The semi-synthetic cannabinoid hexahydrocannabinol (HHC) has become a highly discussed topic in forensic toxicology since 2022 due to its legal availability at this time and its psychoactive effects. This study aimed to investigate the pharmacokinetics, effects, and immunological detectability of HHC after oral (25 mg HHC fruit gum) and inhalative (three puffs from HHC vape) consumption with three participants per group. Serum (up to 48 h), urine (up to five days), and saliva (up to 48 h) samples were collected at different relevant time points and analyzed by HPLC-MS/MS for (9R)/(9S)-HHC, 11-hydroxy-HHC, and (9R)/(9S)-HHC carboxylic acid with a fully validated method. Additionally, immunological detectability was investigated with three different commercially available tests. To address the psychoactive effects, the subjective "high" feeling (scale 0-10) was monitored and different psychophysical tests (e.g. modified Romberg test, walk and turn) were conducted. Overall, the pharmacokinetics and effects of HHC were comparable to tetrahydrocannabinol (THC). However, the route of administration as well as inter-individual factors played a crucial role regarding maximum concentrations, pharmacokinetic profiles, and psychoactive effects.
- Klíčová slova
- Cannabinoids, Forensic toxicology, Hexahydrocannabinol, Pharmacokinetics, Psychophysical tests,
- MeSH
- agonisté kanabinoidních receptorů farmakokinetika farmakologie MeSH
- aplikace inhalační * MeSH
- aplikace orální * MeSH
- dospělí MeSH
- emoce účinky léků MeSH
- farmakokinetika * MeSH
- imunologické testy MeSH
- kanabinoidy * analýza krev farmakokinetika farmakologie moč MeSH
- kapalinová chromatografie-hmotnostní spektrometrie MeSH
- lidé MeSH
- psychofyziologie * MeSH
- psychotropní léky * analýza krev farmakokinetika farmakologie moč MeSH
- sliny chemie MeSH
- tetrahydrokanabinol farmakokinetika farmakologie MeSH
- Check Tag
- dospělí MeSH
- lidé MeSH
- mužské pohlaví MeSH
- ženské pohlaví MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- agonisté kanabinoidních receptorů MeSH
- kanabinoidy * MeSH
- psychotropní léky * MeSH
- tetrahydrokanabinol MeSH
Analysis of new psychoactive substances (NPS), which is essential for toxicological and forensic reasons, can be made complicated by the presence of isomers. Ion mobility has been used as a standalone technique or coupled to mass spectrometry to detect and identify NPS. However, isomer separation has so far chiefly relied on chromatography. Here we report on the determination of isomeric ratios using cyclic ion mobility-mass spectrometry without any chromatographic separation. Isomers were distinguished by mobility separation of lithium adducts. Alternatively, we used arrival time distribution (ATD) profiles that were characteristic of individual isomers and were acquired for protonated molecules or fragment ions. Both approaches provided comparable results. Calculations were used to determine the structures and collision cross sections of both protonated and lithiated isomers that accurately characterized their ion mobility properties. The applicability of ATD profiles to isomer differentiation was demonstrated using direct infusion and flow injection analysis with electrospray of solutions, as well as desorption electrospray of solid samples. Data processing was performed by applying multiple linear regression to the ATD profiles. Using the proposed ATD profile-based approach, the relationships between the determined and given content of isomers showed good linearity with coefficients of determination typically greater than 0.99. Flow injection analysis using an autosampler allowed us to rapidly determine isomeric ratios in a sample containing two isomeric pairs with a minor isomer of 10% (determined 9.3% of 3-MMC and 11.0% of 3-FMC in a mixture with buphedrone and 4-FMC). The proposed approach is not only useful for NPS, but also may be applicable to small isomeric molecules analyzed by ion mobility when complete separation of isomers is not achieved.
