Synthetic cannabinoids: Analysis and metabolites

Life Sciences

Volumn 97, Issue 1, 2014, Pages 78-90

  ElSohly, Mahmoud A ^a,b,c   Gul, Waseem ^a,b   Wanas, Amira S ^b,d   Radwan, Mohamed M ^b,e  

^a ElSohly Laboratories Incorporated   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

^c UNIVERSITY OF MISSISSIPPI   (United States)

^d Minia University   (Egypt)

^e Alexandria University Faculty of Pharmacy   (Egypt)

Author keywords

Analysis; Herbal products; Metabolites; Synthetic cannabinoids

Indexed keywords

ANALYSIS; HERBAL PRODUCTS; METABOLITES; SYNTHETIC CANNABINOIDS;

ANIMALS; CANNABINOID RECEPTOR MODULATORS; CANNABINOIDS; DESIGNER DRUGS; DRUG DESIGN; HUMANS; RECEPTOR, CANNABINOID, CB1; RECEPTOR, CANNABINOID, CB2;

EID: 84894061625     PISSN: 00243205     EISSN: 18790631     Source Type: Journal    
DOI: 10.1016/j.lfs.2013.12.212     Document Type: Review

References (47)

1. J. Ammann, J.M. McLaren, D. Gerostamoulos, and J. Beyer Detection and quantification of new designer drugs in human blood: part 1 - synthetic cannabinoids J Anal Toxicol 36 2012 372 380
2. A. Arntson, B. Ofsa, D. Lancaster, R. Simon, M. McMullin, and B. Logan Validation of a novel immunoassay for the detection of synthetic cannabinoids and metabolites in urine specimens J Anal Toxicol 37 5 2013 284 290
3. K.P. Bateman, J. Castro-Perez, M. Wrona, J.P. Shockcor, K. Yu, and R. Oballa et al. MSE with mass defect filtering for in vitro and in vivo metabolite identification Rapid Commun Mass Spectrom 21 9 2007 1485 1496 (Pubitemid 46761970)
4. N. Brabanter, S. Esposito, E. Tudela, L. Lootens, P. Meuleman, and G. Leroux-Roels et al. In vivo and in vitro metabolism of the synthetic cannabinoid JWH-200 Rapid Commun Mass Spectrom 27 18 2013 2115 2126
5. F. Carroll, A. Lewin, W. Mascarella, H. Seltzman, and P. Reddy Designer drugs: a medicinal chemistry perspective Ann N Y Acad Sci 1248 2012 18 38
6. H. Choi, S. Heo, S. Choe, W. Yang, Y. Park, and E. Kim et al. Simultaneous analysis of synthetic cannabinoids in the materials seized during drug trafficking using GC-MS Anal Bioanal Chem 405 12 2013 3937 3944
7. S. Dresen, S. Kneisel, W. Weinmann, R. Zimmermann, and V. Auwärter 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 J Mass Spectrom 46 2011 163 171
8. S.J.B. Dunham, P.D. Hooker, and R.M. Hyde Identification, extraction and quantification of the synthetic cannabinoid JWH-018 from commercially available herbal marijuana alternatives Forensic Sci Int 223 2012 241 244
9. M.A. ElSohly, W. Gul, K. ElSohly, T.P. Murphy, V.L.M. Madgula, and S.I. Khan Liquid chromatography-tandem mass spectrometry analysis of urine specimens for K2 (JWH-018) metabolites J Anal Toxicol 35 2011 487 495
10. D. Favretto, J. Pascali, and F. Tagliaro New challenges and innovations in forensic toxicology: focus on the "new psychoactive substances" J Chromatogr A 1287 2013 84 95
11. S. Gandhi, Z. Mingshe, P. Shaokun, A. Wohlfarth, K. Scheidweiler, and F. Liu et al. First characterization of AKB-48 metabolism, a novel synthetic cannabinoid, using human hepatocytes and high-resolution mass spectrometry AAPS J 2013 10.1208/s12248-013-9516-0
12. R. Gottardo, A. Chiarini, I. Dal Prá, C. Seri, C. Rimondo, and G. Serpelloni Direct screening of herbal blends for new synthetic cannabinoids by MALDI-TOF MS J Mass Spectrom 47 2012 141 146
