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- Novel synthetic opioids – toxicological aspects and analysisPublication . Tabarra, Inês; Soares, Sofia; Rosado, Tiago; Gonçalves, Joana; Luís, Ângelo; Malaca, Sara; Barroso, Mário; Keller, Thomas; Restolho, José; Gallardo, EugeniaOver the past few years, there has been an emerging number of new psychoactive drugs. These drugs are frequently mentioned as “legal highs”, “herbal highs”, “bath salts” and “research chemicals”. They are mostly sold and advertised on online forums and on the dark web. The emerging new psychoactive substances are designed to mimic the effects of psy- choactive groups, which are often abused drugs. Novel synthetic opioids are a new trend in this context and represent an alarming threat to public health. Given the wide number of fatalities related to these compounds reported within the last few years, it is an important task to accurately identify these compounds in biologic matrices in order to administer an effective treatment and reverse the respiratory depression caused by opioid related substan- ces. Clinicians dealing with fentanyl intoxication cases should consider that it could, in fact, be a fentanyl analogue. For this reason, it is a helpful recommendation to include synthetic opioids in the routine toxicological screening procedures, including analysis in alternative matrices, if available, to investigate poly-drug use and possible tolerance to opioids. To address this public health problem, better international collaboration, effective legislation, effective investigation, control of suspicious “research chemicals” online forums and continu- ous community alertness are required. This article aims to review diverse reported fatalities associated with new synthetic opioids describing them in terms of pharmacology, metabol- ism, posology, available forms, as well as their toxic effects, highlighting the sample proce- dures and analytical techniques available for their detection and quantification in biological matrices
- Evaluation of the Cytotoxicity of Ayahuasca BeveragesPublication . Simão, Ana Y.; Gonçalves, Joana; Gradillas, Ana; García, Antonia; Restolho, José; Fernández, Nicolás; Rodilla, Jesus M.; Barroso, Mário; Duarte, Ana Paula; Cristóvão, Ana C.; Gallardo, EugeniaAyahuasca is a beverage consumed at shamanic ceremonies and currently has gained popularity on recreational scenarios. It contains beta-carboline alkaloids and N,N-dimethyltryptamine, which possesses hallucinogenic effects. Only a few studies have elicited the psychoactive effects and the dose of such compounds on neurological dopaminergic cells or animals. In this work, we aimed to study the cytotoxic effects of these compounds present in ayahuasca beverages and on five different teas (Banisteriopsis caapi, Psychotria viridis, Peganum harmala, Mimosa tenuiflora and Dc Ab (commercial name)) preparations on dopaminergic immortalized cell lines. Moreover, a characterization of the derivative alkaloids was also performed. All the extracts were characterized by chromatographic systems and the effect of those compounds in cell viability and total protein levels were analyzed in N27 dopaminergic neurons cell line. This is the first article where cytotoxicity of ayahuasca tea is studied on neurological dopaminergic cells. Overall, results showed that both cell viability and protein contents decreased when cells were exposed to the individual compounds, as well as to the teas and to the two mixtures based on the traditional ayahuasca beverages. View Full-Tex
- Stability of Cocaine, Opiates, and Metabolites in Dried Saliva SpotsPublication . Almeida, Ema; Soares, Sofia; Gonçalves, Joana; Rosado, Tiago; Fernández, Nicolás; Rodilla, Jesus M.; Passarinha, Luís A.; Barroso, Mário; Gallardo, EugeniaDrug abuse still represents a global problem, and it is associated with an increased risk of diseases, injuries, and deaths. Cocaine (COC) and opiates are the most abused drugs and account for a significant number of fatalities. Therefore, it is important to develop methods capable of effectively identifying and quantifying these substances. The present study aims to evaluate the long- term stability of COC, ecgonine methylester (EME), benzoylecgonine (BEG), cocaethylene (COET), norcocaine (NCOC), morphine (MOR), codeine (COD) and 6-monoacetylmorphine (6-MAM) in oral fluid samples. The analytes of interest were isolated from the matrix (50 μL) using the dried saliva spots (DSS) sampling approach and were