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Forensic Toxicology

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Open Access 01-07-2020 | Short Communication

Spectroscopic and crystallographic characterization of a new cathinone derivative: 1-phenyl-2-(butylamino)hexan-1-one hydrochloride (N-butylhexedrone)

Authors: Marcin Rojkiewicz, Piotr Kuś, Joachim Kusz, Maria Książek, Aleksander Sochanik

Published in: Forensic Toxicology | Issue 2/2020

Abstract

Purpose

In this study, a new cathinone derivative, N-butylhexedrone, emerged on new psychoactive substances (NPS) market in Poland was described and characterized.

Methods

The compound was analyzed by gas chromatography—mass spectrometry, X-ray crystallography and infrared, Raman, ultraviolet-visible and nuclear magnetic resonance spectroscopic approaches.

Results

We confirmed the presence of the compound in the seized material and obtained detailed and comprehensive physicochemical characterization of N-butylhexedrone—new cathinone derivative available on the NPS market.

Conclusions

In this study, we presented chromatographic, spectroscopic and crystallographic characterization of a new cathinone derivative that emerged on the NPS market in 2019. The obtained analytical data should be useful for forensic and toxicological purposes in quick and reliable compound identification.

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Adamowicz P, Geroń J, Gil D, Lechowicz W, Skulska A, Tokarczyk B (2016) The prevalence of new psychoactive substances in biological material—a three-year review of casework in Poland. Drug Test Anal 8:63–70. https://doi.org/10.1002/dta.1924 CrossRefPubMed

Zawilska J, Wojcieszak J (2017) α-Pyrrolidinophenones: a new wave of designer cathinones. Forensic Toxicol 35:201–216. https://doi.org/10.1007/s11419-016-0353-6 CrossRef

Couto RAS, Gonçalves LM, Carvalho F, Rodrigues JA, Rodrigues CMP, Quinaz MB (2018) The analytical challenge in the determination of cathinones, key-players in the worldwide phenomenon of novel psychoactive substances. Crit Rev Anal Chem 48:372–390. https://doi.org/10.1080/10408347.2018.1439724 CrossRefPubMed

Zawilska JB, Wojcieszak J (2013) Designer cathinones—an emerging class of novel recreational drugs. Forensic Sci Int 231:42–53. https://doi.org/10.1016/j.forsciint.2013.04.015 CrossRefPubMed

Romanek K, Stenzel J, Schmoll S, Schrettl V, Geith S, Eyer F, Rabe C (2017) Synthetic cathinones in Southern Germany—characteristics of users, substance-patterns, co-ingestions, and complications. Clin Toxicol 55:573–578. https://doi.org/10.1080/15563650.2017.1301463 CrossRef

Glicksberg L, Winecker R, Miller C, Kerrigan S (2018) Postmortem distribution and redistribution of synthetic cathinones. Forensic Toxicol 36:291–303. https://doi.org/10.1007/s11419-018-0403-3 CrossRef

Rojkiewicz M, Kuś P, Kusz J, Książek M (2018) Spectroscopic and crystallographic characterization of two cathinone derivatives: 1-(4-fluorophenyl)-2-(methylamino)pentan-1-one (4-FPD) hydrochloride and 1-(4-methylphenyl)-2-(ethylamino)pentan-1-one (4-MEAP) hydrochloride. Forensic Toxicol 36:141–150. https://doi.org/10.1007/s11419-017-0393-6(open access article) CrossRefPubMed

Kuś P, Rojkiewicz M, Kusz J, Książek M, Sochanik A (2019) Spectroscopic characterization and crystal structures of four hydrochloride cathinones: N-ethyl-2-amino-1-phenylhexan-1-one (hexen, NEH), N-methyl-2-amino-1-(4-methylphenyl)-3-methoxypropan-1-one (mexedrone), N-ethyl-2-amino-1-(3,4-methylenedioxyphenyl)pentan-1-one (ephylone) and N-butyl-2-amino-1-(4-chlorophenyl)propan-1-one (4-chlorobutylcathinone). Forensic Toxicol 37:456–464. https://doi.org/10.1007/s11419-019-00477-y(open access article) CrossRef

Nycz JE, Małecki G, Zawiązalec M, Paździorek T (2011) X-ray structures and computational studies of several cathinones. J Mol Struct 1002:10–18. https://doi.org/10.1016/j.molstruc.2011.06.030 CrossRef

10.

