Recent developments in urinalysis of metabolites of new psychoactive substances using LC-MS

Bioanalysis

Volumn 6, Issue 15, 2014, Pages 2083-2107

  Peters, Frank T ^a  

^a JENA UNIVERSITY HOSPITAL   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1 BUTYL 3 (1 NAPHTHOYL)INDOLE; 3 (1 NAPHTHOYL) 1 PENTYLINDOLE; 3,4 DIMETHYLMETHCATHINONE; 4' METHYLMETHCATHINONE; ACETONITRILE; AM 2201; CANNABINOID DERIVATIVE; DESIGNER DRUG; DESOXYPIPRADROL; DRUG METABOLITE; FLUBROMAZEPAM; JWH 019; JWH 122; JWH 200; JWH 203; JWH 210; JWH 250; JWH 251; JWH 398; METHIOPROPAMINE; METHYLENEDIOXYPYROVALERONE; NEW DRUG; PSYCHOTROPIC AGENT; PYRROLIDINOPENTIOPHENONE; RCS 4; RECREATIONAL DRUG; UNCLASSIFIED DRUG; UR 144; XLR 11;

ANALYTIC METHOD; ANALYTICAL RESEARCH; DATA ANALYSIS; DRUG CONJUGATION; DRUG DESIGN; DRUG DETERMINATION; DRUG MONITORING; DRUG SCREENING; DRUG STABILITY; DRUG URINE LEVEL; ELECTROSPRAY MASS SPECTROMETRY; ENANTIOSELECTIVITY; HUMAN; IN VITRO STUDY; INTERMETHOD COMPARISON; LIQUID CHROMATOGRAPHY; LIQUID LIQUID EXTRACTION; MASS SPECTROMETRY; METABOLITE; MOLECULAR STABILITY; PROCESS CONTROL; PROCESS DESIGN; PROCESS DEVELOPMENT; PROCESS MONITORING; PROCESS OPTIMIZATION; REVIEW; SEPARATION TECHNIQUE; SOLID PHASE EXTRACTION; SPECTRAL SENSITIVITY; STANDARD; TANDEM MASS SPECTROMETRY; TOXICOLOGY; URINALYSIS; VALIDATION PROCESS; ADDICTION; ANIMAL; METABOLOMICS; PROCEDURES; SUBSTANCE ABUSE; URINE;

ANIMALS; CHROMATOGRAPHY, LIQUID; HUMANS; METABOLOMICS; PSYCHOTROPIC DRUGS; SUBSTANCE ABUSE DETECTION; SUBSTANCE-RELATED DISORDERS; TANDEM MASS SPECTROMETRY; URINALYSIS;

EID: 84908054042     PISSN: 17576180     EISSN: 17576199     Source Type: Journal    
DOI: 10.4155/BIO.14.168     Document Type: Review

References (97)

1. Schep LJ, Slaughter RJ, Vale JA, Beasley DM, Gee P. The clinical toxicology of the designer "party pills" benzylpiperazine and trifluoromethylphenylpiperazine. Clin. Toxicol. (Phila.) 49(3), 131-141 (2011).
2. Lin JC, Jan RK, Kydd RR, Russell BR. Subjective effects in humans following administration of party pill drugs BZP and TFMPP alone and in combination. Drug Test. Anal. 3(9), 582-585 (2011).
3. De Boer D, Bosman IJ, Hidvegi E et al. Piperazine-like compounds: a new group of designer drugs-of-abuse on the European market. Forensic Sci. Int. 121(1-2), 47-56 (2001).
4. Staack RF, Maurer HH. Metabolism of designer drugs of abuse. Curr. Drug Metab. 6(3), 259-274 (2005).
5. Peters FT, Martinez-Ramirez JA. Analytical toxicology of emerging drugs of abuse. Ther. Drug Monit. 32(5), 532-539 (2010).
6. Johansen SS, Hansen AC, Muller IB, Lundemose JB, Franzmann MB. Three fatal cases of PMA and PMMA poisoning in Denmark. J Anal. Toxicol. 27(4), 253-256 (2003).
7. Kraner JC, McCoy DJ, Evans MA, Evans LE, Sweeney BJ. Fatalities caused by the MDMA-related drug paramethoxyamphetamine (PMA). J. Anal. Toxicol. 25(7), 645-648 (2001).
