An analysis of the 'legal high' mephedrone

Gibbons, Simon and Zloh, Mire (2010) An analysis of the 'legal high' mephedrone. Bioorganic & Medicinal Chemistry Letters, 20 (14). pp. 4135-4139. ISSN 0960-894X

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'Legal highs' are compounds, plant or fungal material which can be readily bought from the internet without legal restriction and the single chemicals may be structurally related to illegal drugs of abuse such as the amphetamines. Several recent deaths in the UK have been attributed to these legal highs and unfortunately there is little chemical or biological literature on these materials or certified standards. Here, we detail the analysis of the widely consumed synthetic N-methyl-cathinone analogue known as mephedrone ((1) 2-aminomethyl-1-tolyl-propan-1-one (4′-methylmethcathinone)) and report its spectral data and molecular properties. Material was purchased from an internet site and examined by extensive one- and two-dimensional NMR studies, high-resolution mass spectrometry, elemental analysis and optical rotation, which demonstrated the sample to be of high purity and racemic in nature. Additionally, we report the molecular modelling properties of methyl-cathinones and compare them to their corresponding methyl-amphetamine series. This indicated that the methyl-cathinones are considerably more hydrophilic than the methyl-amphetamines which may account for the higher doses that are needed to demonstrate similar effects. The presence of a ketone in the side chain introduces a far more planar quality to the methyl-cathinones which is absent in the methyl-amphetamine series, and this planarity may contribute to toxicity.

Item Type: Article
Uncontrolled Keywords: 4′-methylmethcathinone,butylone,legal highs,mdpv,mephedrone,methedrone,methyl-cathinones,methylone,biochemistry,molecular medicine,molecular biology,pharmaceutical science,drug discovery,clinical biochemistry,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1300/1303
Faculty \ School: Faculty of Science > School of Pharmacy
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Depositing User: LivePure Connector
Date Deposited: 15 Jul 2020 23:39
Last Modified: 22 Oct 2022 06:29
DOI: 10.1016/j.bmcl.2010.05.065

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