinoids in human urine--an Australian perspective. J. Chromatogr. B 2012, 897, 22.
13. J. Newberry, A. Wodak, D. Sellman, G. Robinson. New Zealand's regulation of new psychoactive substances. Brit. Med. J. 2014, 348, g1534.
14. World Anti-Doping Agency. The 2010 Prohibited List International Standard. Available at: http://www.wada-ama.org/en/Science-Medicine/Prohibited-List/ [1May 2014].
15. M. Hermanns-Clausen, S. Kneisel, B. Szabo, V. Auwärter. Acute toxicity due to the confirmed consumption of synthetic cannabinoids: clinical and laboratory findings. Addiction 2013, 108, 534.
16. S.L. Kacinko, A. Xu, J.W. Homan, M.M. McMullin, D.M. Warrington, B.K. Logan. 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. J. Anal. Toxicol. 2011, 35, 386.
17. F. Musshoff, B. Madea, G. Kernbach-Wighton, W. Bicker, S. Kneisel, M. Hutter, V. Auwärter. Driving under the influence of synthetic cannabinoids (" Spice" ): A case series. Int. J. Legal Med. 2013, 128, 59.
18. S. Kneisel, V. Auwärter. Analysis of 30 synthetic cannabinoids in serum by liquid chromatography-electrospray ionization tandem mass spectrometry after liquid-liquid extraction. J. Mass Spectrom. 2012, 47, 825.
19. J. Teske, J.-P. Weller, A. Fieguth, T. Rothaemel, Y. Schulz, H.D. Troeger. 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. J. Chromatogr. B 2010, 878, 2659.
20. C. Coulter, M. Garnier, C. Moore. Synthetic cannabinoids in oral fluid. J. Anal. Toxicol. 2011, 35, 424.
21. W. Rodrigues, P. Catbagan, S. Rana, G. Wang, C. Moore. Detection of synthetic cannabinoids in oral fluid using ELISA and LC-MS-MS. J. Anal. Toxicol. 2011, 35, 424.
22. R. Gottardo, D. Sorio, G. Musile, E. Trapani, C. Seri, G. Serpelloni, F. Tagliaro. Screening for synthetic cannabinoids in hair by using LC-QTOF MS: A new and powerful approach to study the penetration of these new psychoactive substances in the population. Med. Sci. Law 2013, 54, 22.
23. M. Hutter, S. Kneisel, V. Auwärter, M.A. Neukamm. Determination of 22 synthetic cannabinoids in human hair by liquid chromatography-tandem mass spectrometry. J. Chromatogr. B 2012, 903, 95.
24. A. Salomone, C. Luciano, D. Di Corcia, E. Gerace, M. Vincenti. Hair analysis as a tool to evaluate the prevalence of synthetic cannabinoids in different populations of drug consumers. Drug Test. Anal. 2014, 6, 126.
25. K.C. Chimalakonda, C.L. Moran, P.D. Kennedy, G.W. Endres, A. Uzieblo, P.J. Dobrowolski, E.K. Fifer, J. Lapoint, L.S. Nelson, R.S. Hoffman, L.P. James, A. Radominska-Pandya, J.H. Moran. Solid-phase extraction and quantitative measurement of omega and omega-1 Metabolites of JWH-018 and JWH-073 in human urine. Anal.Chem. 2011, 83, 6381.
26. A. Grigoryev, P. Kavanagh, A. Melnik. 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 Test. Anal. 2012, 4, 519.
27. A. Grigoryev, P. Kavanagh, A. Melnik. 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 Test. Anal. 2013, 5, 110.
28. M. Hutter, B. Moosmann, S. Kneisel, V. Auwärter. Characteristics of the designer drug and synthetic cannabinoid receptor agonist AM-2201 regarding its chemistry and metabolism. J. Mass Spectrom. 2013, 48, 885.
29. M. Jang, W. Yang, H. Choi, H. Chang, S. Lee, E. Kim, H. Chung. Monitoring of urinary metabolites of JWH-018 and JWH-073 in legal cases. Forensic Sci. Int. 2013, 231, 13.