8. Lin DL, Liu HC, Yin HL. Recent paramethoxymethamphetamine (PMMA) deaths in Taiwan. J. Anal. Toxicol. 31(2), 109-113 (2007).
9. EMCDDA-Europol. EMCDDA-Europol 2011 Annual Report on the implementation of Council Decision 2005/387/JHA (2012).http://www.emcdda.europa.eu/attachements.cfm/att-212366-EN-EMCDDA-Europol%202012%20Annual%20Report-final.pdf
10. Valente MJ, Guedes De Pinho P, De Lourdes Bastos M, Carvalho F, Carvalho M. Khat and synthetic cathinones: a review. Arch. Toxicol. 88(1), 15-45 (2014).
11. Spiller HA, Ryan ML, Weston RG, Jansen J. Clinical experience with and analytical confirmation of "bath salts" and "legal highs" (synthetic cathinones) in the United States. Clin. Toxicol. (Phila.) 49(6), 499-505 (2011).
12. Prosser JM, Nelson LS. The toxicology of bath salts: a review of synthetic cathinones. J. Med. Toxicol. 8(1), 33-42 (2012).
13. Winder GS, Stern N, Hosanagar A. Are "bath salts" the next generation of stimulant abuse? J. Subst. Abuse Treat. 44(1), 42-45 (2013).
14. Zuba D, Byrska B, Maciow M. Comparison of "herbal highs" composition. Anal. Bioanal. Chem. 400(1), 119-126 (2011).
15. Ernst L, Kruger K, Lindigkeit R, Schiebel HM, Beuerle T. Synthetic cannabinoids in "spice-like" herbal blends: first appearance of JWH-307 and recurrence of JWH-018 on the German market. Forensic Sci. Int. 222(1-3), 216-222 (2012).
16. Seely KA, Patton AL, Moran CL et al. Forensic investigation of K2, Spice, and "bath salt" commercial preparations: a three-year study of new designer drug products containing synthetic cannabinoid, stimulant, and hallucinogenic compounds. Forensic Sci. Int. 233(1-3), 416-422 (2013).
17. Helander A, Beck O, Hagerkvist R, Hulten P. Identification of novel psychoactive drug use in Sweden based on laboratory analysis - initial experiences from the STRIDA project. Scand. J. Clin. Lab. Invest. 73(5), 400-406 (2013).
18. Auwarter V, Dresen S, Weinmann W, Muller M, Putz M, Ferreiros N. 'Spice' and other herbal blends: harmless incense or cannabinoid designer drugs? J. Mass Spectrom. 44(5), 832-837 (2009).
19. Elliott S. Cat and mouse: the analytical toxicology of designer drugs. Bioanalysis 3(3), 249-251 (2011).
20. Kronstrand R, Roman M, Andersson M, Eklund A. Toxicological findings of synthetic cannabinoids in recreational users. J. Anal. Toxicol. 37(8), 534-541 (2013).
21. Favretto D, Pascali JP, Tagliaro F. New challenges and innovation in forensic toxicology: focus on the "new psychoactive substances". J. Chromatogr. A 1287, 84-95 (2013).
22. Staack RF, Fritschi G, Maurer HH. Studies on the metabolism and toxicological detection of the new designer drug N-benzylpiperazine in urine using gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 773(1), 35-46 (2002).
23. Vorce S P, Holler JM, Levine B, Past MR. Detection of 1-benzylpiperazine and 1-(3-trifluoromethylphenyl)-piperazine in urine analysis specimens using GC-MS and LC-ESI-MS. J. Anal. Toxicol. 32(6), 444-450 (2008).
24. Bell C, George C, Kicman AT, Traynor A. Development of a rapid LC-MS/MS method for direct urinalysis of designer drugs. Drug Test. Anal. 3(7-8), 496-504 (2011).
25. Kerrigan S, Mellon MB, Banuelos S, Arndt C. Evaluation of commercial enzyme-linked immunosorbent assays to identify psychedelic phenethylamines. J. Anal. Toxicol. 35(7), 444-451 (2011).
26. Grigoryev A, Melnik A, Savchuk S, Simonov A, Rozhanets V. 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 Analyt. Technol. Biomed. Life Sci. 879(25), 2519-2526 (2011).
27. Arntson A, Ofsa B, Lancaster D, Simon JR, Mcmullin M, Logan B. Validation of a novel immunoassay for the detection of synthetic cannabinoids and metabolites in urine specimens. J. Anal. Toxicol. 37(5), 284-290 (2013).
