{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,8]],"date-time":"2026-01-08T19:53:28Z","timestamp":1767902008317,"version":"3.49.0"},"reference-count":18,"publisher":"Wiley","issue":"11-12","license":[{"start":{"date-parts":[[2021,9,15]],"date-time":"2021-09-15T00:00:00Z","timestamp":1631664000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100007641","name":"Minist\u00e8re de l'Int\u00e9rieur","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100007641","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Drug Testing and Analysis"],"published-print":{"date-parts":[[2021,11]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>\u0394<jats:sup>8<\/jats:sup>\u2010Tetrahydrocannabinol (\u0394<jats:sup>8<\/jats:sup>\u2010THC) as isomer of the well\u2010known \u0394<jats:sup>9<\/jats:sup>\u2010THC has a similar mode of action, and the potency was estimated to be two thirds compared with \u0394<jats:sup>9<\/jats:sup>\u2010THC. Content of \u0394<jats:sup>8<\/jats:sup>\u2010THC in plant material is low, but formulations containing \u0394<jats:sup>8<\/jats:sup>\u2010THC in high concentrations are gaining popularity. \u0394<jats:sup>8<\/jats:sup>\u2010THC is to be regarded as prohibited substance according to the Prohibited List of the World Anti\u2010Doping Agency (WADA). Contradictory results between initial testing procedure and confirmatory quantitation for 11\u2010Nor\u20109\u2010carboxy\u2010\u0394<jats:sup>9<\/jats:sup>\u2010tetrahydrocannabinol (\u0394<jats:sup>9<\/jats:sup>\u2010THC\u2010COOH) of a doping control sample gave rise for follow\u2010up testing procedures. After alkaline hydrolysis and liquid\u2013liquid extraction, the sample was analyzed by high\u2010performance liquid chromatography tandem mass spectrometry (HPLC\u2010MS\/MS) using isocratic elution instead of gradient elution, which is used for standard procedure. Isocratic elution resulted in two peaks instead of one using gradient elution. Both peaks showed same fragmentation. Using certified reference materials, one peak could be assigned to \u0394<jats:sup>9<\/jats:sup>\u2010THC\u2010COOH and the other one with higher intensity to the less common 11\u2010Nor\u20109\u2010carboxy\u2010\u0394<jats:sup>8<\/jats:sup>\u2010Tetrahydrocannabinol (\u0394<jats:sup>8<\/jats:sup>\u2010THC\u2010COOH) in a concentration of approximately 1200\u2009ng\/ml. As complementary method, gas chromatography tandem mass spectrometry (GC\u2010MS\/MS) can also be used for identification. Here \u0394<jats:sup>8<\/jats:sup>\u2010 and \u0394<jats:sup>9<\/jats:sup>\u2010THC\u2010COOH can be distinguished by chromatography and by fragmentation. Additional investigations of doping control samples containing \u0394<jats:sup>9<\/jats:sup>\u2010THC\u2010COOH revealed the simultaneous presence of \u0394<jats:sup>8<\/jats:sup>\u2010THC\u2010COOH in low concentrations (0.22\u20138.91\u2009ng\/ml) presumably due to plant origin. Percentage of \u0394<jats:sup>8<\/jats:sup>\u2010THC\u2010COOH varies from 0.05 to 2.83%. In vitro experiments using human liver microsomes showed that \u0394<jats:sup>8<\/jats:sup>\u2010THC is metabolized in the same way as \u0394<jats:sup>9<\/jats:sup>\u2010THC.<\/jats:p>","DOI":"10.1002\/dta.3159","type":"journal-article","created":{"date-parts":[[2021,9,8]],"date-time":"2021-09-08T05:52:07Z","timestamp":1631080327000},"page":"1936-1943","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["Emergence of the less common cannabinoid \u0394<sup>8<\/sup>\u2010Tetrahydrocannabinol in a doping sample"],"prefix":"10.1002","volume":"13","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1540-393X","authenticated-orcid":false,"given":"Sebastian","family":"Rzeppa","sequence":"first","affiliation":[{"name":"Institute of Doping Analysis and Sport Biochemistry  Kreischa Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Joachim","family":"Gro\u00dfe","sequence":"additional","affiliation":[{"name":"Institute of Doping Analysis and Sport Biochemistry  Kreischa Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Claudia","family":"Rautenberg","sequence":"additional","affiliation":[{"name":"Institute of Doping Analysis and Sport Biochemistry  Kreischa Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Detlef","family":"Thieme","sequence":"additional","affiliation":[{"name":"Institute of Doping Analysis and Sport Biochemistry  Kreischa Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Triin","family":"Lepp","sequence":"additional","affiliation":[{"name":"Estonian Center for Integrity in Sports  Tallinn Estonia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Henn","family":"Vallim\u00e4e","sequence":"additional","affiliation":[{"name":"Estonian Center for Integrity in Sports  Tallinn Estonia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2157-4711","authenticated-orcid":false,"given":"Annekathrin M.","family":"Keiler","sequence":"additional","affiliation":[{"name":"Institute of Doping Analysis and Sport Biochemistry  Kreischa Germany"},{"name":"Environmental Monitoring and Endocrinology, Faculty of Biology Technische Universit\u00e4t Dresden  Dresden Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2021,9,15]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jpba.2017.07.021"},{"key":"e_1_2_6_3_1","unstructured":"WebsterGR SarnaL MechoulamR.Conversion of CBD to delta8\u2010THC and delta9\u2010THC. 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