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Erschienen in: Forensic Toxicology 2/2017

06.03.2017 | Original Article

Identification and structural characterization of four novel synthetic cathinones: α-methylaminohexanophenone (hexedrone, HEX), 4-bromoethcathinone (4-BEC), 4-chloro-α-pyrrolidinopropiophenone (4-Cl-PPP), and 4-bromo-α-pyrrolidinopentiophenone (4-Br-PVP) after their seizures

verfasst von: Agata Błażewicz, Elżbieta Bednarek, Jerzy Sitkowski, Magdalena Popławska, Karolina Stypułkowska, Wojciech Bocian, Lech Kozerski

Erschienen in: Forensic Toxicology | Ausgabe 2/2017

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Abstract

Over 560 new psychoactive substances have been detected via the European Union Early Warning System (EU-EWS) of the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) between 2005 and 2015. Among them, 103 synthetic cathinones have been identified, which are the second largest group monitored by EMCDDA. National Medicines Institute in Poland analyzed over six thousands samples of designer drugs containing psychoactive substances from 2008 to 2015 by applying complementary techniques, i.e., liquid chromatography with high resolution mass spectrometry, gas chromatography with mass spectrometry, and nuclear magnetic resonance spectroscopy. Among over 150 identified psychoactive substances from different groups, the largest was an ensemble of substituted cathinones containing 48 items. Most of them were cathinones not covered by the Act on Counteracting Drug Addiction in Poland at the time of identification; however, they have been added successively to the list of banned compounds in the consecutive amendments of the Act. The present study describes the structure identification and spectral characterization of four novel substituted cathinones: hexedrone [2-methylamino-1-(phenyl)hexan-1-one], 4-BEC [1-(4-bromophenyl)-2-(ethylamino)propan-1-one], 4-Cl-PPP [1-(4-chlorophenyl)-2-(pyrrolidin-1-yl)propan-1-one], and 4-Br-PVP [1-(4-bromophenyl)-2-(pyrrolidin-1-yl)pentan-1-one], seized prior to being sold on the drug market. They were identified for the first time by us and reported to EU-EWS EMCDDA.
Literatur
2.
Zurück zum Zitat Hassan NA, Gunaid AA, Murray-Lyon IM (2007) Khat (Catha edulis): health aspects of khat chewing. East Mediterr Health J 13:706–718PubMed Hassan NA, Gunaid AA, Murray-Lyon IM (2007) Khat (Catha edulis): health aspects of khat chewing. East Mediterr Health J 13:706–718PubMed
6.
Zurück zum Zitat Zaitsu K, Katagi M, Tsuchihashi H, Ishii A (2014) Recently abused synthetic cathinones, α-pyrrolidinophenone derivatives: a review of their pharmacology, acute toxicity, and metabolism. Forensic Toxicol 32:1–8. doi:10.1007/s11419-013-0218-1 CrossRef Zaitsu K, Katagi M, Tsuchihashi H, Ishii A (2014) Recently abused synthetic cathinones, α-pyrrolidinophenone derivatives: a review of their pharmacology, acute toxicity, and metabolism. Forensic Toxicol 32:1–8. doi:10.​1007/​s11419-013-0218-1 CrossRef
12.
14.
Zurück zum Zitat Uchiyama N, Matsuda S, Kawamura M, Shimokawa Y, Kikura-Hanajiri R, Aritake K, Urade Y, Goda Y (2014) Characterization of four new designer drugs, 5-chloro-NNEI, NNEI indazole analog, α-PHPP and α-POP, with 11 newly distributed designer drugs in illegal products. Forensic Sci Int 243:1–13. doi:10.1016/j.forsciint.2014.03.013 CrossRefPubMed Uchiyama N, Matsuda S, Kawamura M, Shimokawa Y, Kikura-Hanajiri R, Aritake K, Urade Y, Goda Y (2014) Characterization of four new designer drugs, 5-chloro-NNEI, NNEI indazole analog, α-PHPP and α-POP, with 11 newly distributed designer drugs in illegal products. Forensic Sci Int 243:1–13. doi:10.​1016/​j.​forsciint.​2014.​03.​013 CrossRefPubMed
15.
Zurück zum Zitat Gaspar H, Bronze S, Ciríaco S, Queirós CR, Matias A, Rodrigues J, Oliveira C, Cordeiro C, Santos S (2015) 4F-PBP (4′-fluoro-α-pyrrolidinobutyrophenone), a new substance of abuse: structural characterization and purity NMR profiling. Forensic Sci Int 252:168–176. doi:10.1016/j.forsciint.2015.05.003 CrossRefPubMed Gaspar H, Bronze S, Ciríaco S, Queirós CR, Matias A, Rodrigues J, Oliveira C, Cordeiro C, Santos S (2015) 4F-PBP (4′-fluoro-α-pyrrolidinobutyrophenone), a new substance of abuse: structural characterization and purity NMR profiling. Forensic Sci Int 252:168–176. doi:10.​1016/​j.​forsciint.​2015.​05.​003 CrossRefPubMed
16.
