{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,18]],"date-time":"2026-07-18T17:05:38Z","timestamp":1784394338837,"version":"3.55.0"},"reference-count":39,"publisher":"Walter de Gruyter GmbH","issue":"8","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2024,7,26]]},"abstract":"<jats:title>Abstract<\/jats:title>\n               <jats:sec id=\"j_cclm-2023-1360_abs_001\">\n                  <jats:title>Objectives<\/jats:title>\n                  <jats:p>N-piperidinyl etonitazene (etonitazepipne) is a newly synthesized opioid related to the 2-benzylbenzimidazole analog class. Etonitazepipne has been formally notified and placed under intensive monitoring in Europe in January 2022. Nitazenes have high affinity at \u00b5-opioid receptor (MOR). Etonitazepipne, specifically shows a EC<jats:sub>50<\/jats:sub> of 2.49\u202fnM, suggesting about 50 times higher potency combined with higher efficacy compared to morphine. Antinociceptive potency l (\u2018hot plate test\u2019 with rats) was 192-fold greater than that of morphine.<\/jats:p>\n               <\/jats:sec>\n               <jats:sec id=\"j_cclm-2023-1360_abs_002\">\n                  <jats:title>Methods<\/jats:title>\n                  <jats:p>Here we report on a post-mortem case involving etonitazepipne and its quantification using a standard addition method (SAM) through liquid chromatography tandem mass spectrometry (LC-MS\/MS). In addition, characterization and identification of phase I human metabolites using <jats:italic>in\u00a0vitro<\/jats:italic> assay based on pooled human liver microsomes (pHLM) was performed along with the analysis of authentic urine samples by means of high-performance liquid chromatography high-resolution tandem mass spectrometry (LC-HRMS\/MS).<\/jats:p>\n               <\/jats:sec>\n               <jats:sec id=\"j_cclm-2023-1360_abs_003\">\n                  <jats:title>Results<\/jats:title>\n                  <jats:p>The concentration of etonitazepipne in post-mortem blood and urine was 8.3 and 11\u202fng\/mL, respectively. SAM was validated by assessing the following parameters: intraday and interday repeatability, matrix effect and recovery rate in post-mortem blood. A total of 20 and 14 metabolites were identified after pHLM incubation and urine analysis, respectively. Most pronounced <jats:italic>in\u00a0vitro<\/jats:italic> and <jats:italic>in\u00a0vivo<\/jats:italic> transformations were O-deethylation, hydroxylation, ketone reduction, and combinations thereof.<\/jats:p>\n               <\/jats:sec>\n               <jats:sec id=\"j_cclm-2023-1360_abs_004\">\n                  <jats:title>Conclusions<\/jats:title>\n                  <jats:p>Considering small traces of the parent drug often found in real cases, the identification of metabolic biomarkers is crucial to identify exposure to this drug. O-deethylated, oxidated metabolites, and combination thereof are proposed as urinary biomarkers along with the parent compound.<\/jats:p>\n               <\/jats:sec>","DOI":"10.1515\/cclm-2023-1360","type":"journal-article","created":{"date-parts":[[2024,2,5]],"date-time":"2024-02-05T05:10:39Z","timestamp":1707109839000},"page":"1580-1590","source":"Crossref","is-referenced-by-count":25,"title":["<i>In vitro<\/i>, <i>in\u00a0vivo<\/i> metabolism and quantification of the novel synthetic opioid N-piperidinyl etonitazene (etonitazepipne)"],"prefix":"10.1515","volume":"62","author":[{"given":"Diletta","family":"Berardinelli","sequence":"first","affiliation":[{"name":"Department of Biomedical Sciences and Public Health , Marche Polytechnic University , Ancona , Italy"},{"name":"Forensic Toxicology , Institute for Legal Medicine, Medical Center \u2013 University of Freiburg, Faculty of Medicine, University of Freiburg , Freiburg , Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Omayema","family":"Taoussi","sequence":"additional","affiliation":[{"name":"Department of Biomedical Sciences and Public Health , Marche Polytechnic University , Ancona , Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jeremy","family":"Carlier","sequence":"additional","affiliation":[{"name":"Department of Biomedical Sciences and Public Health , Marche Polytechnic University , Ancona , Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anastasio","family":"Tini","sequence":"additional","affiliation":[{"name":"Department of Biomedical Sciences and Public Health , Marche Polytechnic University , Ancona , Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Simona","family":"Zaami","sequence":"additional","affiliation":[{"name":"Department of Anatomical, Histological, Forensic and Orthopaedic Sciences , Sapienza University of Rome , Rome , Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tom","family":"Sundermann","sequence":"additional","affiliation":[{"name":"Institute of Forensic and Traffic Medicine, Heidelberg University Hospital , Heidelberg , Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Francesco Paolo","family":"Busard\u00f2","sequence":"additional","affiliation":[{"name":"Department of Biomedical Sciences and Public Health , Marche Polytechnic University , Ancona , Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Volker","family":"Auw\u00e4rter","sequence":"additional","affiliation":[{"name":"Forensic Toxicology , Institute for Legal Medicine, Medical Center \u2013 University of Freiburg, Faculty of Medicine, University of Freiburg , Freiburg , Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"374","published-online":{"date-parts":[[2024,2,5]]},"reference":[{"key":"2024071605441144030_j_cclm-2023-1360_ref_001","unstructured":"European Monitoring Centre for Drugs and Drug, Addiction. 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Clin Chem Lab Med 2023;61:e200\u20132. https:\/\/doi.org\/10.1515\/cclm-2023-0186.","DOI":"10.1515\/cclm-2023-0186"},{"key":"2024071605441144030_j_cclm-2023-1360_ref_020","doi-asserted-by":"crossref","unstructured":"Vandeputte, MM, Krotulski, AJ, Walther, D, Glatfelter, GC, Papsun, D, Walton, SE, et al.. Pharmacological evaluation and forensic case series of N-pyrrolidino etonitazene (etonitazepyne), a newly emerging 2-benzylbenzimidazole \u2018nitazene\u2019 synthetic opioid. Arch Toxicol 2022;96:1845\u201363. https:\/\/doi.org\/10.1007\/s00204-022-03276-4.","DOI":"10.1007\/s00204-022-03276-4"},{"key":"2024071605441144030_j_cclm-2023-1360_ref_021","doi-asserted-by":"crossref","unstructured":"Grafinger, KE, Wilde, M, Otte, L, Auw\u00e4rter, V. Pharmacological and metabolic characterization of the novel synthetic opioid brorphine and its detection in routine casework. 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