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Article ; Online: Intriguing Cytotoxicity of the Street Dissociative Anesthetic Methoxphenidine: Unexpected Impurities Spotted.

Jurásek, Bronislav / Rimpelová, Silvie / Babor, Martin / Čejka, Jan / Bartůněk, Vilém / Kuchař, Martin

International journal of molecular sciences

2022 Volume 23, Issue 4

Abstract: The black market for new psychoactive substances has been constantly evolving and the substances that appear on this market cause a considerable number of issues, in extreme cases leading to human deaths. While monitoring the drug black market, we ... ...

Abstract	The black market for new psychoactive substances has been constantly evolving and the substances that appear on this market cause a considerable number of issues, in extreme cases leading to human deaths. While monitoring the drug black market, we detected a sample of a dissociative anesthetic methoxphenidine, the salt of which contained an unusual anion in the form of bromo- and chloro-zincate complex. Concerning the unknown and potentially hazardous properties of this sample, we performed an in vitro cytotoxicity screening in cell lines of various origins (e.g., kidney, liver, bladder) which was compared with the toxicity results of the methoxphenidine standard prepared for this purpose. The street methoxphenidine sample exhibited markedly higher toxicity than the standard, which was probably caused by the anion impurity. Since it is not usual to analyze anions in salts of novel psychoactive substances, but such samples may be commonly available at the drug black market, we have developed a method for their identification with X-ray powder diffraction (XRPD), which also enabled us to distinguish between different polymorphs/solvates of methoxphenidine that were crystallized in the laboratory. XRPD offers additional data about samples, which may not be discovered by routine techniques, and in some cases, they may help to find out essential information.
MeSH term(s)	Anesthetics, Dissociative/adverse effects ; Cells, Cultured ; Humans ; Illicit Drugs/adverse effects ; Piperidines/adverse effects ; Psychotropic Drugs/adverse effects ; X-Ray Diffraction/methods
Chemical Substances	Anesthetics, Dissociative ; Illicit Drugs ; Piperidines ; Psychotropic Drugs ; 1-(1-(2-methoxyphenyl)-2-phenylethyl)piperidine (H2W7A6GZGX)
Language	English
Publishing date	2022-02-14
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2019364-6
ISSN	1422-0067 ; 1422-0067 ; 1661-6596
ISSN (online)	1422-0067
ISSN	1422-0067 ; 1661-6596
DOI	10.3390/ijms23042083
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Article: X-Ray powder diffraction – A non-destructive and versatile approach for the identification of new psychoactive substances

Jurásek, Bronislav / Martin Kuchař / Štěpán Huber / Vilém Bartůněk

Talanta. 2019 Apr. 01, v. 195

2019

Abstract: A considerable number of fatal intoxications have recently been connected with the growing popularity of new psychoactive substances (NPS). Therefore, there is a significant demand for the development of fast and facile field detection methods for NPS. ... ...

Abstract	A considerable number of fatal intoxications have recently been connected with the growing popularity of new psychoactive substances (NPS). Therefore, there is a significant demand for the development of fast and facile field detection methods for NPS. These substances are often sold as blends (with inorganic or organic cutting agents), which may further complicate detection. X-Ray powder diffraction (XRPD) was evaluated as a suitable and easily employable analytical method for the identification of NPS. XRPD has been successfully used for the differentiation of eight synthetic cathinones with a similar molecular structure. Moreover, this method was also used for the identification of four drugs in authentic street samples. XRPD is a facile non-destructive method that can identify not only NPS in mixtures but also the cutting agents. The small amount of substances needed for the measurement, which can be re-used for other analyses, further enhances the versatility of this method.
Keywords	chemical structure ; cutting agents ; nondestructive methods ; psychotropic agents ; X-ray diffraction
Language	English
Dates of publication	2019-0401
Size	p. 414-418.
Publishing place	Elsevier B.V.
Document type	Article
ZDB-ID	1500969-5
ISSN	1873-3573 ; 0039-9140
ISSN (online)	1873-3573
ISSN	0039-9140
DOI	10.1016/j.talanta.2018.11.063
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Article ; Online: Gradient supercritical fluid chromatography coupled to mass spectrometry with a gradient flow of make-up solvent for enantioseparation of cathinones.

