In vitro characterization of potential CYP- and UGT-derived metabolites of the psychoactive drug 25B-NBOMe using LC-high resolution MS

Drug Testing and Analysis

Volumn 8, Issue 2, 2016, Pages 248-256

  Boumrah, Yacine ^a,b   Humbert, Luc ^c   Phanithavong, Melodie ^c   Khimeche, Kamel ^d   Dahmani, Abdallah ^a   Allorge, Delphine ^c,e  

^a UNIVERSITY OF SCIENCES AND TECHNOLOGY HOUARI BOUMEDIENE   (Algeria)

^b Institut National de Criminalistique et de Criminologie   (Algeria)

^c LILLE UNIVERSITY HOSPITAL   (France)

^d ECOLE MILITAIRE POLYTECHNIQUE   (Algeria)

^e UFR3S Pharmacie   (France)

Author keywords

25B NBOMe; Human liver microsomes; In vitro; Metabolism; UHPLC Q TOF MS

Indexed keywords

ACETYLATION; ALKYLATION; BIOMOLECULES; DETOXIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITES; PHYSIOLOGY;

25B-NBOME; BIOLOGICAL MATRIXES; BIOLOGICAL SAMPLES; DETECTION WINDOWS; FALSE NEGATIVES; HIGH RESOLUTION; HUMAN LIVER MICROSOMES; IN-VITRO; UHPLC-Q-TOF/MS; VITRO CHARACTERIZATION;

METABOLISM;

2 (4 BROMO 2,5 DIMETHOXYPHENYL) N [(2 METHOXYPHENYL)METHYL]ETHANAMINE; CYTOCHROME P450; DRUG METABOLITE; GLUCURONOSYLTRANSFERASE; PSYCHOTROPIC AGENT; UNCLASSIFIED DRUG; 2-(4-BROMO-2,5-DIMETHOXYPHENYL)-N-((2-METHOXYPHENYL)METHYL)ETHANAMINE; ANISOLE DERIVATIVE; DESIGNER DRUG; GLUTATHIONE; PHENETHYLAMINE DERIVATIVE; SULFATE;

ARTICLE; AUTOANALYSIS; CONTROLLED STUDY; DEMETHYLATION; DRUG ANALYSIS; DRUG DETERMINATION; DRUG HYDROXYLATION; DRUG IDENTIFICATION; DRUG METABOLISM; HUMAN; HUMAN TISSUE; IN VITRO STUDY; LIVER MICROSOME; ONLINE ANALYSIS; PRIORITY JOURNAL; QUADRUPOLE TIME OF FLIGHT MASS SPECTROMETRY; TIME OF FLIGHT MASS SPECTROMETRY; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; ACETYLATION; BIOTRANSFORMATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLISM; METHYLATION; PROCEDURES; SUBSTANCE ABUSE; TANDEM MASS SPECTROMETRY;

ACETYLATION; ANISOLES; BIOTRANSFORMATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; DESIGNER DRUGS; GLUCURONOSYLTRANSFERASE; GLUTATHIONE; HUMANS; IN VITRO TECHNIQUES; METHYLATION; MICROSOMES, LIVER; PHENETHYLAMINES; PSYCHOTROPIC DRUGS; SUBSTANCE ABUSE DETECTION; SULFATES; TANDEM MASS SPECTROMETRY;

EID: 84958760123     PISSN: 19427603     EISSN: 19427611     Source Type: Journal    
DOI: 10.1002/dta.1865     Document Type: Article

References (28)

