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

Analytical and Bioanalytical Chemistry

Volumn 405, Issue 14, 2013, Pages 4691-4706

  Kneisel, Stefan ^a,b   Speck, Michael ^b   Moosmann, Bjoern ^b   Corneillie, Todd M ^c   Butlin, Nathaniel G ^c   Auwärter, Volker ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

^b UNIVERSITY OF FREIBURG   (Germany)

^c Biophor Diagnostics Inc   (United States)

Author keywords

'Spice'; Detection window; LC ESI MS MS; Neat oral fluid; Synthetic cannabinoids

Indexed keywords

LIQUID CHROMATOGRAPHY; METABOLITES;

CHROMATOGRAPHIC SEPARATIONS; DETECTION WINDOWS; LC/ESI-MS/MS; LIMITS OF DETECTION; ORAL FLUIDS; PROTEIN PRECIPITATION; SYNTHETIC CANNABINOID; SYNTHETIC CANNABINOIDS;

BLOOD;

CANNABINOID; DRUG MIXTURE;

ARTICLE; CHEMISTRY; DRUG MIXTURE; ELECTROSPRAY MASS SPECTROMETRY; LIMIT OF DETECTION; LIQUID CHROMATOGRAPHY; METHODOLOGY; PILOT STUDY; REPRODUCIBILITY; SALIVA; SUBSTANCE ABUSE; TANDEM MASS SPECTROMETRY; ANALYSIS; PROCEDURES;

CANNABINOIDS; CHROMATOGRAPHY, LIQUID; COMPLEX MIXTURES; LIMIT OF DETECTION; PILOT PROJECTS; REPRODUCIBILITY OF RESULTS; SALIVA; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SUBSTANCE ABUSE DETECTION; TANDEM MASS SPECTROMETRY;

EID: 84891718087     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-013-6887-0     Document Type: Article

References (68)

