Ivan Langa

Cooperativa de Ensino Superior Politécnico e Universitário

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Cláudia Ribeiro

Cooperativa de Ensino Superior Politécnico e Universitário

Maria Elizabeth Tiritan

Cooperativa de Ensino Superior Politécnico e Universitário

Virgínia M. F. Gonçalves

Cooperativa de Ensino Superior Politécnico e Universitário

João Soares Carrola

University of Trás-os-Montes and Alto Douro

Ariana Pérez‐Pereira

University of Trás-os-Montes and Alto Douro

Bruno B. Castro

University of Minho

Ricardo Gonçalves

Cooperativa de Ensino Superior Politécnico e Universitário

Mónica Torres-Ruíz

Centro Nacional de Sanidad Ambiental

Cristiano dos Santos Gomes

Universidade Federal do Rio Grande do Norte

Maria Elisabeth Tiritan

Universidade do Porto

Cooperative Institutions

Cooperativa de Ensino Superior Politécnico e Universitário

Universidade do Porto

Instituto de Investigação e Formação Avançada em Ciências e Tecnologias da Saúde

Unidade em Ciências Biomoleculares Aplicadas

University of Trás-os-Montes and Alto Douro

Centro Interdisciplinar de Investigação Marinha e Ambiental

University of Aveiro

Rede de Química e Tecnologia

Polytechnic Institute of Porto

i3S - Instituto de Investigação e Inovação em Saúde, Universidade do Porto

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Unveil the toxicity induced on early life stages of zebrafish (Danio rerio) exposed to 3,4-methylenedioxymethamphetamine (MDMA) and its enantiomers

The Science of The Total Environment (2024)

Ondina Ribeiro Luís Félix Cláudia Ribeiro Mónica Torres-Ruíz Maria Elizabeth Tiritan

Danio

MDMA

Ecstasy

10.1016/j.scitotenv.2024.176906

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Toxicity of the 3,4-Methylenedioxymethamphetamine and Its Enantiomers to Daphnia magna after Isolation by Semipreparative Chromatography

Molecules (2023)

Ana Rita Fernandes Miranda da Costa Virgínia M. F. Gonçalves Bruno B. Castro João Soares Carrola Ivan Langa

MDMA (3,4-methylenedioxymethamphetamine) is a chiral psychoactive recreational drug sold in illicit markets as racemate. Studies on the impact of MDMA on aquatic organisms are scarce. While enantioselectivity in toxicity in animals and humans has been reported, none is reported on aquatic organisms. This study aimed to investigate the ecotoxicological effects of MDMA and its enantiomers in Daphnia magna. For that, enantiomers (enantiomeric purity > 97%) were separated by liquid chromatography using a homemade semipreparative chiral column. Daphnids were exposed to three concentrations of (R,S)-MDMA (0.1, 1.0 and 10.0 µg L−1) and two concentrations of (R)- and (S)-enantiomers (0.1 and 1.0 µg L−1) over the course of 8 days. Morphophysiological responses were dependent on the substance form and daphnia development stage, and they were overall not affected by the (R)-enantiomer. Changes in swimming behaviour were observed for both the racemate and its enantiomers, but enantioselective effects were not observed. Reproductive or biochemical changes were not observed for enantiomers whereas a significant decrease in acetylcholinesterase and catalase activity was noted at the highest concentration of (R,S)-MDMA (10 µg L−1). Overall, this study showed that sub-chronic exposure to MDMA racemate and its enantiomers can interfere with morphophysiological and swimming behaviour of D. magna. In general, the (R)-enantiomer demonstrated less toxicity than the (S)-enantiomer.

Daphnia magna

MDMA

10.3390/molecules28031457

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Citations (8)

Enantiomeric estimation of drugs consumption by gas chromatography: the role of suspended particulate matter in wastewater epidemiology

RevSALUS - Revista Científica da Rede Académica das Ciências da Saúde da Lusofonia (2022)

Ivan Langa Ana R. Ribeiro Virgínia M. F. Gonçalves Maria Elisabeth Tiritan Cláudia Ribeiro

Consumption

10.51126/revsalus.v4isup.370

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Wastewater analysis of psychoactive drugs: Non-enantioselective vs enantioselective methods for estimation of consumption

Forensic Science International (2021)

Ivan Langa Ricardo Gonçalves Maria Elizabeth Tiritan Cláudia Ribeiro

Consumption

10.1016/j.forsciint.2021.110873

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Citations (22)

