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Published in: Forensic Toxicology 2/2017

01-07-2017 | Original Article

Mass spectrometric identification and structural analysis of the third-generation synthetic cannabinoids on the UK market since the 2013 legislative ban

Authors: Lubertus Bijlsma, María Ibáñez, Bram Miserez, Solomon Ting Fung Ma, Trevor Shine, John Ramsey, Félix Hernández

Published in: Forensic Toxicology | Issue 2/2017

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Abstract

To examine the impact of the second legal ban on synthetic cannabinoids (SCs) in the UK in February 2013, we surveyed the UK legal high market just before and after the change in legislation, looking for new SCs. The technique gas chromatography–mass spectrometry (GC–MS) in electron ionization mode, most widely applied for analysis, was found to be insufficient for the identification of several SCs, and therefore liquid chromatography–high-resolution mass spectrometry (LC–HR-MS) was required. LC–HR-MS(/MS) measurements of the protonated molecules and product ions allowed the detection of up to 27 compounds as the third-generation SCs in the samples analysed as part of this study, including two unknown compounds that were tentatively identified as F2201 and dealkyl-SDB-006. Our results showed that banned compounds were removed from the market on the day when the ban was in place, and were replaced by other SCs immediately after the ban. In only one occasion, a banned compound (UR-144) was detected after the date when the new legislation came into place. It is also noteworthy that regardless of the change in legislation, new compounds continued to enter the market. Product ion spectral information on the third-generation SCs at different collision energies given in this paper will be of help for forensic and clinical laboratories and will facilitate the detection and identification of new SCs by laboratories of control. This information is very valuable for law enforcement and policymakers and will be of help in future prevention programs.
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Literature
1.
go back to reference Uchiyama N, Kikura-Hanajiri R, Kawahara N, Haishima Y, Goda Y (2009) Identification of a cannabinoid analog as a new type of designer drug in a herbal product. Chem Pharm Bull 57:439–441CrossRefPubMed Uchiyama N, Kikura-Hanajiri R, Kawahara N, Haishima Y, Goda Y (2009) Identification of a cannabinoid analog as a new type of designer drug in a herbal product. Chem Pharm Bull 57:439–441CrossRefPubMed
2.
go back to reference Auwärter V, Dresen S, Weinmann W, Müller M, Pütz M, Ferreirós N (2009) ’Spice’ and other herbal blends: harmless incense or cannabinoid designer drugs? J Mass Spectrom 44:832–837CrossRefPubMed Auwärter V, Dresen S, Weinmann W, Müller M, Pütz M, Ferreirós N (2009) ’Spice’ and other herbal blends: harmless incense or cannabinoid designer drugs? J Mass Spectrom 44:832–837CrossRefPubMed
3.
go back to reference Uchiyama N, Kikura-Hanajiri R, Kawahara N, Goda Y (2009) Identification of a cannabimimetic indole as a designer drug in a herbal product. Forensic Toxicol 27:61–66CrossRef Uchiyama N, Kikura-Hanajiri R, Kawahara N, Goda Y (2009) Identification of a cannabimimetic indole as a designer drug in a herbal product. Forensic Toxicol 27:61–66CrossRef
4.
go back to reference Tsujikawa K, Yamamuro T, Kuwayama K, Kanamori T, Iwata YT, Inoue H (2014) Thermal degradation of a new synthetic cannabinoid QUPIC during analysis by gas chromatography–mass spectrometry. Forensic Toxicol 32:201–207CrossRef Tsujikawa K, Yamamuro T, Kuwayama K, Kanamori T, Iwata YT, Inoue H (2014) Thermal degradation of a new synthetic cannabinoid QUPIC during analysis by gas chromatography–mass spectrometry. Forensic Toxicol 32:201–207CrossRef
5.
go back to reference Uchiyama N, Kikura-Hanajiri R, Goda Y (2010) Chemical analysis of synthetic cannabinoids as designer drugs in herbal products. Forensic Sci Int 198:31–38CrossRefPubMed Uchiyama N, Kikura-Hanajiri R, Goda Y (2010) Chemical analysis of synthetic cannabinoids as designer drugs in herbal products. Forensic Sci Int 198:31–38CrossRefPubMed
