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Open Access 01-01-2016 | Original Article

Identification and characterization of new designer drug 4-fluoro-PV9 and α-PHP in the seized materials

Authors: Milena Majchrzak, Marcin Rojkiewicz, Rafał Celiński, Piotr Kuś, Mieczysław Sajewicz

Published in: Forensic Toxicology | Issue 1/2016

Abstract

In this study, we present identification and physicochemical characterization of new cathinone derivatives, 4-fluoro-PV9 and already known α-PHP in seized materials. Although the disclosure of α-PHP from an illegal product had been reported and characterized to some extent, the data on α-PHP are also presented together with those of 4-fluoro-PV9. The data of characterization for the two compounds were obtained by high-performance liquid chromatography (HPLC)–mass spectrometry and HPLC–diode array detection, electrospray ionization/ion trap mass spectrometry in MS² and MS³ modes, gas chromatography–mass spectrometry, thermogravimetric analysis, differential scanning calorimetry, Fourier transform infrared spectroscopy, ultraviolet-visible spectroscopy, and nuclear magnetic resonance spectroscopy. To our knowledge, this is the first report for identification and detailed characterization of 4-fluoro-PV9 circulated on the illegal drug market.

Liechti M (2015) Novel psychoactive substances (designer drugs): overview and pharmacology of modulators of monoamine signaling. Swiss Med Wkly 145:w14043PubMed

Baumann MH, Solis E, Watterson LR, Marusich JA, Fantegrossi WE, Wiley JL (2014) Bath salts, spice, and related designer drugs: the science behind the headlines. J Neurosci 34:15150–15158PubMedPubMedCentralCrossRef

Weaver MF, Hopper JA, Gunderson EW (2015) Designer drugs 2015: assessment and management. Addict Sci Clin Pract. doi:10.1186/s13722-015-0024-7 PubMedPubMedCentral

European Monitoring Centre for Drugs and Drug Addiction (2015) New psychoactive substances in Europe. Publications Office of the European Union, Luxembourg (An update from the EU Early Warning System)

Arbo MD, Bastos ML, Carmo HF (2012) Piperazine compounds as drugs of abuse. Drug Alcohol Depen 122:174–185CrossRef

Schep LJ, Slaughter RJ, Vale JA, Beasley DMG, Gee P (2011) The clinical toxicology of the designer “party pills” benzylpiperazine and trifluoromethylphenylpiperazine. Clin Toxicol 49:131–141CrossRef

Srisuma S, Bronstein AC, Hoyte CO (2015) NBOMe and 2C substitute phenylethylamine exposures reported to the National Poison Data System. Clin Toxicol 53:624–628CrossRef

Zuba D, Sekuła K, Buczek A (2013) 25C-NBOMe—new potent hallucinogenic substance identified on the drug market. Forensic Sci Int 227:7–14PubMedCrossRef

Denooz R, Vanheugen JC, Frederich M, de Tullio P, Charlier C (2013) Identification and structural elucidation of four cannabimimetic compounds (RCS-4, AM-2201, JWH-203 and JWH-210) in seized products. J Anal Toxicol 37:56–63PubMedCrossRef

10.

Adamowicz P, Lechowicz W (2015) The influence of synthetic cannabinoid UR-144 on human psychomotor performance—a case report demonstrating road traffic risks. Traffic Inj Prev. doi:10.1080/15389588.2015.1018990 PubMed

11.

Katz DP, Bhattacharya D, Bhattacharya S, Deruiter J, Clark CR, Suppiramaniam V, Dhanasekaran M (2014) Synthetic cathinones: “a khat and mouse game”. Toxicol Lett 229:349–356PubMedCrossRef

12.

Valente MJ, Guedes de Pinho P, de Lourdes Bastos M, Carvalho F, Carvalho M (2014) Khat and synthetic cathinones: a review. Arch Toxicol 88:15–45PubMedCrossRef

13.

Szendrei K (1980) The chemistry of khat. Bull Narc 32:5–35PubMed

14.

