{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,27]],"date-time":"2025-11-27T13:58:49Z","timestamp":1764251929393,"version":"build-2065373602"},"reference-count":133,"publisher":"MDPI AG","issue":"13","license":[{"start":{"date-parts":[[2025,7,4]],"date-time":"2025-07-04T00:00:00Z","timestamp":1751587200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"FCT","award":["UIDB\/04423\/2020","UIDB\/MULTI\/04378\/2020","UIDP\/04423\/2020","LA\/P\/0140\/2020","2023.00262.BD","CEECINST\/00108\/2021\/CP2794\/CT0001"],"award-info":[{"award-number":["UIDB\/04423\/2020","UIDB\/MULTI\/04378\/2020","UIDP\/04423\/2020","LA\/P\/0140\/2020","2023.00262.BD","CEECINST\/00108\/2021\/CP2794\/CT0001"]}]},{"name":"Scientific Employment Stimulus","award":["UIDB\/04423\/2020","UIDB\/MULTI\/04378\/2020","UIDP\/04423\/2020","LA\/P\/0140\/2020","2023.00262.BD","CEECINST\/00108\/2021\/CP2794\/CT0001"],"award-info":[{"award-number":["UIDB\/04423\/2020","UIDB\/MULTI\/04378\/2020","UIDP\/04423\/2020","LA\/P\/0140\/2020","2023.00262.BD","CEECINST\/00108\/2021\/CP2794\/CT0001"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>New psychoactive substances (NPSs) are emerging narcotics or psychotropics that pose a public health risk. The most commonly reported NPSs are synthetic cannabinoids and synthetic cathinones. Synthetic cannabinoids mimic the effects of \u03949-tetrahydrocannabinol (\u03949-THC), often with greater potency, while synthetic cathinones act as stimulants, frequently serving as cheaper alternatives to amphetamines, 3,4-methylenedioxymethamphetamine (MDMA) and cocaine. While some synthetic cannabinoids exhibit chirality depending on their synthesis precursors, synthetic cathinones are intrinsically chiral. Biotargets can recognize and differentiate between enantiomers, leading to distinct biological responses (enantioselectivity). Understanding these differences is crucial; therefore, the development of enantioresolution methods to assess the biological and toxicological effects of enantiomer is necessary. This work systematically compiles enantioselectivity studies and enantioresolution methods of synthetic cannabinoids and synthetic cathinones, following PRISMA guidelines. The main aim of this review is to explore the impact of chirality on these NPSs, improving our understanding of their toxicological behavior and evaluating advances in analytical techniques for their enantioseparation. Key examples from both groups are presented. This review highlights the importance of continuing research in this field, as demonstrated by the differing properties of synthetic cannabinoid and synthetic cathinone enantiomers, which are closely linked to variations in biological and toxicological outcomes.<\/jats:p>","DOI":"10.3390\/ijms26136471","type":"journal-article","created":{"date-parts":[[2025,7,7]],"date-time":"2025-07-07T08:58:23Z","timestamp":1751878703000},"page":"6471","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Exploring the Impact of Chirality of Synthetic Cannabinoids and Cathinones: A Systematic Review on Enantioresolution Methods and Enantioselectivity Studies"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6826-1854","authenticated-orcid":false,"given":"Ana Sofia","family":"Almeida","sequence":"first","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica e Farmac\u00eautica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia, Universidade do Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"},{"name":"Centro Interdisciplinar de Investiga\u00e7\u00e3o Marinha e Ambiental (CIIMAR), Universidade do Porto, Terminal de Cruzeiros do Porto de Leix\u00f5es, Avenida General Norton de Matos, s\/n, 4450-208 Matosinhos, Portugal"},{"name":"UCIBIO-Applied Molecular Biosciences Unit, Laboratory of Toxicology, Department of Biological Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"},{"name":"Associate Laboratory i4HB\u2014Institute for Health and Bioeconomy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0009-0006-9034-6321","authenticated-orcid":false,"given":"Rita M. G.","family":"Santos","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica e Farmac\u00eautica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia, Universidade do Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"},{"name":"Centro Interdisciplinar de Investiga\u00e7\u00e3o Marinha e Ambiental (CIIMAR), Universidade do Porto, Terminal de Cruzeiros do Porto de Leix\u00f5es, Avenida General Norton de Matos, s\/n, 4450-208 Matosinhos, Portugal"},{"name":"UCIBIO-Applied Molecular Biosciences Unit, Laboratory of Toxicology, Department of Biological Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"},{"name":"Associate Laboratory i4HB\u2014Institute for Health and Bioeconomy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7395-5700","authenticated-orcid":false,"given":"Paula","family":"Guedes de Pinho","sequence":"additional","affiliation":[{"name":"UCIBIO-Applied Molecular Biosciences Unit, Laboratory of Toxicology, Department of Biological Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"},{"name":"Associate Laboratory i4HB\u2014Institute for Health and Bioeconomy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1382-5119","authenticated-orcid":false,"given":"Fernando","family":"Remi\u00e3o","sequence":"additional","affiliation":[{"name":"UCIBIO-Applied Molecular Biosciences Unit, Laboratory of Toxicology, Department of Biological Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"},{"name":"Associate Laboratory i4HB\u2014Institute for Health and Bioeconomy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0940-9163","authenticated-orcid":false,"given":"Carla","family":"Fernandes","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica e Farmac\u00eautica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia, Universidade do Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"},{"name":"Centro Interdisciplinar de Investiga\u00e7\u00e3o Marinha e Ambiental (CIIMAR), Universidade do Porto, Terminal de Cruzeiros do Porto de Leix\u00f5es, Avenida General Norton de Matos, s\/n, 4450-208 Matosinhos, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2025,7,4]]},"reference":[{"key":"ref_1","unstructured":"(2023, June 10). New Psychoactive Substances (NPS). www.emcdda.europa.eu. Available online: https:\/\/www.emcdda.europa.eu\/topics\/nps_en#library."