28. Kronstrand R, Brinkhagen L, Birath-Karlsson C, Roman M, Josefsson M. LC-QTOF-MS as a superior strategy to immunoassay for the comprehensive analysis of synthetic cannabinoids in urine. Anal. Bioanal. Chem. 406(15), 3599-3609 (2014).
29. Meyer MR, Peters FT. Analytical toxicology of emerging drugs of abuse - an update. Ther. Drug Monit. 34(6), 615-621 (2012).
30. Peters FT, Meyer MR. Analytical techniques for the detection of novel psychoactive substances and their metabolites. In: Novel Psychoactive Substances: Classification, Pharmacology and Toxicology. Dargan PI, Wood DM (Eds). Elsevier, CA, USA, 131-157 (2013).
31. Drummer OH. Requirements for bioanalytical procedures in postmortem toxicology. Anal. Bioanal. Chem. 388(7), 1495-1503 (2007).
32. Maurer HH. Position of chromatographic techniques in screening for detection of drugs or poisons in clinical and forensic toxicology and/or doping control [review] Clin. Chem. Lab. Med. 42(11), 1310-1324 (2004).
33. Thevis M, Schanzer W. Mass spectrometry in sports drug testing: structure characterization and analytical assays. Mass Spectrom. Rev. 26(1), 79-107 (2007).
34. Meyer MR, Maurer HH. Metabolism of designer drugs of abuse: an updated review. Curr. Drug Metab. 11(5), 468-482 (2010).
35. Sobolevsky T, Prasolov I, Rodchenkov G. Detection of JWH-018 metabolites in smoking mixture post-administration urine. Forensic Sci. Int. 200(1-3), 141-147 (2010).
36. Hutter M, Broecker S, Kneisel S, Auwarter V. 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(1), 54-65 (2012).
37. Adamowicz P, Zuba D, Sekula K. Analysis of UR-144 and its pyrolysis product in blood and their metabolites in urine. Forensic Sci. Int. 233(1-3), 320-327 (2013).
38. Kavanagh P, Grigoryev A, Melnik A, Savchuk S, Simonov A, Rozhanets V. Detection and tentative identification of urinary phase I metabolites of phenylacetylindole cannabimimetics JWH-203 and JWH-251, by GC-MS and LC-MS/MS. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 934, 102-108 (2013).
39. Stellpflug SJ, Kealey SE, Hegarty CB, Janis GC. 2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl) methyl] ethanamine (25I-NBOMe): clinical case with unique confirmatory testing. J. Med. Toxicol. 10(1), 45-50 (2014).
40. Sobolevsky T, Prasolov I, Rodchenkov G. Detection of urinary metabolites of AM-2201 and UR-144, two novel synthetic cannabinoids. Drug Test. Anal.doi:10.1002/dta.1418 (2012) (Epub ahead of print).
41. Peters FT, Meyer MR. In vitro approaches to studying the metabolism of new psychoactive compounds. Drug Test. Anal. 3(7-8), 483-495 (2011).
42. Wintermeyer A, Moller I, Thevis M et al. In vitro phase I metabolism of the synthetic cannabimimetic JWH-018. Anal. Bioanal. Chem. 398(5), 2141-2153 (2010).
43. Elsohly MA, Gul W, Elsohly KM, Murphy TP, Madgula VL, Khan SI. Liquid chromatography-tandem mass spectrometry analysis of urine specimens for K2 (JWH-018) metabolites. J. Anal. Toxicol. 35(7), 487-495 (2011).
44. Beuck S, Moller I, Thomas A et al. 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(2), 493-505 (2011).
45. Moller I, Wintermeyer A, Bender K et al. Screening for the synthetic cannabinoid JWH-018 and its major metabolites in human doping controls. Drug Test. Anal. 3(9), 609-620 (2011).
46. Chimalakonda KC, Moran CL, Kennedy PD et al. Solid-phase extraction and quantitative measurement of omega and omega-1 metabolites of JWH-018 and JWH-073 in human urine. Anal. Chem. 83(16), 6381-6388 (2011).
47. Chimalakonda KC, Seely KA, Bratton SM et al. Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in K2/Spice: identification of novel cannabinoid receptor ligands. Drug Metab. Dispos. 40(11), 2174-2184 (2012).
48. De Brabanter N, Esposito S, Tudela E et al. In vivo and in vitro metabolism of the synthetic cannabinoid JWH-200. Rapid Commun. Mass Spectrom. 27(18), 2115-2126 (2013).
