Testing for designer stimulants: Metabolic profiles of 16 synthetic cathinones excreted free in human urine

Journal of Analytical Toxicology

Volumn 38, Issue 5, 2014, Pages 233-241

  Uralets, Victor ^a   Rana, Sumandeep ^a   Morgan, Stewart ^a   Ross, Wayne ^a  

^a Redwood Toxicology Laboratory   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DIMETHYLMETHCATHINONE; 3,4 METHYLENEDIOXYPYROVALERONE; 4 METHYL N ETHYLCATHINONE; 4 METHYLBUPHEDRONE; 4' METHYLMETHCATHINONE; ALPHA PYRROLIDINOPENTIOPHENONE; ALPHA \PYRROLIDINOBUTIOPHENONE; BUPHEDRONE; BUTYLONE; CATHINONE; CENTRAL STIMULANT AGENT; DESIGNER DRUG; ETHCATHINONE; ETHYLONE; FLEPHEDRONE; METHYLONE; N ETHYLBUPHEDRONE; PENTEDRONE; PENTYLONE; SYNTHETIC CATHINONE DERIVATIVE; UNCLASSIFIED DRUG; ALKALOID;

ARTICLE; HUMAN; LIQUID LIQUID EXTRACTION; MASS FRAGMENTOGRAPHY; CHROMATOGRAPHY; URINE;

ALKALOIDS; CENTRAL NERVOUS SYSTEM STIMULANTS; CHROMATOGRAPHY; DESIGNER DRUGS; HUMANS;

EID: 84899972013     PISSN: 01464760     EISSN: 19452403     Source Type: Journal    
DOI: 10.1093/jat/bku021     Document Type: Article

References (42)