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"204512532096719","DOI":"10.1177\/2045125320967197","article-title":"New Psychoactive Substances: A Review and Updates","volume":"10","author":"Shafi","year":"2020","journal-title":"Ther. Adv. Psychopharmacol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.drugalcdep.2015.09.030","article-title":"Next Generation of Novel Psychoactive Substances on the Horizon\u2014A Complex Problem to Face","volume":"157","author":"Zawilska","year":"2015","journal-title":"Drug Alcohol Depend."},{"key":"ref_4","unstructured":"(2023, June 10). European Drug Report: Trends and Developments. Available online: https:\/\/www.euda.europa.eu\/publications\/edr\/trends-developments\/2022_en."},{"key":"ref_5","unstructured":"(2024, June 11). EMCDDA New Psychoactive Substances\u2014The Current Situation in Europe (European Drug Report 2024). Available online: https:\/\/www.euda.europa.eu\/publications\/european-drug-report\/2024\/new-psychoactive-substances_en."},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Coppola, M., Mondola, R., Oliva, F., Picci, R.L., Ascheri, D., and Trivelli, F. (2016). Treating the Phenomenon of New Psychoactive Substances. Neuropathology of Drug Addictions and Substance Misuse, Elsevier.","DOI":"10.1016\/B978-0-12-800213-1.00063-8"},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Almeida, A.S., Silva, B., de Pinho, P.G., Remi\u00e3o, F., and Fernandes, C. (2022). Synthetic Cathinones: Recent Developments, Enantioselectivity Studies and Enantioseparation Methods. Molecules, 27.","DOI":"10.3390\/molecules27072057"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"359","DOI":"10.1080\/10408444.2020.1762539","article-title":"The Synthetic Cannabinoids Phenomenon: From Structure to Toxicological Properties. A Review","volume":"50","author":"Alves","year":"2020","journal-title":"Crit. Rev. Toxicol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"220","DOI":"10.1002\/cpt.563","article-title":"Focus on Cannabinoids and Synthetic Cannabinoids","volume":"101","author":"Alexandre","year":"2017","journal-title":"Clin. Pharmacol. Ther."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"187","DOI":"10.1146\/annurev-pharmtox-031122-113758","article-title":"Synthetic Cannabinoids: A Pharmacological and Toxicological Overview","volume":"63","author":"Silva","year":"2023","journal-title":"Annu. Rev. Pharmacol. Toxicol."},{"key":"ref_11","first-page":"123","article-title":"The Therapeutic Use of Cannabis and Cannabinoids","volume":"47","author":"Silva","year":"2022","journal-title":"Rev. Esp. Drogodepend"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"255","DOI":"10.1002\/dta.3403","article-title":"EMCDDA Framework and Practical Guidance for Naming Synthetic Cannabinoids","volume":"15","author":"Pulver","year":"2023","journal-title":"Drug Test. Anal."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Antonides, L.H., Cannaert, A., Norman, C., Vives, L., Harrison, A., Costello, A., Nic Daeid, N., Stove, C.P., Sutcliffe, O.B., and McKenzie, C. (2019). Enantiospecific Synthesis, Chiral Separation, and Biological Activity of Four Indazole-3-Carboxamide-Type Synthetic Cannabinoid Receptor Agonists and Their Detection in Seized Drug Samples. Front. Chem., 7.","DOI":"10.3389\/fchem.2019.00321"},{"key":"ref_14","unstructured":"(2023, September 26). Synthetic Cannabinoids in Europe (Perspectives on Drugs). www.emcdda.europa.eu. Available online: https:\/\/www.emcdda.europa.eu\/publications\/pods\/synthetic-cannabinoids_en."},{"key":"ref_15","unstructured":"(2023, August 30). New Psychoactive Substances\u2014The Current Situation in Europe (European Drug Report 2023). Available online: https:\/\/www.emcdda.europa.eu\/publications\/european-drug-report\/2023\/new-psychoactive-substances_en."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1007\/s00204-013-1163-9","article-title":"Khat and Synthetic Cathinones: A Review","volume":"88","author":"Valente","year":"2014","journal-title":"Arch. Toxicol."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Almeida, A.S., Silva, B., Silva, J.P., Pereira, J.A., Remi\u00e3o, F., and Fernandes, C. (2023). Semi-Preparative Separation, Absolute Configuration, Stereochemical Stability and Effects on Human Neuronal Cells of MDPV Enantiomers. Molecules, 28.","DOI":"10.3390\/molecules28052121"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"552","DOI":"10.1038\/npp.2012.204","article-title":"Powerful Cocaine-Like Actions of 3,4-Methylenedioxypyrovalerone (MDPV), a Principal Constituent of Psychoactive \u2018Bath Salts\u2019 Products","volume":"38","author":"Baumann","year":"2013","journal-title":"Neuropsychopharmacology"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1007\/s11419-022-00639-5","article-title":"A Review of Synthetic Cathinones Emerging in Recent Years (2019\u20132022)","volume":"41","author":"Kuropka","year":"2023","journal-title":"Forensic Toxicol."},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Coelho, M.M., Fernandes, C., Remi\u00e3o, F., and Tiritan, M.E. (2021). Enantioselectivity in Drug Pharmacokinetics and Toxicity: Pharmacological Relevance and Analytical Methods. Molecules, 26.","DOI":"10.3390\/molecules26113113"},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Roberts, J.B., and Colyer, C.L. (2023). Enantioselective Separation of Synthetic Cathinones by Capillary Electrophoresis with Ionic Liquid and Cyclodextrin Buffer Co-Additives. Separations, 10.","DOI":"10.3390\/separations10070417"},{"key":"ref_22","first-page":"535","article-title":"Memoires Sur La Relation Qui Peut Exister Entre La Forme Crystalline et la Composition Chimique, et Sur La Cause de La Polarization Rotatoire","volume":"26","author":"Pasteur","year":"1848","journal-title":"Compt. Rend."