{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,12]],"date-time":"2025-11-12T03:31:11Z","timestamp":1762918271935,"version":"build-2065373602"},"reference-count":47,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2021,8,30]],"date-time":"2021-08-30T00:00:00Z","timestamp":1630281600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006742","name":"CESPU","doi-asserted-by":"publisher","award":["CHIRALBIOACTIVE-PI-3RL-IINFACTS-2019 and MYCOBIOENV-PFT-IINFACTS-2019."],"award-info":[{"award-number":["CHIRALBIOACTIVE-PI-3RL-IINFACTS-2019 and MYCOBIOENV-PFT-IINFACTS-2019."]}],"id":[{"id":"10.13039\/501100006742","id-type":"DOI","asserted-by":"publisher"}]},{"name":"FCT\u2014Foundation for Science and Technology; project PTDC\/CTA-AMB\/6686\/2020","award":["Strategic Funding UID\/Multi\/04423\/2019;"],"award-info":[{"award-number":["Strategic Funding UID\/Multi\/04423\/2019;"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemosensors"],"abstract":"<jats:p>Ketamine (K) and its main metabolite, norketamine (NK), are chiral compounds that have been found in effluents from wastewater treatment plants (WWTPs) and aquatic environments. Little is known about their enantioselective biodegradation during sewage treatment; however, this information is pivotal for risk assessment, the evaluation of WWTP performance and wastewater epidemiological studies. The aim of this study was to investigate the biodegradation pattern of the enantiomers of K by activated sludge (AS) from a WWTP. For that, an enantioselective liquid chromatography with diode array detection (LC-DAD) method was developed and validated to quantify the enantiomers of K and NK. Both K and NK enantiomers were separated, in the same chromatographic run, using a Lux\u00ae 3 \u00b5m cellulose-4 analytical column under isocratic elution mode. The method was demonstrated to be linear (r2 &gt; 0.99) and precise (&lt;11.3%). Accuracy ranged between 85.9 and 113.6% and recovery ranged between 50.1 and 86.9%. The limit of quantification was 1.25 \u00b5g\/mL for the enantiomers of NK and 2.5 \u00b5g\/mL for K. The method was applied to monitor the biodegradation assay of the enantiomers of K by AS for 14 days. K was poorly biodegraded, less than 15% for both enantiomers, and enantioselectivity in the biodegradation was not observed. The metabolite NK and other possible degradation products were not detected. This work reports, for the first time, the behavior of both enantiomers of K in biodegradation studies.<\/jats:p>","DOI":"10.3390\/chemosensors9090242","type":"journal-article","created":{"date-parts":[[2021,8,30]],"date-time":"2021-08-30T11:01:37Z","timestamp":1630321297000},"page":"242","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Enantioselective Monitoring of Biodegradation of Ketamine and Its Metabolite Norketamine by Liquid Chromatography"],"prefix":"10.3390","volume":"9","author":[{"given":"Ariana","family":"P\u00e9rez-Pereira","sequence":"first","affiliation":[{"name":"Instituto de Investiga\u00e7\u00e3o e Forma\u00e7\u00e3o Avan\u00e7ada em Ci\u00eancias e Tecnologias da Sa\u00fade, Cooperativa de Ensino Superior Polit\u00e9cnico e Universit\u00e1rio (CESPU), Rua Central de Gandra, 1317, 4585-116 Gandra, Portugal"},{"name":"TOXRUN\u2014Toxicology Research Unit, University Institute of Health Sciences, CESPU, CRL, 4585-116 Gandra, Portugal"}]},{"given":"Alexandra","family":"Maia","sequence":"additional","affiliation":[{"name":"Instituto de Investiga\u00e7\u00e3o e Forma\u00e7\u00e3o Avan\u00e7ada em Ci\u00eancias e Tecnologias da Sa\u00fade, Cooperativa de Ensino Superior Polit\u00e9cnico e Universit\u00e1rio (CESPU), Rua Central de Gandra, 1317, 4585-116 Gandra, Portugal"},{"name":"TOXRUN\u2014Toxicology Research Unit, University Institute of Health Sciences, CESPU, CRL, 4585-116 Gandra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9151-516X","authenticated-orcid":false,"given":"Virg\u00ednia","family":"Gon\u00e7alves","sequence":"additional","affiliation":[{"name":"Instituto de Investiga\u00e7\u00e3o e Forma\u00e7\u00e3o Avan\u00e7ada em Ci\u00eancias e Tecnologias da Sa\u00fade, Cooperativa de Ensino Superior Polit\u00e9cnico e Universit\u00e1rio (CESPU), Rua Central de Gandra, 1317, 4585-116 Gandra, Portugal"},{"name":"TOXRUN\u2014Toxicology Research Unit, University Institute of Health Sciences, CESPU, CRL, 4585-116 Gandra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7245-4552","authenticated-orcid":false,"given":"Cl\u00e1udia","family":"Ribeiro","sequence":"additional","affiliation":[{"name":"Instituto de Investiga\u00e7\u00e3o e Forma\u00e7\u00e3o Avan\u00e7ada em Ci\u00eancias e Tecnologias da Sa\u00fade, Cooperativa de Ensino Superior Polit\u00e9cnico e Universit\u00e1rio (CESPU), Rua Central de Gandra, 1317, 4585-116 Gandra, Portugal"},{"name":"TOXRUN\u2014Toxicology Research Unit, University Institute of Health Sciences, CESPU, CRL, 4585-116 Gandra, Portugal"},{"name":"Interdisciplinary Center of Marine and Environmental Research (CIIMAR), University of Porto, Edif\u00edcio do Terminal de Cruzeiros do Porto de Leix\u00f5es, Av. General Norton de Matos s\/n, 4050-208 Matosinhos, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3320-730X","authenticated-orcid":false,"given":"Maria Elizabeth","family":"Tiritan","sequence":"additional","affiliation":[{"name":"Instituto de Investiga\u00e7\u00e3o e Forma\u00e7\u00e3o Avan\u00e7ada em Ci\u00eancias e Tecnologias da Sa\u00fade, Cooperativa de Ensino Superior Polit\u00e9cnico e Universit\u00e1rio (CESPU), Rua Central de Gandra, 1317, 4585-116 Gandra, Portugal"},{"name":"Interdisciplinary Center of Marine and Environmental Research (CIIMAR), University of Porto, Edif\u00edcio do Terminal de Cruzeiros do Porto de Leix\u00f5es, Av. General Norton de Matos s\/n, 4050-208 Matosinhos, Portugal"},{"name":"Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica e Farmac\u00eautica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia da Universidade do Porto, Rua Jorge de Viterbo Ferreira 228, 4050-313 Porto, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2021,8,30]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"OECD (2019). Pharmaceutical Residues in Freshwater: Hazards and Policy Responses, OECD Publishing. OECD Studies on Water.","DOI":"10.1787\/74fe3bf8-en"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"2529","DOI":"10.1021\/es981014w","article-title":"Occurrence and environmental behavior of the chiral pharmaceutical drug ibuprofen in surface waters and in wastewater","volume":"33","author":"Buser","year":"1999","journal-title":"Environ. Sci. 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