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Published in: Forensic Toxicology 1/2018

Open Access 01-01-2018 | Review Article

The newest cathinone derivatives as designer drugs: an analytical and toxicological review

Authors: Milena Majchrzak, Rafał Celiński, Piotr Kuś, Teresa Kowalska, Mieczysław Sajewicz

Published in: Forensic Toxicology | Issue 1/2018

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Abstract

Purpose

Currently, among new psychoactive substances, cathinone derivatives constitute the biggest group, which are mainly classified into N-alkylated, 3,4-methylenedioxy-N-alkylated, N-pyrrolidinyl, and 3,4-methylenedioxy-N-pyrrolidinyl derivatives. These derivatives are actively being subjected to minor modifications at the alkyl chains or the aromatic ring to create new synthetic cathinones with the goal of circumventing laws. In this review, the new synthetic cathinones that have appeared on the illegal drug market during the period 2014–2017 are highlighted, and their characterization by gas chromatography–mass spectrometry and liquid chromatography–tandem mass spectrometry is presented.

Methods

Various key words were used to conduct an extensive literature search across a number of databases, specifically for synthetic cathinones that emerged between 2014 and 2017.

Results

More than 30 new cathinone derivatives were discovered. The preexisting parental compounds for the new derivatives are also referenced, and their mass spectral data are compiled in a table to facilitate their identification by forensic toxicologists.

Conclusions

To our knowledge, this is the most current review presenting new synthetic cathinones. Political authorities should take measures to implement and enforce generic scheduling (comprehensive system) laws to control the diversely modified synthetic cathinones. Supplementing the existing databases with new findings can greatly facilitate the efforts of forensic toxicologists.
Literature
1.
go back to reference 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 30:825–828CrossRefPubMedPubMedCentral 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 30:825–828CrossRefPubMedPubMedCentral
2.
go back to reference Feyissa AM, Kelly JP (2008) A review of the neuropharmacological properties of khat. Prog Neuropsychopharmacol Biol Psychiat 32:1147–1166CrossRef Feyissa AM, Kelly JP (2008) A review of the neuropharmacological properties of khat. Prog Neuropsychopharmacol Biol Psychiat 32:1147–1166CrossRef
3.
go back to reference Patel NB (2015) “Natural amphetamine” khat: a cultural tradition or a drug of abuse? Int Rev Neurobiol 120:235–255CrossRefPubMed Patel NB (2015) “Natural amphetamine” khat: a cultural tradition or a drug of abuse? Int Rev Neurobiol 120:235–255CrossRefPubMed
4.
5.
go back to reference Katz DP, Bhattacharya D, Bhattacharya S, Deruiter J, Clark CR, Suppiramaniam V, Dhanasekaran M (2014) Synthetic cathinones: “a khat and mouse game. Toxicol Lett 229:349–356CrossRefPubMed Katz DP, Bhattacharya D, Bhattacharya S, Deruiter J, Clark CR, Suppiramaniam V, Dhanasekaran M (2014) Synthetic cathinones: “a khat and mouse game. Toxicol Lett 229:349–356CrossRefPubMed
6.
go back to reference Valente MJ, Guedes de Pinho P, de Lourdes Bastos M, Carvalho F, Carvalho M (2014) Khat and synthetic cathinones: a review. Arch Toxicol 88:15–45CrossRefPubMed Valente MJ, Guedes de Pinho P, de Lourdes Bastos M, Carvalho F, Carvalho M (2014) Khat and synthetic cathinones: a review. Arch Toxicol 88:15–45CrossRefPubMed
7.
go back to reference Baumann MH, Solis E, Watterson LR, Marusich JA, Fantegrossi WE, Wiley JL (2014) Baths salts, spice, and related designer drugs: the science behind the headlines. J Neurosci 34:15150–15158CrossRefPubMedPubMedCentral Baumann MH, Solis E, Watterson LR, Marusich JA, Fantegrossi WE, Wiley JL (2014) Baths salts, spice, and related designer drugs: the science behind the headlines. J Neurosci 34:15150–15158CrossRefPubMedPubMedCentral
8.
