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26 August / September 2016


UHPSFC technology presents an alternative and orthogonal solution for the separation of synthetic cannabinoids. In particular, when paired with Trefoil column chemistries, UHPSFC offers excellent selectivity for structural analogues and stereoisomers [2]. Here, simple method development was demonstrated for the chiral analysis of selected synthetic cannabinoids including: HU-210, HU- 211, (±)-CP 47,497, (±)-epi CP 47,497, (±)-CP 55,940 and (±)5-epi CP 55,940. Fast stereoisomeric separations, for both enantiomers and diastereomers, were achieved using the Waters ACQUITY UPC2


System with Waters Trefoil chiral


Figure 5: Separations of the stereoisomers of (A) (±)-CP 55,940 and (±)5-epi CP 55,940 on the Trefoil CEL1 column at 13% ethanol isocratic conditions, and (B) (±)-CP 47,497 and (±)-epi CP 47,497 on the Trefoil AMY1 column at 20% ethanol isocratic conditions.


the latest eluting peak in the screen was used to calculate the isocratic method conditions. The CEL1 column was selected for the separation of (±)-CP 55,940 and (±)5-epi CP 55,940 because it showed the best resolution of the (±)5-epi CP 55,940 enantiomers. Based on the retention time of the (+)-CP 55,940 enantiomer at 5.01 min, the co-solvent percentage at elution was 18%, after subtracting 5%, the optimised separation was achieved at 13% isocratic conditions. The AMY1 column was used to separate the (±)-CP 47,497 and (±)-epi CP 47,497 stereoisomers because it showed the most resolution for both sets of enantiomers. As stated earlier, the (+)-epi CP 47,497 didn’t elute during the screen, but it was well separated from the (-)-epi CP 47,497. Because the last two peaks eluted during or well after the 20% hold, 20% isocratic conditions were used for the optimised method. The optimised chromatography can be seen in Figure 5, where all four stereoisomers (enantiomers and diastereomers) of the two cyclohexylphenol (CP) compounds were


separated in approximately 3.5 minutes using Trefoil stationary phases at the calculated isocratic mobile phase conditions.


Conclusion


Synthetic cannabinoids possess a wide range of structural variability, which include structural analogues, structural homologues, positional isomers and stereoisomers [1,4]. Just as with other active pharmaceutical ingredients, the stereochemistry of synthetic cannabinoids affects pharmacological activity. As a result, comprehensive ingredient analysis of these products, including their stereoisomers, is required in regulated environments, forensic laboratories and for pharmaceutical development [1]. In pharmaceutical development, chiral separation is important for the identification and characterisation of impurities, or for purification purposes. Chiral analysis is also important for screening in forensic laboratories, where achiral analysis alone will not result in comprehensive qualitative and quantitative analysis.


columns. Isocratic conditions derived from screening gradients effortlessly resolved the enantiomers of several chiral synthetic cannabinoids and increased analysis speed and efficiency.


References


[1] T. Toyo’oka, R. Kikura-Hanajiri, A Reliable Method for the Separation and Detection of Synthetic Cannabinoids by Supercritical Fluid Chromatography with Mass Spectrometry, and Its Application to Plant Products, Chem. Pharm. Bull. 63 (2015) 762-769


[2] S. Breitenbach, W.F. Rowe, B. McCord, I.S. Lurie, Assessment of ultra high performance supercritical fluid chromatography as a separation technique for the analysis of seized drugs: Applicability to synthetic cannabinoids, Journal of Chromatography A, 1440 (2016) 201-011


[3] J. Schlatter, Synthetic Cannabinoids: Synthesis and Biological Activities, Studies in Natural Products Chemistry, (2014) 291-311


[4] P.D. Kennedy, W. Collin, Automated Ion Trap Screening Method for the Detection of Synthetic Cannabinoids in Commercial Herbal Incense Products, www.caymanchem.com (2010)


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