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Prediction of designer drugs: synthesis and spectroscopic analysis of synthetic cannabinoid analogues of 1H-indol-3-yl(2,2,3,3-tetramethylcyclopropyl) methanone and 1H-indol-3-yl(adamantan-1-yl)methanone
Swedish National Forens Centre NFC, SE-58194 Linkoping, Sweden.
Swedish Def Research Agency, Sweden.
Linköping University, Department of Physics, Chemistry and Biology, Chemistry. Linköping University, Faculty of Science & Engineering.
Swedish National Forens Centre NFC, SE-58194 Linkoping, Sweden.
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2016 (English)In: Drug Testing and Analysis, ISSN 1942-7603, E-ISSN 1942-7611, Vol. 8, no 10, 1015-1029 p.Article in journal (Refereed) Published
Abstract [en]

In this work, emergence patterns of synthetic cannabinoids were utilized in an attempt to predict those that may appear on the drug market in the future. Based on this information, two base structures of the synthetic cannabinoid analogues - (1H-indol-3-yl (2,2,3,3-tetramethylcyclopropyl) methanone and 1H-indol-3-yl(adamantan-1-yl)methanone) - together with three substituents butyl, 4-fluorobutyl and ethyl tetrahydropyran - were selected for synthesis. This resulted in a total of six synthetic cannabinoid analogues that to the authors knowledge have not yet appeared on the drug market. Spectroscopic data, including nuclearmagnetic resonance (NMR), mass spectrometry (MS), and Fourier transforminfrared (FTIR) spectroscopy (solid and gas phase), are presented for the synthesized analogues and some additional related cannabinoids. In this context, the suitability of the employed techniques for the identification of unknowns is discussed and the use of GC-FTIR as a secondary complementary technique to GC-MS is addressed. Examples of compounds that are difficult to differentiate by their mass spectra, but can be distinguished based upon their gas phase FTIR spectra are presented. Conversely, structural homologueswhere mass spectra aremore powerful than gas phase FTIR spectra for unambiguous assignments are also exemplified. This work further emphasizes that a combination of several techniques is the key to success in structural elucidations. Copyright (C) 2015 John Wiley amp; Sons, Ltd.

Place, publisher, year, edition, pages
WILEY-BLACKWELL , 2016. Vol. 8, no 10, 1015-1029 p.
Keyword [en]
drug analysis; proactive; synthetic cannabinoids; synthesis; mass spectrometry
National Category
Pharmaceutical Sciences
URN: urn:nbn:se:liu:diva-132473DOI: 10.1002/dta.1904ISI: 000384806400003PubMedID: 26526273OAI: diva2:1046272

Funding Agencies|Swedish Contingencies Agency (MSB)

Available from: 2016-11-13 Created: 2016-11-12 Last updated: 2016-11-24
In thesis
1. Synthesis and spectroscopic characterization of emerging synthetic cannabinoids and cathinones
Open this publication in new window or tab >>Synthesis and spectroscopic characterization of emerging synthetic cannabinoids and cathinones
2016 (English)Licentiate thesis, comprehensive summary (Other academic)
Abstract [en]

The application of different analytical techniques is fundamental in forensic drug analysis. In the wake of the occurrence of large numbers of new psychoactive substances possessing similar chemical structures as already known ones, focus has been placed on applied criteria for their univocal identification. These criteria vary, obviously, depending on the applied technique and analytical approach. However, when two or more substances are proven to have similar analytical properties, these criteria no longer apply, which imply that complementary techniques have to be used in their differentiation.

This work describes the synthesis of some structural analogues to synthetic cannabinoids and cathinones based on the evolving patterns in the illicit drug market. Six synthetic cannabinoids and six synthetic cathinones were synthesized, that, at the time for this study, were not as yet found in drug seizures. Further, a selection of their spectroscopic data is compared to those of already existing analogues; mainly isomers and homologues. The applied techniques were mass spectrometry (MS), Fourier transformed infrared (FTIR, gas phase) spectroscopy and nuclear magnetic resonance (NMR) spectroscopy. In total, 59 different compounds were analyzed with the  selected techniques.

The results from comparison of spectroscopic data showed that isomeric substances may in some cases be difficult to unambiguously identify based only on their GC-MS EI spectra. On the other hand, GC-FTIR demonstrated more distinguishable spectra. The spectra for the homologous compounds showed however, that the GC-FTIR technique was less successful compared to GC-MS. Also a pronounced fragmentation pattern for some of the cathinones was found.

In conclusion, this thesis highlights the importance of using complementary techniques for the univocal identification of synthetic cannabinoids and cathinones. By increasing the number of analogues investigated, the more may be learnt about the capabilities of different techniques for structural differentiations, and thereby providing important identification criteria leading to trustworthy forensic evidence.

Place, publisher, year, edition, pages
Linköping: Linköping University Electronic Press, 2016. 62 p.
Linköping Studies in Science and Technology. Thesis, ISSN 0280-7971 ; 1766
National Category
Organic Chemistry Analytical Chemistry Materials Chemistry Atom and Molecular Physics and Optics
urn:nbn:se:liu:diva-132781 (URN)10.3384/lic.diva-132781 (DOI)9789176856253 (ISBN)
2016-12-16, Schrödinger, Fysikhuset, Campus Valla, Linköpings universitet, Linköping, 09:00 (Swedish)
Available from: 2016-11-24 Created: 2016-11-24 Last updated: 2016-12-06Bibliographically approved

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