Simultaneous quantification of 37 synthetic cannabinoid metabolites in human urine by liquid chromatography-tandem mass spectrometry

Forensic Toxicology

Volumn 33, Issue 2, 2015, Pages 221-234

  Jang, Moonhee ^a   Shin, Ilchung ^a   Kim, Jihyun ^a   Yang, Wonkyung ^a  

^a National Forensic Service   (South Korea)

Author keywords

LC MS MS; N Hydroxypentyl metabolite; N Pentanoic acid metabolite; Regioisomer separation; Synthetic cannabinoid; Urine

Indexed keywords

1 BUTYL 3 (1 NAPHTHOYL)INDOLE 6 HYDROXYINDOLE; 1 BUTYL 3 (1 NAPHTHOYL)INDOLE N (3 HYDROXYBUTYL); 1 BUTYL 3 (1 NAPHTHOYL)INDOLE N (4 HYDROXYBUTYL); 1 BUTYL 3 (1 NAPHTHOYL)INDOLE N BUTANOIC ACID; 3 (1 NAPHTHOYL) 1 PENTYLINDOLE 6 HYDROXYINDOLE; 3 (1 NAPHTHOYL) 1 PENTYLINDOLE N (4 HYDROXYPENTYL); 3 (1 NAPHTHOYL) 1 PENTYLINDOLE N (5 HYDROXYPENTYL); 3 (1 NAPHTHOYL) 1 PENTYLINDOLE N PENTANOIC ACID; CANNABINOID DERIVATIVE; JWH 019 N (6 HYDROXYHEXYL); JWH 081 N (5 HYDROXYPENTYL); JWH 122 N (4 HYDROXYPENTYL); JWH 122 N (5 HYDROXYPENTYL); JWH 203 N (4 HYDROXYPENTYL); JWH 203 N (5 HYDROXYPENTYL); JWH 203 N PENTANOIC ACID; JWH 210 N (4 HYDROXYPENTYL); JWH 210 N (5 HYDROXYPENTYL); JWH 2201 6 HYDROXYINDOLE; JWH 2201 N (4 HYDROXYPENTYL); JWH 250 N (4 HYDROXYPENTYL); JWH 250 N (5 HYDROXYPENTYL); JWH 250 N PENTANOIC ACID; JWH 398 N (4 HYDROXYPENTYL); JWH 398 N (5 HYDROXYPENTYL); MAM 2201 N (4 HYDROXYPENTYL); MAM 2201 N PENTANOIC ACID; UNCLASSIFIED DRUG; UR 144 N (5 HYDROXYPENTYL); UR 144 N PENTANOIC ACID;

ARTICLE; CONTROLLED STUDY; DRUG USE; FREEZE THAWING; HUMAN; HYDROLYSIS; LIMIT OF DETECTION; LIMIT OF QUANTITATION; LIQUID CHROMATOGRAPHY; MEASUREMENT ACCURACY; METABOLITE; MOLECULAR STABILITY; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; SOLID PHASE EXTRACTION; STORAGE; TANDEM MASS SPECTROMETRY; URINALYSIS; VALIDATION STUDY;

EID: 84937423389     PISSN: 18608965     EISSN: 18608973     Source Type: Journal    
DOI: 10.1007/s11419-015-0265-x     Document Type: Article

References (33)

