Identification of ten new designer drugs by GC‐MS, UPLC‐QTOF‐MS, and NMR as part of a police investigation of a Danish Internet company

Abstract

The ability of forensic laboratories to detect and identify unknown compounds is highly important since new, non-controlled designer drugs are appearing on the market with increasing frequency. In this study, the combined use of gas chromatography-mass spectrometry (GC-MS) and ultra performance liquid chromatography-quadrupole time of flight-mass spectrometry (UPLC-QTOF-MS) was used for screening of new unknowns. In one large seizure from a Danish Internet company, ten different drugs were identified. Several of the compounds were seized for the first time in Denmark. The GC-MS and UPLC-QTOF-MS analyses were supplemented by nuclear magnetic resonance (NMR) spectra for the structural elucidation of p-fluoroamphetamine, mephedrone (4-methylmethcathinone), flephedrone (4-fluoromethcathinone), PPP (α-pyrrolidinopropiophenone), MDPV (3,4-methylenedioxypyrovalerone), Bk-MBDB (2-methylamino-1-(3,4-methylenedioxyphenyl)butan-1-one), pFBT (3-(pfluorobenzoyl)-tropane), and JWH-073 (1-butyl-3-(1-naphthoyl)indol), whereas methylone (3,4-methylenedioxymethcathinone) and N-ethylcathinone matched electron impact-mass spectrometry (EI-MS) library spectra and therefore the screenings were considered sufficient. EI-MS spectra and the proposed main fragmentation patterns are presented as well as QTOF-MS exact masses and fragments and NMR chemical shifts. For the β-ketophenylethylamines (mephedrone, flephedrone, PPP, MDPV, Bk-MBDB, methylone, and N-ethylcathinone) some general fragmentation patterns observed in the EI-MS and QTOF-MS spectra are further discussed and compared to other β-ketophenylethylamines.

Identification of new psychoactive substances (NPS) using handheld Raman spectroscopy employing both 785 and 1064 nm laser sources

“…According to the UNODC, gas chromatography -mass spectrometry (electron ionisation) (GC-MS (EI)) was the predominant analytical technique employed by EU countries for chemical analysis of NPS mixtures. [1] For example, this technique has been shown to successfully discriminate between NPS classes [14][15][16][17] as well as within classes such as cathinones, [18] aminoindanes [19,20] and benzylpiperazines. [21] In circumstances where no reference standards or data were available, nuclear magnetic resonance spectroscopy (NMR) has been used to determine the chemical connectivity of NPS such as cathinones [22] and aminoindanes.…”

Locomotor activity and discriminative stimulus effects of a novel series of synthetic cathinone analogs in mice and rats

“…The present study examines a set of five compounds flagged for study by the United States Drug Enforcement Agency because of their increasing prevalence in drug seizures (Brandt et al, 2011; Kikura-Hanajiri et al, 2014; Odoardi et al, 2016; Reitzel et al, 2012; Schneir et al, 2014). The compounds are synthetic analogues of cathinone (Figure 1), the pyrrolidines α-pyrrolidinohexiophenone (α-PHP), α-pyrrolidinopropiophenone (α-PPP), α-pyrrolidinopentiothiophenone (α-PVT), 3,4-methylenedioxybutiophenone (MDPBP), and the methylenedioxy-substituted compound 3,4-methylenedioxyethcathinone (ethylone).…”

Psychosis from a Bath Salt Product Containing Flephedrone and MDPV with Serum, Urine, and Product Quantification

“…MDPV was made a DEA schedule I drug as of October 21, 2011 [2,7]. Flephedrone is a fluorinated analog of methcathinone and has recently been identified as an emerging designer drug [3,9]. We believe this to be the first report documenting both MDPV and flephedrone in a bath salt product in the USA.…”

“…Several synthetic cathinones have been indentified in these products, including mephedrone, 3,4-methylenedioxypyrovalerone (MDPV), and 4-fluoromethcathinone (flephedrone) [2,3]. While agitation, psychosis, movement disorders, tachycardia, and hypertension have all been attributed to the use of MDPV, there are no reports detailing clinical experience with flephedrone [2,4,5].…”