Zurück zum Zitat Hasegawa K, Wurita A, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Suzuki O, Watanabe K (2014) Identification and quantitation of a new cathinone designer drug PV9 in an “aroma liquid” product, antemortem whole blood and urine specimens, and a postmortem whole blood specimen in a fatal poisoning case. Forensic Toxicol 32:243–250. doi:10.1007/s11419-014-0230-0 CrossRef Hasegawa K, Wurita A, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Suzuki O, Watanabe K (2014) Identification and quantitation of a new cathinone designer drug PV9 in an “aroma liquid” product, antemortem whole blood and urine specimens, and a postmortem whole blood specimen in a fatal poisoning case. Forensic Toxicol 32:243–250. doi:10.​1007/​s11419-014-0230-0 CrossRef
17.
Zurück zum Zitat Uchiyama N, Shimokawa Y, Kawamura M, Kikura-Hanajiri R, Hakamatsuka T (2014) Chemical analysis of a benzofuran derivative, 2-(2-ethylaminopropyl)benzofuran (2-EAPB), eight synthetic cannabinoids, five cathinone derivatives, and five other designer drugs newly detected in illegal products. Forensic Toxicol 32:266–281. doi:10.1007/s11419-014-0238-5 CrossRef Uchiyama N, Shimokawa Y, Kawamura M, Kikura-Hanajiri R, Hakamatsuka T (2014) Chemical analysis of a benzofuran derivative, 2-(2-ethylaminopropyl)benzofuran (2-EAPB), eight synthetic cannabinoids, five cathinone derivatives, and five other designer drugs newly detected in illegal products. Forensic Toxicol 32:266–281. doi:10.​1007/​s11419-014-0238-5 CrossRef
18.
Zurück zum Zitat Minakata K, Yamagishi I, Nozawa H, Hasegawa K, Wurita A, Gonmori K, Suzuki M, Watanabe K, Suzuki O (2015) Determination of new pyrrolidino cathinone derivatives, PVT, F-PVP, MPHP, PV8, PV9 and F-PV9, in human blood by MALDI-Q-TOF mass spectrometry. Forensic Toxicol 33:148–154. doi:10.1007/s11419-014-0248-3 CrossRef Minakata K, Yamagishi I, Nozawa H, Hasegawa K, Wurita A, Gonmori K, Suzuki M, Watanabe K, Suzuki O (2015) Determination of new pyrrolidino cathinone derivatives, PVT, F-PVP, MPHP, PV8, PV9 and F-PV9, in human blood by MALDI-Q-TOF mass spectrometry. Forensic Toxicol 33:148–154. doi:10.​1007/​s11419-014-0248-3 CrossRef
19.
Zurück zum Zitat Minakata K, Yamagishi I, Nozawa H, Hasegawa K, Wurita A, Gonmori K, Suzuki M, Watanabe K, Suzuki O (2014) MALDI-TOF mass spectrometric determination of four pyrrolidino cathinones in human blood. Forensic Toxicol 32:169–175. doi:10.1007/s11419-013-0212-7 CrossRef Minakata K, Yamagishi I, Nozawa H, Hasegawa K, Wurita A, Gonmori K, Suzuki M, Watanabe K, Suzuki O (2014) MALDI-TOF mass spectrometric determination of four pyrrolidino cathinones in human blood. Forensic Toxicol 32:169–175. doi:10.​1007/​s11419-013-0212-7 CrossRef
21.
Zurück zum Zitat Paul M, Bleicher S, Guber S, Ippisch J, Polettini A, Schultis W (2015) Identification of phase I and II metabolites of the new designer drug α-pyrrolidinohexiophenone (α-PHP) in human urine by liquid chromatography quadrupole time-of-flight mass spectrometry (LC-QTOF-MS). J Mass Spectrom 50:1305–1317. doi:10.1002/jms.3642 CrossRefPubMed Paul M, Bleicher S, Guber S, Ippisch J, Polettini A, Schultis W (2015) Identification of phase I and II metabolites of the new designer drug α-pyrrolidinohexiophenone (α-PHP) in human urine by liquid chromatography quadrupole time-of-flight mass spectrometry (LC-QTOF-MS). J Mass Spectrom 50:1305–1317. doi:10.​1002/​jms.​3642 CrossRefPubMed
25.
Zurück zum Zitat Fornal E (2013) Formation of odd-electron product ions in collision-induced fragmentation of electrospray generated protonated cathinone derivatives: aryl α-primary aminoketones. Rapid Commun Mass Spectrom 27:1858–1866. doi:10.1002/rcm.6635 CrossRefPubMed Fornal E (2013) Formation of odd-electron product ions in collision-induced fragmentation of electrospray generated protonated cathinone derivatives: aryl α-primary aminoketones. Rapid Commun Mass Spectrom 27:1858–1866. doi:10.​1002/​rcm.​6635 CrossRefPubMed
Metadaten
Titel
Identification and structural characterization of four novel synthetic cathinones: α-methylaminohexanophenone (hexedrone, HEX), 4-bromoethcathinone (4-BEC), 4-chloro-α-pyrrolidinopropiophenone (4-Cl-PPP), and 4-bromo-α-pyrrolidinopentiophenone (4-Br-PVP) after their seizures
verfasst von
Agata Błażewicz
Elżbieta Bednarek
Jerzy Sitkowski
Magdalena Popławska
Karolina Stypułkowska
Wojciech Bocian
Lech Kozerski
Publikationsdatum
06.03.2017
Verlag
Springer Japan
Erschienen in
Forensic Toxicology / Ausgabe 2/2017
Print ISSN: 1860-8965
Elektronische ISSN: 1860-8973
DOI
https://doi.org/10.1007/s11419-017-0360-2

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