1. Auwärter V, Dresen S, Weinmann W, Müller M, Pütz M, Ferreirós N (2009) 'Spice' and other herbal blends: harmless incense or cannabinoid designer drugs? J Mass Spectrom 44:832-837
2. Uchiyama N, Kikura-Hanajiri R, Kawahara N, Goda Y (2009) Identification of a cannabimimetic indole as a designer drug in a herbal product. Forensic Toxicol 27:61-66
3. Vearrier D, Osterhoudt KC (2010) A teenager with agitation: higher than she should have climbed. Pediatr Emerg Care 26:462-465
4. Hermanns-Clausen M, Kneisel S, Szabo B, Auwärter V (2012) Acute toxicity due to the confirmed consumption of synthetic cannabinoids: clinical and laboratory findings. Addiction. doi:10.1111/j.1360-0443.2012.04078.x
5. Tofighi B, Lee JD (2012) Internet highs-seizures after consumption of synthetic cannabinoids purchased online. J Addict Med 6:240-241
6. Cohen J, Morrison S, Greenberg J, Saidinejad M (2012) Clinical presentation of intoxication due to synthetic cannabinoids. Pediatrics 129:e1064-e1067
7. Forrester MB, Kleinschmidt K, Schwarz E, Young A (2011) Synthetic cannabinoid exposures reported to Texas poison centers. J Addict Dis 30:351-358
8. Forrester M, Kleinschmidt K, Schwarz E, Young A (2012) Synthetic cannabinoid and marijuana exposures reported to poison centers. Hum Exp Toxicol. doi:10.1177/0960327111421945
9. McQuade D, Hudson S, Dargan PI, Wood DM (2012) First European case of convulsions related to analytically confirmed use of the synthetic cannabinoid receptor agonist AM-2201. Eur J Clin Pharmacol. doi:10.1007/s00228-012-1379-2
10. Harris CR, Brown A (2012) Synthetic cannabinoid intoxication: a case series and review. J Emerg Med. doi:10.1016/ j.jemermed.2012.07.061
11. Hoyte CO, Jacob J, Monte AA, Al-Jumaan M, Bronstein AC, Heard KJ (2012) A characterization of synthetic cannabinoid exposures reported to the national poison data system in 2010. Ann Emerg Med 60:435-438
12. Young AC, Schwarz E, Medina G, Obafemi A, Feng S-Y, Kane C, Kleinschmidt K (2012) Cardiotoxicity associated with the synthetic cannabinoid, K9, with laboratory confirmation. AM J Emerg Med 30:1320.e1325-1320.e1327
13. Pant S, Deshmukh A, Dholaria B, Kaur V, Ramavaram S, Ukor M, Teran GA (2012) Spicy seizure. Am J Med Sci 344:67-68
14. Schneir AB, Cullen J, Ly BT (2010) "Spice" girls: synthetic cannabinoid intoxication. J Emerg Med 40:296-299
15. Schneir AB, Baumbacher T (2012) Convulsions associated with the use of a synthetic cannabinoid product. J Med Toxicol 8:62-64
16. Lapoint J, James LP, Moran CL, Nelson LS, Hoffman RS, Moran JH (2011) Severe toxicity following synthetic cannabinoid ingestion. Clin Toxicol 49:760-764
17. Mir A, Obafemi A, Young A, Kane C (2011) Myocardial infarction associated with use of the synthetic cannabinoid K2. Pediatrics 128:e1622-e1627
18. Derungs A, Schwaninger A, Mansella G, Bingisser R, Kraemer T, Liechti M (2012) Symptoms, toxicities, and analytical results for a patient after smoking herbs containing the novel synthetic cannabinoid MAM-2201. Forensic Toxicol. doi:10.1007/s11419-012-0166-1
19. Müller H, Sperling W, Köhrmann M, Huttner HB, Kornhuber J, Maler J-M (2010) The synthetic cannabinoid Spice as a trigger for an acute exacerbation of cannabis induced recurrent psychotic episodes. Schizophr Res 118:309-310
20. Müller H, Huttner HB, Kohrmann M, Wielopolski JE, Kornhuber J, Sperling W (2010) Panic attack after spice abuse in a patient with ADHD. Pharmacopsychiatry 43:152-153
21. Every-Palmer S (2010) Warning: legal synthetic cannabinoidreceptor agonists such as jwh-018 may precipitate psychosis in vulnerable individuals. Addiction 105:1859-1860
22. Every-Palmer S (2011) Synthetic cannabinoid JWH-018 and psychosis: an explorative study. Drug Alcohol Depend 117:152-157
23. Hurst D, Loeffler G, McLay R (2011) Psychosis associated with synthetic cannabinoid agonists: a case series. Am J Psychiat 168:1119
24. Zimmermann US, Winkelmann PR, Pilhatsch M, Nees JA, Spanagel R, Schulz K (2009) Withdrawal phenomena and dependence syndrome after the consumption of "spice gold". Dtsch Arztebl Int 106:464-467
