{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,21]],"date-time":"2026-08-21T12:56:48Z","timestamp":1787317008040,"version":"build-2736575974"},"reference-count":24,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2024,7,1]],"date-time":"2024-07-01T00:00:00Z","timestamp":1719792000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Drug Testing and Analysis"],"published-print":{"date-parts":[[2025,4]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    After the Swiss ban of hexahydrocannabinol (HHC) in March 2023, other semisynthetic dibenzopyran cannabinoids emerged on the Swiss gray market. Hexahydrocannabiphorol (HHCP) was the most prominent of them due to its potent cannabimimetic effects, as anecdotal reports from recreational users suggest. In October 2023, a class wide ban of dibenzopyran cannabinoids was introduced in Switzerland to prevent new similar substances from entering the drug market. Various vendors in online shops claim that HHCP is made from CBD, even though they possess different alkyl chain lengths. An HHCP sample was analyzed by gas chromatography coupled to mass spectrometry\u00a0(GC\u2010MS), showing that a mixture of molecules with the same or a similar molecular mass as HHCP was present. Six different substances could be isolated from this sample using column chromatography. Four phenols ((9\n                    <jats:italic>R<\/jats:italic>\n                    )\u2010HHCP,\n                    <jats:italic>iso<\/jats:italic>\n                    \u2010HHCP,\n                    <jats:italic>cis<\/jats:italic>\n                    \u2010HHCP, and\n                    <jats:italic>abn<\/jats:italic>\n                    \u2010HHCP) and two ketones (possible intermediates to (9\n                    <jats:italic>R<\/jats:italic>\n                    )\u2010HHCP and\n                    <jats:italic>abn<\/jats:italic>\n                    \u2010HHCP) were identified by various nuclear magnetic resonance spectroscopy (NMR) techniques. (9\n                    <jats:italic>S<\/jats:italic>\n                    )\u2010HHCP was obtained in an impure fraction. In addition, a fraction was obtained that showed characteristic molecular and fragment ions consistent with bisalkylated products from the synthesis of similar compounds. The presence of abnormal cannabinoids (\n                    <jats:italic>abn<\/jats:italic>\n                    \u2010HHCP) and bisalkylated cannabinoids is a confirmation that this sample was produced purely synthetically as initially suspected, as these compounds have not been reported in\n                    <jats:italic>Cannabis<\/jats:italic>\n                    . Chiral derivatization of the phenols with Mosher acid chlorides showed that only\n                    <jats:italic>iso<\/jats:italic>\n                    \u2010HHCP was present as a scalemic mixture, indicating a good stereocontrol of this synthetic procedure.\n                  <\/jats:p>","DOI":"10.1002\/dta.3759","type":"journal-article","created":{"date-parts":[[2024,7,1]],"date-time":"2024-07-01T05:35:31Z","timestamp":1719812131000},"page":"531-543","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Isolation and characterization of synthesis intermediates and side products in hexahydrocannabiphorol"],"prefix":"10.1002","volume":"17","author":[{"ORCID":"https:\/\/orcid.org\/0009-0004-5579-2217","authenticated-orcid":false,"given":"Willi","family":"Schirmer","sequence":"first","affiliation":[{"name":"Institute of Forensic Medicine, Forensic Toxicology and Chemistry University of Bern  Bern Switzerland"},{"name":"Department of Chemistry, Biochemistry and Pharmaceutical Sciences University of Bern  Bern Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ilche","family":"Gjuroski","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Biochemistry and Pharmaceutical Sciences University of Bern  Bern Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0796-1643","authenticated-orcid":false,"given":"Martina","family":"Vermathen","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Biochemistry and Pharmaceutical Sciences University of Bern  Bern Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2096-0618","authenticated-orcid":false,"given":"Julien","family":"Furrer","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Biochemistry and Pharmaceutical Sciences University of Bern  Bern Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5109-4623","authenticated-orcid":false,"given":"Stefan","family":"Sch\u00fcrch","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Biochemistry and Pharmaceutical Sciences University of Bern  Bern Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8659-1304","authenticated-orcid":false,"given":"Wolfgang","family":"Weinmann","sequence":"additional","affiliation":[{"name":"Institute of Forensic Medicine, Forensic Toxicology and Chemistry University of Bern  Bern Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,7]]},"reference":[{"key":"e_1_2_6_2_1","unstructured":"Schweizerische Eidgenossenschaft.Verordnung des EDI \u00fcber die Verzeichnisse der Bet\u00e4ubungsmittel psychotropen Stoffe Vorl\u00e4uferstoffe und Hilfschemikalien (Bet\u00e4ubungsmittelverzeichnisverordnung BetmVV\u2010EDI) vom 30. 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