13. R. Gottardo, D. Sorio, G. Musile, E. Trapani, C. Seri, and G. Serpelloni et al. 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 10.1177/0025802413477396
14. M. Grabenauer, W.L. Krol, J.L. Wiley, and B.F. Thomas Analysis of synthetic cannabinoids using high-resolution mass spectrometry and mass defect filtering: implications for nontargeted screening of designer drugs Anal Chem 84 2012 5574 5581
15. A. Grigoryev, S. Savchuk, and A. Melnik All-Russian conference 'analytical chromatography and capillary electrophoresis' 2010 Office-Alliance Krasnodar 143
16. A. Grigoryev, S. Savchuk, A. Melnik, N. Moskaleva, J. Dzhurko, and M. Ershov Chromatography-mass spectrometry studies on the metabolism of synthetic cannabinoids JWH-018 and JWH-073, psychoactive components of smoking mixtures J Chromatogr B 879 2011 1126 1136
17. A. Grigoryev, A. Melnik, S. Savchuk, A. Simonov, and V. Rozhants Gas and liquid chromatography-mass spectrometry studies on the metabolism of the synthetic phenylacetylindole cannabimimetic JWH-250, psychoactive component of smoking mixtures J Chromatogr B 879 2011 2519 2526
18. M. Hutter, S. Broecker, S. Kneisel, and 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 47 2012 54 65
19. M. Jin, J. Lee, K. In, and H. Yoo Characterization of in vitro metabolites of CP 47,497, a synthetic cannabinoid, in human liver microsomes by LC-MS/MS J Forensic Sci 58 1 2013 195 199
20. S. Kneisel, and V. Auwärter Analysis of 30 synthetic cannabinoids in serum by liquid chromatography-electrospray ionization tandem mass spectrometry after liquid-liquid extraction J Mass Spectrom 47 2012 825 835
21. S. Kneisel, M. Speck, B. Moosmann, M. Corneillie Todd, G. Butlin, and V. Auwaerter LC/ESI-MS/MS method for quantification of 28 synthetic cannabinoids in neat oral fluid and its application to preliminary studies on their detection windows Anal Bioanal Chem 405 14 2013 4691 4706
22. T. Kraemer, K.Y. Rust, M. Meyer, D. Wissenbach, D. Bregel, and M. Hopf et al. 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 LC/MS techniques Ann Toxicol Anal 21 S1 2009 21
23. B.K. Logan, L.E. Reinhold, A. Xu, and F.X. Diamond Identification of synthetic cannabinoids in herbal incense blends in the United States J Forensic Sci 57 5 2012 1168 1180
24. D. Lovett, Y. Yanes, H. Herbelin, T. Knoerzer, and J. Levisky A 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 226 1-3 2013 81 87
25. G. Merola, Z. Aturki, G. D'Orazio, R. Gottardo, T. Macchia, and F. Tagliaro et al. Analysis of synthetic cannabinoids in herbal blends by means of nano-liquid chromatography J Pharm Biomed Anal 71 2012 45 53
26. I. Möller, A. Wintermeyer, K. Bender, M. Jübner, A. Thomas, and O. Krug et al. Screening for the synthetic cannabinoid JWH-018 and its major metabolites in human doping controls Drug Test Anal 3 2010 609 620
27. B. Moosmann, S. Kneisel, A. Wohlfarth, V. Brecht, and V. Auwärter A fast and inexpensive procedure for the isolation of synthetic cannabinoids from 'Spice' products using a flash chromatography system Anal Bioanal Chem 1 2012 1 7
28. B. Moosmann, S. Kneisel, U. Girreser, V. Brecht, F. Westphal, and 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 220 2012 e17 e22
29. R.A. Musah, M.A. Domin, M.A. Walling, and J.R.E. Shepard Rapid identification of synthetic cannabinoids in herbal samples via direct analysis in real time mass spectrometry Rapid Commun Mass Spectrom 26 2012 1109 1114