Kolderová, Natalie / Jurásek, Bronislav / Kuchař, Martin / Lindner, Wolfgang / Kohout, Michal

Journal of chromatography. A

2020 Volume 1625, Page(s) 461286

Abstract: In the past two decades, supercritical fluid chromatography has evolved from a niche application to a comprehensive technology and a fully-fledged alternative to conventional high-performance liquid chromatography. In this study, we have focused on ... ...

Abstract	In the past two decades, supercritical fluid chromatography has evolved from a niche application to a comprehensive technology and a fully-fledged alternative to conventional high-performance liquid chromatography. In this study, we have focused on chiral separation of synthetic cathinones in gradient supercritical fluid chromatography coupled to mass spectrometry using an inverse gradient of a make-up solvent. Synthetic cathinones possess an amphetamine-like effect and, therefore, are frequently being offered on the Internet as a replacement for illicit drugs. Cathinones are chiral compounds, however, they are usually marketed and used as racemic mixtures. Since the effect of individual enantiomers can significantly vary, there is a need for the development of enantioseparation methods enabling to study the biological effects of individual enantiomers. Since cathinones are basic molecules, they are easily protonated (positively charged) under weakly acidic mobile phase conditions, which is a typical feature of supercritical mobile phases with an alcohol as an organic modifier. The positively charged species represent ideal analytes for ion exchangers, such as chiral zwitterion ion exchangers Chiralpak ZWIX (+) and Chiralpak ZWIX (-), which possess a positively and negatively charged unit in the molecular structure of the selectors. The presence of the positive charge in the selector's structure, functioning as a counter-ion for the positively charged analytes, significantly reduces the required amount of a buffer, which is plausible for hyphenation of such a separation system with mass spectrometry. For mass spectrometry hyphenated to supercritical fluid chromatography, the use of a make-up solvent is required to avoid analyte precipitation when using a low concentration of an organic co-solvent (modifier) in the super-/subcritical mobile phase. Hereby, we introduce a unique approach, which is based on the gradient introduction of the make-up to the post-column effluent. Using this approach, it is possible to keep constant the overall amount of the organic solvent (modifier and make-up) introduced into the mass spectrometer when using a gradient of the organic modifier. We show that the developed gradient elution method facilitates the chiral separation of all employed analytes, while the mobile-phase gradient compensation by the inverse make-up gradient enables their detection with high signal intensities.
MeSH term(s)	Alkaloids/chemical synthesis ; Alkaloids/chemistry ; Alkaloids/isolation & purification ; Chromatography, High Pressure Liquid ; Chromatography, Supercritical Fluid/methods ; Mass Spectrometry/methods ; Pressure ; Rheology ; Solvents/chemistry ; Stereoisomerism ; Temperature
Chemical Substances	Alkaloids ; Solvents ; cathinone (540EI4406J)
Keywords	covid19
Language	English
Publishing date	2020-06-02
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	1171488-8
ISSN	1873-3778 ; 0021-9673
ISSN (online)	1873-3778
ISSN	0021-9673
DOI	10.1016/j.chroma.2020.461286
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Article ; Online: Counterfeit benzodiazepines-A phantom menace.

Jurásek, Bronislav / Čmelo, Ivan / Hájková, Kateřina / Kofroňová, Edita / Kuchař, Martin

International journal of clinical practice

2020 Volume 74, Issue 10, Page(s) e13575

Language	English
Publishing date	2020-06-28
Publishing country	England
Document type	Letter
ZDB-ID	1386246-7
ISSN	1742-1241 ; 1368-5031
ISSN (online)	1742-1241
ISSN	1368-5031
DOI	10.1111/ijcp.13575
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Article: Gradient supercritical fluid chromatography coupled to mass spectrometry with a gradient flow of make-up solvent for enantioseparation of cathinones

Kolderová, Natalie / Jurásek, Bronislav / Kuchař, Martin / Lindner, Wolfgang / Kohout, Michal