},{"key":"ref_23","first-page":"1640","article-title":"Chromatographic separation of racemic thalidomide and teratogenic activity of its enantiomers (author\u2019s transl)","volume":"29","author":"Blaschke","year":"1979","journal-title":"Arzneimittelforschung"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1802","DOI":"10.1016\/S0140-6736(04)16308-3","article-title":"Thalidomide","volume":"363","author":"Franks","year":"2004","journal-title":"Lancet"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"733","DOI":"10.1007\/s10311-024-01808-1","article-title":"Toxicity and Environmental Fate of the Less Toxic Chiral Neonicotinoid Pesticides: A Review","volume":"23","author":"Chen","year":"2025","journal-title":"Environ. Chem. Lett."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"33429","DOI":"10.1039\/D4RA05694A","article-title":"The Significance of Chirality in Contemporary Drug Discovery-a Mini Review","volume":"14","author":"Senkuttuvan","year":"2024","journal-title":"RSC Adv."},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Pinto, M.M.M., Fernandes, C., and Tiritan, M.E. (2020). Chiral Separations in Preparative Scale: A Medicinal Chemistry Point of View. Molecules, 25.","DOI":"10.3390\/molecules25081931"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"115783","DOI":"10.1016\/j.trac.2019.115783","article-title":"Analysis of Chiral Drugs in Environmental Matrices: Current Knowledge and Trends in Environmental, Biodegradation and Forensic Fields","volume":"124","author":"Ribeiro","year":"2020","journal-title":"TrAC Trends Anal. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1093\/jat\/bkx074","article-title":"Chiral Resolution and Enantioselectivity of Synthetic Cathinones: A Brief Review","volume":"42","author":"Silva","year":"2018","journal-title":"J. Anal. Toxicol."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"n71","DOI":"10.1136\/bmj.n71","article-title":"The PRISMA 2020 Statement: An Updated Guideline for Reporting Systematic Reviews","volume":"372","author":"Page","year":"2021","journal-title":"BMJ"},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"Almeida, A.S., Pinho, P.G., Remi\u00e3o, F., and Fernandes, C. (2025). Uncovering the Metabolic Footprint of New Psychoactive Substances by Metabolomics: A Systematic Review. Molecules, 30.","DOI":"10.3390\/molecules30020290"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"38","DOI":"10.1186\/s12995-024-00436-3","article-title":"Metabolomics and Proteomics in Occupational Medicine: A Comprehensive Systematic Review","volume":"19","author":"Rodrigues","year":"2024","journal-title":"J. Occup. Med. Toxicol."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"117553","DOI":"10.1016\/j.cca.2023.117553","article-title":"Metabolic Signature Biomarkers for Predicting the Recurrence of Urological Cancers","volume":"549","author":"Amaro","year":"2023","journal-title":"Clin. Chim. Acta"},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Almeida, A.S., Guedes de Pinho, P., Remi\u00e3o, F., and Fernandes, C. (2025). Metabolomics as a Tool for Unraveling the Impact of Enantioselectivity in Cellular Metabolism. Crit. Rev. Anal. Chem., 1\u201321.","DOI":"10.1080\/10408347.2025.2468926"},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Santos, R.M.G., Lima, R., Cravo, S., Fernandes, P.A., Remi\u00e3o, F., and Fernandes, C. (2025). Binding Affinity of Synthetic Cannabinoids to Human Serum Albumin: Site Characterization and Interaction Insights. Pharmaceuticals, 18.","DOI":"10.3390\/ph18040581"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"123836","DOI":"10.1016\/j.jchromb.2023.123836","article-title":"Binding Studies of Synthetic Cathinones to Human Serum Albumin by High-Performance Affinity Chromatography","volume":"1227","author":"Cardoso","year":"2023","journal-title":"J. Chromatogr. B"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"3277","DOI":"10.1007\/s00204-019-02566-8","article-title":"Metabolic Signature of Methylone in Primary Mouse Hepatocytes, at Subtoxic Concentrations","volume":"93","author":"Carvalho","year":"2019","journal-title":"Arch. Toxicol."},{"key":"ref_38","doi-asserted-by":"crossref","unstructured":"Almeida, A.S., Silva, B., Remi\u00e3o, F., and Fernandes, C. (2023). Assessment of the Permeability of 3,4-Methylenedioxypyrovalerone (MDPV) across the Caco-2 Monolayer for Estimation of Intestinal Absorption and Enantioselectivity. Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms24032680"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"100145","DOI":"10.1016\/j.jcoa.2024.100145","article-title":"Enantiomeric Profile of Promethazine in Metabolic Studies in Liver Microsomes","volume":"6","author":"Coelho","year":"2024","journal-title":"J. Chromatogr. Open"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"115442","DOI":"10.1016\/j.taap.2021.115442","article-title":"S-(+)-Pentedrone and R-(+)-Methylone as the Most Oxidative and Cytotoxic Enantiomers to Dopaminergic SH-SY5Y Cells: Role of MRP1 and P-Gp in Cathinones Enantioselectivity","volume":"416","author":"Silva","year":"2021","journal-title":"Toxicol. Appl. Pharmacol."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"143","DOI":"10.1016\/j.chroma.2012.07.058","article-title":"Resolution and Determination of Enantiomeric Purity of New Chiral Derivatives of Xanthones Using Polysaccharide-Based Stationary Phases","volume":"1269","author":"Fernandes","year":"2012","journal-title":"J. Chromatogr. A"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"463555","DOI":"10.1016\/j.chroma.2022.463555","article-title":"Chromatographic Supports for Enantioselective Liquid Chromatography: Evolution and Innovative Trends","volume":"1684","author":"Fernandes","year":"2022","journal-title":"J. Chromatogr. A"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"2081","DOI":"10.1021\/jo00006a021","article-title":"Synthesis of Both Enantiomers of Nabilone from a Common Intermediate. Enantiodivergent Synthesis of Cannabinoids","volume":"56","author":"Huffman","year":"1991","journal-title":"J. Org. