Synthesis, full chemical characterisation and development of validated methods for the quantification of (±)-4′-methylmethcathinone (mephedrone): A new "legal high"

Journal of Pharmaceutical and Biomedical Analysis

Volumn 56, Issue 2, 2011, Pages 246-255

  Santali, Eman Y ^a   Cadogan, Anna Karina ^a   Daeid, Niamh Nic ^a   Savage, Kathleen A ^a   Sutcliffe, Oliver B ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

Analytical profiling; Cathinone; HPLC; Legal high; Mephedrone

Indexed keywords

4' METHYLMETHCATHINONE; BROMIDE; ILLICIT DRUG; MEPHEDRONE HYDROBROMIDE; NICOTINAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHROMATOGRAPHY; CONTROLLED STUDY; DRUG MANUFACTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS FRAGMENTOGRAPHY; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; SYNTHESIS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DESIGNER DRUGS; DRUG CONTAMINATION; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MAGNETIC RESONANCE SPECTROSCOPY; METHAMPHETAMINE; MOLECULAR STRUCTURE; REPRODUCIBILITY OF RESULTS; SPECTROPHOTOMETRY, ULTRAVIOLET; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SUBSTANCE ABUSE DETECTION; TECHNOLOGY, PHARMACEUTICAL;

EID: 79960071348     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2011.05.022     Document Type: Article

References (23)

1. Hillebrand J., Olszewski D., Sedefov R. Legal highs on the internet. Subst. Use Misuse 2010, 45:330-340.
2. Fleming N. Miaow-miaow on trial: truth or trumped-up charges?. New Sci. 2010, http://www.newscientist.com/article/dn18712-miaowmiaow-on-trial-truth-or-trumpedup-charges.html (accessed 10.02.11).
3. P. Deluca, F. Schifano, Z. Davey, O. Corazza, L. di Furia, M. Farre, L. Flesland, M. Mannonen, A. Majava, V. Minelli, S. Pagani, T. Peltonieme, N. Scherbaum, H. Siemann, A. Skutle, M. Torrens, C. Pezzolesi, P. van der Kreeft, Mephedrone Report, Psychonaut Web Mapping Research Project. 2010 (accessed 10.02.11). http://194.83.136.209/documents/reports/Mephedrone.pdf.
4. Meyer M.R., Peters F.T., Maurer H.H. Metabolism of the new designer drug mephedrone and toxicological detection of the beta keto designer drugs mephedrone, butylone and methylone in urine. Ann. Toxicol. Anal. 2009, 21:22-23.
5. "Consideration of the cathinones" Advisory Council on the Misuse of Drugs (ACMD) Report. 2010 (accessed 10.02.11). http://www.homeoffice.gov.uk/publications/drugs/acmd1/acmd-cathinodes-report-2010%3Fview=Binary.
6. Dickson A.J., Vorce S.P., Levine B., Past M.R. Multiple-drug toxicity caused by the coadministration of 4-methylmethcathinone (mephedrone) and heroin. J. Anal. Toxicol. 2010, 34:162-168.
7. Wood D.M., Davis S., Puchnarewicz M., Button J., Archer R., Ovaska H., Ramsey J., Lee T., Holt D.W., Dargan P.I. Recreational use of mephedrone (4-methylmethcathinone 4-MMC) with associated sympathomimetic toxicity. J. Med. Toxicol. 2010, 6:327-330.
8. Torrance H., Cooper G. The detection of mephedrone (4-methylmethcathinone) in 4 fatalities in Scotland. Forensic Sci. Int. 2010, 202:e62.
9. Camilleri A., Johnston M.R., Brennan M., Davis S., Caldicott D.G.E. Chemical analysis of four capsules containing the controlled substance analogues 4-methylmethcathinone, 2-fluoromethamphetamine, alpha-phthalimidopropiophenone and N-ethylcathinone. Forensic Sci. Int. 2010, 197:59-66.
10. Deruiter J., Hayes L., Valaer A., Clark C.R., Noggle F.T. Methcathinone and designer analogues: synthesis, stereochemical analysis, and analytical properties. J. Chromatogr. Sci. 1994, 32:552-564.
11. Gibbons S., Zloh M. An analysis of the 'legal high' mephedrone. Bioorg. Med. Chem. Lett. 2010, 20:4135-4139.
12. Brandt S.D., Sumnall H.R., Measham F., Cole J. Analyses of second-generation 'legal highs' in the UK: Initial findings. Drug Testing Anal. 2010, 2:377-382.
13. Kalendra D.M., Sickles B.R. Diminished reactivity of ortho-substituted phenacyl bromides toward nucleophilic displacement. J. Org. Chem. 2003, 68:1594-1596.
14. Ogawa K., Terada T., Yamazaki T., Yamada S., Honna T., Ohta S., Okamoto M. Synthesis of novel 5- and 6-substituted 3-arylidene-1 4-oxathiin-2(3H)-ones. J. Chem. Soc. (Perkin Trans. 1) 1985, 11:2417-2423.
15. Archer R.P. Fluoromethcathinone, a new substance of abuse. Forensic Sci. Int. 2009, 185:10-20.
16. Scott A.I. Interpretation of the Ultraviolet Spectra of Natural Products 1964, Pergamon, New York.
17. Singh N., Day P., Katta V.R., Mohammed G.P., Lough W.J. LC purity and related substances screening for mephedrone. J. Pharm. Pharmacol. 2010, 62:1209-1210.
18. Wood D.M., Davies S., Greene S.L., Button J., Holt D.W., Ramsey J., Dargan P.I. Case series of individuals with analytically confirmed acute mephedrone toxicity. Clin. Toxicol. 2010, 48:924-927.
19. Paul B.D., Cole K.A. Cathinone (Khat) and methcathinone (CAT) in urine specimens: a gas chromatographic-mass spectrometric detection procedure. J. Anal. Toxicol. 2001, 6:525-530.
20. Kikura-Hanajiri R., Kawamura M., Saisho K., Kodama Y., Goda Y. The disposition into hair of new designer drugs; methylone, MBDB and methcathinone. J. Chromatogr. B 2007, 855:121-126.
21. Trenerry V.C., Robertson J., Wells R.J. Analysis of illicit amphetamine seizures by capillary electrophoresis. J. Chromatogr. A 1995, 708:169-176.
22. Beyer J., Peters F.T., Kraemer T., Maurer H.H. Detection and validated quantification of nine herbal phenalkylamines and methcathinone in human blood plasma by LC-MS/MS with electrospray ionization. J. Mass Spectrom. 2007, 42:150-160.
23. N. Nic Daeid, Personal communication (2010).