Psilocybin, psilocin, baeocystin, norbaeocystin, and aeruginascin are tryptamines structurally similar to the neurotransmitter serotonin. Psilocybin and its pharmacologically active metabolite psilocin in particular are known for their psychoactive effects. These substances typically occur in most species of the genus Psilocybe (Fungi, Strophariaceae). Even the sclerotia of some of these fungi known as "magic truffles" are of growing interest in microdosing due to them improving cognitive function studies. In addition to microdosing studies, psilocybin has also been applied in clinical studies, but only its pure form has been administrated so far. Moreover, the determination of tryptamine alkaloids is used in forensic analysis. In this study, freshly cultivated fruit bodies of Psilocybe cubensis were used for monitoring stability (including storage and processing conditions of fruiting bodies). Furthermore, mycelium and the individual parts of the fruiting bodies (caps, stipes, and basidiospores) were also examined. The concentration of tryptamines in final extracts was analyzed using ultra-high-performance liquid chromatography coupled with mass spectrometry. No tryptamines were detected in the basidiospores, and only psilocin was present at 0.47 wt.% in the mycelium. The stipes contained approximately half the amount of tryptamine alkaloids (0.52 wt.%) than the caps (1.03 wt.%); however, these results were not statistically significant, as the concentration of tryptamines in individual fruiting bodies is highly variable. The storage conditions showed that the highest degradation of tryptamines was seen in fresh mushrooms stored at -80°C, and the lowest decay was seen in dried biomass stored in the dark at room temperature.
- Klíčová slova
- LC-MS, mushrooms, psilocybin, stability, tryptamines,
- MeSH
- biomasa MeSH
- Psilocybe chemie růst a vývoj MeSH
- psilocybin analýza izolace a purifikace MeSH
- psychotropní léky analýza izolace a purifikace MeSH
- tandemová hmotnostní spektrometrie MeSH
- vysokoúčinná kapalinová chromatografie MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- psilocybin MeSH
- psychotropní léky MeSH
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.
- Klíčová slova
- Dream Market, MPF-47700, dark web, darknet, new psychoactive substances,
- MeSH
- hmotnostní spektrometrie MeSH
- internet MeSH
- lidé MeSH
- magnetická rezonanční spektroskopie MeSH
- obchodování s drogami * MeSH
- odhalování abúzu drog MeSH
- psychotropní léky analýza zásobování a distribuce MeSH
- spektrofotometrie ultrafialová MeSH
- zakázané drogy analýza zásobování a distribuce MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- psychotropní léky MeSH
- zakázané drogy MeSH
Consumption of alcohol and new psychoactive substances (NPS) in a population or during special events (music festivals) is usually monitored through individual questionnaires, forensic and toxicological data, and drug seizures. However, consumption estimates have some biases due mostly to the unknown composition of drug pills for NPS and stockpiling for alcohol. The aim of this study was to evaluate for the first time the real use of alcohol and the occurrence of NPS in Slovakia by wastewater-based epidemiology (WBE). Urban wastewater samples were collected from nine Slovak cities over two years (2017-2018) and during three music festivals. The study included about 20% of the Slovak population and 50 000 festival attendees. The urinary alcohol biomarker ethyl sulfate (EtS) and thirty NPS were analyzed by liquid chromatography tandem mass spectrometry (LC - MS/MS). EtS concentrations were used for estimating the per capita alcohol consumption in each city. The average alcohol consumption in the selected cities and festivals in 2017-2018 ranged between 7 and 126 L/day/1000 inhabitants and increased during the weekends and music festivals. Five NPS belonging to the classes of synthetic cathinones (mephedrone, methcathinone, buphedrone and pentedrone) and phenethylamines (25-iP-NBoMe) were found in the low ng/L range. Methcathinone was the most frequently detected NPS, while the highest normalized mass load corresponded to mephedrone (3.1 mg/day/1000 inhabitants). Wastewater-based epidemiology can provide timely information on alcohol consumption and NPS occurrence at the community level that is complementary to epidemiology-based monitoring techniques (e.g. population surveys, police seizures, sales statistics).