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"716","DOI":"10.1080\/15563650.2019.1687903","article-title":"Effects of Vitamin K1 Treatment on Plasma Concentrations of Long-Acting Anticoagulant Rodenticide Enantiomers Following Inhalation of Contaminated Synthetic Cannabinoids","volume":"58","author":"Feinstein","year":"2020","journal-title":"Clin. Toxicol."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"461256","DOI":"10.1016\/j.chroma.2020.461256","article-title":"Separation of Enantiomers and Positional Isomers of Novel Psychoactive Substances in Solid Samples by Chromatographic and Electrophoretic Techniques\u2014A Selective Review","volume":"1624","author":"Schmid","year":"2020","journal-title":"J. Chromatogr. A"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"342901","DOI":"10.1016\/j.aca.2024.342901","article-title":"Chromatographic Enantioresolution and Stereochemical Characterization of Synthetic Cannabinoid Receptor Agonists with Whelk-O\u00ae1 Chiral Stationary Phases under Mass Spectrometry Compatible Reversed-Phase Conditions: A Study Case with Seized Samples","volume":"1317","author":"Varfaj","year":"2024","journal-title":"Anal. Chim. Acta"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"344","DOI":"10.1007\/s11419-016-0321-1","article-title":"Absolute Configuration of the Synthetic Cannabinoid MDMB-CHMICA with Its Chemical Characteristics in Illegal Products","volume":"34","author":"Andernach","year":"2016","journal-title":"Forensic Toxicol."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"2808","DOI":"10.3762\/bjoc.12.279","article-title":"Characterization of the Synthetic Cannabinoid MDMB-CHMCZCA","volume":"12","author":"Weber","year":"2016","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1016\/j.chroma.2016.10.049","article-title":"Enantioseparation of the Carboxamide-Type Synthetic Cannabinoids N -(1-Amino-3-Methyl-1-Oxobutan-2-Yl)-1-(5-Fluoropentyl)-1 H -Indazole-3-Carboxamide and Methyl [1-(5-Fluoropentyl)-1 H -Indazole-3-Carbonyl]-Valinate in Illicit Herbal Products","volume":"1473","author":"Doi","year":"2016","journal-title":"J. Chromatogr. A"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1007\/s11419-017-0378-5","article-title":"Evaluation of Carboxamide-Type Synthetic Cannabinoids as CB1\/CB2 Receptor Agonists: Difference between the Enantiomers","volume":"36","author":"Doi","year":"2018","journal-title":"Forensic Toxicol."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"201","DOI":"10.1016\/j.chroma.2016.02.047","article-title":"Assessment of Ultra High Performance Supercritical Fluid Chromatography as a Separation Technique for the Analysis of Seized Drugs: Applicability to Synthetic Cannabinoids","volume":"1440","author":"Breitenbach","year":"2016","journal-title":"J. Chromatogr. A"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"762","DOI":"10.1248\/cpb.c15-00170","article-title":"A Reliable Method for the Separation and Detection of Synthetic Cannabinoids by Supercritical Fluid Chromatography with Mass Spectrometry, and Its Application to Plant Products","volume":"63","year":"2015","journal-title":"Chem. Pharm. Bull."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"9390","DOI":"10.1021\/ac4024704","article-title":"Targeted Metabolomic Approach for Assessing Human Synthetic Cannabinoid Exposure and Pharmacology","volume":"85","author":"Patton","year":"2013","journal-title":"Anal. Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"415","DOI":"10.1016\/S0165-022X(02)00144-6","article-title":"Enantiomeric Resolution of a Novel Chiral Cannabinoid Receptor Ligand","volume":"54","author":"Thakur","year":"2002","journal-title":"J. Biochem. Biophys. Methods"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"389","DOI":"10.1002\/chir.20939","article-title":"Preparative Enantiomeric Separation of New Selective CB2 Receptor Agonists by Liquid Chromatography on Polysaccharide-Based Chiral Stationary Phases: Determination of Enantiomeric Purity and Assignment of Absolute Stereochemistry by X-Ray Structure Analysis","volume":"23","author":"Stern","year":"2011","journal-title":"Chirality"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"848","DOI":"10.1016\/j.jpba.2007.01.044","article-title":"Chiral Resolution of the Enantiomers of New Selective CB(2) Receptor Agonists by Liquid Chromatography on Amylose Stationary Phases","volume":"46","author":"Stern","year":"2008","journal-title":"J. Pharm. Biomed. Anal."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"239","DOI":"10.1007\/s10311-011-0352-0","article-title":"Chiral Pharmaceuticals in the Environment","volume":"10","author":"Ribeiro","year":"2012","journal-title":"Environ. Chem. Lett."},{"key":"ref_58","doi-asserted-by":"crossref","unstructured":"Teixeira, J., Tiritan, M.E., Pinto, M.M.M., and Fernandes, C. (2019). Chiral Stationary Phases for Liquid Chromatography: Recent Developments. Molecules, 24.","DOI":"10.3390\/molecules24050865"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1002\/jssc.202100593","article-title":"Recent Progress in the Development of Chiral Stationary Phases for High-performance Liquid Chromatography","volume":"45","author":"Zhang","year":"2022","journal-title":"J. Sep. Sci."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"1561","DOI":"10.1351\/pac200779091561","article-title":"Polysaccharide Derivatives as Useful Chiral Stationary Phases in High-Performance Liquid Chromatography","volume":"79","author":"Chen","year":"2007","journal-title":"Pure Appl. Chem."