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)-MSn

Analytical and Bioanalytical Chemistry

Volumn 406, Issue 7, 2014, Pages 1957-1974

  Welter, Jessica ^a   Meyer, Markus R ^a   Kavanagh, Pierce ^b   Maurer, Hans H ^a  

^a SAARLAND UNIVERSITY   (Germany)

^b ST JAMES S HOSPITAL   (Ireland)

Author keywords

Designer drugs; GC MS; Metabolism; Methyl amphetamine

Indexed keywords

ACETYLATION; AMINES; AROMATIC COMPOUNDS; BIOMOLECULES; CONTROLLED DRUG DELIVERY; DRUG PRODUCTS; GAS CHROMATOGRAPHY; HYDROXYLATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; METABOLITES; PHASE SEPARATION; PLANTS (BOTANY); RATS; RISK ASSESSMENT; TARGETED DRUG DELIVERY;

AROMATIC HYDROXYLATION; DESIGNER DRUGS; GAS CHROMATOGRAPHY-MASS SPECTROMETRIES (GC-MS); GC-MS; LINEAR ION TRAP MASS SPECTROMETRIES; METHYL-AMPHETAMINE; RISK ASSESSMENT REPORTS; SOLID-PHASE EXTRACTION;

ISOMERS;

RATTUS;

1 (4 METHYLPHENYL)PROPANE 2 AMINE; 1-(4-METHYLPHENYL)PROPANE-2-AMINE; 2 METHYLAMPHETAMINE; 2-METHYLAMPHETAMINE; 3 METHYLAMPHETAMINE; 3-METHYLAMPHETAMINE; AMPHETAMINE DERIVATIVE; CYTOCHROME P450;

ANIMAL; ARTICLE; DRUG DETOXIFICATION; DRUG EFFECT; ELECTROSPRAY MASS SPECTROMETRY; ENZYMOLOGY; EQUIPMENT; HUMAN; ISOMERISM; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; MALE; MASS FRAGMENTOGRAPHY; METABOLISM; METHODOLOGY; RAT; SUBSTANCE ABUSE; URINE; WISTAR RAT;

AMPHETAMINES; ANIMALS; CHROMATOGRAPHY, LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; ISOMERISM; MALE; METABOLIC DETOXICATION, PHASE I; METABOLIC DETOXICATION, PHASE II; MICROSOMES, LIVER; RATS; RATS, WISTAR; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SUBSTANCE ABUSE DETECTION;

EID: 84898040669     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-013-7595-5     Document Type: Article

References (32)