1. Zuba D, Byrska B (2013) Analysis of the prevalence and coexistence of synthetic cannabinoids in “herbal high” products in Poland. Forensic Toxicol 31:21–30
2. Kikura-Hanajiri R, Uchiyama N, Kawamura M, Goda Y (2013) Changes in the prevalence of synthetic cannabinoids and cathinone derivatives in Japan until early 2012. Forensic Toxicol 31:44–53
3. Chung H, Choi H, Heo S, Kim E, Lee J (2014) Synthetic cannabinoids abused in South Korea: drug identifications by the National Forensic Service from 2009 to June 2013. Forensic Toxicol 32:82–88
4. Uchiyama N, Shimokawa Y, Kawamura M, Kikura-Hanajiri R, Hakamatsuka T (2014) Chemical analysis of a benzofuran derivative, 2-(2-ethylaminopropyl)benzofuran (2-EAPB), eight synthetic cannabinoids, five cathinone derivatives, and five other designer drugs newly detected in illegal products. Forensic Toxicol 32:266–281
5. 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
6. Castaneto MS, Gorelick DA, Desrosiers NA, Hartman RL, Pirard S, Huestis MA (2014) Synthetic cannabinoids: epidemiology, pharmacodynamics, and clinical implications. Drug Alcohol Depend 144:12–41
7. Brents LK, Reichard EE, Zimmerman SM, Moran JH, Fantegrossi WE, Prather PL (2011) 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 6:e21917
8. Brents LK, Gallus-Zawada A, Radominska-Pandya A, Vasiljevik T, Prisinzano TE, Fantegrossi WE, Moran JH, Prather PL (2012) Monohydroxylated metabolites of the K2 synthetic cannabinoid JWH-073 retain intermediate to high cannabinoid 1 receptor (CB1R) affinity and exhibit neutral antagonist to partial agonist activity. Biochem Pharmacol 83:952–961
9. Dresen S, Ferreirós N, Pütz M, Westphal F, Zimmermann R, Auwärter V (2010) Monitoring of herbal mixtures potentially containing synthetic cannabinoids as psychoactive compounds. J Mass Spectrom 45:1186–1194
10. Gurney SMR, Scott KS, Kacinko SL, Presley BC, Logan BK (2014) Pharmacology, toxicology, and adverse effects of synthetic cannabinoid drugs. Forensic Sci Rev 26:53–78
11. Saito T, Namera A, Miura N, Ohta S, Miyazaki S, Osawa M, Inokuchi S (2013) A fatal case of MAM-2201 poisoning. Forensic Toxicol 31:333–337
12. Sasaki C, Saito T, Shinozuka T, Irie W, Murakami C, Maeda K, Nakamaru N, Oishi M, Nakamura S, Kurihara K (2015) A case of death caused by abuse of a synthetic cannabinoid N-1-naphthalenyl-1-pentyl-1H-indole-3-carboxamide. Forensic Toxicol 33:165–169
13. Arntson A, Ofsa B, Lancaster D, Simon JR, McMullin M, Logan B (2013) Validation of a novel immunoassay for the detection of synthetic cannabinoids and metabolites in urine specimens. J Anal Toxicol 37:284–290
14. Barnes AJ, Young S, Spinelli E, Martin TM, Klette KL, Huestis MA (2014) Evaluation of a homogenous enzyme immunoassay for the detection of synthetic cannabinoids in urine. Forensic Sci Int 241:27–34
15. 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
16. Kneisel S, Speck M, Moosmann B, Corneillie TM, Butlin NG, Auwärter V (2013) 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 405:4691–4706
17. Kim J, Park Y, Park M, Kim E, Yang W, Baeck S, Lee S, Han S (2015) Simultaneous determination of five naphthoylindole-based synthetic cannabinoids and metabolites and their deposition in human and rat hair. J Pharm Biomed Anal 102:162–175
18. Mazzarino M, de la Torre X, Botrè F (2014) A liquid chromatography-mass spectrometry method based on class characteristic fragmentation pathways to detect the class of indole-derivative synthetic cannabinoids in biological samples. Anal Chim Acta 837:70–82
19. Huppertz LM, Kneisel S, Auwärter V, Kempf J (2014) 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 49:117–127
20. Simões SS, Silva I, Ajenjo AC, Dias MJ (2014) Validation and application of an UPLC-MS/MS method for the quantification of synthetic cannabinoids in urine samples and analysis of seized materials from the Portuguese market. Forensic Sci Int 243:117–125
21. Scheidweiler KB, Jarvis MJ, Huestis MA (2015) Nontargeted SWATH acquisition for identifying 47 synthetic cannabinoid metabolites in human urine by liquid chromatography-high-resolution tandem mass spectrometry. Anal Bioanal Chem 407:883–897
22. Sundström M, Pelander A, Angerer V, Hutter M, Kneisel S, Ojanperä I (2013) 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 405:8463–8474
23. Kronstrand R, Brinkhagen L, Birath-Karlsson C, Roman M, Josefsson M (2014) LC-QTOF-MS as a superior strategy to immunoassay for the comprehensive analysis of synthetic cannabinoids in urine. Anal Bioanal Chem 406:3599–3609
24. Chimalakonda KC, Moran CL, Kennedy PD, Endres GW, Uzieblo A, Dobrowolski PJ, Fifer EK, Lapoint J, Nelson LS, Hoffman RS, James LP, Radominska-Pandya A, Moran JH (2011) Solid-phase extraction and quantitative measurement of omega and omega-1 metabolites of JWH-018 and JWH-073 in human urine. Anal Chem 83:6381–6388
25. Hutter M, Moosmann B, Kneisel S, Auwärter V (2013) Characteristics of the designer drug and synthetic cannabinoid receptor agonist AM-2201 regarding its chemistry and metabolism. J Mass Spectrom 48:885–894
26. Jang M, Yang W, Shin I, Choi H, Chang H, Kim E (2014) Determination of AM-2201 metabolites in urine and comparison with JWH-018 abuse. Int J Legal Med 128:285–294
27. Jang M, Shin I, Yang W, Chang H, Yoo HH, Lee J, Kim E (2014) Determination of major metabolites of MAM-2201 and JWH-122 in in vitro and in vivo studies to distinguish their intake. Forensic Sci Int 244:85–91
28. Peters FT, Drummer OH, Musshoff F (2007) Validation of new methods. Forensic Sci Int 165:216–224
29. 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
30. Viswanathan CT, Bansal S, Booth B, DeStefano AJ, Rose MJ, Sailstad J, Shah VP, Skelly JP, Swann PG, Weiner R (2007) Quantitative bioanalytical methods validation and implementation: best practices for chromatographic and ligand binding assays. Pharm Res 24:1962–1973
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. Yanes EG, Lovett DP (2012) High-throughput bioanalytical method for analysis of synthetic cannabinoid metabolites in urine using salting-out sample preparation and LC-MS/MS. J Chromatogr B 909:42–50
33. Scheidweiler KB, Huestis MA (2014) 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 1327:105–117