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1080\/15422119.2017.1326939","article-title":"Chiral Stationary Phases Based on Small Molecules: An Update of the Last 17 Years","volume":"47","author":"Fernandes","year":"2018","journal-title":"Sep. Purif. Rev."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"462413","DOI":"10.1016\/j.chroma.2021.462413","article-title":"Enantioseparation of Cloprostenol on the Polysaccharide Chiral Stationary Phase: Influence of the Mobile Phase on Enantioselective Adsorption","volume":"1653","author":"Wang","year":"2021","journal-title":"J. Chromatogr. A"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"3092","DOI":"10.1039\/C9RA08985C","article-title":"Mass Spectrometry-Based Metabolomics in Health and Medical Science: A Systematic Review","volume":"10","author":"Zhang","year":"2020","journal-title":"RSC Adv."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"379","DOI":"10.1016\/S0021-9673(00)00951-1","article-title":"Enantioselective Chromatography as a Powerful Alternative for the Preparation of Drug Enantiomers","volume":"906","author":"Francotte","year":"2001","journal-title":"J. Chromatogr. A"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"871","DOI":"10.1007\/s10337-013-2469-8","article-title":"Small Molecules as Chromatographic Tools for HPLC Enantiomeric Resolution: Pirkle-Type Chiral Stationary Phases Evolution","volume":"76","author":"Fernandes","year":"2013","journal-title":"Chromatographia"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"628","DOI":"10.1002\/dta.2965","article-title":"Shape Matters: The Application of Activity-based in Vitro Bioassays and Chiral Profiling to the Pharmacological Evaluation of Synthetic Cannabinoid Receptor Agonists in Drug-infused Papers Seized in Prisons","volume":"13","author":"Antonides","year":"2021","journal-title":"Drug Test. Anal."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"2063","DOI":"10.1039\/D3MD00758H","article-title":"Synthesis and Functional Evaluation of Proteinogenic Amino Acid-Derived Synthetic Cannabinoid Receptor Agonists Related to MPP-5F-PICA, MMB-5F-PICA, and MDMB-5F-PICA","volume":"15","author":"Sparkes","year":"2024","journal-title":"RSC Med. Chem."},{"key":"ref_68","doi-asserted-by":"crossref","unstructured":"Salomone, A. (2015). Detection of New Psychoactive Substances. Hair Analysis in Clinical and Forensic Toxicology, Elsevier.","DOI":"10.1016\/B978-0-12-801700-5.00011-X"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"443","DOI":"10.1016\/S0026-895X(25)10492-6","article-title":"Comparison of the Pharmacology and Signal Transduction of the Human Cannabinoid CB1 and CB2 Receptors","volume":"48","author":"Felder","year":"1995","journal-title":"Mol. Pharmacol."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1016\/0014-2999(96)00111-2","article-title":"Electrophysiological Effects of a Cannabinoid on Neural Activity in the Globus Pallidus","volume":"304","author":"Miller","year":"1996","journal-title":"Eur. J. Pharmacol."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"715","DOI":"10.1007\/s002109900135","article-title":"Inhibitory Effect of the Cannabinoid Receptor Agonist WIN 55,212-2 on Pentagastrin-Induced Gastric Acid Secretion in the Anaesthetized Rat","volume":"360","author":"Coruzzi","year":"1999","journal-title":"Naunyn-Schmiedeberg\u2019s Arch. Pharmacol."},{"key":"ref_72","doi-asserted-by":"crossref","unstructured":"Ellert-Miklaszewska, A., Ciechomska, I.A., and Kaminska, B. (2021). Synthetic Cannabinoids Induce Autophagy and Mitochondrial Apoptotic Pathways in Human Glioblastoma Cells Independently of Deficiency in TP53 or PTEN Tumor Suppressors. Cancers, 13.","DOI":"10.3390\/cancers13030419"},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"161","DOI":"10.1002\/glia.10177","article-title":"Cannabinoids Ablate Release of TNFalpha in Rat Microglial Cells Stimulated with Lypopolysaccharide","volume":"41","author":"Facchinetti","year":"2003","journal-title":"Glia"},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"1352","DOI":"10.1016\/S0022-3565(25)10152-3","article-title":"Aminoalkylindole Binding in Rat Cerebellum: Selective Displacement by Natural and Synthetic Cannabinoids","volume":"264","author":"Kuster","year":"1993","journal-title":"J. Pharmacol. Exp. Ther."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"2987","DOI":"10.1523\/JNEUROSCI.19-08-02987.1999","article-title":"Cannabinoids and Neuroprotection in Global and Focal Cerebral Ischemia and in Neuronal Cultures","volume":"19","author":"Nagayama","year":"1999","journal-title":"J. Neurosci."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"432","DOI":"10.1016\/j.pain.2004.02.020","article-title":"Activation of Peripheral Cannabinoid Receptors Attenuates Cutaneous Hyperalgesia Produced by a Heat Injury","volume":"109","author":"Johanek","year":"2004","journal-title":"Pain"},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"3825","DOI":"10.1073\/pnas.89.9.3825","article-title":"Cannabinoids Inhibit N-Type Calcium Channels in Neuroblastoma-Glioma Cells","volume":"89","author":"Mackie","year":"1992","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"257","DOI":"10.1038\/sj.bjp.0705778","article-title":"Cannabinoid Receptor-independent Actions of the Aminoalkylindole WIN 55,212-2 on Trigeminal Sensory Neurons","volume":"142","author":"Price","year":"2004","journal-title":"Br. J. Pharmacol."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"35797","DOI":"10.1074\/jbc.M507959200","article-title":"The Synthetic Cannabinoid R(+)WIN 55,212-2 Inhibits the Interleukin-1 Signaling Pathway in Human Astrocytes in a Cannabinoid Receptor-Independent Manner","volume":"280","author":"Curran","year":"2005","journal-title":"J. Biol. Chem."