30. M. Jang, W. Yang, I. Shin, H. Choi, H. Chang, E. Kim. Determination of AM-2201 metabolites in urine and comparison with JWH-018 abuse. Int. J. Legal Med. 2014, 128, 285.
31. D. Lovett, E. Yanes, T. Herbelin, T. Knoerzer, J. Levisky. Structure elucidation and identification of a common metabolite for naphthoylindole-based synthetic cannabinoids using LC-TOF and comparison to a synthetic reference standard. Forensic Sci. Int. 2013, 226, 81.
32. M.A. ElSohly, W. Gul, K.M. Elsohly, T.P. Murphy, V.L. Madgula, S.I. Khan. Liquid chromatography-tandem mass spectrometry analysis of urine specimens for K2 (JWH-018) metabolites. J. Anal. Toxicol. 2011, 35, 487.
33. P. Kavanagh, A. Grigoryev, A. Melnik, A. Simonov. The identification of the urinary metabolites of 3-(4-methoxybenzoyl)-1-pentylindole (RCS-4), a novel cannabimimetic, by gas chromatography-mass spectrometry. J. Anal. Toxicol. 2012, 36, 303.
34. M. Hutter, S. Broecker, S. Kneisel, V. Auwärter. 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. J. Mass Spectrom. 2012, 47, 54.
35. T. Sobolevsky, I. Prasolov, G. Rodchenkov. Detection of urinary metabolites of AM-2201 and UR-144, two novel synthetic cannabinoids. Drug Test. Anal. 2012, 10, 745.
36. M. Hermanns-Clausen, S. Kneisel, M. Hutter, B. Szabo, V. Auwärter. Acute intoxication by synthetic cannabinoids - Four case reports. Drug Test. Anal. 2013, 5, 790.
37. J.K. Yeakel, B.K. Logan. Blood synthetic cannabinoid concentrations in cases of suspected impaired driving. J. Anal. Toxicol. 2013, 37, 547.
38. S. Kneisel, J. Teske, V. Auwärter. Analysis of synthetic cannabinoids in abstinence control: Long drug detection windows in serum and implications for practitioners. Drug Test. Anal. 2014, 6, 135.
39. M.M. Bergamaschi, E.L. Karschner, R.S. Goodwin, K.B. Scheidweiler, J. Hirvonen, R.H. Queiroz, M.A. Huestis. Impact of prolonged cannabinoid excretion in chronic daily cannabis smokers' blood on per se drugged driving laws. Clin. Chem. 2013, 59, 519.
40. M. Smith. Immunoassay. In Principles of Forensic Toxicology, (Ed: B. Levine ). AACC: Washington DC, 2013, pp. 149-169.
41. F. Guale, S. Shahreza, J.P. Walterscheid, H.H. Chen, C. Arndt, A. T. Kelly, A. Mozayani. Validation of LC-TOF-MS screening for drugs, metabolites, and collateral compounds in forensic toxicology specimens. J. Anal. Toxicol. 2013, 37, 17.
42. L.M. Huppertz, S. Kneisel, V. Auwärter, J. Kempf. A comprehensive library-based, automated screening procedure for 46 synthetic cannabinoids in serum employing liquid chromatography-quadrupole ion trap mass spectrometry with high-temperature electrospray ionization. J. Mass Spectrom. 2014, 49, 117.
43. R. Kronstrand, L. Brinkhagen, C. Birath-Karlsson, M. Roman, M. Josefsson. LC-QTOF-MS as a superior strategy to immunoassay for the comprehensive analysis of synthetic cannabinoids in urine. Anal. Bioanal. Chem. 2014, 405, 3599.
44. M. Sundström, A. Pelander, V. Angerer, M. Hutter, S. Kneisel, I. Ojanperä. A high-sensitivity ultra-high performance liquid chromatography/high-resolution time-of-flight mass spectrometry (UHPLC-HR-TOFMS) method for screening synthetic cannabinoids and other drugs of abuse in urine. Anal. Bioanal. Chem. 2013, 405, 8463.
45. A. Wohlfarth, K.B. Scheidweiler, X. Chen, H.F. Liu, M.A. Huestis. Qualitative confirmation of 9 synthetic cannabinoids and 20 metabolites in human urine using LC-MS/MS and library search. Anal. Chem. 2013, 85, 3730.