go back to reference Favretto D, Pascali JP, Tagliaro F (2013) New challenges and innovation in forensic toxicology: focus on the “new psychoactive substances”. J Chromatogr A 1287:84–95CrossRefPubMed Favretto D, Pascali JP, Tagliaro F (2013) New challenges and innovation in forensic toxicology: focus on the “new psychoactive substances”. J Chromatogr A 1287:84–95CrossRefPubMed
9.
go back to reference Paillet-Loilier M, Cesbron A, Le Boisselier R, Bourgine J (2014) Emerging drugs of abuse: current perspectives on substituted cathinones. Subst Abuse Rehabil 5:37–52PubMedPubMedCentral Paillet-Loilier M, Cesbron A, Le Boisselier R, Bourgine J (2014) Emerging drugs of abuse: current perspectives on substituted cathinones. Subst Abuse Rehabil 5:37–52PubMedPubMedCentral
10.
go back to reference Vardakou I, Pistos C, Spiliopoulou C (2011) Drugs for youth via internet and the example of mephedrone. Toxicol Lett 201:191–195CrossRefPubMed Vardakou I, Pistos C, Spiliopoulou C (2011) Drugs for youth via internet and the example of mephedrone. Toxicol Lett 201:191–195CrossRefPubMed
12.
go back to reference Zawilska JB, Wojcieszak J (2013) Designer cathinones–an emerging class of novel recreational drugs. Forensic Sci Int 231:42–53CrossRefPubMed Zawilska JB, Wojcieszak J (2013) Designer cathinones–an emerging class of novel recreational drugs. Forensic Sci Int 231:42–53CrossRefPubMed
13.
go back to reference Simmler LD, Buser TA, Donzelli M, Schramm Y, Dieu LH, Huwyler J, Chaboz S, Hoener MC, Liechti ME (2013) Pharmacological characterization of designer cathinones in vitro. Br J Pharmacol 168:458–470CrossRefPubMed Simmler LD, Buser TA, Donzelli M, Schramm Y, Dieu LH, Huwyler J, Chaboz S, Hoener MC, Liechti ME (2013) Pharmacological characterization of designer cathinones in vitro. Br J Pharmacol 168:458–470CrossRefPubMed
14.
go back to reference Baumann MH, Ayestas MA Jr, Partilla JS, Sink JR, Shulgin AT, Daley PF, Brandt SD, Rothman RB, Ruoho RAE, Cozzi NV (2012) The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue. Neuropsychopharmacology 37:1192–1203CrossRefPubMed Baumann MH, Ayestas MA Jr, Partilla JS, Sink JR, Shulgin AT, Daley PF, Brandt SD, Rothman RB, Ruoho RAE, Cozzi NV (2012) The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue. Neuropsychopharmacology 37:1192–1203CrossRefPubMed
15.
go back to reference Baumann MH, Partilla JS, Lehner KR, Thorndike EB, Hoffman AF, Holy M, Rothman RB, Goldberg SR, Lupica CR, Sitte HH, Brandt SD, Tella SR, Cozzi NV, Schindler CW (2013) Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive ‘bath salts’ products. Neuropsychopharmacology 38:552–562CrossRefPubMed Baumann MH, Partilla JS, Lehner KR, Thorndike EB, Hoffman AF, Holy M, Rothman RB, Goldberg SR, Lupica CR, Sitte HH, Brandt SD, Tella SR, Cozzi NV, Schindler CW (2013) Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive ‘bath salts’ products. Neuropsychopharmacology 38:552–562CrossRefPubMed
16.