49. De Brabanter N, Esposito S, Geldof L et al. In vitro and in vivo metabolisms of 1-pentyl-3-(4-methyl-1-naphthoyl) indole (JWH-122). Forensic Toxicol. 31(2), 212-222 (2013).
50. Pedersen AJ, Reitzel LA, Johansen SS, Linnet K. In vitro metabolism studies on mephedrone and analysis of forensic cases. Drug Test. Anal. 5(6), 430-438 (2013).
51. Strano-Rossi S, Cadwallader AB, De La Torre X, Botre F. Toxicological determination and in vitro metabolism of the designer drug methylenedioxypyrovalerone (MPDV) by gas chromatography/mass spectrometry and liquid chromatography/quadrupole time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 24(18), 2706-2714 (2010).
52. Meyer MR, Du P, Schuster F, Maurer HH. Studies on the metabolism of the alpha-pyrrolidinophenone designer drug methylenedioxy-pyrovalerone (MDPV) in rat and human urine and human liver microsomes using GC-MS and LC-high-resolution MS and its detectability in urine by GC-MS. J. Mass Spectrom. 45(12), 1426-1442 (2010).
53. Tyrkko E, Pelander A, Ketola RA, Ojanpera I. In silico and in vitro metabolism studies support identification of designer drugs in human urine by liquid chromatography/quadrupole-time-of-flight mass spectrometry. Anal. Bioanal. Chem. 405(21), 6697-6709 (2013).
54. Moosmann B, Huppertz LM, Hutter M, Buchwald A, Ferlaino S, Auwarter V. Detection and identification of the designer benzodiazepine flubromazepam and preliminary data on its metabolism and pharmacokinetics. J. Mass Spectrom. 48(11), 1150-1159 (2013).
55. Emerson B, Durham B, Gidden J, Lay JO Jr. Gas chromatography-mass spectrometry of JWH-018 metabolites in urine samples with direct comparison to analytical standards. Forensic Sci. Int. 229(1-3), 1-6 (2013).
56. Grigoryev A, Savchuk S, Melnik A et al. Chromatography-mass spectrometry studies on the metabolism of synthetic cannabinoids JWH-018 and JWH-073, psychoactive components of smoking mixtures. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 879(15-16), 1126-1136 (2011).
57. Jang M, Yang W, Choi H et al. Monitoring of urinary metabolites of JWH-018 and JWH-073 in legal cases. Forensic Sci. Int. 231(1-3), 13-19 (2013).
58. Jang M, Yang W, Shin I, Choi H, Chang H, Kim E. Determination of AM-2201 metabolites in urine and comparison with JWH-018 abuse. Int. J. Legal Med. 128(2), 285-294 (2014).
59. Moran CL, Le VH, Chimalakonda KC et al. Quantitative measurement of JWH-018 and JWH-073 metabolites excreted in human urine. Anal. Chem. 83(11), 4228-4236 (2011).
60. Patton AL, Seely KA, Chimalakonda KC et al. Targeted metabolomic approach for assessing human synthetic cannabinoid exposure and pharmacology. Anal. Chem. 85(19), 9390-9399 (2013).
61. Scheidweiler KB, Huestis MA. 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 (2014).
62. Strano-Rossi S, Anzillotti L, Castrignano E, Romolo FS, Chiarotti M. Ultra high performance liquid chromatography-electrospray ionization-tandem mass spectrometry screening method for direct analysis of designer drugs, "spice" and stimulants in oral fluid. J. Chromatogr. A 1258, 37-42 (2012).
63. Wohlfarth A, Scheidweiler KB, Chen X, Liu H F, Huestis MA. Qualitative confirmation of 9 synthetic cannabinoids and 20 metabolites in human urine using LC-MS/MS and library search. Anal. Chem. 85(7), 3730-3738 (2013).
64. Yanes EG, Lovett DP. High-throughput bioanalytical method for analysis of synthetic cannabinoid metabolites in urine using salting-out sample preparation and LC-MS/MS. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 909, 42-50 (2012).
65. Gandhi AS, Zhu M, Pang S et al. First characterization of AKB-48 metabolism, a novel synthetic cannabinoid, using human hepatocytes and high-resolution mass spectrometry. AAPS J. 15(4), 1091-1098 (2013).