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"61438","DOI":"10.18632\/oncotarget.11367","article-title":"Inhibition of Interleukin-1\u03b2-Induced Endothelial Tissue Factor Expression by the Synthetic Cannabinoid WIN 55,212-2","volume":"7","author":"Scholl","year":"2016","journal-title":"Oncotarget"},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"301","DOI":"10.1007\/s00210-003-0787-3","article-title":"Analysis of the Respiratory Effects of Cannabinoids in Rats","volume":"368","author":"Schmid","year":"2003","journal-title":"Naunyn-Schmiedeberg\u2019s Arch. Pharmacol."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"1831","DOI":"10.1038\/sj.bjp.0702478","article-title":"Effects of the Endogeneous Cannabinoid, Anandamide, on Neuronal Activity in Rat Hippocampal Slices","volume":"126","author":"Ameri","year":"1999","journal-title":"Br. J. Pharmacol."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"2111","DOI":"10.1016\/0024-3205(95)00196-D","article-title":"Inhibition of Noxious Stimulus-Evoked Activity of Spinal Cord Dorsal Horn Neurons by the Cannabinoid WIN 55,212-2","volume":"56","author":"Hohmann","year":"1995","journal-title":"Life Sci."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"179","DOI":"10.1016\/0014-2999(95)00151-A","article-title":"Effects of a Cannabinoid on Spontaneous and Evoked Neuronal Activity in the Substantia Nigra Pars Reticulata","volume":"279","author":"Miller","year":"1995","journal-title":"Eur. J. Pharmacol."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"472","DOI":"10.1152\/jn.1999.82.1.472","article-title":"Cannabinoid WIN 55,212-2 Inhibits the Activity-Dependent Facilitation of Spinal Nociceptive Responses","volume":"82","author":"Strangman","year":"1999","journal-title":"J. Neurophysiol."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"82","DOI":"10.1016\/j.brainres.2006.04.103","article-title":"A Nitric Oxide Synthase Inhibitor (L-NAME) Attenuates Abstinence-Induced Withdrawal from Both Cocaine and a Cannabinoid Agonist (WIN 55212-2) in Planaria","volume":"1099","author":"Rawls","year":"2006","journal-title":"Brain Res."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"25440","DOI":"10.1074\/jbc.M112.371757","article-title":"The Synthetic Cannabinoid R(+)WIN55,212-2 Augments Interferon-\u03b2 Expression via Peroxisome Proliferator-Activated Receptor-\u03b1","volume":"287","author":"Downer","year":"2012","journal-title":"J. Biol. Chem."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"5813","DOI":"10.1021\/jm0502743","article-title":"Synthesis and Structure\u2212Activity Relationship of a Novel Series of Aminoalkylindoles with Potential for Imaging the Neuronal Cannabinoid Receptor by Positron Emission Tomography","volume":"48","author":"Willis","year":"2005","journal-title":"J. Med. Chem."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"6386","DOI":"10.1021\/jm050135l","article-title":"Potent Cannabinergic Indole Analogues as Radioiodinatable Brain Imaging Agents for the CB1 Cannabinoid Receptor","volume":"48","author":"Deng","year":"2005","journal-title":"J. Med. Chem."},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"1061","DOI":"10.1038\/sj.bjp.0707303","article-title":"Species-specific in Vitro Pharmacological Effects of the Cannabinoid Receptor 2 (CB 2) Selective Ligand AM1241 and Its Resolved Enantiomers","volume":"151","author":"Bingham","year":"2007","journal-title":"Br. J. Pharmacol."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1208\/s12248-009-9170-8","article-title":"Antinociceptive Effects of Racemic AM1241 and Its Chirally Synthesized Enantiomers: Lack of Dependence upon Opioid Receptor Activation","volume":"12","author":"Rahn","year":"2010","journal-title":"AAPS J."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"9584","DOI":"10.1073\/pnas.86.23.9584","article-title":"Nonpsychotropic Cannabinoid Acts as a Functional N-Methyl-D-Aspartate Receptor Blocker","volume":"86","author":"Feigenbaum","year":"1989","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"736","DOI":"10.1016\/S0026-895X(25)09130-8","article-title":"Identification of a Functionally Relevant Cannabinoid Receptor on Mouse Spleen Cells That Is Involved in Cannabinoid-Mediated Immune Modulation","volume":"42","author":"Kaminski","year":"1992","journal-title":"Mol. Pharmacol."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"66","DOI":"10.1034\/j.1600-0773.2003.930202.x","article-title":"The CB 1 Cannabinoid Receptor Agonist, HU-210, Reduces Levodopa-Induced Rotations in 6-Hydroxydopamine-Lesioned Rats","volume":"93","author":"Melamed","year":"2003","journal-title":"Pharmacol. Toxicol."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"R7","DOI":"10.1016\/0014-2999(94)90666-1","article-title":"The Action of Synthetic Cannabinoids on the Induction of Long-Term Potentiation in the Rat Hippocampal Slice","volume":"259","author":"Collins","year":"1994","journal-title":"Eur. J. Pharmacol."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1006\/cbir.1996.0019","article-title":"Cannabinoid Enantiomer Action on the Cytoarchitecture","volume":"20","author":"Wilson","year":"1996","journal-title":"Cell Biol. Int."},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"517","DOI":"10.1016\/S0022-3565(25)20242-7","article-title":"Spinal and Supraspinal Components of Cannabinoid-Induced Antinociception","volume":"258","author":"Lichtman","year":"1991","journal-title":"J. Pharmacol. Exp. Ther."},{"key":"ref_98","unstructured":"Buchler, I.P., Hayes, M.J., Hedge, S.G., Hockerman, S.L., Jones, D., Kortum, S.W., Rico, J.G., TenBrink, R.E., and Wu, K.K. (2009). Indazole Derivatives as CB1 Receptor Modulators and Their Preparation and Use in the Treatment of CB1-Mediated Diseases. Eur. Pat. Appl."},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"1546","DOI":"10.1021\/acschemneuro.5b00112","article-title":"Pharmacology of Indole and Indazole Synthetic Cannabinoid Designer Drugs AB-FUBINACA, ADB-FUBINACA, AB-PINACA, ADB-PINACA, 5F-AB-PINACA, 5F-ADB-PINACA, ADBICA, and 5F-ADBICA","volume":"6","author":"Banister","year":"2015","journal-title":"ACS Chem. Neurosci."