go back to reference López-Arnau R, Martínez-Clemente J, Pubill D, Escubedo E, Camarasa J (2012) Comparative neuropharmacology of three psychostimulant cathinone derivatives: butylone, mephedrone and methylone. Br J Pharmacol 167:407–420CrossRefPubMedPubMedCentral López-Arnau R, Martínez-Clemente J, Pubill D, Escubedo E, Camarasa J (2012) Comparative neuropharmacology of three psychostimulant cathinone derivatives: butylone, mephedrone and methylone. Br J Pharmacol 167:407–420CrossRefPubMedPubMedCentral
17.
go back to reference Martinez-Clemente J, Escubedo E, Pubill D, Camarasa J (2012) Interaction of mephedrone with dopamine and serotonin targets in rats. Eur Neuropsychopharmacol 22:231–236CrossRefPubMed Martinez-Clemente J, Escubedo E, Pubill D, Camarasa J (2012) Interaction of mephedrone with dopamine and serotonin targets in rats. Eur Neuropsychopharmacol 22:231–236CrossRefPubMed
18.
go back to reference Meyer MR, Wilhelm J, Peters FT, Maurer HH (2010) Beta-keto amphetamines: studies on the metabolism of the designer drug mephedrone and toxicological detection of mephedrone, butylone, and methylone in urine using gas chromatography-mass spectrometry. Anal Bioanal Chem 397:1225–1233CrossRefPubMed Meyer MR, Wilhelm J, Peters FT, Maurer HH (2010) Beta-keto amphetamines: studies on the metabolism of the designer drug mephedrone and toxicological detection of mephedrone, butylone, and methylone in urine using gas chromatography-mass spectrometry. Anal Bioanal Chem 397:1225–1233CrossRefPubMed
19.
go back to reference Gibbons S, Zloh M (2010) An analysis of the “legal high” mephedrone. Bioorg Med Chem 20:4135–4139CrossRef Gibbons S, Zloh M (2010) An analysis of the “legal high” mephedrone. Bioorg Med Chem 20:4135–4139CrossRef
20.
go back to reference Dargan PI, Sedefov R, Gallegos A, Wood DM (2011) The pharmacology and toxicology of the synthetic cathinone mephedrone (4-methylmethcathinone). Drug Test Anal 3:454–463CrossRefPubMed Dargan PI, Sedefov R, Gallegos A, Wood DM (2011) The pharmacology and toxicology of the synthetic cathinone mephedrone (4-methylmethcathinone). Drug Test Anal 3:454–463CrossRefPubMed
22.
go back to reference 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 38:233–241CrossRefPubMed 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 38:233–241CrossRefPubMed
23.
go back to reference Lusthof KJ, Oosting R, Maes A, Verschraagen M, Dijkhuizen A, Sprong AGA (2011) A case of extreme agitation and death after the use of mephedrone in The Netherlands. Forensic Sci Int 206:e93–e95CrossRefPubMed Lusthof KJ, Oosting R, Maes A, Verschraagen M, Dijkhuizen A, Sprong AGA (2011) A case of extreme agitation and death after the use of mephedrone in The Netherlands. Forensic Sci Int 206:e93–e95CrossRefPubMed
24.
go back to reference Shima N, Kakehashi H, Matsuta S, Kamata H, Nakano S, Sasaki K, Kamata T, Nishioka H, Zaitsu K, Sato T, Miki A, Katagi M, Tsuchihashi H (2015) Urinary excretion and metabolism of the α-pyrrolidinophenone designer drug 1-phenyl-2-(pyrrolidin-1-yl)octan-1-one (PV9) in humans. Forensic Toxicol 33:279–294CrossRef Shima N, Kakehashi H, Matsuta S, Kamata H, Nakano S, Sasaki K, Kamata T, Nishioka H, Zaitsu K, Sato T, Miki A, Katagi M, Tsuchihashi H (2015) Urinary excretion and metabolism of the α-pyrrolidinophenone designer drug 1-phenyl-2-(pyrrolidin-1-yl)octan-1-one (PV9) in humans. Forensic Toxicol 33:279–294CrossRef
25.