1. Westphal F, Schaefer T, Zechlin L, Stoll S (2011) Identification of 4-methylamphetamine in a seized amphetamine mixture. Toxichem Krimtech 35:306-315
2. Wee S, Anderson KG, Baumann MH, Rothman RB, Blough BE, Woolverton WL (2005) Relationship between the serotonergic activity and reinforcing effects of a series of amphetamine analogs. J Pharmacol Exp Ther 313:848-854
3. Rothman RB, Baumann MH (2006) Balance between dopamine and serotonin release modulates behavioral effects of amphetamine-type drugs. Ann N Y Acad Sci 1074:245-260
4. Baumann MH, Clark RD, Woolverton WL, Wee S, Blough BE, Rothman RB (2011) In vivo effects of amphetamine analogs reveal evidence for serotonergic inhibition of mesolimbic dopamine transmission in the rat. J Pharmacol Exp Ther 337:218-225
5. Kimmel HL, Manvich DF, Blough BE, Negus SS, Howell LL (2009) Behavioral and neurochemical effects of amphetamine analogs that release monoamines in the squirrel monkey. Pharmacol Biochem Behav 94:278-284
6. Wellman PJ, Davis KW, Clifford PS, Rothman RB, Blough BE (2009) Changes in feeding and locomotion induced by amphetamine analogs in rats. Drug Alcohol Depend 100:234-239
7. Negus SS, Mello NK, Blough BE, Baumann MH, Rothman RB (2007) Monoamine releasers with varying selectivity for dopamine/norepinephrine versus serotonin release as candidate "agonist" medications for cocaine dependence: studies in assays of cocaine discrimination and cocaine self-administration in rhesus monkeys. J Pharmacol Exp Ther 320:627-636
8. Marsh DF, Herring DA (1950) The pharmacological activity of the ring methyl substituted phenisopropylamines. J Pharmacol Exp Ther 100:298-308
9. Higgs RA, Glennon RA (1990) Stimulus properties of ring-methyl amphetamine analogs. Pharmacol Biochem Behav 37:835-837
10. European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) (2012) Europol Joint Report on a new psychoactive substance: 4-methylamphetamine. http://www.emcdda.europa.eu/attachements.cfm/att-191982-EN-TDAS12001ENN.PDF Accessed December 2013
11. Davis S, Blakey K, Rands-Trevor K (2012) GC-MS and GC-IRD analysis of 2-, 3- and 4-methylmethamphetamine and 2-, 3- and 4-methylamphetamine. Forensic Sci Int 220:67-73
12. Pedersen AJ, Dalsgaard PW, Rode AJ, Rasmussen BS, Muller IB, Johansen SS, Linnet K (2013) Screening for illicit and medicinal drugs in whole blood using fully automated SPE and ultra-high-performance liquid chromatography with TOF-MS with data-independent acquisition. J Sep Sci 36:2081-2089
13. Strano-Rossi S, Anzillotti L, Castrignano E, Romolo FS, Chiarotti M (2012) 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
14. Wissenbach DK, Meyer MR, Remane D, Weber AA, Maurer HH (2011) Development of the first metabolite-based LC-MSn urine drug screening procedure - exemplified for antidepressants. Anal Bioanal Chem 400:79-88
15. Wissenbach DK, Meyer MR, Remane D, Philipp AA, Weber AA, Maurer HH (2011) Drugs of abuse screening in urine as part of a metabolite-based LC-MS(n) screening concept. Anal Bioanal Chem 400:3481-3489
16. Power JD, Clarke K, McDermott SD, McGlynn P, Barry M, White C, O'Brien J, Kavanagh P (2013) The identification of 4-methylamphetamine and its synthesis by-products in forensic samples. Forensic Sci Int 228:115-131
17. Welter J, Meyer MR, Wolf E, Weinmann W, Kavanagh P, Maurer HH (2013) 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 405:3125-3135
18. Maurer HH, Pfleger K, Weber AA (2011) Mass spectral and GC data of drugs, poisons, pesticides, pollutants and their metabolites. Wiley-VCH, Weinheim
19. Ewald AH, Ehlers D, Maurer HH (2008) Metabolism and toxicological detection of the designer drug 4-chloro-2,5-dimethoxyamphetamine in rat urine using gas chromatography-mass spectrometry. Anal Bioanal Chem 390:1837-1842
20. Meyer MR, Peters FT, Maurer HH (2010) Automated mass spectral deconvolution and identification system for GC-MS screening for drugs, poisons, and metabolites in urine. Clin Chem 56:575-584
21. Peters FT, Schaefer S, Staack RF, Kraemer T, Maurer HH (2003) Screening for and validated quantification of amphetamines and of amphetamine- and piperazine-derived designer drugs in human blood plasma by gas chromatography/mass spectrometry. J Mass Spectrom 38:659-676
22. Meyer MR, Wilhelm J, Peters FT, Maurer HH (2010) 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 397:1225-1233
23. McLafferty FW, Turecek F (1993) Interpretation of mass spectra. University Science, Mill Valley
24. Smith RM, Busch KL (1999) Understanding mass spectra - a basic approach. Wiley, New York
25. Caldwell J, Dring LG, Williams RT (1972) Metabolism of [C-14]methamphetamine in man, guinea-pig and rat. Biochemical Journal 129:11-12
26. Dring LG, Smith RL, Williams RT (1970) The metabolic fate of amphetamine in man and other species. Biochem J 116:425-435
27. Shimosato K, Tomita M, Ijiri I (1986) Urinary excretion of p-hydroxylated methamphetamine metabolites in man. I. A method for determination by high-performance liquid chromatography-electrochemistry. Arch Toxicol 59:135-140
28. Pedersen AJ, Reitzel LA, Johansen SS, Linnet K (2013) In vitro metabolism studies on mephedrone and analysis of forensic cases. Drug Test Anal 5:430-438
29. Shima N, Katagi M, Kamata H, Zaitsu K, Kamata T, Nishikawa M, Miki A, Tsuchihashi H, Sakuma T, Nemoto N (2008) Urinary excretion of the main metabolites of 3,4-methylenedioxymethamphetamine (MDMA), including the sulfate and glucuronide of 4-hydroxy-3-methoxymethamphetamine (HMMA), in humans and rats. Xenobiotica 38:314-324
30. Meyer MR, Bach M, Welter J, Bovens M, Turcant A, Maurer HH (2013) Ketamine-derived designer drug methoxetamine: metabolism including isoenzyme kinetics and toxicological detectability using GC-MS and LC-(HR-)MSn. Anal Bioanal Chem 405:6307-6321
31. Law MY, Slawson MH, Moody DE (2000) Selective involvement of cytochrome P450 2D subfamily in in vivo 4-hydroxylation of amphetamine in rat. Drug Metab Dispos 28:348-353
32. Sharma V, McNeill JH (2009) To scale or not to scale: the principles of dose extrapolation. Br J Pharmacol 157:907-921