30. L. Nico, L. Rainer, S. Martin, E. Ludger, and B. Till Identification and quantification of synthetic cannabinoids in 'spice-like' herbal mixtures: a snapshot of the German situation in the autumn of 2012 Drug Test Anal 2013 10.1002/dta.1499
31. H.J. Penn, L.J. Langman, D. Unold, J. Shields, and J.H. Nichols Detection of synthetic cannabinoids in herbal incense products Clin Biochem 44 2011 1163 1165
32. E.T. Peters, and H.H. Maurer Bioanalytical method validation and its implication for forensic and clinical toxicology: a review Accredit Qual Assur 7 2002 441 449 (Pubitemid 36165305)
33. E.T. Peters, O.H. Drummer, and F. Musshoff Validation of new methods Forensic Sci Int 7 2007 216 224 (Pubitemid 46073540)
34. F.T. Peters, M. Hartung, M. Herbold, G. Schmitt, T. Daldrup, and F. Mußhoff Anhang B zu den Richtlinien der GTFCh zur Qualitässicherung bei forensisch-toxikologischen Untersuchungen; Anforderungen an die Validierung von Analysenmethoden Toxichem Krimtech 76 3 2009 185
35. C. Rollins, S. Spuhler, K. Clemens, D. Predecki, and J. Richardson Qualitative and quantitative analysis of fluorine containing synthetic cannabinoids using NMR 245th ACS National Meeting & Exposition, New Orleans, LA, United States, April 7-11, 2013 2013 [CHED-1398]
36. A. Salomone, E. Gerace, F. D'Urso, D. Di Corcia, and M. Vincenti 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 J Mass Spectrom 47 2012 604 610
37. K.A. Seely, L.K. Brents, A. Radominska-Pandya, G.W. Endres, G.S. Keyes, and J.H. Moran et al. A major glucuronidated metabolite of JWH-018 is a neutral antagonist at CB1 receptors Chem Res Toxicol 25 2012 825 827
38. T.G. Sobolevskii, I.S. Prasolov, and G.M. Rodchenkov Application of mass spectrometry to the structural identification of the metabolites of the synthetic cannabinoid JWH-018 and the determination of them in human urine J Anal Chem 66 13 2011 1314 1323
39. T. Sobolevsky, I. Prasolov, and G. Rodchenkov Detection of JWH-018 metabolites in smoking mixture post-administration urine Forensic Sci Int 200 2010 141
40. M. Spaderna, P. Addy, and D. D'Souza Spicing things up: synthetic cannabinoids Psychopharmacology (Berl) 228 2013 525 540
41. J. Teske, J.P. Weller, A. Fieguth, T. Rothämel, Y. Schulz, and H.D. Tröger et al. J Chromatogr B 878 2010 2959
42. U.S. Department of Health, Human Sevices Guidance for Industry Bioanalytical Method Validation 2001 [Washington, DC]
43. N. Uchiyama, M. Kawamura, R. Kikura-Hanajiri, and Y. Goda URB-754. A new class of designer drug and 12 synthetic cannabinoids detected in illegal products Forensic Sci Int 227 2013 21 32
44. D. Wells, and C. Ott The "new" marijuana Ann Pharmacother 45 2011 414 417
45. A. Wohlfarth, B. Scheidweiler, X. Chen, H. Liu, and A. Huestis Qualitative confirmation of 9 synthetic cannabinoids and 20 metabolites in human urine using LC-MS/MS and library search Anal Chem 85 7 2013 3730 3738
46. H.Y. Zhang, D.L. Zhang, and K. Ray A software filter to remove interference ions from drug metabolites in accurate mass liquid chromatography/mass spectrometric analyses J Mass Spectrom 38 10 2003 1110 1112 (Pubitemid 37407706)
47. M.S. Zhu, L. Ma, D.L. Zhang, K. Ray, W.P. Zhao, and W.G. Humphreys et al. Detection and characterization of metabolites in biological matrices using mass defect filtering of liquid chromatography/high resolution mass spectrometry data Drug Metab Dispos 34 10 2006 1722 1733 (Pubitemid 44427475)