go back to reference Gustaffsson D, Escher C (2009) Mephedrone-Internet drug that seems to have come to stay (in Swedish). Läkartidningen 106:2769–2771 Gustaffsson D, Escher C (2009) Mephedrone-Internet drug that seems to have come to stay (in Swedish). Läkartidningen 106:2769–2771
26.
go back to reference Schifano F, Corkery J, Ghodse AH (2012) Suspected and confirmed fatalities associated with mephedrone (4-methylmethcathinone, “meow meow”) in the United Kingdom. J Clin Psychopharmacol 32:710–714CrossRefPubMed Schifano F, Corkery J, Ghodse AH (2012) Suspected and confirmed fatalities associated with mephedrone (4-methylmethcathinone, “meow meow”) in the United Kingdom. J Clin Psychopharmacol 32:710–714CrossRefPubMed
27.
go back to reference Adamowicz P, Tokarczyk B, Stanaszek R, Slopianka M (2013) Fatal mephedrone intoxication—a case report. J Anal Toxicol 37:37–42CrossRefPubMed Adamowicz P, Tokarczyk B, Stanaszek R, Slopianka M (2013) Fatal mephedrone intoxication—a case report. J Anal Toxicol 37:37–42CrossRefPubMed
28.
go back to reference Young AC, Schwarz ES, Velez LI, Gardner M (2013) Two cases of disseminated intravascular coagulation due to “bath salts” resulting in fatalities, with laboratory confirmation. Am J Emerg Med 31:445.e3–445.e5CrossRef Young AC, Schwarz ES, Velez LI, Gardner M (2013) Two cases of disseminated intravascular coagulation due to “bath salts” resulting in fatalities, with laboratory confirmation. Am J Emerg Med 31:445.e3–445.e5CrossRef
29.
go back to reference Cawrse BM, Levine B, Jufer RA, Fowler DR, Vorce SP, Dickson AJ, Holler JM (2012) Distribution of methylone in four postmortem cases. J Anal Toxicol 36:434–439CrossRefPubMed Cawrse BM, Levine B, Jufer RA, Fowler DR, Vorce SP, Dickson AJ, Holler JM (2012) Distribution of methylone in four postmortem cases. J Anal Toxicol 36:434–439CrossRefPubMed
30.
go back to reference Murray BL, Murphy CM, Beuhler MC (2012) Death following recreational use of designer drug “bath salts” containing 3,4-methylenedioxypyrovalerone (MDPV). J Med Toxicol 8:69–75CrossRefPubMedPubMedCentral Murray BL, Murphy CM, Beuhler MC (2012) Death following recreational use of designer drug “bath salts” containing 3,4-methylenedioxypyrovalerone (MDPV). J Med Toxicol 8:69–75CrossRefPubMedPubMedCentral
31.
go back to reference Hasegawa K, Wurita A, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Watanabe K, Suzuki O (2015) Postmortem distribution of PV9, a new cathinone derivative, in human solid tissues in a fatal poisoning case. Forensic Toxicol 33:141–147CrossRef Hasegawa K, Wurita A, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Watanabe K, Suzuki O (2015) Postmortem distribution of PV9, a new cathinone derivative, in human solid tissues in a fatal poisoning case. Forensic Toxicol 33:141–147CrossRef
32.
go back to reference Kudo K, Usumoto Y, Kikura-Hanajiri R, Sameshima N, Tsuji A, Ikeda N (2015) A fatal case of poisoning related to new cathinone designer drugs, 4-methoxy PV8, PV9, and 4-methoxy PV9, and a dissociative agent, diphenidine. Leg Med 17:421–426CrossRef Kudo K, Usumoto Y, Kikura-Hanajiri R, Sameshima N, Tsuji A, Ikeda N (2015) A fatal case of poisoning related to new cathinone designer drugs, 4-methoxy PV8, PV9, and 4-methoxy PV9, and a dissociative agent, diphenidine. Leg Med 17:421–426CrossRef
33.