1. S. Gibbons. 'Legal highs'-novel and emerging psychoactive drugs: A chemical overview for the toxicologist. Clin. Toxicol. (Phila.) 2012, 50, 15.
2. H.A. Spiller, M.L. Ryan, R.G. Weston, J. Jansen. Clinical experience with and analytical confirmation of 'bath salts' and 'legal highs' (synthetic cathinones) in the United States. Clin. Toxicol. (Phila.). 2011, 49, 499.
3. G.G. Davis. Drug abuse: newly-emerging drugs and trends. Clin. Lab. Med. 2012, 32, 407.
4. M.E. Nelson, S.M. Bryant, S.E. Aks. Emerging drugs of abuse. Emerg. Med. Clin. North Am. 2014, 32, 1.
5. S.D. Brandt, L.A. King, M. Evans-Brown. The new drug phenomenon. Drug Test. Anal. 2014, 6, 587.
6. P. Griffiths, M. Evans-Brown, R. Sedefov. Getting up to speed with the public health and regulatory challenges posed by new psychoactive substances in the information age. Addiction. 2013, 108, 1700.
7. T. Néfau, M. Martinez. Nouveaux produits de synthèse identifiés en France depuis 2000. Note d'information SINTES, 2014.
8. A. Shulgin, T. Manning, P. Daley. The Shulgin Index Vol 1: Psychedelic Phenethylamines and Related Compounds, Transform Press, Berkeley, CA, USA 2011.
9. A. Ninnemann, G.L. Stuart. The NBOMe series: a novel, dangerous group of hallucinogenic drugs. J. Stud. Alcohol Drugs. 2013, 74, 977.
10. GPHIN. What is NBOME?, Factivia, The Press, Christchurch, New Zealand 2013.
11. World Health Organization. 25B-NBOMe, Critical Review Report. 36th ECDD Agenda Item 4.18. 2014.
12. M.R. Meyer, H.H. Maurer. Metabolism of designer drugs of abuse: an updated review. Curr. Drug Metab. 2010, 11, 468.
13. M.H. Tang, C.K. Ching, M.S.H. Tsui, F.K.C. Chu, T.W.L. Mak. Two cases of severe intoxication associated with analytically confirmed use of the novel psychoactive substances 25B-NBOMe and 25C-NBOMe. Clin. Toxicol. 2014, 52, 561.
14. Y.N.A. Soh, S. Elliot. An investigation of the stability of emerging new psychoactive substances. Drug Test. Anal. 2014, 6, 696.
15. S.J. Stellpflug, S. E. Kealey, C.B. Hegarty, G.C. Janis. 2-(4-Iodo-2, 5-dimethoxyphenyl)-N-[(2 methoxyphenyl)methyl]ethanamine (25I-NBOMe): Clinical Case with Unique Confirmatory Testing. J. Med. Toxicol. 2013, 10, 45.
16. J.L. Poklis, C.R. Nanco, M.M. Troendle, C.E. Wolf, A. Poklis. Determination of 4-bromo-2, 5-dimethoxy-N-[(2-methoxyphenyl)methyl]-benzeneethanamine (25B-NBOMe) in serum and urine by high performance liquid chromatography with tandem mass spectrometry in a case of severe intoxication. Drug Test. Anal. 2014, 6, 764.
17. N.B. Holm, A.J. Pedersen, P.W. Dalsgaard, K. Linnet. Metabolites of 5F-AKB-48, a synthetic cannabinoid receptor agonist, identified in human urine and liver microsomal preparations using liquid chromatography high-resolutionmassspectrometry. Drug Test. Anal. 2015, 7, 199.
18. T. Sobolevsky, I. Prasolov, G. Rodchenkov. Study on the phase I metabolism of novel synthetic cannabinoids, APICA and its fluorinated analogue. Drug Test. Anal. 2015, 7, 131.
19. A.G. Helfer, A. Turcant, D. Boels, S. Ferec, B. Lelièvre, J. Welter, M.R. Meyer, H.H. Maurer. Elucidation of the metabolites of the novel psychoactive substance 4-methyl-N-ethyl-cathinone (4-MEC) inhuman urine and pooledliver microsomesby GC-MS and LC-HR-MS/MS techniques and of its detectability by GC-MS or LC-MSn standard screening approaches. Drug Test. Anal. 2014. DOI:10.1002/dta.1682.
20. 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 designerdrug, N-(adamantan-1-yl)-1-(5-fluoropentyl)-1H-indole-3-carboxamide (STS-135), using cryopreservedhumanhepatocytes and assessment of metabolic stability withhumanliver microsomes. Drug Test. Anal. 2014. DOI:10.1002/dta.1662.
21. A.J. Pedersen, L.A. Reitzel, S.S. Johansen, K. Linnet. In vitro metabolism studies on mephedrone and analysis of forensic cases. Drug Test. Anal. 2013, 5, 430.
22. J. Vacek, B. Papoušková, P. Kosina, A. Galandáková, J. Ulrichová. Mass spectrometric investigation of chelerythrine and dihydrochelerythrine biotransformation patterns in human hepatocytes. J. Chromatogr. B Biomed. Sci. Appl. 2013, 941, 17.
23. J. Vacek, B. Papoušková, J. Vrba, M. Zatloukalová, V. Křen, J. Ulrichová. LC/MS metabolic study on quercetin and taxifolin galloyl esters using human hepatocytes as toxicity and biotransformation in vitro cell model. J. Pharm. Biomed. Anal. 2013, 86, 135.
24. P. Kosina, J. Vacek, B. Papoušková, M. Stiborová, J. Stýskala, P. Cankař, E. Vrublová, J. Vostálová, V. Simánek, J. Ulrichová. Identification of benzo[c]phenanthridine metabolites in human hepatocytes by liquid chromatography with electrospray ion-trap and quadrupole time-of-flight mass spectrometry. J. Chromatogr. B Biomed. Sci. Appl. 2011, 879, 1077.
25. Y. Li, L. Wu, Y. Gu, D. Si, C. Liu. Metabolism of aildenafil in vivo in rats and in vitro in mouse, rat, dog, and human liver microsomes. Drug Test. Anal. 2014, 6, 552.
26. M.R. Meyer, J. Dinger, A.E. Schwaninger, D.K. Wissenbach, J. Zapp, G. Fritschi, H.H. Maurer. Qualitative studies on the metabolism and the toxicological detection of the fentanyl-derived designer drugs 3-methylfentanyl and isofentanyl inratsusing liquid chromatography-linear ion trap-mass spectrometry (LC-MS(n)). Anal. Bioanal. Chem. 2012, 402, 1249.
27. A.T. Caspar, A.G. Helfer, J.A. Michelely, V. Auwärter, S.D. Brandt, M.R. Meyer, H.H. Maurer. Studies on the metabolism and toxicological detection of the new psychoactive designer drug 2-(4-iodo-2, 5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine (25I-NBOMe) in human and rat urine using GC-MS, LC-MSn, and LC-HR-MS/MS. Anal. Bioanal. Chem. 2015. DOI:10.1007/s00216-015-8828-6.
28. C. Emoto, N. Murayama, A. Rostami-Hodjegan, H. Yamazaki. Methodologies for Investigating Drug Metabolism at the Early Drug Discovery Stage: Prediction of Hepatic Drug Clearance and P450 Contribution. Curr. Drug Metab. 2010, 11, 678.