66. Meyer MR, Bach M, Welter J, Bovens M, Turcant A, Maurer HH. Ketamine-derived designer drug methoxetamine: metabolism including isoenzyme kinetics and toxicological detectability using GC-MS and LC-(HR-)MSn. Anal. Bioanal. Chem. 405(19), 6307-6321 (2013).
67. Meyer MR, Caspar A, Brandt SD, Maurer HH. A qualitative/quantitative approach for the detection of 37 tryptamine-derived designer drugs, 5 beta-carbolines, ibogaine, and yohimbine in human urine and plasma using standard urine screening and multi-analyte approaches. Anal. Bioanal. Chem. 406(1), 225-237 (2014).
68. Meyer MR, Lindauer C, Welter J, Maurer HH. Dimethocaine, a synthetic cocaine analogue: studies on its in-vivo metabolism and its detectability in urine by means of a rat model and liquid chromatography-linear ion-trap (high-resolution) mass spectrometry. Anal. Bioanal. Chem. 406(7), 1845-1854 (2014).
69. Meyer MR, Mauer S, Meyer GM et al. The in vivo and in vitro metabolism and the detectability in urine of 3′,4′-methylenedioxy-alpha-pyrrolidinobutyrophenone (MDPBP), a new pyrrolidinophenone-type designer drug, studied by GC-MS and LC-MS. Drug Test. Anal. 6(7-8), 746-756 (2014).
70. Meyer MR, Prosser D, Maurer HH. Studies on the metabolism and detectability of the designer drug beta-naphyrone in rat urine using GC-MS and LC-HR-MS/MS. Drug Test. Anal. 5(4), 259-265 (2013).
71. Meyer MR, Schmitt S, Maurer HH. Studies on the metabolism and detectability of the emerging drug of abuse diphenyl-2-pyrrolidinemethanol (D2PM) in rat urine using GC-MS and LC-HR-MS/MS. J. Mass Spectrom. 48(2), 243-249 (2013).
72. Meyer MR, Wilhelm J, Peters FT, Maurer HH. Beta-keto amphetamines: studies on the metabolism of the designer drug mephedrone and toxicological detection of mephedrone, butylone, and methylone in urine using gas chromatography-mass spectrometry. Anal. Bioanal. Chem. 397(3), 1225-1233 (2010).
73. Welter J, Meyer MR, Wolf EU, Weinmann W, Kavanagh P, Maurer HH. 2-methiopropamine, a thiophene analogue of methamphetamine: studies on its metabolism and detectability in the rat and human using GC-MS and LC-(HR)-MS techniques. Anal. Bioanal. Chem. 405(10), 3125-3135 (2013).
74. Welter J, Meyer MR, Kavanagh P, Maurer HH. Studies on the metabolism and the detectability of 4-methyl-amphetamine and its isomers 2-methyl-amphetamine and 3-methyl-amphetamine in rat urine using GC-MS and LC-(high-resolution)-MS. Anal. Bioanal. Chem. 406(7), 1957-1974 (2014).
75. Antia U, Lee HS, Kydd RR, Tingle MD, Russell BR. Pharmacokinetics of 'party pill' drug N-benzylpiperazine (BZP) in healthy human participants. Forensic Sci. Int. 186(1-3), 63-67 (2009).\
76. Antia U, Tingle MD, Russell BR. Validation of an LC-MS method for the detection and quantification of BZP and TFMPP and their hydroxylated metabolites in human plasma and its application to the pharmacokinetic study of TFMPP in humans. J. Forensic Sci. 55(5), 1311-1318 (2010).
77. De Jager AD, Warner JV, Henman M, Ferguson W, Hall A. LC-MS/MS method for the quantitation of metabolites of eight commonly-used synthetic cannabinoids in human urine - an Australian perspective. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 897, 22-31 (2012).
78. Hutter M, Moosmann B, Kneisel S, Auwarter V. Characteristics of the designer drug and synthetic cannabinoid receptor agonist AM-2201 regarding its chemistry and metabolism. J. Mass Spectrom. 48(7), 885-894 (2013).
79. Moosmann B, Hutter M, Huppertz LM, Ferlaino S, Redlingshöfer L, Auwärter V. Characterization of the designer benzodiazepine pyrazolam and its detectability in human serum and urine. Forensic Toxicol. 31(2), 263-271 (2013).
80. Sundstrom M, Pelander A, Angerer V, Hutter M, Kneisel S, Ojanpera I. 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(26), 8463-8474 (2013).