go back to reference Dickson AJ, Vorce SP, Levine B, Past MR (2010) Multiple-drug toxicity caused by the coadministration of 4-methylmethcathinone (mephedrone) and heroin. J Anal Toxicol 34:162–168CrossRefPubMed Dickson AJ, Vorce SP, Levine B, Past MR (2010) Multiple-drug toxicity caused by the coadministration of 4-methylmethcathinone (mephedrone) and heroin. J Anal Toxicol 34:162–168CrossRefPubMed
34.
go back to reference Wyman JF, Lavins ES, Engelhart D, Armstrong EJ, Snell KD, Boggs PD, Taylor SM, Norris RN, Miller FP (2013) Postmortem tissue distribution of MDPV following lethal intoxication by bath salts. J Anal Toxicol 37:182–185CrossRefPubMed Wyman JF, Lavins ES, Engelhart D, Armstrong EJ, Snell KD, Boggs PD, Taylor SM, Norris RN, Miller FP (2013) Postmortem tissue distribution of MDPV following lethal intoxication by bath salts. J Anal Toxicol 37:182–185CrossRefPubMed
35.
go back to reference Rojek S, Kłys M, Strona M, Maciów M, Kula K (2012) “Legal Highs”–toxicity in the clinical and medico-legal aspect as exemplified by suicide with bk-MDMA administration. Forensic Sci Int 22:e1–e6CrossRef Rojek S, Kłys M, Strona M, Maciów M, Kula K (2012) “Legal Highs”–toxicity in the clinical and medico-legal aspect as exemplified by suicide with bk-MDMA administration. Forensic Sci Int 22:e1–e6CrossRef
36.
go back to reference Usui K, Hayashizaki Y, Hashiyada M, Funayama M (2012) Rapid drug extraction from human whole blood using a modified QuEChERS extraction method. Leg Med 14:286–296CrossRef Usui K, Hayashizaki Y, Hashiyada M, Funayama M (2012) Rapid drug extraction from human whole blood using a modified QuEChERS extraction method. Leg Med 14:286–296CrossRef
37.
go back to reference Kudo K, Usumoto Y, Usui K, Hayashida M, Kurisaki E, Saka K, Tsuji A, Ikeda N (2013) Rapid and simultaneous extraction of acidic and basic drugs from human whole blood for reliable semi-quantitative NAGINATA drug screening by GC–MS. Forensic Toxicol 32:97–104CrossRef Kudo K, Usumoto Y, Usui K, Hayashida M, Kurisaki E, Saka K, Tsuji A, Ikeda N (2013) Rapid and simultaneous extraction of acidic and basic drugs from human whole blood for reliable semi-quantitative NAGINATA drug screening by GC–MS. Forensic Toxicol 32:97–104CrossRef
38.
go back to reference Jankovics P, Váradi A, Tölgyesi L, Lohner S, Németh-Palotás J, Kőszegi-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 210:213–220CrossRefPubMed Jankovics P, Váradi A, Tölgyesi L, Lohner S, Németh-Palotás J, Kőszegi-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 210:213–220CrossRefPubMed
39.
go back to reference 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 81–82:13–19CrossRefPubMed 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 81–82:13–19CrossRefPubMed
40.
go back to reference Westphal F, Junge T, Rosner P, Fritschi G, Klein B, Girresee 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 169:32–42CrossRefPubMed Westphal F, Junge T, Rosner P, Fritschi G, Klein B, Girresee 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 169:32–42CrossRefPubMed
41.
go back to reference 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. Trends Anal Chem 57:107–117CrossRef 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. Trends Anal Chem 57:107–117CrossRef
42.
go back to reference Lesiak AD, Musah RA, Cody RB, Domin MA, Dane AJ, Shepard JRE (2013) Direct analysis in real time mass spectrometry (DART-MS) of “bath salt” cathinone drug mixtures. Analyst 138:3424–3432CrossRefPubMed Lesiak AD, Musah RA, Cody RB, Domin MA, Dane AJ, Shepard JRE (2013) Direct analysis in real time mass spectrometry (DART-MS) of “bath salt” cathinone drug mixtures. Analyst 138:3424–3432CrossRefPubMed
43.