},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"6608","DOI":"10.1021\/jm300763w","article-title":"7-Oxo-[1,4]Oxazino [2,3,4-Ij ]Quinoline-6-Carboxamides as Selective CB 2 Cannabinoid Receptor Ligands: Structural Investigations around a Novel Class of Full Agonists","volume":"55","author":"Baraldi","year":"2012","journal-title":"J. Med. Chem."},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"3672","DOI":"10.1021\/acschemneuro.0c00591","article-title":"Exploring Stereochemical and Conformational Requirements at Cannabinoid Receptors for Synthetic Cannabinoids Related to SDB-006, 5F-SDB-006, CUMYL-PICA, and 5F-CUMYL-PICA","volume":"11","author":"Ametovski","year":"2020","journal-title":"ACS Chem. Neurosci."},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"7327","DOI":"10.1016\/j.bmcl.2010.10.061","article-title":"Design, Synthesis, and Structure\u2013Activity Relationship Study of Bicyclic Piperazine Analogs of Indole-3-Carboxamides as Novel Cannabinoid CB1 Receptor Agonists","volume":"20","author":"Moir","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"4918","DOI":"10.1016\/j.bmcl.2010.06.067","article-title":"Design, Synthesis, and Structure-Activity Relationship Study of Conformationally Constrained Analogs of Indole-3-Carboxamides as Novel CB1 Cannabinoid Receptor Agonists","volume":"20","author":"Kiyoi","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_104","doi-asserted-by":"crossref","first-page":"70","DOI":"10.1021\/jm050467q","article-title":"Novel 4-Oxo-1,4-Dihydroquinoline-3-Carboxamide Derivatives as New CB2 Cannabinoid Receptors Agonists: Synthesis, Pharmacological Properties and Molecular Modeling","volume":"49","author":"Stern","year":"2006","journal-title":"J. Med. Chem."},{"key":"ref_105","doi-asserted-by":"crossref","first-page":"5471","DOI":"10.1021\/jm070387h","article-title":"Pharmacomodulations around the 4-Oxo-1,4-Dihydroquinoline-3-Carboxamides, a Class of Potent CB2-Selective Cannabinoid Receptor Ligands: Consequences in Receptor Affinity and Functionality","volume":"50","author":"Stern","year":"2007","journal-title":"J. Med. Chem."},{"key":"ref_106","doi-asserted-by":"crossref","unstructured":"Brandon, A.M., Antonides, L.H., Riley, J., Epemolu, O., McKeown, D.A., Read, K.D., and McKenzie, C. (2021). A Systematic Study of the In Vitro Pharmacokinetics and Estimated Human In Vivo Clearance of Indole and Indazole-3-Carboxamide Synthetic Cannabinoid Receptor Agonists Detected on the Illicit Drug Market. Molecules, 26.","DOI":"10.3390\/molecules26051396"},{"key":"ref_107","doi-asserted-by":"crossref","first-page":"2003","DOI":"10.1021\/acsomega.4c07879","article-title":"Chiral Recognition of Butylone by Methylated \u03b2-Cyclodextrin Inclusion Complexes: Molecular Calculations and Two-Level Factorial Designs","volume":"10","author":"Lawtrakul","year":"2025","journal-title":"ACS Omega"},{"key":"ref_108","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1007\/s11419-023-00677-7","article-title":"Determination of 3- and 4-Chloromethcathinone Interactions with Plasma Proteins: Study Involving Analytical and Theoretical Methods","volume":"42","author":"Holowinski","year":"2024","journal-title":"Forensic Toxicol."},{"key":"ref_109","doi-asserted-by":"crossref","first-page":"343380","DOI":"10.1016\/j.aca.2024.343380","article-title":"Advantages of Dimethyl Carbonate as Organic Modifier for Enantioseparation of Novel Psychoactive Substances in Sub\/Supercritical Fluid Chromatography","volume":"1332","author":"Seibert","year":"2024","journal-title":"Anal. Chim. Acta"},{"key":"ref_110","doi-asserted-by":"crossref","first-page":"1721","DOI":"10.1002\/elps.202400092","article-title":"Enantiomeric Separation of Nefopam and Cathinone Derivatives Using a Supramolecular Deep Eutectic Solvent as a Chiral Selector in Capillary Electrophoresis","volume":"45","author":"Ioannou","year":"2024","journal-title":"Electrophoresis"},{"key":"ref_111","doi-asserted-by":"crossref","unstructured":"Ioannou, K.A., Ioannou, G.D., Christou, A., Stavrou, I.J., Schmid, M.G., and Kapnissi-Christodoulou, C.P. (2024). Stereoselective Separation of Psychoactive Substances: Multivariate Optimization and Validation of a Capillary Electrophoresis Method Using Carboxymethyl-\u03b2-CD\/Deep Eutectic Solvent Dual System. J. Pharm. Biomed. Anal., 239.","DOI":"10.1016\/j.jpba.2023.115897"},{"key":"ref_112","doi-asserted-by":"crossref","unstructured":"Folprechtov\u00e1, D., Schmid, M.G., Armstrong, D.W., and Kal\u00edkov\u00e1, K. (2023). The Enantioselective Potential of NicoShell and TeicoShell Columns for Basic Pharmaceuticals and Forensic Drugs in Sub\/Supercritical Fluid Chromatography. Molecules, 28.","DOI":"10.3390\/molecules28031202"},{"key":"ref_113","doi-asserted-by":"crossref","first-page":"2392","DOI":"10.1002\/elps.202200182","article-title":"Evaluation of Cyclodextrin- and Cyclofructan-based Chiral Selectors for the Enantioseparation of Psychoactive Substances in Capillary Electrophoresis","volume":"43","author":"Ioannou","year":"2022","journal-title":"Electrophoresis"},{"key":"ref_114","doi-asserted-by":"crossref","first-page":"112351","DOI":"10.1016\/j.forsciint.2024.112351","article-title":"NMR-Based Structure Elucidation and Chiral Separation of N-Cyclohexylmethylone, a Novel Designer Drug","volume":"367","author":"Seibert","year":"2025","journal-title":"Forensic Sci. Int."