46. Centers for Disease Control and Prevention. Acute kidney injury associated with synthetic cannabinoid use - multiple states, 2012. MMWR Morb. Mortal. Wkly Rep. 2013, 62, 93.
47. K.B. Scheidweiler, M.A. Huestis. Simultaneous quantification of 20 synthetic cannabinoids and 21 metabolites, and semi-quantification of 12 alkyl hydroxy metabolites in human urine by liquid chromatography-tandem mass spectrometry. J. Chromatogr. A 2014, 1327, 105.
48. K.N. Ellefsen, S. Anizan, M.S. Castaneto, N.A. Desrosiers, T.M. Martin, K.L. Klette, M.A. Huestis. Validation of the only commercially available immunoassay for synthetic cathinones in urine: Randox drugs of abuse V biochip array technology. Drug Test. Anal. 2014, 6, 728.
49. S. Beuck, I. Moeller, A. Thomas, A. Klose, N. Schloerer, W. Schaenzer, M. Thevis. 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. Anal. Bioanal. Chem. 2011, 401, 493.
50. K.C. Chimalakonda, K.A. Seely, S.M. Bratton, L.K. Brents, C.L. Moran, G.W. Endres, L.P. James, P.F. Hollenberg, P.L. Prather, A. Radominska-Pandya, J.H. Moran. Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in K2/Spice: identification of novel cannabinoid receptor ligands. Drug Metab. Dispos. 2012, 40, 2174.
51. B.K. Logan, L.E. Reinhold, A. Xu, F.X. Diamond. Identification of synthetic cannabinoids in herbal incense blends in the United States. J. Forensic Sci. 2012, 57, 1168.
52. L.K. Brents, E.E. Reichard, S.M. Zimmerman, J.H. Moran, W.E. Fantegrossi, P.L. Prather. Phase I hydroxylated metabolites of the K2 synthetic cannabinoid JWH -018 retain in vitro and in vivo cannabinoid 1 receptor affinity and activity. PLoS One 2011, 6, e21917.
53. C.L. Moran, V.-H. Le, K.C. Chimalakonda, A.L. Smedley, F.D. Lackey, S.N. Owen, P.D. Kennedy, G.W. Endres, F.L. Ciske, J.B. Kramer, A.M. Kornilov, L.D. Bratton, P.J. Dobrowolski, W.D. Wessinger, W.E. Fantegrossi, P.L. Prather, L.P. James, A. Radominska-Pandya, J.H. Moran. Quantitative measurement of JWH-018 and JWH-073 metabolites excreted in human urine. Anal. Chem. 2011, 83, 4228.
54. A.S. Gandhi, A. Wohlfarth, M. Zhu, S. Pang, M. Castaneto, K.B. Scheidweiler, M.A. Huestis. High-resolution mass spectrometric metabolite profiling of a novel synthetic designer drug, N-(adamantan-1-yl)-1-(5-fluoropentyl)-1H-indole-3-carboxamide (STS-135), using cryopreserved human hepatocytes and assessment of metabolic stability with human liver microsomes. Drug Test. Anal. 2014, doi:10.1002/dta.1662
55. A.S. Gandhi, M. Zhu, S. Pang, A. Wohlfarth, K.B. Scheidweiler, H.F. Liu, M.A. Huestis. First characterization of AKB-48 metabolism, a novel synthetic cannabinoid, using human hepatocytes and high-resolution mass spectrometry. AAPS J. 2013, 15, 1091.
56. A. Wohlfarth, S. Pang, M. Zhu, A.S. Gandhi, K.B. Scheidweiler, H.F. Liu, M.A. Huestis. First metabolic profile of XLR-11, a novel synthetic cannabinoid, obtained by using human hepatocytes and high-resolution mass spectrometry. Clin. Chem. 2013, 59, 1638.
57. P. Adamowicz, D. Zuba, K. Sekula. Analysis of UR-144 and its pyrolysis product in blood and their metabolites in urine. Forensic Sci. Int. 2013, 233, 320.