go back to reference Namera A, Kawamura M, Nakamoto A, Saito T, Nagao M (2015) Comprehensive review of the detection methods for synthetic cannabinoids and cathinones. Forensic Toxicol 33:175–194CrossRefPubMedPubMedCentral Namera A, Kawamura M, Nakamoto A, Saito T, Nagao M (2015) Comprehensive review of the detection methods for synthetic cannabinoids and cathinones. Forensic Toxicol 33:175–194CrossRefPubMedPubMedCentral
44.
go back to reference Toole KE, Fu S, Shimmon RG, Kraymen N, Taflaga S (2012) Color test for the preliminary identification of methcathinone and analogues of methcathinone. Microgram J 9:27–32 Toole KE, Fu S, Shimmon RG, Kraymen N, Taflaga S (2012) Color test for the preliminary identification of methcathinone and analogues of methcathinone. Microgram J 9:27–32
45.
go back to reference Apollonio LG, Whittall IR, Pianca DJ, Kyd JM, Maher WA (2007) Matrix effect and cross-reactivity of select amphetamine-type substances, designer analogues, and putrefactive amines using the Bio-Quant direct ELISA presumptive assays for amphetamine and methamphetamine. J Anal Toxicol 31:208–213CrossRefPubMed Apollonio LG, Whittall IR, Pianca DJ, Kyd JM, Maher WA (2007) Matrix effect and cross-reactivity of select amphetamine-type substances, designer analogues, and putrefactive amines using the Bio-Quant direct ELISA presumptive assays for amphetamine and methamphetamine. J Anal Toxicol 31:208–213CrossRefPubMed
46.
go back to reference Ellefsen KN, Anizan S, Castaneto MS, Desrosiers NA, Martin LTM, Klette CKL, Huestis MA (2014) Validation of the only commercially available immunoassay for synthetic cathinones in urine: Randox Drugs of Abuse V Biochip Array technology. Drug Test Anal 6:728–738CrossRefPubMedPubMedCentral Ellefsen KN, Anizan S, Castaneto MS, Desrosiers NA, Martin LTM, Klette CKL, Huestis MA (2014) Validation of the only commercially available immunoassay for synthetic cathinones in urine: Randox Drugs of Abuse V Biochip Array technology. Drug Test Anal 6:728–738CrossRefPubMedPubMedCentral
47.
go back to reference Swortwood MJ, Hearn WL, DeCaprio AP (2014) Cross-reactivity of designer drugs, including cathinone derivatives, in commercial enzyme-linked immunosorbent assays. Drug Test Anal 6:716–727CrossRefPubMed Swortwood MJ, Hearn WL, DeCaprio AP (2014) Cross-reactivity of designer drugs, including cathinone derivatives, in commercial enzyme-linked immunosorbent assays. Drug Test Anal 6:716–727CrossRefPubMed
48.
go back to reference Zuba D (2012) Identification of cathinones and other active components of “legal highs” by mass spectrometric methods. Trends Anal Chem 32:15–30CrossRef Zuba D (2012) Identification of cathinones and other active components of “legal highs” by mass spectrometric methods. Trends Anal Chem 32:15–30CrossRef
49.
go back to reference Kohyama E, Chikumoto T, Kitaichi K, Horiuchi T, Ito T (2016) Differentiation of the isomers of N-alkylated cathinones by GC-EI-MS-MS and LC-PDA. Anal Sci 32:831–837CrossRefPubMed Kohyama E, Chikumoto T, Kitaichi K, Horiuchi T, Ito T (2016) Differentiation of the isomers of N-alkylated cathinones by GC-EI-MS-MS and LC-PDA. Anal Sci 32:831–837CrossRefPubMed
50.
