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, 35 (1), 114-124

Spectroscopic Characterization and Crystal Structures of Two Cathinone Derivatives: N-ethyl-2-amino-1-phenylpropan-1-one (Ethcathinone) Hydrochloride and N-ethyl-2-amino-1-(4-chlorophenyl)propan-1-one (4-CEC) Hydrochloride

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Spectroscopic Characterization and Crystal Structures of Two Cathinone Derivatives: N-ethyl-2-amino-1-phenylpropan-1-one (Ethcathinone) Hydrochloride and N-ethyl-2-amino-1-(4-chlorophenyl)propan-1-one (4-CEC) Hydrochloride

Piotr Kuś et al. Forensic Toxicol.

Abstract

Comprehensive chemical characterization for two cathinone derivatives, N-ethyl-2-amino-1-phenylpropan-1-one (ethcathinone) hydrochloride and N-ethyl-2-amino-1-(4-chlorophenyl)-propan-1-one (4-chloroethcathinone, 4-CEC) hydrochloride, in material seized by drug enforcement agencies was performed by nuclear magnetic resonance (NMR) spectroscopy, infrared spectroscopy, gas chromatography-mass spectrometry in positive electron ionization mode, liquid chromatography-mass spectrometry in positive electrospray ionization mode and X-ray crystallography. The examined samples of these two compounds proved to be very pure for ethcathinone and mixed with very small quantities of other substances for 4-CEC by NMR spectroscopy and mass spectrometry. X-ray crystallographic studies confirmed the occurrence of both compounds as racemic mixtures. These spectroscopic and crystallographic data seem very useful for their identification. Especially for 4-CEC, this is the first description on its spectroscopic characterization in a scientific context to our knowledge.

Keywords: 4-CEC; 4-Chlorocathinone; Ethcathinone; MS; NMR; X-ray crystallography.

Conflict of interest statement

The authors have no financial or other relations that could lead to a conflict of interest. Ethical approval This article does not contain any studies with human participants or animals performed by any of the authors.

Figures

Fig. 1
Fig. 1
Structures of N-ethyl-2-amino-1-phenylpropan-1-one (ethcathinone) hydrochloride (compound 1) and N-ethyl-2-amino-1-(4-chlorophenyl)propan-1-one (4-CEC) hydrochloride (compound 2)
Fig. 2
Fig. 2
1H Nuclear magnetic resonance (NMR; upper) and 13C NMR (lower) spectra of compound 1 in D2O
Fig. 3
Fig. 3
1H NMR (upper) and 13C NMR (lower) spectra of compound 2 in dimethyl sulfoxide-d 6
Fig. 4
Fig. 4
Electron ionization (EI) mass spectra of a compound 1 and b compound 2
Fig. 5
Fig. 5
EI fragmentation pathways of compound 1
Fig. 6
Fig. 6
Electrospray ionization (ESI) mass spectra of a compound 1 and b compound 2
Fig. 7
Fig. 7
Proposed fragmentation pathways of compounds 1 and 2 in ESI-MSn modes
Fig. 8
Fig. 8
a The molecule of an (S) enantiomer of compound 1 in the crystal. b The molecule of an (R) enantiomer of compound 2 in the crystal. Ellipsoids correspond to 50% probability levels
Fig. 9
Fig. 9
Packing diagrams of a compound 1 and b compound 2
Fig. 10
Fig. 10
Schematic representation of a single chloride ion surrounded by compound 1 molecules. The dotted lines show short contacts of the chloride ion with hydrogen atoms from four nearest molecules
Fig. 11
Fig. 11
a Two molecules forming half an elementary cell of compound 2 with short interatomic distances are shown. b Three molecules of compound 2 surrounding the chloride anion in the crystallographic structure. The dotted lines show short contacts of chloride ion with hydrogen atoms from three adjacent molecules

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References

    1. European Monitoring Centre for Drugs and Drug Addiction (2015) European drug report. http://www.emcdda.europa.eu/attachements.cfm/att_239505_EN_TDAT15001ENN.pdf. Accessed June 2015 - PubMed
    1. Zawilska J, Wojcieszak J. Designer cathinones—an emerging class of novel psychoactive substances. Forensic Sci Int. 2013;231:42–53. doi: 10.1016/j.forsciint.2013.04.015. - DOI - PubMed
    1. Valente MJ, Geudes de Pinho P, Carvalho F, Carvalho M. Khat and synthetic cathinones: a review. Arch Toxicol. 2014;88:15–45. doi: 10.1007/s00204-013-1163-9. - DOI - PubMed
    1. Prosser JM, Nelson LS. The toxicology of bath salts: a review of synthetic cathinones. J Med Toxicol. 2012;8:33–42. doi: 10.1007/s13181-011-0193-z. - DOI - PMC - PubMed
    1. http://gis.gov.pl/images/%C5%9Brodki_zast%C4%99pcze/%C5%9Bz/gis_raport_2013-2014.pdf. Accessed June 2015

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