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[1-(Tetrahydropyran-4-ylmethyl)-1H-indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone: a new synthetic cannabinoid identified on the drug market

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Abstract

A new synthetic cannabinoid, [1-(tetrahydropyran-4-ylmethyl)-1H-indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone, was identified in several resinous samples seized by law enforcement officers in Poland. Its identification was based on liquid chromatography–electrospray ionization–quadrupole time-of-flight–mass spectrometry, gas chromatography–electron ionization–mass spectrometry, one-dimensional and two-dimensional nuclear magnetic resonance spectroscopy, and Fourier-transform infrared spectroscopy. The reported substance was first developed by Abbott Laboratories and patented under the name “A-834,735”. It is a potent agonist of both CB1 and CB2 receptors. Although A-834,735 shows moderate selectivity to CB2 receptor, it exhibits a CB1 affinity similar to that of ∆9-tetrahydrocannabinol. The drug has recently become available in online shops. To our knowledge, this is the first report to disclose a synthetic cannabinoid containing a (tetrahydropyran-4-yl)methyl structure in products seized from the drug market.

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Authors and Affiliations

  1. Institute of Forensic Research, Westerplatte 9, 31-033, Kraków, Poland

    Dariusz Zuba & Karolina Sekuła

  2. Chair and Department of Forensic Medicine, The Poznań University of Medical Sciences, Poznań, Poland

    Bogna Geppert & Czesław Żaba

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  1. Dariusz Zuba
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  2. Bogna Geppert
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  4. Czesław Żaba
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Correspondence to Dariusz Zuba.

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Zuba, D., Geppert, B., Sekuła, K. et al. [1-(Tetrahydropyran-4-ylmethyl)-1H-indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone: a new synthetic cannabinoid identified on the drug market. Forensic Toxicol 31, 281–291 (2013). https://doi.org/10.1007/s11419-013-0191-8

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