go back to reference Zweipfenning PG, Wilderink AH, Horsthuis P, Franke JP, de Zeeuw RA (1994) Toxicological analysis of whole blood samples by means of bond-elut certify columns and gas chromatography with nitrogen–phosphorus detection. J Chromatogr A 674:87–95CrossRefPubMed Zweipfenning PG, Wilderink AH, Horsthuis P, Franke JP, de Zeeuw RA (1994) Toxicological analysis of whole blood samples by means of bond-elut certify columns and gas chromatography with nitrogen–phosphorus detection. J Chromatogr A 674:87–95CrossRefPubMed
51.
go back to reference 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 209:126–132CrossRefPubMed 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 209:126–132CrossRefPubMed
52.
go back to reference Westphal F, Junge T, Girreser U, Greibl W, Doering C (2012) Mass, NMR and IR spectroscopic characterization of pentedrone and pentylone and identification of their isocathinone by-products. Forensic Sci Int 217:157–167CrossRefPubMed Westphal F, Junge T, Girreser U, Greibl W, Doering C (2012) Mass, NMR and IR spectroscopic characterization of pentedrone and pentylone and identification of their isocathinone by-products. Forensic Sci Int 217:157–167CrossRefPubMed
53.
go back to reference Majchrzak M, Rojkiewicz M, Celiński R, Kuś P, Sajewicz M (2016) Identification and characterization of new designer drug 4-fluoro-PV9 and α-PHP in the seized materials. Forensic Toxicol 34:115–124CrossRefPubMed Majchrzak M, Rojkiewicz M, Celiński R, Kuś P, Sajewicz M (2016) Identification and characterization of new designer drug 4-fluoro-PV9 and α-PHP in the seized materials. Forensic Toxicol 34:115–124CrossRefPubMed
54.
go back to reference Gambaro V, Casagni E, Dell’Acqua L, Roda G, Tamborini L, Visconti GL, Demartin F (2016) Identification and characterization of a new designer drug thiothinone in seized products. Forensic Toxicol 34:174–178CrossRef Gambaro V, Casagni E, Dell’Acqua L, Roda G, Tamborini L, Visconti GL, Demartin F (2016) Identification and characterization of a new designer drug thiothinone in seized products. Forensic Toxicol 34:174–178CrossRef
55.
go back to reference 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 243:1–13CrossRefPubMed 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 243:1–13CrossRefPubMed
56.
go back to reference Uchiyama N, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2014) Identification of two new-type designer drugs, piperazine derivative MT-45 (I-C6) and synthetic peptide Noopept (GVS-111), with synthetic cannabinoid A-834735, cathinone derivative 4-methoxy-α-PVP, and phenethylamine derivative 4-methylbuphedrine from illegal products. Forensic Toxicol 32:9–18CrossRef Uchiyama N, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2014) Identification of two new-type designer drugs, piperazine derivative MT-45 (I-C6) and synthetic peptide Noopept (GVS-111), with synthetic cannabinoid A-834735, cathinone derivative 4-methoxy-α-PVP, and phenethylamine derivative 4-methylbuphedrine from illegal products. Forensic Toxicol 32:9–18CrossRef
57.
go back to reference 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 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
58.
go back to reference Uchiyama N, Shimokawa Y, Kikura-Hanajiri R, Demizu Y, Goda Y, Hakamatsuka T (2015) A synthetic cannabinoid FDU-NNEI, two 2H-indazole isomers of synthetic cannabinoids AB-CHMINACA and NNEI indazole analog (MN-18), a phenethylamine derivative N-OH-EDMA, and a cathinone derivative dimethoxy-α-PHP, newly identified in illegal products. Forensic Toxicol 33:244–259CrossRefPubMedPubMedCentral Uchiyama N, Shimokawa Y, Kikura-Hanajiri R, Demizu Y, Goda Y, Hakamatsuka T (2015) A synthetic cannabinoid FDU-NNEI, two 2H-indazole isomers of synthetic cannabinoids AB-CHMINACA and NNEI indazole analog (MN-18), a phenethylamine derivative N-OH-EDMA, and a cathinone derivative dimethoxy-α-PHP, newly identified in illegal products. Forensic Toxicol 33:244–259CrossRefPubMedPubMedCentral
59.
