'Smoking' mephedrone: The identification of the pyrolysis products of 4-methylmethcathinone hydrochloride

Drug Testing and Analysis

Volumn 5, Issue 5, 2013, Pages 291-305

  Kavanagh, Pierce ^a   O'Brien, John ^b   Power, John D ^c   Talbot, Brian ^b   Mcdermott, Seán D ^c  

^a ST JAMES S HOSPITAL   (Ireland)

^b TRINITY COLLEGE DUBLIN   (Ireland)

^c Forensic Science Laboratory Dulin Ireland   (Ireland)

Author keywords

Analysis; Drug; Forensic; Mephedrone; Pyrolysis; Smoke

Indexed keywords

DRUG PRODUCTS; FORENSIC SCIENCE; KETONES;

ANALYSE; CATHINONE; CONDITION; DIMERIZATIONS; DRUG; FORENSIC; MEPHEDRONE; PYRAZINE DERIVATIVE; PYROLYSIS PRODUCTS; RECREATIONAL DRUGS;

PYROLYSIS;

4' METHYLMETHCATHINONE; CHLORIDE;

ARTICLE; DIMERIZATION; HEATING; OXIDATION; PRIORITY JOURNAL; PYROLYSIS; SMOKING;

EID: 84878232773     PISSN: 19427603     EISSN: 19427611     Source Type: Journal    
DOI: 10.1002/dta.1373     Document Type: Article

References (22)

1. EMCDDA, Report on the risk assessment of mephedrone in the framework of the Council Decision on new psychoactive substances. Available at: http://www.emcdda.europa.eu [9 April 2012].
2. M.H. Baumann, M.A. Ayestas Jr, J.S. Partilla, J.R. Sink, A.T. Shulgin, P.F. Daley, et al. The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue. Neuropsychopharmacology 2012, 37, 1192.
3. J. Martínez-Clemente, E. Escubedo, D. Pubill, J. Camarasa. Interaction of mephedrone with dopamine and serotonin targets in rats. Eur. Neuropsychopharm. 2012, 22, 231.
4. G.C. Hadlock, K.M. Webb, L.M. McFadden, P.W. Chu, J.D. Ellis, S.C. Allen, et al. 4-Methylmethcathinone (mephedrone): Neuropharmacological effects of a designer stimulant of abuse. J. Pharmacol. Exp. Ther. 2011, 339, 530.
5. T.P. Freeman, C.J. Morgan, J. Vaughn-Jones, N. Hussain, K. Karimi, H.V. Curran. Cognitive and subjective effects of mephedrone and factors influencing use of a 'new legal high'. Addiction 2012, 107, 792.
6. A.J. Dickson, S.P. Vorce, B. Levine, M.R. Past. Multiple-drug toxicity caused by the co-administration of 4-methylmethcathinone (mephedrone) and heroin. J. Anal. Toxicol. 2010, 34, 162.
7. K.J. Lusthof, R. Oosting, A. Maes, M. Verschraagen, A. Dijkhuizwn, A.G. Sprong. A case of extreme agitation and death after the use of mephedrone in The Netherlands. Forensic Sci. Int. 2011, 206, e93-e95. Available at: http://dx.doi.org/10.1016/j.forsciint.2010.12.014 [9 April 2012].
8. F. Measham, K. Moore, R. Newcombe, Z. Welch. Tweaking, bombing, dabbing and stockpiling: The emergence of mephedrone and the perversity of prohibition. Drugs Alcohol Today 2010, 10, 14.
9. D.M. Wood, S.L. Greene, P.I. Dargan. Clinical pattern of toxicity associated with the novel synthetic cathinone, mephedrone. Emerg. Med. J. 2011, 28, 280.
10. Drugs-forum.com. Available at: www.drugs-forum.com [9 April 2012]. (search terms: mephedrone, smoking).
11. Erowid.org. Available at: www.erowid.org/experiences/exp.php?ID=85440 [9 April 2012].
12. Anonymous. Emergency department visits after use of a drug sold as "bath salts"-Michigan, November 13, 2010-March 31. Morbid. Mortal. Wkly Rep. 2011, 60, 624.
13. NIDA Monograph173, Pharmacokinetics, Metabolism, and Pharmaceutics of Drugs of Abuse, pp. 201-224. Available at: http://archives.drugabuse.gov/pdf/monographs/monograph173/201-224_Meng.pdf [9 April 2012].
14. S. Motoyasu, H. Minemasa, H. Nagase. Analysis of pyrolysis products of methamphetamine. J. Anal. Toxicol. 2004, 28, 638.
15. L.C. Chen, J.F. Graefe, J. Shojaie, J. Willetts, R.W. Wood. Pulmonary effects of the cocaine pyrolysis product, methylecgonidine, in guinea pigs. Life Sci. 1994, 56, PL7.
16. E.C. Wolters, F.C. Stam, R.J. Lousberg, G.K. van Wyngaarden, H. Rengelink, M.E.I. Schipper, et al. Leucoencephalopathy after inhaling 'heroin' pyrolysate. Lancet 1982, 8310, 1233.
17. S.D. McDermott, J.D. Power, P. Kavanagh, J. O'Brien. The analysis of substituted cathinones, Part 2: An investigation into the phenylacetone based isomers of 4-methylmethcathinone and N-ethylcathinone. Forensic Sci. Int. 2011, 212, 13.
18. Annex 1 to the Risk assessment report: Technical report on Mephedrone. Prepared by Dr Paul Dargan and Dr David Wood, Guy's and St Thomas' NHS Foundation Trust, London, UK. July 2010. Available at: http://www.emcdda.europa.eu [9 April 2012].
19. C.L. Stevens, R.D. Elliot, B.L. Winch. Aminoketone rearrangements. II. The rearrangement of phenyl α-aminoketones. J. Am. Chem. Soc. 1963, 85, 1464.
20. A.K. Nigam, M.V.S. Suryanarayana, P.K. Gutch, S.P. Sharma, L.N.S. Tomar, R. Vijayaraghavan. Thermal decomposition studies of riot control agent ω-chloroacetophenone (CN) by pyrolysis-gas chromatography-mass spectrometry. J. Hazard. Mater. 2010, 184, 506.
21. A.R. Butler, E.H. Brown. Condensation of 2-hydroxy-2'- aminoacetophenone to form a dihydropyrazine. Arkivoc 2002, 166. Available at: www.arkat-usa.org/get-file/19009/ [9 April 2012].
22. J.W. Lown, M.H. Akhtar, R.S. McDaniell. Stereochemistry and mechanism of the thermal [1, 3] alkyl shift of stable1, 4-dialkyl-1, 4-dihydropyrazines. J. Org. Chem. 1974, 14, 1998.