The analytical investigation of synthetic street drugs containing cathinone analogs Amanda M. Leffler, Philip B. Smith, Adriana de Armas, Frank L. Dorman * The Pennsylvania State University, University Park, PA 16802, United States 1. Introduction A variety of retail establishments across the United States are carrying new products sold under the names of ‘‘bath salts’’, ‘‘plant food’’, and ‘‘jewelry cleaner’’. These products contain synthetic drugs which have been becoming prevalent in the United States since 2009 when they were brought over from Europe [1]. The drug names (i.e. bath salts) illustrate the variety of marketing tactics that manufacturers employ in order to lure customers. Products exhibit colorful packaging labels (ex. Doves Original, Diablo XXX Extreme) and every bag states that the product is ‘‘Not for Human Consumption’’ to allow for legal possession and recreational use by circumventing potential control mechanisms [2]. These products are not only sold in ‘‘head shops’’, but also are also carried in gas stations, adult stores, independently owned convenience stores, and online retailers [3]. The online market provides an easy means for users to obtain drugs by circulating new compounds quickly and effectively. In March 2009, there were reportedly fewer than ten online vendors; by June 2009 that number had grown to dozens, with new sites opening every week [4]. The products are mainly composed of synthetic cathinones. Cathinone (Fig. 1) is a naturally occurring compound that is extracted from Khat, a plant that has been used in eastern and central Africa and areas of the Arabian Peninsula for years [5]. The cathinone backbone can be functionalized in four different places to create hundreds of possible compounds. Additional functionali- ty includes substituents on the aromatic ring and/or the alpha carbon, N-alkylation, and the incorporation of the nitrogen atom in a ring structure (Fig. 1). Numerous compounds have already been identified in the products by other studies [6]. U.S. Congress passed the S. 3187:Food and Drug Administration Safety and Innovation Act which listed 3,4-methylenedioxypyrovalerone (MDPV) and 4- methylmethcathinone (mephedrone) as schedule I drugs [7]. These are the only permanently banned synthetic cathinones so far. Also referred to as ‘‘legal highs,’’ these stimulants are taken by individuals who desire effects similar to ecstasy and amphetamine. The products are sold as tablets, capsules, and powders and modes of abuse include ingestion, inhalation, injection, and insufflation [8]. They have also been combined with other illicit controlled substances, such as ecstasy, in tablets and capsules and sold by independent dealers. In 2011, hundreds of calls per month were made to poison control centers across the country and there have been reported deaths in some cases, mostly due to conjugation of Forensic Science International 234 (2014) 50–56 A R T I C L E I N F O Article history: Received 2 May 2013 Received in revised form 20 August 2013 Accepted 23 August 2013 Available online 19 September 2013 Keywords: Bath salts Synthetic cathinones GC–MS MDPV MDPBP PVP A B S T R A C T Synthetic drugs, often marketed as ‘‘legal highs,’’ are entering the drug market at an accelerated pace. Analysis of these ‘‘designer drugs’’ and the determination of their composition are necessary in order to aid law enforcement and also to understand what potential users may be subjected to. Ten synthetic cathinones were identified in 14 separate street samples analyzed utilizing a variety of techniques, including gas chromatography with mass spectrometric detection (GC–MS) and flame ionization (GC- FID). Additionally, preparatory high performance liquid chromatography (HPLC) for the fractionation of multi-component samples and the use of direct infusion tandem mass spectrometry (MS/MS) was necessary to identify compounds which were not available as reference materials. These cathinones include 3,4-methylenedioxy pyrovalerone (MDPV), 3,4-methylenedioxy-a-pyrrolidinobutiophenone (MDPBP), 4-fluoromethcathinone (4-FMC), butylone, mephedrone, naphyrone, 4-methylethcathinone (4-MEC), ethcathinone, a-pyrrolidinopentiophenone (a-PVP), and 3-methyl-a-pyrrolidinopropiophe- none (3-MPPP). Concentrations of the active compounds varied between samples. For example, MDPV was determined to be the most common cathinone. It was found in five of the 14 samples and ranged from 11% to 73% between samples. ß 2013 Elsevier Ireland Ltd. All rights reserved. * Corresponding author at: 107 Whitmore Labs, University Park, PA 16802, United States. Tel.: +1 814 863 6805. E-mail addresses: aml357@psu.edu (A.M. Leffler), pbs13@psu.edu (P.B. Smith), fld3@psu.edu, frank@peak-diagnostics.com (F.L. Dorman). Contents lists available at ScienceDirect Forensic Science International jou r nal h o mep age: w ww.els evier .co m/lo c ate/fo r sc iin t 0379-0738/$ – see front matter ß 2013 Elsevier Ireland Ltd. All rights reserved. http://dx.doi.org/10.1016/j.forsciint.2013.08.021