81. Jin MJ, Jin C, Kim JY, In MK, Kwon OS, Yoo HH. A quantitative method for simultaneous determination of 5-methoxy-N, N-diisopropyltryptamine and its metabolites in urine using liquid chromatography-electrospray ionization-tandem mass spectrometry. J. Forensic Sci. 56(4), 1044-1048 (2011).
82. Lovett DP, Yanes EG, Herbelin TW, Knoerzer TA, Levisky JA. 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), 81-87 (2013).
83. Shima N, Katagi M, Kamata H et al. Metabolism of the newly encountered designer drug α-pyrrolidinovalerophenone in humans: identification and quantitation of urinary metabolites. Forensic Toxicol. 32(1), 59-67 (2013).
84. Zaitsu K, Katagi M, Kamata HT et al. Determination of the metabolites of the new designer drugs bk-MBDB and bk-MDEA in human urine. Forensic Sci. Int. 188(1-3), 131-139 (2009).
85. Shima N, Katagi M, Kamata H et al. Urinary excretion and metabolism of the newly encountered designer drug 3,4-dimethylmethcathinone in humans. Forensic Toxicol. 31(1), 101-112 (2012).
86. Concheiro M, Anizan S, Ellefsen K, Huestis MA. Simultaneous quantification of 28 synthetic cathinones and metabolites in urine by liquid chromatography-high resolution mass spectrometry. Anal. Bioanal. Chem. 405(29), 9437-9448 (2013).
87. Heltsley R, Shelby MK, Crouch DJ et al. Prevalence of synthetic cannabinoids in U.S. athletes: initial findings. J. Anal. Toxicol. 36(8), 588-593 (2012).
88. Kikura-Hanajiri R, Kawamura M, Miyajima A, Sunouchi M, Goda Y. Determination of a new designer drug, N-hydroxy-3,4-methylenedioxymethamphetamine and its metabolites in rats using ultra-performance liquid chromatography-tandem mass spectrometry. Forensic Sci. Int. 198(1-3), 62-69 (2010).
89. Grigoryev A, Kavanagh P, Melnik A, Savchuk S, Simonov A. Gas and liquid chromatography-mass spectrometry setection of the urinary metabolites of UR-144 and its,ajor pyrolysis product. J. Anal. Toxicol. 37(5), 265-276 (2013).
90. Wiley JL, Marusich JA, Lefever TW, Grabenauer M, Moore KN, Thomas BF. Cannabinoids in disguise: Delta9-tetrahydrocannabinol-like effects of tetramethylcyclopropyl ketone indoles. Neuropharmacology 75, 145-154 (2013).
91. Meyer MR, Vollmar C, Schwaninger AE, Wolf E, Maurer HH. New cathinone-derived designer drugs 3-bromomethcathinone and 3-fluoromethcathinone: studies on their metabolism in rat urine and human liver microsomes using GC-MS and LC-high-resolution MS and their detectability in urine. J. Mass Spectrom. 47(2), 253-262 (2012).
92. Zaitsu K, Katagi M, Tsuchihashi H, Ishii A. Recently abused synthetic cathinones, α-pyrrolidinophenone derivatives: a review of their pharmacology, acute toxicity, and metabolism. Forensic Toxicol. 32(1), 1-8 (2013).
93. Kim U, Jin MJ, Lee J, Han SB, In MK, Yoo HH. 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 (2012).
94. Wissenbach DK, Meyer MR, Remane D, Philipp AA, Weber AA, Maurer HH. Drugs of abuse screening in urine as part of a metabolite-based LC-MS(n) screening concept. Anal. Bioanal. Chem. 400(10), 3481-3489 (2011).
95. Wissenbach DK, Meyer MR, Remane D, Weber AA, Maurer HH. Development of the first metabolite-based LC-MS(n) urine drug screening procedure-exemplified for antidepressants. Anal. Bioanal. Chem. 400(1), 79-88 (2011).
96. Wohlfarth A, Pang S, Zhu M et al. First metabolic profile of XLR-11, a novel synthetic cannabinoid, obtained by using human hepatocytes and high-resolution mass spectrometry. Clin. Chem. 59(11), 1638-1648 (2013).
97. Hermanns-Clausen M, Kneisel S, Szabo B, Auwarter V. Acute toxicity due to the confirmed consumption of synthetic cannabinoids: clinical and laboratory findings. Addiction 108(3), 534-544 (2013).