Journal of chromatography. 2020 Aug. 16, v. 1625

2020

Abstract	In the past two decades, supercritical fluid chromatography has evolved from a niche application to a comprehensive technology and a fully-fledged alternative to conventional high-performance liquid chromatography.In this study, we have focused on chiral separation of synthetic cathinones in gradient supercritical fluid chromatography coupled to mass spectrometry using an inverse gradient of a make-up solvent. Synthetic cathinones possess an amphetamine-like effect and, therefore, are frequently being offered on the Internet as a replacement for illicit drugs. Cathinones are chiral compounds, however, they are usually marketed and used as racemic mixtures. Since the effect of individual enantiomers can significantly vary, there is a need for the development of enantioseparation methods enabling to study the biological effects of individual enantiomers. Since cathinones are basic molecules, they are easily protonated (positively charged) under weakly acidic mobile phase conditions, which is a typical feature of supercritical mobile phases with an alcohol as an organic modifier. The positively charged species represent ideal analytes for ion exchangers, such as chiral zwitterion ion exchangers Chiralpak ZWIX (+) and Chiralpak ZWIX (−), which possess a positively and negatively charged unit in the molecular structure of the selectors. The presence of the positive charge in the selector's structure, functioning as a counter-ion for the positively charged analytes, significantly reduces the required amount of a buffer, which is plausible for hyphenation of such a separation system with mass spectrometry. For mass spectrometry hyphenated to supercritical fluid chromatography, the use of a make-up solvent is required to avoid analyte precipitation when using a low concentration of an organic co-solvent (modifier) in the super-/subcritical mobile phase. Hereby, we introduce a unique approach, which is based on the gradient introduction of the make-up to the post-column effluent. Using this approach, it is possible to keep constant the overall amount of the organic solvent (modifier and make-up) introduced into the mass spectrometer when using a gradient of the organic modifier. We show that the developed gradient elution method facilitates the chiral separation of all employed analytes, while the mobile-phase gradient compensation by the inverse make-up gradient enables their detection with high signal intensities.
Keywords	Internet ; alcohols ; chemical species ; enantiomers ; liquids ; mass spectrometry ; solvents ; spectrometers ; supercritical fluid chromatography ; zwitterions
Language	English
Dates of publication	2020-0816
Publishing place	Elsevier B.V.
Document type	Article
Note	NAL-AP-2-clean
ZDB-ID	218139-3
ISSN	0021-9673 ; 0378-4355 ; 0376-737X
ISSN	0021-9673 ; 0378-4355 ; 0376-737X
DOI	10.1016/j.chroma.2020.461286
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Article ; Online: X-Ray powder diffraction - A non-destructive and versatile approach for the identification of new psychoactive substances.

Jurásek, Bronislav / Bartůněk, Vilém / Huber, Štěpán / Kuchař, Martin

Talanta

2018 Volume 195, Page(s) 414–418

Abstract	A considerable number of fatal intoxications have recently been connected with the growing popularity of new psychoactive substances (NPS). Therefore, there is a significant demand for the development of fast and facile field detection methods for NPS. These substances are often sold as blends (with inorganic or organic cutting agents), which may further complicate detection. X-Ray powder diffraction (XRPD) was evaluated as a suitable and easily employable analytical method for the identification of NPS. XRPD has been successfully used for the differentiation of eight synthetic cathinones with a similar molecular structure. Moreover, this method was also used for the identification of four drugs in authentic street samples. XRPD is a facile non-destructive method that can identify not only NPS in mixtures but also the cutting agents. The small amount of substances needed for the measurement, which can be re-used for other analyses, further enhances the versatility of this method.
MeSH term(s)	Alkaloids/analysis ; Central Nervous System Stimulants/analysis ; Powder Diffraction ; Psychotropic Drugs/analysis ; X-Ray Diffraction
Chemical Substances	Alkaloids ; Central Nervous System Stimulants ; Psychotropic Drugs ; cathinone (540EI4406J)
Language	English
Publishing date	2018-11-22
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	1500969-5
ISSN	1873-3573 ; 0039-9140
ISSN (online)	1873-3573
ISSN	0039-9140
DOI	10.1016/j.talanta.2018.11.063
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Article ; Online: New psychoactive substances on dark web markets: From deal solicitation to forensic analysis of purchased substances.

Jurásek, Bronislav / Čmelo, Ivan / Svoboda, Jan / Čejka, Jan / Svozil, Daniel / Kuchař, Martin

Drug testing and analysis

2020 Volume 13, Issue 1, Page(s) 156–168

Abstract: The dark web scene has been drawing the attention of law enforcement agencies and researchers alike. To date, most of the published works on the dark web are based on data gained by passive observation. To gain a more contextualized perspective, a study ... ...