go back to reference Nycz JE, Malecki G, Zawiazalec M, Pazdziorek T (2011) X-ray structures and computational studies of several cathinones. J Mol Struct 1002:10–18CrossRef Nycz JE, Malecki G, Zawiazalec M, Pazdziorek T (2011) X-ray structures and computational studies of several cathinones. J Mol Struct 1002:10–18CrossRef
60.
go back to reference Doi T, Asada A, Takeda A, Tagami T, Katagi M, Matsuta S, Kamata H, Kawaguchi M, Satsuki Y, Sawabe Y, Obana H (2016) Identification and characterization of α-PVT, α-PBT, and their bromothienyl analogs found in illicit drug products. Forensic Toxicol 34:76–93CrossRef Doi T, Asada A, Takeda A, Tagami T, Katagi M, Matsuta S, Kamata H, Kawaguchi M, Satsuki Y, Sawabe Y, Obana H (2016) Identification and characterization of α-PVT, α-PBT, and their bromothienyl analogs found in illicit drug products. Forensic Toxicol 34:76–93CrossRef
61.
go back to reference Liu C, Jia W, Li T, Hua Z, Qian Z (2017) Identification and analytical characterization of nine synthetic cathinone derivatives N-ethylhexedrone, 4-Cl-pentedrone, 4-Cl-EAPP, propylone, N-ethylnorpentylone, 6-MeO-bk-MDMA, α-PiHP, 4-Cl-α-PHP and 4-F-α-PHP. Drug Test Anal 9:1162–1171CrossRefPubMed Liu C, Jia W, Li T, Hua Z, Qian Z (2017) Identification and analytical characterization of nine synthetic cathinone derivatives N-ethylhexedrone, 4-Cl-pentedrone, 4-Cl-EAPP, propylone, N-ethylnorpentylone, 6-MeO-bk-MDMA, α-PiHP, 4-Cl-α-PHP and 4-F-α-PHP. Drug Test Anal 9:1162–1171CrossRefPubMed
62.
go back to reference Błażewicz A, Bednarek E, Sitowski J, Popławska M, Stypułkowska K, Bocian W, Kozerski L (2017) 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. Forensic Toxicol 35:317–332CrossRef Błażewicz A, Bednarek E, Sitowski J, Popławska M, Stypułkowska K, Bocian W, Kozerski L (2017) 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. Forensic Toxicol 35:317–332CrossRef
63.
go back to reference Apirakkan O, Frinculescu A, Shine T, Parkin MC, Cillibrizi A, Frascione N, Abbate V (2017) Analytical characterization of three cathinone derivatives, 4-MPD, 4F-PHP and bk-EPDP, purchased as bulk powder from online vendors. Drug Test Anal. doi:10.1002/dta.2218 PubMed Apirakkan O, Frinculescu A, Shine T, Parkin MC, Cillibrizi A, Frascione N, Abbate V (2017) Analytical characterization of three cathinone derivatives, 4-MPD, 4F-PHP and bk-EPDP, purchased as bulk powder from online vendors. Drug Test Anal. doi:10.​1002/​dta.​2218 PubMed
Metadata
Title
The newest cathinone derivatives as designer drugs: an analytical and toxicological review
Authors
Milena Majchrzak
Rafał Celiński
Piotr Kuś
Teresa Kowalska
Mieczysław Sajewicz
Publication date
01-01-2018
Publisher
Springer Japan
Published in
Forensic Toxicology / Issue 1/2018
Print ISSN: 1860-8965
Electronic ISSN: 1860-8973
DOI
https://doi.org/10.1007/s11419-017-0385-6

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