1. Consideration of the cathinones. Advisory council on the misuse of drugs. http://www.homeoffice.gov.uk/acmd1/acmd-cathinodesreport-2010?view=Binary (accessed January 2013).
2. European Monitoring Centre on Drugs and Drug Addiction. EMCDDA-Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA. http://www.emcdda.europa.eu/attachements.cfm/att_132857_EN_EMCDDA-Europol%20Annual%20Report%202010A.pdf (accessed January 2013).
3. European Monitoring Centre on Drugs and Drug Addiction. EMCDDA-drug profiles-synthetic cathinones. http://www.emcdda.europa.eu/publications/drug-profiles/synthetic-cathinones (accessed January 2013).
4. Torrance, H., Cooper, G. (2010) The detection of mephedrone (4-methylmethcathinone) in 4 fatalities in Scotland. Forensic Science International, 202, e62-e63.
5. Maskell, P.D., De Paoli, G., Seneviratne, C., Pounder, D.J. (2011) Mephedrone (4-methylcathinone)-related deaths. Journal of Analytical Toxicology, 35, 188-191.
6. DEA Press release (Oct 21, 2011). 'Chemicals used in 'bath salts' now under federal control and regulation'. http://www.justice.gov/dea/pubs/pressrel/pr102111.html (accessed January 2013).
7. Dal Cason, T.A., Young, R., Glennon, R.A. (1997) Cathinone: an investigation of several N-alkyl and methylenedioxy-substituted analogs. Pharmacology Biochemistry & Behavior, 58, 1109-1116.
8. Cozzi, N.V., Sievert, M.K., Shulgin, A.T., Jacob, P., III, Ruoho, A.E. (1998) Methcathinone and 2 methylamino-1-(3,4-methylenedioxyphenyl)propan-1-one (methylone) selectively inhibit plasma membrane catecholamine reuptake transporters. The Society for Neuroscience Abstract, 24, 341-348.
9. 3H]serotonin uptake into human platelets. American Chemical Society Abstracts, Division of Medicinal Chemistry, 215, 152.
10. Coppola, M., Mondola, R. (2012) 3,4-Methylenedioxypyrovalerone (MDPV): chemistry, pharmacology and toxicology of a new designer drug of abuse marketed online. Toxicology Letters, 208, 12-15.
11. Brandt, S.D., Sumnall, H.R., Measham, F., Cole, J. (2010) Analyses of second-generation 'legal highs' in the UK: initial findings. Drug Testing and Analysis, 2, 377-382.
12. Brenneisen, R., Fish, H.U., Kö bling, U., Giesshusler, S., Kalix, P. (1990) Amphetamine-like effects in humans of the Khat alkaloids cathinone. British Journal of Clinical Pharmacology, 30, 825-828.
13. Brenneisen, R., Geisshÿsler, S., Schorno, X. (1986) Metabolism of cathinone to (-)-norephedrine and (-)-norpseudoephedrine. Journal of Pharmacy and Pharmacology, 38, 298-300.
14. Mathys,K.,Brenneisen,R. (1992)DetectionofS-(-)-cathinoneanditsmain metabolites (R,S)-(-)-norephedrine and (R,S)-(-)norpseudoephedrine in urine by high-performance liquid chromatography with photodiode-array detection. Journal of Chromatography, 593, 70-85.
15. Toennes, S.W., Kauert, G.F. (2002) Excretion and detection of cathinone, cathine and phenylpropanolamine in urine after khat chewing. Clinical Chemistry, 48, 1715-1719.
16. Testa, B., Beckett, A.H. (1973) Metabolism and excretion of diethylpropion in man under acidic urine conditions. Journal of Pharmacy and Pharmacology, 25, 119-124.
17. Markantonis, S.L., Kyroudis, A., Beckett, A.H. (1986) The stereoselective metabolism of dimethylpropion and monomethylpropion. Biochemical Pharmacology, 35, 529-532.
18. Beckett, A.H., Stanojcić , M. (1987) Re-evaluation of the metabolism and excretion of diethylpropion in non-sustained and sustained release formulations. Journal of Pharmacy and Pharmacology, 39, 409-415.
19. Yu, H., Rothman, R.B., Dersch, C.M., Partilla, J.S., Rice, K.C. (2000) Uptake and release effects of diethylpropion and its metabolites with biogenic amine transporters. Bioorganic & Medicinal Chemistry, 8, 2689-2692.
20. Strano-Rossi, S., Cadwallader, A., De La Torre, X., Botrè , F. (2010) Toxicological determination and in vitro metabolism of the designer drug methylenedioxypyrovalerone (MPDV) by gas chromatography/ mass spectrometry and liquid chromatography/quadrupole timeof-flight mass spectrometry. Rapid Communications in Mass Spectrometry, 24, 2706-2714.
21. Pawlik, E., Plässer, G., Mahler, H., Daldrup, T. (2012) Studies on the phase I metabolism of the new designer drug 3-fluoromethcathinone using rabbit liver slices. The International Journal of Legal Medicine, 126, 231-240.
22. Meyer, M.R., Du, P., Schuster, F., Maurer, H.H. (2010) Studies on the metabolism of the a-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. Journal of Mass Spectrometry, 45, 1426-1442.
23. Meyer, M.R., Vollmar, C., Schwaninger, A.E., Wolf, E., Maurer, H.H. (2012) New cathinone-derived designer drugs 3-bromomethcathinone and 3-fluoromethcathinone: studies on their metabolism in rat and humanliver microsomes using GC-MS and LC-high-resolution MS and their detectability in urine. Journal of Mass Spectrometry, 202, 253-262.
24. Sauer, C., Peters, F.T., Haas, C., Meyer, M.R., Fritschi, G., Maurer, H.H. (2009) New designer drug a-pyrrolidinovalerophenone (a -PVP): studies on its metabolism and toxicological detection in rat urine using gas chromatographic-mass spectrometric techniques'. Journal of Mass Spectrometry, 44, 952-964.
25. Kamata, H., Shima, N., Zaitsu, K., Kamata, T., Miki, A., Nishikawa, M. et al. (2006) Metabolism of the recently encountered drug methylone in humans and rats. Xenobiotica, 36, 709-723.
26. Zaitsu, K., Katagi, M., Kamata, H., Kamata, T., Shima, N., Miki, A. et al. (2009) Determination of the metabolites of the new designer drugs bk-MBDB and bk-MDEA in human urine. Forensic Science International, 188, 131-139.
27. Meyer, M.R., Wilhelm, J., Peters, F.T., Maurer, H.H. (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. Analytical and Bioanalytical Chemistry, 397, 1225-1233.
28. Katagi, M., Zaitsu, K., Shima, N., Kamata, H., Kamata, T., Nakanishi, K. et al. (2010) Metabolism and forensic toxicological analysis of the extensively abused designer drug methylone. TIAFT Bulletin, 40, No.1, 30-35.
29. Meyer, M.R., Maurer, H.H. (2010) Metabolism of designer drugs of abuse: an updated review. Current Drug Metabolism, 2010, 468-482.
30. Zaitsu, K., Katagi, M., Tatsuno, M., Sato, T., Tsuchihashi, H., Suzuki, K. (2011) Recently abused b-keto derivatives of 3,4-methylendioxyphenylalkylamines: a review of their metabolism and toxicological analysis. Forensic Toxicology, 29, 73-84.
31. Saem de Burnaga Sanchez, J. (1929) Sur un homologue de l'éphé -drine. Bulletin de la Societé Chimique de France., 45, 284-286.
32. Hyde, J.F., Browning, E., Adams, R. (1928) Synthetic homologs of d,l-ephedrine. Journal of the American Chemical Society, 50, 2287-2292.
33. Maheux, C.R., Copeland, C.R. (2012) Chemical analysis of two new designer drugs: buphedrone and pentedrone. Drug Testing and Analysis, 4, 17-23.
34. Westphal, F., Junge, T., Girreser, U., Greibl, W., Doering, C. (2012) Mass, NMR and IR spectroscopic characterization of pentedrone and pentylone and identification of their isocathinone by-products. Forensic Science International, 217, 157-167.
35. Jankovics, P., Váradi, A., Tö lgyesi, L., Lohner, S., Németh-Palotá s, J., Koszegi-Szalai, H. (2011) Identification and characterization of the new designer drug 40-methylethcathinone (4-MEC) and elaboration of a novel liquid chromatography-tandem mass spectrometry (LC-MS/MS) screening method for seven different methcathinone analogs. Forensic Science International, 210, 213-220.
36. Locos, O., Reynolds, D. (2012) The characterization of 3,4-dimethylmethcathinone (3,4-DMMC). Journal of Forensic Science, 57, 1303-1306.
37. Archer, R.P. (2009) Fluoromethcathinone, a new substance of abuse. Forensic Science International, 185, 10-20.
38. Westphal, F., Junge, T., Girreser, U., Jacobsen-Bauer, A., Rö Sner, P. (2010) 'Bathsalts' for snorting-fluoromethcathinone-now on German market. TIAFT Bulletin, 40, 28-33.
39. Substituted phenyl-a-amino ketones. British Patent GB 1085135 (1969).
40. Brandt, S.D., Freeman, S., Sumnall, H.R., Measham, F., Cole, J. (2011) Analysis of NRG 'legal highs' in the UK: identification and formation of novel cathinones. Drug Testing and Analysis, 3, 569-575.
41. Ernst Seeger. α-Pyrrolidinyl ketones. US Patent 3314970
42. Westphal, F., Junge, T., Rö sner, P., Sö nnichsen, F., Schuster, F. (2009) Mass and NMR spectroscopic characterization of 3,4-methylenedioxypyrovalerone: a designer drug with alpha-pyrrolidinophenone structure. Forensic Science International, 190, 1-8.