- Klíčová slova
- Alcohol, Festivals, Liquid chromatography-tandem mass spectrometry, New psychoactive substances, Urban wastewater,
- MeSH
- chromatografie kapalinová metody MeSH
- dovolená MeSH
- epidemiologie odpadních vod * MeSH
- estery kyseliny sírové analýza moč MeSH
- ethanol analýza MeSH
- lidé MeSH
- odpadní voda chemie MeSH
- pití alkoholu epidemiologie MeSH
- psychotropní léky analýza moč MeSH
- tandemová hmotnostní spektrometrie metody MeSH
- velkoměsta MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- Geografické názvy
- Slovenská republika MeSH
- velkoměsta MeSH
- Názvy látek
- diethyl sulfate MeSH Prohlížeč
- estery kyseliny sírové MeSH
- ethanol MeSH
- odpadní voda MeSH
- psychotropní léky MeSH
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.
- Klíčová slova
- Cathinones, Drug analysis, Drug identification, New psychoactive substances, X-Ray powder diffraction,
- MeSH
- alkaloidy analýza MeSH
- difrakce rentgenového záření MeSH
- prášková difrakce MeSH
- psychotropní léky analýza MeSH
- stimulanty centrálního nervového systému analýza MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- alkaloidy MeSH
- cathinone MeSH Prohlížeč
- psychotropní léky MeSH
- stimulanty centrálního nervového systému MeSH
BACKGROUND: The emergence of psychoactive designer drugs has significantly increased over the last few years. Customs officials are responsible for the control of products entering the European Union (EU) market. This control applies to chemicals in general, pharmaceutical products and medicines. Numerous products imported from non-EU countries, often declared as 'bath salts' or 'fertilizers', contain new psychoactive substance (NPS). REVIEW: These are not necessarily controlled under international law, but may be subject to monitoring in agreement with EU legislation. This situation imposes substantial challenges, for example, for the maintenance of spectral libraries used for their detection by designated laboratories. The chemical identification of new substances, with the use of powerful instrumentation, and the time needed for detailed analysis and interpretation of the results, demands considerable commitment. The EU Joint Research Centre endeavors to provide scientific support to EU Customs laboratories to facilitate rapid identification and characterisation of seized samples. In addition to analysing known NPS, several new chemical entities have also been identified. Frequently, these belong to NPS classes already notified to the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) by the European Early- Warning System (EWS). CONCLUSION: The aim of this paper is to discuss the implementation of workflow mechanisms that are in place in order to facilitate the monitoring, communication and management of analytical data. The rapid dissemination of this information between control authorities strives to help protect EU citizens against the health risks posed by harmful substances.
- Klíčová slova
- JRC, New psychoactive substances, chemical identification, cheminformatic, cheminformatics, customs.,
- MeSH
- biomedicínský výzkum metody trendy MeSH
- Evropská unie * MeSH
- lidé MeSH
- mezisektorová spolupráce * MeSH
- poruchy spojené s užíváním psychoaktivních látek epidemiologie prevence a kontrola MeSH
- psychotropní léky analýza chemie MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- dopisy MeSH
- Názvy látek
- psychotropní léky MeSH
Achievements of supercritical fluid chromatography with mass spectrometric detection made in the field of forensic science during the last decade are reviewed. The main topics include analysis of traditional drugs of abuse (e.g. cannabis, methamphetamine) as well as new psychoactive substances (synthetic cannabinoids, cathinones and phenethylamines), doping agents (anabolic steroids, stimulants, diuretics, analgesics etc.) and chemical warfare agents. Control of food authenticity, detection of adulteration and identification of toxic substances in food are also pointed out. Main aspects of an analytical workflow, such as sample preparation, separation and detection are discussed. A special attention is paid to the performance characteristics and validation parameters of supercritical fluid chromatography-mass spectrometric methods in comparison with other separation techniques.