Trzybiński D, Niedziałkowski P, Ossowski T, Trynda A, Sikorski A (2013) Single-crystal X-ray diffraction analysis of designer drugs: hydrochlorides of metaphedrone and pentedrone. Forensic Sci Int 232:e28–e32. https://doi.org/10.1016/j.forsciint.2013.07.012 CrossRefPubMed

11.

Siczek M, Siczek M, Szpot P, Zawadzki M, Wachełko O (2019) Crystal structures and spectroscopic characterization of four synthetic cathinones: 1-(4-chlorophenyl)-2-(dimethylamino)propan-1-one (N-methyl-clephedrone, 4-CDC), 1-(1,3-benzodioxol-5-yl)-2-(tert-butylamino)propan-1-one (tBuONE, tertylone, MDPT), 1-(4-fluorophenyl)-2-(pyrrolidin-1-yl)hexan-1-one (4F-PHP) and 2-(ethylamino)-1-(3-methylphenyl)propan-1-one (3-methyl-ethylcathinone, 3-MEC). Crystals 9:555. https://doi.org/10.3390/cryst9110555(open access article) CrossRef

12.

National Forensic Laboratory, Slovenia (2019) Analytical report: butylhexedrone. https://www.policija.si/apps/nfl_response_web/0_Analytical_Reports_final/Butylhexedrone-ID-2065-19_report.pdf. Accessed 12 Nov 2019

13.

Sheldrick GM (2015) Crystal structure refinement with SHELXL Acta Cryst C71:3–8. https://doi.org/10.1107/S2053229614024218(open access article) CrossRef

14.

Matsuta S, Katagi M, Nishioka H, Kamata H, Sasaki K, Shima N, Kamata T, Miki A, Tatsuno M, Zaitsu K, Tsuboi K, Tsuchihashi H, Suzuki K (2014) Structural characterization of cathinone-type designer drugs by EI mass spectrometry. Jpn J Forensic Sci Technol 19:77–89. https://doi.org/10.3408/jafst.19.77(open access article, in Japanese with English abstract) CrossRef

15.

Fornal E (2014) Study of collision-induced dissociation of electrospray-generated protonated cathinones. Drug Test Anal 6:705–715. https://doi.org/10.1002/dta.1573 CrossRefPubMed

16.

Fornal E (2013) Formation of odd-electron product ions in collision-induced fragmentation of electrospray-generated protonated cathinone derivatives: aryl α-primary amino ketones. Rapid Commun Mass Spectrom 27:1858–1866. https://doi.org/10.1002/rcm.6635 CrossRefPubMed

17.

Kuś P, Kusz J, Książek M, Pieprzyca E, Rojkiewicz M (2018) Spectroscopic characterization and crystal structures of two cathinone derivatives: 1-(4-chlorophenyl)-2-(1-pyrrolidinyl)pentan-1-one (4-chloro-α-PVP) sulfate and 1-(4methylphenyl)-2-(dimethylamino)propan-1-one (4-MDMC) hydrochloride salts, seized on illicit drug market. Forensic Toxicol 36:178–184. https://doi.org/10.1007/s11419-017-0381-x(open access article) CrossRefPubMed

18.

Shevyrin V, Eltsov O, Shafran Y (2020) Identification and analytical characterization of the synthetic cathinone N-butylhexedrone. Drug Test Anal 12:159–163. https://doi.org/10.1002/dta.2712 CrossRefPubMed

Title: Spectroscopic and crystallographic characterization of a new cathinone derivative: 1-phenyl-2-(butylamino)hexan-1-one hydrochloride (N-butylhexedrone)
Authors: Marcin Rojkiewicz
Piotr Kuś
Joachim Kusz
Maria Książek
Aleksander Sochanik
Publication date: 01-07-2020
Publisher: Springer Singapore
Published in: Forensic Toxicology / Issue 2/2020
Print ISSN: 1860-8965
Electronic ISSN: 1860-8973
DOI: https://doi.org/10.1007/s11419-020-00525-y

ACC 2024 Congress

Springer Medicine

Spectroscopic and crystallographic characterization of a new cathinone derivative: 1-phenyl-2-(butylamino)hexan-1-one hydrochloride (N-butylhexedrone)

Abstract

Purpose

Methods

Results

Conclusions

ACC 2024 Congress

Springer Medicine

Abstract

Purpose

Methods

Results

Conclusions

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