{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T14:54:45Z","timestamp":1786978485614,"version":"build-2736575974"},"reference-count":37,"publisher":"Wiley","issue":"7","license":[{"start":{"date-parts":[[2024,2,11]],"date-time":"2024-02-11T00:00:00Z","timestamp":1707609600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Rapid Comm Mass Spectrometry"],"published-print":{"date-parts":[[2024,4,15]]},"abstract":"<jats:sec>\n                    <jats:title>Context<\/jats:title>\n                    <jats:p>\n                      Hexahydrocannabinol (HHC), a compound derived from synthetic production using cannabidiol (CBD) or delta\u20109\u2010tetrahydrocannabinol (\u0394\n                      <jats:sup>9<\/jats:sup>\n                      \u2010THC), has gained recent attention due to its presence in seized materials across Europe. Sold legally in various forms, HHC poses potential health risks, particularly as a legal alternative to THC in some countries. Despite its historical description in the 1940s, limited toxicology data, pharmacological understanding, and analytical methods for HHC exist.\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Method<\/jats:title>\n                    <jats:p>\n                      This study proposes analytical techniques using mass spectrometry to detect, identify, and quantify (9\n                      <jats:italic>R<\/jats:italic>\n                      )\u2010HHC and (9\n                      <jats:italic>S<\/jats:italic>\n                      )\u2010HHC, concurrently with THC and CBD in various matrices, including oral fluid, whole blood, and seized material. Three distinct methods were employed for different matrices: GC\/MS for seized material, GC\/MS\/MS for whole blood, and UHPLC\/MS\/MS for oral fluid. Methods were validated qualitatively for oral fluid with a FLOQSwab\u00ae device and quantitatively in whole blood and seized material according to Peters et al's recommendations and ICH guidelines.\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Results<\/jats:title>\n                    <jats:p>\n                      Validated methods were considered reliable in detecting and quantifying HHC isomers in terms of repeatability, reproducibility, and linearity with\n                      <jats:italic>r<\/jats:italic>\n                      <jats:sup>2<\/jats:sup>\n                      systematically &gt;0.992. These methods were applied to authentic cases, including seized materials and biological samples from traffic control (whole blood and oral fluid). In seized materials, (9\n                      <jats:italic>R<\/jats:italic>\n                      )\u2010HHC levels ranged from 2.09% to 8.85% and (9\n                      <jats:italic>R<\/jats:italic>\n                      )\u2010HHC\/(9\n                      <jats:italic>S<\/jats:italic>\n                      )\u2010HHC ratios varied from 1.36 to 2.68. In whole blood sample, (9\n                      <jats:italic>R<\/jats:italic>\n                      )\u2010HHC and (9\n                      <jats:italic>S<\/jats:italic>\n                      )\u2010HHC concentrations were, respectively, 2.38 and 1.39\u2009ng\/mL. For all analyzed samples, cannabinoids such as THC and CBD were also detected.\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Conclusion<\/jats:title>\n                    <jats:p>\n                      This research contributes analytical insights into differentiating and simultaneously analyzing (9\n                      <jats:italic>R<\/jats:italic>\n                      )\u2010HHC and (9\n                      <jats:italic>S<\/jats:italic>\n                      )\u2010HHC, using widely applicable mass spectrometric methods. The study emphasizes the need for vigilance among toxicologists, as new semisynthetic cannabinoids continue to emerge in Europe, with potential health implications. The findings underscore the importance of reliable analytical methods for monitoring these compounds in forensic and clinical settings.\n                    <\/jats:p>\n                  <\/jats:sec>","DOI":"10.1002\/rcm.9711","type":"journal-article","created":{"date-parts":[[2024,2,11]],"date-time":"2024-02-11T22:59:01Z","timestamp":1707692341000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Identification and quantification of both isomers of hexahydrocannabinol, (9\n                    <i>R<\/i>\n                    )\u2010hexahydrocannabinol and (9\n                    <i>S<\/i>\n                    )\u2010hexahydrocannabinol, in three different matrices by mass spectrometry"],"prefix":"10.1002","volume":"38","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4779-0666","authenticated-orcid":false,"given":"Charline","family":"Bottinelli","sequence":"first","affiliation":[{"name":"LATLUMTOX Laboratory  Bron France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pauline","family":"Baradian","sequence":"additional","affiliation":[{"name":"LATLUMTOX Laboratory  Bron France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Am\u00e9lie","family":"Poly","sequence":"additional","affiliation":[{"name":"LATLUMTOX Laboratory  Bron France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Guillaume","family":"Hoizey","sequence":"additional","affiliation":[{"name":"LATLUMTOX Laboratory  Bron France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Camille","family":"Chatenay","sequence":"additional","affiliation":[{"name":"LATLUMTOX Laboratory  Bron France"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,2,11]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.26434\/chemrxiv\u20102022\u2010v4zqc\u2010v2"},{"key":"e_1_2_9_3_1","unstructured":"European Monitoring Centre for Drugs and Drug Addiction (EMCDDA).Technical expert meeting on hexahydrocannabinol (HHC) and related cannabinoids.2022. 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