25. Castellanos D, Singh S, Thornton G, Avila M, Moreno A (2011) Synthetic cannabinoid use: a case series of adolescents. J Adolesc Health 49:347-349
26. Castellanos D, Thornton G (2012) Synthetic cannabinoid use: recognition and management. J Psychiat Pract 18:86-93
27. Hutter M, Ippisch J, Schultis H-W, Auwärter V (2012) Evaluation of an ELISA for synthetic cannabinoids applied to urine samples by comparison with a comprehensive and highly sensitive LC-MS/ MS method (Poster). Presented at the 50th Annual Meeting of The International Association of Forensic Toxicologists (TIAFT), Hamamatsu, Japan, 3-8 June, 2012
28. Möller I, Wintermeyer A, Bender K, Jübner M, Thomas A, Krug O, SchänzerWet al (2010) Screening for the synthetic cannabinoid JWH-018 and its major metabolites in human doping controls. Drug Test Anal 3:609-620
29. Moran CL, Le V-H, Chimalakonda KC, Smedley AL, Lackey FD, Owen SN, Kennedy PD et al (2011) Quantitative measurement of JWH-018 and JWH-073 metabolites excreted in human urine. Anal Chem 83:4228-4236
30. ElSohly MA, Gul W, ElSohly KM, Murphy TP, Madgula VLM, Khan SI (2011) Liquid chromatography-tandem mass spectrometry analysis of urine specimens for K2 (JWH-018) metabolites. J Anal Toxicol 35:487-495
31. de Jager AD, Warner JV, 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. J Chromatogr B 897:22-31
32. Heltsley R, Shelby MK, Crouch DJ, Black DL, Robert TA,Marshall L, Bender CL et al (2012) Prevalence of synthetic cannabinoids in U.S. athletes: initial findings. J Anal Toxicol 36:588-593
33. Wintermeyer A, Möller I, Thevis M, Jübner M, Beike J, Rothschild M, Bender K (2010) In vitro phase I metabolism of the synthetic cannabimimetic JWH-018. Anal Bioanal Chem 398:2141-2153
34. Beuck S, Möller I, Thomas A, Klose A, Schlörer 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. Anal Bioanal Chem 401:493-505
35. Sobolevsky T, Prasolov I, Rodchenkov G (2011) 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 66:1314-1323
36. Grigoryev A, Savchuk S, Melnik A, Nj M, Dzhurko J, Ershov M, Nosyrev A et al (2011) Chromatography-mass spectrometry studies on the metabolism of synthetic cannabinoids JWH-018 and JWH-073, psychoactive components of smoking mixtures. J Chromatogr B 879:1126-1136
37. Grigoryev A,Melnik A, Savchuk S, Simonov A, Rozhanets V (2011) Gas and liquid chromatography-mass spectrometry studies on the metabolism of the synthetic phenylacetylindole cannabimimetic JWH-250, the psychoactive component of smoking mixtures. J Chromatogr B 879:2519-2526
38. HutterM, Broecker S, Kneisel S, Auwärter V (2012) Identification of themajor urinarymetabolites inman of seven synthetic cannabinoids of the aminoalkylindole type present as adulterants in 'herbal mixtures' using LC-MS/MS techniques. J Mass Spectrom 47:54-65
39. 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 Test Anal. doi:10.1002/dta.1336
40. 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 Test Anal 4:519-524
41. 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. J Anal Toxicol 36:303-311
42. Sobolevsky T, Prasolov I, Rodchenkov G (2012) Detection of urinary metabolites of AM-2201 and UR-144, two novel synthetic cannabinoids. Drug Test Anal. doi:10.1002/dta.1418
43. Jin MJ, Lee J, In MK, Yoo HH (2012) Characterization of in vitro metabolites of CP 47,497, a synthetic cannabinoid, in human liver microsomes by LC-MS/MS. J Forensic Sci. doi:10.1111/j.1556-4029.2012.02261.x
44. Kim U, Jin MJ, Lee J, Han SB, In MK, Yoo HH (2012) Tentative identification of phase I metabolites of HU-210, a classical synthetic cannabinoid, by LC-MS/MS. J Pharm Biomed Anal 64-65:26-34
45. Auwärter V, Kneisel S, Hutter M, Thierauf A (2012) Synthetische cannabinoide: forensische relevanz und interpretation analytischer befunde. Rechtsmedizin 22:259-271
46. Kneisel S, Teske J, Auwärter V (2012) Analysis of synthetic cannabinoids in abstinence control: long drug detection windows in serum and implications for practitioners. Drug Test Anal. doi:10.1002/dta.1445
47. Neukamm MA, Muerdter TE, Kabbe C, Wehner H, Wehner F (2009) Quantitative detection of the active "Spice" ingredient JWH-018 in serum by means of liquid chromatography-tandem mass spectrometry. Blutalkohol 46:373-379