subsequently analyzed by gas chromatography coupled with tandem mass spectrometry (GC–MS/MS). The parameters that could influence the stability of the target compounds were studied, and these were storage temperature, light, use of preservatives (and respective concentrations), and time. The effects of each parameter were evaluated using the design of experiments (DOE) approach. The stability of the target analytes was improved when the DSS were stored at room temperature, in the presence of light and using 1% sodium fluoride. The best conditions were then adopted for the DSS storage and long-term stability was assessed. COD was only stable for 1 day, EME was stable for 3 days, COC, COET, NCOC and 6-MAM were stable for 7 days, MOR for 14 days and BEG remained stable throughout the study (136 days). This is the first study that evaluates the stability of these compounds in oral fluid samples after application in DSS cards, and optimizes the conditions in order to improve their stability
- Deteção e quantificação dos principais constituintes de Ayahuasca com recurso a QuEChERS e HPLC-DADPublication . Gonçalves, Joana; Rosado, Tiago; Barroso, Mário; Restolho, José; Luís, Ângelo; Duarte, Ana Paula; Gallardo, EugeniaA Ayahuasca é uma bebida psicoativa originalmente consumida na bacia amazónica. Esta decocção possui N,N-dimetiltriptamina (DMT), responsável pelos efeitos psicoativos, e alcaloides β-carbolínicos, que inibem a Monoamina Oxidase A (MAO-A), permitindo que o DMT aceda ao sistema nervoso central. A legislação que regula o consumo de Ayahuasca é pouco rigorosa, uma vez que esta também é consumida em contexto religioso, levando muitas vezes a um consumo não controlado. Este estudo tem como objetivo a quantificação simultânea de DMT, tetrahidroharmina (THH), harmina, harmalina, harmol e harmalol em amostras de Ayahuasca. Assim, inicialmente foram comparadas três técnicas de extração: microextração líquido-líquido dispersiva (DLLME), microextração em seringa empacotada (MEPS) e Quick, Easy, Cheap, Effective, Rugged and Safe (QuEChERS). Esta última mostrou ser a mais promissora, portanto foi submetida a um processo de otimização, onde foram testadas três variáveis (volume de solvente extrator, quantidade de amina primária secundária (PSA) e tempo de vórtex). As condições finais utilizadas foram 500 μL de solvente extrator, 85 mg de PSA e 4 segundos de agitação por vórtex. Posteriormente, foi utilizada cromatografia líquida de alta eficiência acoplada a um detetor de diode array (HPLC-DAD). O método analítico foi validado, apresentando linearidade entre 10 e 0,16 μg/mL (1 e 0,016 μg/mL para o DMT) com coeficientes de determinação superiores a 0,99. Os limites de deteção e quantificação foram de 0,16 μg/mL para as β-carbolinas e 0,016 μg/mL para o DMT e as eficiências de extração variaram entre 60 e 88 %. Este é o primeiro estudo que quantifica os principais constituintes de ayahuasca recorrendo à técnica de QuEChERS.
- Evaluation of Antipsychotic Drugs’ Stability in Oral Fluid SamplesPublication . Gameiro, Carina; Gonçalves, Joana; Soares, Sofia; Rosado, Tiago; Araujo, André R. T. S.; Passarinha, Luís A.; Barroso, Mário; Gallardo, EugeniaAntipsychotics have narrow therapeutic windows, and their monitoring in biological fluids is therefore important; consequently, stability in those fluids must be investigated during method development and validation. This work evaluates the stability of chlorpromazine, levomepromazine, cyamemazine, clozapine, haloperidol, and quetiapine in oral fluid (OF) samples, using the dried saliva spots (DSS) sampling approach and gas chromatography coupled to tandem mass spectrometry. Since many parameters can influence the stability of the target analytes, design of experiments was adopted to check the crucial factors that affect that stability in a multivariate fashion. The studied parameters were the presence of preservatives at different concentrations, temperature, light, and time. It was possible to observe that antipsychotic stability improved when OF samples in DSS were stored at 4 °C, with a low ascorbic acid concentration, and in the absence of light. With these conditions, chlorpromazine and quetiapine were stable for 14 days, clozapine and haloperidol were stable for 28 days, levomepromazine remained stable for 44 days, and cyamemazine was stable for the entire monitored period (146 days). This is the first study that evaluates the stability of these antipsychotics in OF samples after application to DSS cards.