Abstract	The dark web scene has been drawing the attention of law enforcement agencies and researchers alike. To date, most of the published works on the dark web are based on data gained by passive observation. To gain a more contextualized perspective, a study was conducted in which three vendors were selected on the "Dream Market" dark web marketplace, from whom subsequently several new psychoactive substances (NPS) were ordered. All transactions were documented from the initial drug deal solicitation to the final qualitative analysis of all received samples. From the selected vendors, a total of nine NPS samples was obtained, all of which were analyzed by NMR, HRMS, LC-UV, and two also by x-ray diffraction. According to our analyses, four of the five substances offered under already known NPS names contained a different NPS. The selected vendors therefore either did not know about their product, or deliberately deceived the buyers. Furthermore, two of three obtained samples of purportedly novel NPS were identified as already documented substances sold under a different name. However, the third characterized substance sold as "MPF-47700" was a novel, yet uncharacterized, NPS. Finally, we received a single undeclared substance, later identified as 5F-ADB. In addition to chemical analysis of the nine obtained NPS samples, the methodology used also yielded contextual information about the accessibility of NPS on the dark web, the associated purchase process, and the modus operandi of three NPS vendors. Direct participation in dark web marketplaces seems to provide additional layers of information useful for forensic studies.
MeSH term(s)	Drug Trafficking ; Humans ; Illicit Drugs/analysis ; Illicit Drugs/supply & distribution ; Internet ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Psychotropic Drugs/analysis ; Psychotropic Drugs/supply & distribution ; Spectrophotometry, Ultraviolet ; Substance Abuse Detection
Chemical Substances	Illicit Drugs ; Psychotropic Drugs
Language	English
Publishing date	2020-08-07
Publishing country	England
Document type	Journal Article
ZDB-ID	2462336-2
ISSN	1942-7611 ; 1942-7603
ISSN (online)	1942-7611
ISSN	1942-7603
DOI	10.1002/dta.2901
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Article ; Online: Synthesis and identification of deschloroketamine metabolites in rats' urine and a quantification method for deschloroketamine and metabolites in rats' serum and brain tissue using liquid chromatography tandem mass spectrometry.

Hájková, Kateřina / Jurásek, Bronislav / Čejka, Jan / Štefková, Kristýna / Páleníček, Tomáš / Sýkora, David / Kuchař, Martin

Drug testing and analysis

2020 Volume 12, Issue 3, Page(s) 343–360

Abstract: Deschloroketamine (2-(methylamino)-2-phenyl-cyclohexanone) is a ketamine analog belonging to a group of dissociative anesthetics, which have been distributed within the illicit market since 2015. However, it was also being sold as 'ketamine' misleading ... ...

Abstract	Deschloroketamine (2-(methylamino)-2-phenyl-cyclohexanone) is a ketamine analog belonging to a group of dissociative anesthetics, which have been distributed within the illicit market since 2015. However, it was also being sold as 'ketamine' misleading people to believe that they were getting genuine ketamine. Dissociative anesthetics have also come to the attention of the psychiatric field due to their potential properties in the treatment of depression. At present, there is a dearth of information on deschloroketamine related to its metabolism, biodistribution, and its mechanism of action. We have therefore carried out a metabolomics study for deschloroketamine via non-targeted screening of urine samples employing liquid chromatography combined with high-resolution mass spectrometry. We developed and validated a multiple reaction monitoring method using a triple quadrupole instrument to track metabolites of deschloroketamine. Furthermore, significant metabolites of deschloroketamine, (trans-dihydrodeschloroketamine, cis- and trans-dihydronordeschloroketamine, and nordeschloroketamine), were synthesized in-house. The prepared standards were utilized in the developed multiple reaction monitoring method. The quantification method for serum samples provided intra-day accuracy ranging from 86% to 112% with precision of 3% on average. The concentrations of cis/trans-dihydronordeschloroketamines and trans-dihydrodeschloroketamine were lower than 10 ng/mL, nordeschloroketamine and deschloroketamine ranged from 0.5 to 860 ng/mL in real samples. The quantification method for brain tissue provided intra-day accuracy ranging from 80% to 125% with precision of 7% on average. The concentrations of cis/trans-dihydronordeschloroketamines and trans-dihydrodeschloroketamine ranged from 0.5 to 70 ng/g, nordeschloroketamine and deschloroketamine varied from 0.5 to 4700 ng/g in real samples.
MeSH term(s)	Animals ; Brain/metabolism ; Chromatography, Liquid ; Ketamine/agonists ; Ketamine/blood ; Ketamine/chemical synthesis ; Ketamine/pharmacokinetics ; Male ; Rats ; Tandem Mass Spectrometry/instrumentation ; Tissue Distribution
Chemical Substances	Ketamine (690G0D6V8H)
Language	English
Publishing date	2020-01-15
Publishing country	England
Document type	Journal Article
ZDB-ID	2462336-2
ISSN	1942-7611 ; 1942-7603
ISSN (online)	1942-7611
ISSN	1942-7603
DOI	10.1002/dta.2726
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Article: Gradient supercritical fluid chromatography coupled to mass spectrometry with a gradient flow of make-up solvent for enantioseparation of cathinones

