{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,19]],"date-time":"2026-03-19T12:20:43Z","timestamp":1773922843236,"version":"3.50.1"},"reference-count":15,"publisher":"Wiley","issue":"11","license":[{"start":{"date-parts":[[2025,7,14]],"date-time":"2025-07-14T00:00:00Z","timestamp":1752451200000},"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":["Drug Testing and Analysis"],"published-print":{"date-parts":[[2025,11]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Since around 2021, products such as e\u2010cigarette liquid cartridges, herbal products, and gummy products, claiming to contain tetrahydrocannabinol (THC) analogues, have been seen for sale on the internet. Recently, products claiming to contain other THC derivatives have appeared. In this study, we identified the ingredients in products distributed on the internet that claim to contain THC derivatives. The e\u2010cigarette cartridge product analyzed in this study was obtained from Japan in September 2024. One milligram of the oil product was treated with 1\u2009mL of acetonitrile under ultrasonication. The resulting solutions were used for gas chromatography\u2013mass spectrometry (GC\n                    <jats:bold>\u2013<\/jats:bold>\n                    MS) and liquid chromatography\u2013photodiode array\u2013mass spectrometry (LC\n                    <jats:bold>\u2013<\/jats:bold>\n                    PDA\n                    <jats:bold>\u2013<\/jats:bold>\n                    MS) measurements. After isolating and purifying unknown components from the product, structural analysis was performed by measuring\n                    <jats:sup>1<\/jats:sup>\n                    H,\n                    <jats:sup>13<\/jats:sup>\n                    C nuclear magnetic resonance (NMR) and various two\u2010dimensional NMR (COSY, HMQC, HMBC, and NOESY) and LC with hybrid quadrupole time\u2010of\u2010flight MS. The analysis revealed that chlorinated HHCs (i.e., (9R)\u20102\u2010chloro\u2010HHC, (9S)\u20102\u2010chloro\u2010HHC, (9R)\u20104\u2010chloro\u2010HHC, (9S)\u20104\u2010chloro\u2010HHC, (9R)\u20102,4\u2010dichloro\u2010HHC, and (9S)\u20102,4\u2010dichloro\u2010HHC) were the major components, and chlorinated dihydro\u2010\n                    <jats:italic>iso<\/jats:italic>\n                    \u2010THCs (i.e., 10\u2010chloro\u2010dihydro\u2010\n                    <jats:italic>iso<\/jats:italic>\n                    \u2010THC, 8\u2010chloro\u2010dihydro\u2010\n                    <jats:italic>iso<\/jats:italic>\n                    \u2010THC, and 8,10\u2010dichloro\u2010\n                    <jats:italic>iso<\/jats:italic>\n                    \u2010THC) were the minor components isolated and identified from the product. Furthermore, \u0394\n                    <jats:sup>9<\/jats:sup>\n                    \u2010THCB\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010butanoate, a compound in which the hydroxyl group at the C1 position of \u0394\n                    <jats:sup>9<\/jats:sup>\n                    THCB was butanoylated, was detected.\n                  <\/jats:p>","DOI":"10.1002\/dta.3927","type":"journal-article","created":{"date-parts":[[2025,7,14]],"date-time":"2025-07-14T23:39:57Z","timestamp":1752536397000},"page":"2170-2177","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Identification of Novel THC Analogs: Chloro Derivatives of Hexahydrocannabinol and Tetrahydrocannabibutol Butanoate in an Oil Product Obtained in Japan"],"prefix":"10.1002","volume":"17","author":[{"ORCID":"https:\/\/orcid.org\/0009-0000-6432-2867","authenticated-orcid":false,"given":"Rie","family":"Tanaka","sequence":"first","affiliation":[{"name":"Division of Pharmacognosy, Phytochemistry and Narcotics National Institute of Health Sciences  Kawasaki Kanagawa Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Maiko","family":"Kawamura","sequence":"additional","affiliation":[{"name":"Division of Pharmacognosy, Phytochemistry and Narcotics National Institute of Health Sciences  Kawasaki Kanagawa Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Michiho","family":"Ito","sequence":"additional","affiliation":[{"name":"Division of Pharmacognosy, Phytochemistry and Narcotics National Institute of Health Sciences  Kawasaki Kanagawa Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ruri","family":"Kikura\u2010Hanajiri","sequence":"additional","affiliation":[{"name":"Division of Pharmacognosy, Phytochemistry and Narcotics National Institute of Health Sciences  Kawasaki Kanagawa Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2025,7,14]]},"reference":[{"key":"e_1_2_9_2_1","unstructured":"EMCDDA \u201cHexahydrocannabinol (HHC) and Related Substances \u201d Publications Office Luxembourg 2023 https:\/\/www.emcdda.europa.eu\/publications\/technical\u2010reports\/hhc\u2010and\u2010related\u2010substances_en."},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/dta.3519"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.0c00436"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11419\u2010023\u201000667\u20109"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1248\/yakushi.24\u201000029"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1093\/jat\/bkac036"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/dta.3883"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.1007\/s13181\u2010023\u201000974\u2010y"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/dta.3777"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.forc.2024.100595"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/dta.3759"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.3390\/psychoactives3040030"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.46.1462"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.43.335"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.47.1641"}],"container-title":["Drug Testing and Analysis"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/dta.3927","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,11,3]],"date-time":"2025-11-03T02:12:06Z","timestamp":1762135926000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/dta.3927"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,7,14]]},"references-count":15,"journal-issue":{"issue":"11","published-print":{"date-parts":[[2025,11]]}},"alternative-id":["10.1002\/dta.3927"],"URL":"https:\/\/doi.org\/10.1002\/dta.3927","archive":["Portico"],"relation":{},"ISSN":["1942-7603","1942-7611"],"issn-type":[{"value":"1942-7603","type":"print"},{"value":"1942-7611","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,7,14]]},"assertion":[{"value":"2025-04-08","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-07-03","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-07-14","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}