- Klíčová slova
- Adulteration, Doping control, Drug of abuse, Food authenticity, New psychoactive substance,
- MeSH
- analýza potravin MeSH
- doping ve sportu MeSH
- hmotnostní spektrometrie metody MeSH
- lidé MeSH
- odhalování abúzu drog MeSH
- oleje rostlin chemie MeSH
- psychotropní léky analýza MeSH
- superkritická fluidní chromatografie metody MeSH
- zakázané drogy analýza MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- přehledy MeSH
- Názvy látek
- oleje rostlin MeSH
- psychotropní léky MeSH
- zakázané drogy MeSH
New psychoactive substances represent serious social and health problem as tens of new compounds are detected in Europe annually. They often show structural proximity or even isomerism, which complicates their analysis. Two methods based on ultra high performance supercritical fluid chromatography and ultra high performance liquid chromatography with mass spectrometric detection were validated and compared. A simple dilute-filter-and-shoot protocol utilizing propan-2-ol or methanol for supercritical fluid or liquid chromatography, respectively, was proposed to detect and quantify 15 cathinones and phenethylamines in human urine. Both methods offered fast separation (<3 min) and short total analysis time. Precision was well <15% with a few exceptions in liquid chromatography. Limits of detection in urine ranged from 0.01 to 2.3 ng/mL, except for cathinone (5 ng/mL) in supercritical fluid chromatography. Nevertheless, this technique distinguished all analytes including four pairs of isomers, while liquid chromatography was unable to resolve fluoromethcathinone regioisomers. Concerning matrix effects and recoveries, supercritical fluid chromatography produced more uniform results for different compounds and at different concentration levels. This work demonstrates the performance and reliability of supercritical fluid chromatography and corroborates its applicability as an alternative tool for analysis of new psychoactive substances in biological matrixes.
- Klíčová slova
- cathinones, isomers, mass spectrometry, phenethylamines, quantitative analysis,
- MeSH
- alkaloidy MeSH
- analýza moči metody MeSH
- fenethylaminy moč MeSH
- hmotnostní spektrometrie MeSH
- kalibrace MeSH
- lidé MeSH
- limita detekce MeSH
- methanol moč MeSH
- psychotropní léky analýza MeSH
- reprodukovatelnost výsledků MeSH
- rozpouštědla MeSH
- superkritická fluidní chromatografie * MeSH
- vysokoúčinná kapalinová chromatografie * MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- alkaloidy MeSH
- cathinone MeSH Prohlížeč
- fenethylaminy MeSH
- methanol MeSH
- psychotropní léky MeSH
- rozpouštědla MeSH
The aim of this study was to analyze 26 various illicit drugs, psychopharmaceuticals and metabolites thereof in sewer from 17 selected wastewater treatment plants (WWTPs) in the Slovak and Czech Republics. Urinary bio-markers used were analyzed using liquid chromatography coupled with the tandem mass spectrometry (LC-MS/MS). We then compared our results with data obtained in other parts of Europe and the world. The present study shows that the Slovak and Czech Republics have one of the highest methamphetamine consumption rates in Europe. Within Slovakia, the highest level of methamphetamine consumption was found in Dunajská Streda with the mean specific load of the drug in sewage being up to 479mg/day/1000 inhabitants; the next highest load was detected in Trnava (354mg/day/1000 inhabitants). The methamphetamine, ecstasy and cannabis consumptions in our study were comparable to those found in other European cities, whereas cocaine consumption was lower. Among all of the studied psychopharmaceuticals, tramadol and venlafaxine were represented in the highest concentrations. The highest mean specific load of tramadol was detected in the spa town of Piešťany (371mg/day/1000 inhabitants) and Košice (372mg/day/1000 inhabitants), while the highest mean loads of venlafaxine were recorded for the towns of Trenčín (230mg/day/1000 inhabitants) and Piešťany (108mg/day/1000 inhabitants).
- Klíčová slova
- Drug monitoring, LC–MS/MS, Methamphetamine, Sewage biomarker analysis, Wastewater analysis,
- MeSH
- chromatografie kapalinová MeSH
- lidé MeSH
- monitorování životního prostředí metody MeSH
- odhalování abúzu drog metody MeSH
- odpadní voda chemie MeSH
- psychotropní léky analýza MeSH
- tandemová hmotnostní spektrometrie MeSH
- tetrahydrokanabinol analogy a deriváty analýza MeSH
- zakázané drogy analýza MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- Geografické názvy
- Slovenská republika MeSH
- Názvy látek
- 11-nor-delta(9)-tetrahydrocannabinol-9-carboxylic acid MeSH Prohlížeč
- odpadní voda MeSH
- psychotropní léky MeSH
- tetrahydrokanabinol MeSH
- zakázané drogy MeSH