},{"key":"ref_115","doi-asserted-by":"crossref","unstructured":"P\u00e9rez-Pereira, A., Gon\u00e7alves, V.M.F., Ribeiro, A.R.L., Fernandes, C., Carrola, J.S., Ribeiro, C., and Tiritan, M.E. (2024). Development of an Enantioselective Method by Liquid Chromatography to Monitor 3,4-Methylenedioxypyrovalerone in Culture Media from Ecotoxicity Assays. Separations, 11.","DOI":"10.3390\/separations11080248"},{"key":"ref_116","doi-asserted-by":"crossref","first-page":"e23646","DOI":"10.1002\/chir.23646","article-title":"Synthesis and Absolute Configuration of Cyclic Synthetic Cathinones Derived from \u03b1-Tetralone","volume":"36","author":"Kohout","year":"2024","journal-title":"Chirality"},{"key":"ref_117","doi-asserted-by":"crossref","first-page":"112128","DOI":"10.1016\/j.forsciint.2024.112128","article-title":"Amphetamine-like Substances and Synthetic Cathinones in Portuguese Wastewater Influents: Enantiomeric Profiling and Role of Suspended Particulate Matter","volume":"361","author":"Langa","year":"2024","journal-title":"Forensic Sci. Int."},{"key":"ref_118","doi-asserted-by":"crossref","first-page":"100139","DOI":"10.1016\/j.jcoa.2024.100139","article-title":"Tuning Parameters of Single Quadrupole Mass Detector Hyphenated to Supercritical Fluid Chromatography for Enantioseparation of Synthetic Cathinones","volume":"5","author":"Kohout","year":"2024","journal-title":"J. Chromatogr. Open"},{"key":"ref_119","doi-asserted-by":"crossref","first-page":"e23679","DOI":"10.1002\/chir.23679","article-title":"Exploring a Lux\u00ae i-Amylose-3 Column in Normal Phase and Polar-organic Mode for Chiral Separation of Cathinone Derivatives and Pyrovalerones Using High-performance Liquid Chromatography","volume":"36","author":"Seibert","year":"2024","journal-title":"Chirality"},{"key":"ref_120","doi-asserted-by":"crossref","first-page":"106906","DOI":"10.1016\/j.aquatox.2024.106906","article-title":"Toxicity of Butylone and Its Enantiomers to Daphnia Magna and Its Degradation\/Toxicity Potential Using Advanced Oxidation Technologies","volume":"271","author":"Carvalho","year":"2024","journal-title":"Aquat. Toxicol."},{"key":"ref_121","doi-asserted-by":"crossref","unstructured":"Dob\u0161\u00edkov\u00e1, K., Javorsk\u00e1, \u017d., Pa\u0161kan, M., Sp\u00e1lovsk\u00e1, D., Trembulakov\u00e1, P., Hercikov\u00e1, J., Kucha\u0159, M., Kozm\u00edk, V., Kohout, M., and Setni\u010dka, V. (2023). Enantioseparation and a Comprehensive Spectroscopic Analysis of Novel Synthetic Cathinones Laterally Substituted with a Trifluoromethyl Group. Spectrochim. Acta Part A Mol. Biomol. Spectrosc., 291.","DOI":"10.1016\/j.saa.2023.122320"},{"key":"ref_122","doi-asserted-by":"crossref","first-page":"123986","DOI":"10.1016\/j.talanta.2022.123986","article-title":"Development and Validation of a Chiral LC-MS\/MS Method for the Separation and Quantification of Four Synthetic Cathinones in Human Whole Blood and Its Application in Stability Analysis","volume":"253","author":"Aldubayyan","year":"2023","journal-title":"Talanta"},{"key":"ref_123","doi-asserted-by":"crossref","unstructured":"Pa\u0161kan, M., Rimpelov\u00e1, S., Svobodov\u00e1 Pavl\u00ed\u010dkov\u00e1, V., Sp\u00e1lovsk\u00e1, D., Setni\u010dka, V., Kucha\u0159, M., and Kohout, M. (2022). 4-Isobutylmethcathinone\u2014A Novel Synthetic Cathinone with High In Vitro Cytotoxicity and Strong Receptor Binding Preference of Enantiomers. Pharmaceuticals, 15.","DOI":"10.3390\/ph15121495"},{"key":"ref_124","doi-asserted-by":"crossref","first-page":"463506","DOI":"10.1016\/j.chroma.2022.463506","article-title":"Sugammadex Analogue Cyclodextrins as Chiral Selectors for Enantioseparation of Cathinone Derivatives by Capillary Electrophoresis","volume":"1683","author":"Ujj","year":"2022","journal-title":"J. Chromatogr. A"},{"key":"ref_125","doi-asserted-by":"crossref","unstructured":"Langa, I., Tiritan, M.E., Silva, D., and Ribeiro, C. (2021). Gas Chromatography Multiresidue Method for Enantiomeric Fraction Determination of Psychoactive Substances in Effluents and River Surface Waters. Chemosensors, 9.","DOI":"10.3390\/chemosensors9080224"},{"key":"ref_126","doi-asserted-by":"crossref","first-page":"121994","DOI":"10.1016\/j.talanta.2020.121994","article-title":"Enantiodetermination of R,S-3,4-Methylenedioxypyrovalerone in Urine Samples by High Pressure in-Line Solid-Phase Extraction Capillary Electrophoresis-Mass Spectrometry","volume":"225","author":"Borrull","year":"2021","journal-title":"Talanta"},{"key":"ref_127","doi-asserted-by":"crossref","unstructured":"Czerwinska, J., Parkin, M.C., Cilibrizzi, A., George, C., Kicman, A.T., Dargan, P.I., and Abbate, V. (2020). Pharmacokinetics of Mephedrone Enantiomers in Whole Blood after a Controlled Intranasal Administration to Healthy Human Volunteers. Pharmaceuticals, 14.","DOI":"10.3390\/ph14010005"},{"key":"ref_128","doi-asserted-by":"crossref","first-page":"110528","DOI":"10.1016\/j.forsciint.2020.110528","article-title":"Determination of the R- and S-Enantiomers of Methylone and Ethylone in Seized Drugs by Enantioselective Liquid Chromatography Tandem Mass Spectrometry Analysis","volume":"317","author":"Lin","year":"2020","journal-title":"Forensic Sci. Int."},{"key":"ref_129","doi-asserted-by":"crossref","first-page":"85","DOI":"10.59566\/IJBS.2006.2085","article-title":"Chiral Drugs: An Overview","volume":"2","author":"Nguyen","year":"2006","journal-title":"Int. J. Biomed. Sci."},{"key":"ref_130","doi-asserted-by":"crossref","first-page":"815","DOI":"10.1007\/s10337-012-2261-1","article-title":"Chiral Recognition Mechanisms in Analytical Separation Sciences","volume":"75","author":"Scriba","year":"2012","journal-title":"Chromatographia"},{"key":"ref_131","doi-asserted-by":"crossref","first-page":"571","DOI":"10.1016\/S1359-6446(05)03407-0","article-title":"Enantioselective Chromatography in Drug Discovery","volume":"10","author":"Zhang","year":"2005","journal-title":"Drug Discov. Today"},{"key":"ref_132","doi-asserted-by":"crossref","first-page":"1623","DOI":"10.1080\/10408347.2022.2038072","article-title":"Liquid-Phase Microextraction Approaches for Preconcentration and Analysis of Chiral Compounds: A Review on Current Advances","volume":"53","author":"Bayatloo","year":"2023","journal-title":"Crit. Rev. Anal. 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