48. Teske J, Weller J-P, Fieguth A, Rothämel T, Schulz Y, Tröger HD (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. J Chromatogr B 878:2659-2663
49. Dresen S, Kneisel S, Weinmann W, Zimmermann R, Auwärter 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. J Mass Spectrom 46:163-171
50. Kacinko SL, Xu A, Homan JW, McMullin MM, Warrington DM, Logan BK (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. J Anal Toxicol 35:386-393
51. Ammann J, McLaren JM, Gerostamoulos D, Beyer J (2012) Detection and quantification of new designer drugs in human blood: part 1-synthetic cannabinoids. J Anal Toxicol 36:372-380
52. Shanks KG, Dahn T, Terrell AR (2012) Detection of JWH-018 and JWH-073 by UPLC-MS-MS in postmortem whole blood casework. J Anal Toxicol 36:145-152
53. Kneisel S, Auwärter V (2012) Analysis of 30 synthetic cannabinoids in serum by liquid chromatography-electrospray ionization tandem mass spectrometry after liquid-liquid extraction. J Mass Spectrom 47:825-835
54. Coulter C, Garnier M, Moore C (2011) Synthetic cannabinoids in oral fluid. J Anal Toxicol 35:424-430
55. Kneisel S, Auwärter V, Kempf J (2012) Analysis of 30 synthetic cannabinoids in oral fluid using liquid chromatographyelectrospray ionization tandem mass spectrometry. Drug Test Anal. doi:10.1002/dta.1429
56. Crouch DJ (2005) Oral fluid collection: the neglected variable in oral fluid testing. Forensic Sci Int 150:165-173
57. Quintela O, Crouch DJ, Andrenyak DM (2006) Recovery of drugs of abuse from the Immunalysis Quantisal™ oral fluid collection device. J Anal Toxicol 30:614-616
58. Kauert GF, Iwersen-Bergmann S, Toennes SW (2006) Assay of Δ9-tetrahydrocannabinol (THC) in oral fluid-evaluation of the OraSure oral specimen collection device. J Anal Toxicol 30:274-277
59. Dickson S, Park A, Nolan S, Kenworthy S, Nicholson C, Midgley J, Pinfold R et al (2007) The recovery of illicit drugs from oral fluid sampling devices. Forensic Sci Int 165:78-84
60. Langel K, Engblom C, Pehrsson A, Gunnar T, Ariniemi K, Lillsunde P (2008) Drug testing in oral fluid-evaluation of sample collection devices. J Anal Toxicol 32:393-401
61. Kempf J, Wuske T, Schubert R, Weinmann W (2009) Preanalytical stability of selected benzodiazepines on a polymeric oral fluid sampling device. Forensic Sci Int 186:81-85
62. Moosmann B, Kneisel S, Girreser U, Brecht V, Westphal F, Auwärter V (2012) Separation and structural characterization of the synthetic cannabinoids JWH-412 and 1-[(5-fluoropentyl)-1Hindol-3yl]-(4-methylnaphthalen-1-yl)methanone using GC-MS, NMR analysis and a flash chromatography system. Forensic Sci Int 220:e17-e22
63. Moosmann B, Kneisel S,Wohlfarth A, Brecht V, Auwärter V (2012) A fast and inexpensive procedure for the isolation of synthetic cannabinoids from 'Spice' products using a flash chromatography system. Anal Bioanal Chem. doi:10.1007/s00216-012-6462-0
64. Peters FT, Hartung M, Herbold M, Schmitt G, Daldrup T, Mußhoff F (2009) Anhang B zu den Richtlinien der GTFCh zur Qualitätssicherung bei forensisch-toxikologischen untersuchungen; anforderungen an die validierung von analysenmethoden. Toxichem Krimtech 76(3):185-208
65. Matuszewski BK, Constanzer ML, Chavez-Eng CM (2003) Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS. Anal Chem 75:3019-3030
66. Speck M, Kneisel S, Butlin NG, Auwärter V (2012) Stability of 26 synthetic cannabinoids of the aminoalkylindole type, JWH-307 and methanandamide in oral fluid under different storage conditions (Poster). Presented at the 50th Annual Meeting of The International Association of Forensic Toxicologists (TIAFT), Hamamatsu, Japan, 3-8 June, 2012
67. Niedbala RS, Kardos KW, Fritch DF, Kardos S, Fries T, Waga J, Robb J et al (2001) Detection of marijuana use by oral fluid and urine analysis following single-dose administration of smoked and oral marijuana. J Anal Toxicol 25:289-303
68. HuestisMA, Cone EJ (2004) Relationship ofΔ9-tetrahydrocannabinol concentrations in oral fluid and plasma after controlled administration of smoked cannabis. J Anal Toxicol 28:394-399