6.
go back to reference Shanks KG, Dahn T, Behonick G, Terrell A (2012) Analysis of first and second generation legal highs for synthetic cannabinoids and synthetic stimulants by ultra-performance liquid chromatography and time of flight mass spectrometry. J Anal Toxicol 36:360–371CrossRefPubMed Shanks KG, Dahn T, Behonick G, Terrell A (2012) Analysis of first and second generation legal highs for synthetic cannabinoids and synthetic stimulants by ultra-performance liquid chromatography and time of flight mass spectrometry. J Anal Toxicol 36:360–371CrossRefPubMed
7.
go back to reference Ibáñez M, Bijlsma L, van Nuijs ALN, Sancho JV, Haro G, Covaci A, Hernández F (2013) Quadrupole-time-of-flight mass spectrometry screening for synthetic cannabinoids in herbal blends. J Mass Spectrom 48:685–694CrossRefPubMed Ibáñez M, Bijlsma L, van Nuijs ALN, Sancho JV, Haro G, Covaci A, Hernández F (2013) Quadrupole-time-of-flight mass spectrometry screening for synthetic cannabinoids in herbal blends. J Mass Spectrom 48:685–694CrossRefPubMed
8.
go back to reference Penn HJ, Langman LJ, Unold D, Shields J, Nichols JH (2011) Detection of synthetic cannabinoids in herbal incense products. Clin Biochem 44:1163–1165CrossRefPubMed Penn HJ, Langman LJ, Unold D, Shields J, Nichols JH (2011) Detection of synthetic cannabinoids in herbal incense products. Clin Biochem 44:1163–1165CrossRefPubMed
9.
go back to reference Grabenauer M, Krol WL, Wiley JL, Thomas BF (2012) Analysis of synthetic cannabinoids using high-resolution mass spectrometry and mass defect filtering: implications for nontargeted screening of designer drugs. Anal Chem 84:5574–5581CrossRefPubMedPubMedCentral Grabenauer M, Krol WL, Wiley JL, Thomas BF (2012) Analysis of synthetic cannabinoids using high-resolution mass spectrometry and mass defect filtering: implications for nontargeted screening of designer drugs. Anal Chem 84:5574–5581CrossRefPubMedPubMedCentral
10.
go back to reference Hudson S, Ramsey J, King L, Timbers S, Maynard S, Dargan PI, Wood DM (2010) Use of high-resolution accurate mass spectrometry to detect reported and previously unreported cannabinomimetics in “herbal high” products. J Anal Toxicol 34:252–260CrossRefPubMed Hudson S, Ramsey J, King L, Timbers S, Maynard S, Dargan PI, Wood DM (2010) Use of high-resolution accurate mass spectrometry to detect reported and previously unreported cannabinomimetics in “herbal high” products. J Anal Toxicol 34:252–260CrossRefPubMed
11.
go back to reference Gottardo R, Chiarini A, Dal Prà I, Seri C, Rimondo C, Serpelloni G, Armato U, Tagliaro F (2012) Direct screening of herbal blends for new synthetic cannabinoids by MALDI-TOF MS. J Mass Spectrom 47:141–146CrossRefPubMed Gottardo R, Chiarini A, Dal Prà I, Seri C, Rimondo C, Serpelloni G, Armato U, Tagliaro F (2012) Direct screening of herbal blends for new synthetic cannabinoids by MALDI-TOF MS. J Mass Spectrom 47:141–146CrossRefPubMed
14.
go back to reference Kikura-Hanajiri R, Uchijama N, Kawamura M, Goda Y (2014) Changes in the prevalence of new psychoactive substances before and after the introduction of generic scheduling of synthetic cannabinoids in Japan. Drug Test Anal 6:832–839CrossRefPubMed Kikura-Hanajiri R, Uchijama N, Kawamura M, Goda Y (2014) Changes in the prevalence of new psychoactive substances before and after the introduction of generic scheduling of synthetic cannabinoids in Japan. Drug Test Anal 6:832–839CrossRefPubMed
Metadata
Title
Mass spectrometric identification and structural analysis of the third-generation synthetic cannabinoids on the UK market since the 2013 legislative ban
Authors
Lubertus Bijlsma
María Ibáñez
Bram Miserez
Solomon Ting Fung Ma
Trevor Shine
John Ramsey
Félix Hernández
Publication date
01-07-2017
Publisher
Springer Japan
Published in
Forensic Toxicology / Issue 2/2017
Print ISSN: 1860-8965
Electronic ISSN: 1860-8973
DOI
https://doi.org/10.1007/s11419-017-0368-7

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