Gas Chromatography Multiresidue Method for Enantiomeric Fraction Determination of Psychoactive Substances in Effluents and River Surface Waters

Chemosensors (2021)

Ivan Langa Maria Elizabeth Tiritan Diana Dias da Silva Cláudia Ribeiro

Determination of psychoactive substances (PAS) and/or their metabolites in surface waters is crucial for environmental risk assessment, and disclosure of their enantiomeric fractions (EF) allows discrimination between consumption, direct disposal, and synthesis pathways. The aim of this study was to develop and validate an indirect method by gas chromatography coupled to mass spectrometry (GC–MS) based on derivatization using (R)-(−)-α-methoxy-α-(trifluoromethyl) phenylacetyl chloride as chiral derivatization reagent, for enantiomeric quantification of amphetamine (AMP), methamphetamine (MAMP), 3,4-methylenedioxymethamphetamine (MDMA), norketamine, buphedrone (BPD), butylone, 3,4-dimethylmethcathinone (3,4-DMMC), 3-methylmethcathinone, and quantification of 1-benzylpiperazine and 1-(4-metoxyphenyl)-piperazine. The method allowed to evaluate the occurrence, spatial distribution, and the EF of the target chiral PAS in Portuguese surface waters and in effluents from 2 wastewater treatment plants (WWTP). For that, water samples were pre-concentrated by solid phase extraction using OASIS® MCX cartridges, derivatized and further analyzed by GC–MS. Both enantiomers of AMP, (R)-MDMA, (S)-MAMP, and the first eluted enantiomer of BPD (configuration not assigned) were found in surface waters, while effluent samples showed both enantiomers of MDMA, (S)-MAMP, (R)-AMP, and the first eluted enantiomer of BPD and 3,4-DMMC. According to our knowledge, this is the first multiresidue analytical method by CG–MS enrolling cathinones, amphetamines, and piperazines. The presence of illicit synthetic cathinones in Douro River estuary is here reported for the first time, along with other amphetamine derivatives. The potential of the method to monitor consumption of the target PAS was demonstrated.

Designer drug

Solid phase extraction

10.3390/chemosensors9080224

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Citations (19)

Enantioselectivity in the Ecotoxicity of Amphetamine Using Daphnia magna as the Aquatic Model Organism: Morphophysiological, Behavioral, Reproductive and Biochemical Parameters

Environmental Toxicology and Chemistry (2023)

Cláudia Ribeiro Cristiano dos Santos Gomes Ariana Pérez‐Pereira João Soares Carrola Maria Elizabeth Tiritan

Amphetamine (AMP) is a chiral psychoactive substance that exhibits enantioselectivity in its pharmacological properties. It has been detected in wastewaters and surface waters and can occur as enantiomeric mixtures, but little is known about its environmental risk and potential enantioselective toxicity to aquatic organisms. Our study aimed to target enantioselectivity in AMP toxicity to the freshwater invertebrate Daphnia magna. Daphnids were subchronically exposed to the racemate (rac-AMP: 0.1, 1.0, and 10 µg/L) and pure enantiomers, (R)-AMP and (S)-AMP (0.1, and 1.0 µg/L, respectively), for 8 days. Morphophysiological, swimming behavior, reproductive and biochemical variables were evaluated during critical life stages (juveniles vs. adults). Some responses were context-dependent and often enantioselective, varying between racemate and enantiomers and across the life stage of the organisms. Overall, rac-AMP stimulated D. magna growth, decreased heart rate and area, affected behavior, and stimulated reproduction. The effect of enantiomers was totally or partially concordant with rac-AMP, except for swimming behavior and reproduction. Enantioselectivity was observed for body size, number of eggs/daphnia, and heart rate (steeper decrease caused by (R)-AMP on day 3). Changes in biochemical parameters were also observed: AMP caused a significant decrease in catalase activity as racemate or pure enantiomers, whereas a decrease in acetylcholinesterase activity was found only for rac-AMP. Evidence for oxidative stress was contradictory, although both enantiomers caused a significant decrease in reactive oxygen species (unlike rac-AMP). Overall, these results show that AMP can interfere in an enantioselective way with aquatic organisms at low concentrations (e.g., 0.1 µg/L), demonstrating the relevance of this kind of study to an accurate environmental risk assessment regarding medium- to long-term exposure to this psychoactive drug. Environ Toxicol Chem 2023;42:1743-1754. © 2023 SETAC.

Daphnia magna

Ecotoxicity

Model Organism

Daphnia pulex

10.1002/etc.5646

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Citations (4)