Synthesis, characterization and differentiation of the structural isomers of valine and tert‐leucine derived synthetic cannabinoids

The identification of the synthetic cannabinoids receptor agonists (SCRAs) has always posed a great challenge to drug testing laboratories with slight structural modifications aimed at evading drug legislation. In addition, the most prevalent synthetic cannabinoids have valine and tert‐leucine amino...

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Veröffentlicht in:Drug testing and analysis 2024-04, Vol.16 (4), p.420-434
Hauptverfasser: Sim, Sui Boon Derek, Lee, Hui Zhi Shirley, Ong, Mei Ching, Zhang, Shuhua, Lim, Kheng Aik, Lim, Jong Lee Wendy, Yap, Tiong Whei Angeline
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Sprache:eng
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Zusammenfassung:The identification of the synthetic cannabinoids receptor agonists (SCRAs) has always posed a great challenge to drug testing laboratories with slight structural modifications aimed at evading drug legislation. In addition, the most prevalent synthetic cannabinoids have valine and tert‐leucine amino acid moieties where re‐arrangement of the carbon chains can result in structural isomers that are very similar to the parent synthetic cannabinoids. This makes their analysis and identification challenging, and the problem is compounded with the difficulty in purchasing reference standards quickly and a lack of literature for comparison. Therefore, in this investigation, four series of synthetic cannabinoids (AB‐PINACA, AB‐CHMINACA, MMB‐FUBINACA and 5‐fluoro‐MDMB‐PINACA) and their alkyl chain structural isomers at the amino acid moieties were synthesized and characterized using various analytical techniques—gas chromatography–mass spectrometry (GC–MS), gas chromatography–infrared detection (GC–IRD) and nuclear magnetic resonance (NMR) spectroscopy to evaluate the ability of each analytical technique to differentiate the respective isomers for their identification. A total of 12 isomers were synthesized and analysed together with the four parent synthetic cannabinoids. NMR was able to differentiate between all the compounds, whereas GC–IRD was able to discern between most of the synthetic cannabinoids and their isomers. GC–MS had the least discriminating power and was not able to differentiate some of the compounds that has very similar mass spectra. The results from this work will be useful to other drug testing laboratories that are facing the identification of related synthetic cannabinoids. Synthesis and characterization of AB‐PINACA, AB‐CHMINACA, MMB‐FUBINACA and 5‐fluoro‐MDMB‐PINACA and their structural isomers at the amino acid derived side chain was done using various techniques including GC–MS, GC–IRD and NMR spectroscopy.
ISSN:1942-7603
1942-7611
DOI:10.1002/dta.3561