Unexpected identification of a bupivacaine analog from smuggling by using single-crystal X-ray diffraction analysis: N-(2, 6-dimethylphenyl)−1-phenethylpiperidine-2-carboxamide. (September 2021)

• Record Type: Journal Article
• Authors: Yen, Yao-Te; Liu, Mei-Chun; Liu, Chun-Yi; Hung, Cheng-Han; Chen, Pei-Lin; Chyueh, San-Chong
• Is Part Of: Forensic science international. Volume 326(2021)
• Publication Date: 2021-09
• Subjects: Bupivacaine -- Anesthetic -- Discrimination -- Mass spectrometry -- X-ray crystallography; Medical jurisprudence -- Periodicals; Chemistry, Forensic -- Periodicals; Forensic Medicine -- Periodicals; Médecine légale -- Périodiques; Chimie légale -- Périodiques; Gerechtelijke geneeskunde; Gerechtelijke chemie; Gerechtelijke psychiatrie; Chemistry, Forensic; Medical jurisprudence; Electronic journals; Periodicals; Electronic journals; 614.1
• DOI: 10.1016/j.forsciint.2021.110917
• Languages: English
• ISSNs: 0379-0738

Abstract

Highlights: ● A suspicious "unknown" powder was identified as N -(2, 6-dimethylphenyl)−1-phenethylpiperidine-2-carboxamide. ● This is the first report of this drug from a seizure, that has similar pharmacological effects to those of absued drugs. ● Single-crystal X-ray diffraction can be used for structural determination, especially for "new" drugs. Graphical Abstract: A suspicious "unknown" powder seized from smuggling is identified as N -(2, 6-dimethylphenyl)−1-phenethylpiperidine-2-carboxamide by using single-crystal X-ray diffraction, that has similar pharmacological effects to those of cocaine, ketamine, and morphine. ga1 Abstract: The identification of new psychoactive substances (NPSs) is essential against drug abuse, especially for "new" drugs that are not regulated by international drug conventions. A suspicious powder seized by the officers of Taipei Customs Administration of Taiwan was sent to this laboratory for analysis by using gas chromatography-mass spectrometry (GCMS), liquid chromatography-high resolution mass spectrometry (LCHRMS), proton nuclear magnetic resonance (1H NMR), carbon-13 nuclear magnetic resonance (13C NMR) with distortionless enhancement by polarization transfer (DEPT) at proton pulses of 45°, 90°, and 135°, two-dimensional correlation NMR measurements (2D_COSY), and heteronuclear single-quantum correlation NMR measurements (2D_HSQC). However, the structure of this "unknown" sample was difficult to identify. Alternatively, single‐crystal X‐ray crystallography was applied for structural determination after the crystallization of the compound in methanol. The structure was thus identified as N -(2, 6-dimethylphenyl)−1-phenethylpiperidine-2-carboxamide (NDMPPPC), an analog of bupivacaine with similar pharmacological effects to those of cocaine, ketamine and morphine. The identification of NDMPPPC is in accordance with all mass fragments and NMR signal data, demonstrating that single-crystal X-ray diffraction can be used for structural determination, especially for complicated structures of "new" drugs or "unknown" samples. The seizure of NDMPPPC from smuggling indicates a great potential to become part of the next generation of NPSs.