Patel NB (2015) “Natural amphetamine” khat: a cultural tradition or a drug of abuse? Int Rev Neurobiol 120:235–255PubMedCrossRef

15.

Brenneisen R, Fisch HU, Koelbing U, Geisshüsler S, Kalix P (1990) Amphetamine-like effects in humans of the khat alkaloid cathinone. Br J Clin Pharmacol 30:825–828PubMedPubMedCentralCrossRef

16.

Vardakou I, Pistos C, Spiliopoulou C (2011) Drugs for youth via Internet and the example of mephedrone. Toxicol Lett 201:191–195PubMedCrossRef

17.

Gibbons S, Zloh M (2010) An analysis of the “legal high” mephedrone. Bioorg Med Chem Lett 20:4135–4139PubMedCrossRef

18.

Westphal F, Junge T, Klein B, Fritschi G, Girreser U (2011) Spectroscopic characterization of 3,4-methylenedioxypyrrolidinobutyrophenone: a new designer drug with α-pyrrolidinophenone structure. Forensic Sci Int 209:126–132PubMedCrossRef

19.

Kaizaki A, Tanaka S, Numazawa S (2014) New recreational drug 1-phenyl-2-(1-pyrrolidinyl)-1-pentanone (alpha-PVP) activates central nervous system via dopaminergic neuron. J Toxicol Sci 39:1–6PubMedCrossRef

20.

Uralets V, Rana S, Morgan S, Ross W (2014) Testing for designer stimulants: metabolic profiles of 16 synthetic cathinones excreted free in human urine. J Anal Toxicol 38:233–241PubMedCrossRef

21.

Jankovics P, Váradi A, Tölgyesi L, Lohner S, Németh-Palotás J, Koszegi-Szalai H (2011) Identification and characterization of the new designer drug 4′-methylethcathinone (4-MEC) and elaboration of a novel liquid chromatography–tandem mass spectrometry (LC–MS/MS) screening method for seven different methcathinone analogs. Forensic Sci Int 210:213–220PubMedCrossRef

22.

Ibáñez M, Sancho JV, Bijlsma L, Van Nuijs ALN, Covaci A, Hernández F (2014) Comprehensive analytical strategies based on high-resolution time-of-flight mass spectrometry to identify new psychoactive substances. Trac-Trend Anal Chem 57:107–117CrossRef

23.

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 243:1–13PubMedCrossRef

24.

Fornal E (2013) Identification of substituted cathinones: 3,4-methylenedioxy derivatives by high performance liquid chromatography–quadrupole time of flight mass spectrometry. J Pharm Biomed Anal 81–82:13–19PubMedCrossRef

25.

Zuba D (2012) Identification of cathinones and other active components of “legal highs” by mass spectrometric methods. Trac-Trend Anal Chem 32:15–30CrossRef

26.

Westphal F, Junge T, Rösner P, Fritschi G, Klein B, Girreser U (2007) Mass spectral and NMR spectral data of two new designer drugs with an α-aminophenone structure: 4′-methyl-α-pyrrolidinohexanophenone and 4′-methyl-α-pyrrolidinobutyrophenone. Forensic Sci Int 169:32–42PubMedCrossRef

27.

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 32:266–281CrossRef

28.

Cayman Chemical (2015) Cayman spectral library. https://www.caymanchem.com/app/template/SpectralLibrary.vm. Accessed 6 Mar 2015

Title: Identification and characterization of new designer drug 4-fluoro-PV9 and α-PHP in the seized materials
Authors: Milena Majchrzak
Marcin Rojkiewicz
Rafał Celiński
Piotr Kuś
Mieczysław Sajewicz
Publication date: 01-01-2016
Publisher: Springer Japan
Published in: Forensic Toxicology / Issue 1/2016
Print ISSN: 1860-8965
Electronic ISSN: 1860-8973
DOI: https://doi.org/10.1007/s11419-015-0295-4

Keynote webinar | Spotlight on medication adherence

Springer Medicine

Identification and characterization of new designer drug 4-fluoro-PV9 and α-PHP in the seized materials

Abstract

Keynote webinar | Spotlight on medication adherence

Springer Medicine

Abstract

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