Targeting misuse of 2-amino-N-ethyl-1-phenylbutane in urine samples: In vitro-in vivo correlation of metabolic profiles and development of LC-TOF-MS method

Drug Testing and Analysis

Volumn 7, Issue 2, 2015, Pages 89-94

  Kobayashi, Masaki ^a,b,c   Pelander, Anna ^a   Ketola, Raimo A ^a   Leinonen, Antti ^c   Kuuranne, Tiia ^c  

^a UNIVERSITY OF HELSINKI   (Finland)

^b KYOTO PREFECTURAL UNIVERSITY OF MEDICINE   (Japan)

^c Doping Control Laboratory   (Finland)

Author keywords

2 amino N ethyl 1 phenylbutane; Designer drugs; Doping control; High resolution mass spectrometry; LC TOF MS; Metabolism; Phenethylamine derivatives

Indexed keywords

BIOMOLECULES; DIETARY SUPPLEMENTS; GAS CHROMATOGRAPHY; HYDROXYLATION; INDUCTIVELY COUPLED PLASMA; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM;

2-AMINO-N-ETHYL-1-PHENYLBUTANE; DESIGNER DRUGS; DOPING CONTROL; HIGH RESOLUTION MASS SPECTROMETRY; IN-VITRO; LC-TOF-MS; PHENETHYLAMINE DERIVATIVE; PHENETHYLAMINES; URINE SAMPLE; VITRO-IN VIVO CORRELATION;

METABOLITES;

2 AMINO N ETHYL 1 PHENYLBUTANE; AMPHETAMINE; AMPHETAMINE DERIVATIVE; CYTOCHROME P450 2D6; DRUG METABOLITE; GLUCURONIDE; METHAMPHETAMINE; NOREPHEDRINE; PHENETHYLAMINE DERIVATIVE; UNCLASSIFIED DRUG; BUTYLAMINE; N-ETHYL-ALPHA-ETHYL-PHENETHYLAMINE;

ADULT; ARTICLE; CASE REPORT; CONTROLLED STUDY; DEALKYLATION; DOPING; DRUG ABSORPTION; DRUG ABUSE; DRUG BLOOD LEVEL; DRUG EXCRETION; DRUG HALF LIFE; DRUG METABOLISM; DRUG URINE LEVEL; GAS CHROMATOGRAPHY; HUMAN; HUMAN CELL; HUMAN TISSUE; HYDROLYSIS; HYDROXYLATION; IN VITRO STUDY; IN VIVO STUDY; LIQUID CHROMATOGRAPHY; MALE; MASS SPECTROMETRY; OXIDATION; PRIORITY JOURNAL; SINGLE DRUG DOSE; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; URINALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIVER MICROSOME; METABOLISM; METABOLOMICS; PROCEDURES; SUBSTANCE ABUSE; URINE;

ADULT; BUTYLAMINES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DOPING IN SPORTS; HUMANS; MALE; MASS SPECTROMETRY; METABOLOMICS; MICROSOMES, LIVER; SUBSTANCE ABUSE DETECTION;

EID: 84922041438     PISSN: 19427603     EISSN: 19427611     Source Type: Journal    
DOI: 10.1002/dta.1642     Document Type: Article

References (14)

1. L.J. Schep, R.J. Slaughter, D.M. Beasley. The clinical toxicology of metamfetamine. Clin. Toxicol. (Phila.) 2010, 48, 675.
2. R. Oberlender, D.E. Nichols. (+)-N-methyl-1-(1, 3-benzodioxol-5-yl)-2-butanamine as a discriminative stimulus in studies of 3, 4-methylenedioxy-methamphetamine-like behavioral activity. J. Pharmacol. Exp. Ther. 1990, 255, 1098.
3. World Anti-Doping Agency. 2012 Anti-Doping Testing Figures Report. Available at: http://www.wada-ama.org/Documents/Resources/Testing-Figures/WADA-2012-Anti-Doping-Testing-Figures-Report-EN.pdf [20 October 2013].
4. P.A. Cohen, J.C. Travis, B.J. Venhuis. A methamphetamine analog (N, alpha-diethyl-phenylethylamine) identified in a mainstream dietary supplement. Drug Test. Anal. 2013. DOI: 10.1002/dta.1578
5. T. Kuuranne, A. Leinonen, W. Schanzer, M. Kamber, R. Kostiainen, M. Thevis. Aryl-propionamide-derived selective androgen receptor modulators: Liquid chromatography-tandem mass spectrometry characterization of the in vitro synthesized metabolites for doping control purposes. Drug Metab. Dispos. 2008, 36, 571.
6. T. Kuuranne, M. Kurkela, M. Thevis, W. Schanzer, M. Finel, R. Kostiainen. Glucuronidation of anabolic androgenic steroids by recombinant human UDP-glucuronosyltransferases. Drug Metab. Dispos. 2003, 31, 1117.
7. M. Vahermo, T. Suominen, A. Leinonen, J. Yli-Kauhaluoma. Synthesis and characterization of hydroxylated mesocarb metabolites for doping control. Arch. Pharm. 2009, 342, 201.
8. M. Kolmonen, A. Leinonen, T. Kuuranne, A. Pelander, I. Ojanpera. Generic sample preparation and dual polarity liquid chromatography-time-of-flight mass spectrometry for high-throughput screening in doping analysis. Drug Test. Anal. 2009, 1, 250.
9. L. Li, T. Everhart, P. Jacob III, R. Jones, J. Mendelson. Stereoselectivity in the human metabolism of methamphetamine. Brit. J. Clin. Pharmacol. 2010, 69, 187.
10. E. Tyrkko, A. Pelander, R.A. Ketola, I. Ojanpera. 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. 2013, 405, 6697.
11. T. Shoda, K. Fukuhara, Y. Goda, H. Okuda. 4-hydroxy-3-methoxymethamphetamine glucuronide as a phase II metabolite of 3, 4-methylenedioxymethamphetamine: Enzyme-assisted synthesis and involvement of human hepatic uridine 5'-diphosphate-glucuronosyltransferase 2B15 in the glucuronidation. Chem. Pharm. Bull. (Tokyo) 2009, 57, 472.
12. A.E. Schwaninger, M.R. Meyer, H.H. Maurer. Investigation on the enantioselectivity of the sulfation of the methylenedioxymethamphetamine metabolites 3, 4-dihydroxymethamphetamine and 4-hydroxy-3-methoxymethamphetamine using the substrate-depletion approach. Drug Metab. Dispos. 2011, 39, 1998.
13. A.E. Schwaninger, M.R. Meyer, J. Zapp, H.H. Maurer. Investigations on the stereoselectivity of the phase II metabolism of the 3, 4-methylenedioxyethylamphetamine (MDEA) metabolites 3, 4-dihydroxyethylamphetamine (DHEA) and 4-hydroxy-3-methoxyethylamphetamine (HMEA). Toxicol. Lett. 2012, 212, 38.
14. A.E. Schwaninger, M.R. Meyer, A.J. Barnes, E.A. Kolbrich-Spargo, D.A. Gorelick, R.S. Goodwin, M.A. Huestis, H.H. Maurer. Urinary excretion kinetics of 3, 4-methylenedioxymethamphetamine (MDMA, ecstasy) and its phase I and phase II metabolites in humans following controlled MDMA administration. Clin. Chem. 2011, 57, 1748.