- Comparative study of sample preparation procedures to determine the main compounds in ayahuasca beverages by QuEChERS and high‐performance liquid chromatography analysisPublication . Gonçalves, Joana; Rosado, Tiago; Barroso, Mário; Restolho, José; Fernández, Nicolás; Luís, Ângelo; Gallardo, Eugenia; Duarte, Ana PaulaIntroduction : Ayahuasca is a psychoactive drink originally consumed by indigenous people of the Amazon. The lack of regulation of this drink leads to uncontrolled consumption, and it is often consumed in religious contexts. Objective :The aim of this work is to compare three miniaturised extraction techniques for extracting the main ayahuasca compounds from beverages. Methodology:Three sample pretreatment techniques were evaluated (dispersive liquid–liquid microextraction [DLLME], microextraction by packed sorbent [MEPS] and QuEChERS [Quick, Easy, Cheap, Effective, Rugged and Safe]) for the simultaneous extraction of N,N-dimethyltryptamine (DMT), tetrahydroharmine (THH), harmine, harmaline, harmol and harmalol from ayahuasca beverage samples. Then, the most promising technique (QuEChERS) was chosen to pre-concentrate the analytes, subsequently detected by high-performance liquid chromatography coupled to a diode array detector (HPLC-DAD). Results: The procedure was optimised, with the final conditions being 500 μL of extractor solvent, 85 mg of primary secondary amine (PSA) and 4 s of vortexing. The analytical method was validated, showing to be linear between 0.16 and 10 μg/mL for β-carbolines and between 0.016 and 1 μg/mL for DMT, with coefficients of determination (R2) between 0.9968 and 0.9993. The limit of detection (LOD) and lower limit of quantification (LLOQ) were 0.16 μg/mL for all compounds, except for DMT (0.016 μg/mL) and extraction efficiencies varied between 60.2% and 88.0%. Conclusion: The analytical methodology proved to be accurate and precise, with good linearity, LODs and LLOQs. This method has been fully validated and successfully applied to ayahuasca beverage samples.
- Volumetric Absorptive Microsampling in ToxicologyPublication . Pires, Bruno; Catarro, Gonçalo; Soares, Sofia; Gonçalves, Joana; Rosado, Tiago; Barroso, Mário; Araujo, André R. T. S.; Gallardo, EugeniaVolumetric absorptive microsampling (VAMS) is an emerging technique in clinical and forensic toxicology. It is recognized as a promising alternative to traditional sampling methods, offering an accurate and minimally invasive means of collecting small volumes of biological samples, such as blood, urine, and saliva. Unlike conventional methods, VAMS provides advantages in terms of sample stability, storage, and transportation, as it enables samples to be collected outside laboratory environments without requiring refrigeration. This review explores several VAMS methodologies, with a particular focus on its application for the quantification of drugs and other substances in clinical and forensic toxicology. It compares VAMS to other microsampling techniques, such as dried blood spots (DBSs), highlighting VAMS's superiority in addressing issues related to sample volume consistency and environmental impact. Despite its advantages, VAMS also presents certain limitations, including higher costs and difficulties in detecting underfilled samples. Overall, VAMS stands out as a microsampling technique with the potential to enhance patient compliance and operational efficiency, positioning itself as a viable tool for toxicological analysis in both clinical and forensic contexts.