Kolderová, Natalie / Jurásek, Bronislav / Kuchar, Martin / Lindner, Wolfgang / Kohout, Michal

J Chromatogr A

Abstract	In the past two decades, supercritical fluid chromatography has evolved from a niche application to a comprehensive technology and a fully-fledged alternative to conventional high-performance liquid chromatography. In this study, we have focused on chiral separation of synthetic cathinones in gradient supercritical fluid chromatography coupled to mass spectrometry using an inverse gradient of a make-up solvent. Synthetic cathinones possess an amphetamine-like effect and, therefore, are frequently being offered on the Internet as a replacement for illicit drugs. Cathinones are chiral compounds, however, they are usually marketed and used as racemic mixtures. Since the effect of individual enantiomers can significantly vary, there is a need for the development of enantioseparation methods enabling to study the biological effects of individual enantiomers. Since cathinones are basic molecules, they are easily protonated (positively charged) under weakly acidic mobile phase conditions, which is a typical feature of supercritical mobile phases with an alcohol as an organic modifier. The positively charged species represent ideal analytes for ion exchangers, such as chiral zwitterion ion exchangers Chiralpak ZWIX (+) and Chiralpak ZWIX (-), which possess a positively and negatively charged unit in the molecular structure of the selectors. The presence of the positive charge in the selector's structure, functioning as a counter-ion for the positively charged analytes, significantly reduces the required amount of a buffer, which is plausible for hyphenation of such a separation system with mass spectrometry. For mass spectrometry hyphenated to supercritical fluid chromatography, the use of a make-up solvent is required to avoid analyte precipitation when using a low concentration of an organic co-solvent (modifier) in the super-/subcritical mobile phase. Hereby, we introduce a unique approach, which is based on the gradient introduction of the make-up to the post-column effluent. Using this approach, it is possible to keep constant the overall amount of the organic solvent (modifier and make-up) introduced into the mass spectrometer when using a gradient of the organic modifier. We show that the developed gradient elution method facilitates the chiral separation of all employed analytes, while the mobile-phase gradient compensation by the inverse make-up gradient enables their detection with high signal intensities.
Keywords	covid19
Publisher	WHO
Document type	Article
Note	WHO #Covidence: #32709336
Database	COVID19

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Article: Can X-Ray Powder Diffraction Be a Suitable Forensic Method for Illicit Drug Identification?

Jurásek, Bronislav / Bartůněk, Vilém / Huber, Štěpán / Fagan, Patrik / Setnička, Vladimír / Králík, František / Dehaen, Wim / Svozil, Daniel / Kuchař, Martin

Frontiers in chemistry

2020 Volume 8, Page(s) 499

Abstract: New psychoactive substances (NPSs) are associated with a significant number of intoxications. With the number of readily available forms of these drugs rising every year, there are even risks for the general public. Consequently, there is a high demand ... ...

Abstract	New psychoactive substances (NPSs) are associated with a significant number of intoxications. With the number of readily available forms of these drugs rising every year, there are even risks for the general public. Consequently, there is a high demand for methods sufficiently sensitive to detect NPSs in samples found at the crime scene. Infrared (IR) and Raman spectroscopies are commonly used for such detection, but they have limitations; for example, fluorescence in Raman can overlay the signal and when the sample is a mixture sometimes neither Raman nor IR is able to identify the compounds. Here, we investigate the potential of X-ray powder diffraction (XRPD) to analyse samples seized on the black market. A series of psychoactive substances (heroin, cocaine, mephedrone, ephylone, butylone, JWH-073, and naphyrone) was measured. Comparison of their diffraction patterns with those of the respective standards showed that XRPD was able to identify each of the substances. The same samples were analyzed using IR and Raman, which in both cases were not able to detect the compounds in all of the samples. These results suggest that XRPD could be a valuable addition to the range of forensic tools used to detect these compounds in illicit drug samples.
Language	English
Publishing date	2020-06-23
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2711776-5
ISSN	2296-2646
ISSN	2296-2646
DOI	10.3389/fchem.2020.00499
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