{"title":"新型四氢大麻酚类似物的鉴定:日本某油品中六氢大麻酚和四氢大麻醇丁酸酯的氯衍生物。","authors":"Rie Tanaka, Maiko Kawamura, Michiho Ito, Ruri Kikura-Hanajiri","doi":"10.1002/dta.3927","DOIUrl":null,"url":null,"abstract":"<p><p>Since around 2021, products such as e-cigarette 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-cigarette cartridge product analyzed in this study was obtained from Japan in September 2024. One milligram of the oil product was treated with 1 mL of acetonitrile under ultrasonication. The resulting solutions were used for gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-photodiode array-mass spectrometry (LC-PDA-MS) measurements. After isolating and purifying unknown components from the product, structural analysis was performed by measuring <sup>1</sup>H, <sup>13</sup>C nuclear magnetic resonance (NMR) and various two-dimensional NMR (COSY, HMQC, HMBC, and NOESY) and LC with hybrid quadrupole time-of-flight MS. The analysis revealed that chlorinated HHCs (i.e., (9R)-2-chloro-HHC, (9S)-2-chloro-HHC, (9R)-4-chloro-HHC, (9S)-4-chloro-HHC, (9R)-2,4-dichloro-HHC, and (9S)-2,4-dichloro-HHC) were the major components, and chlorinated dihydro-iso-THCs (i.e., 10-chloro-dihydro-iso-THC, 8-chloro-dihydro-iso-THC, and 8,10-dichloro-iso-THC) were the minor components isolated and identified from the product. Furthermore, Δ<sup>9</sup>-THCB-O-butanoate, a compound in which the hydroxyl group at the C1 position of Δ<sup>9</sup>THCB was butanoylated, was detected.</p>","PeriodicalId":160,"journal":{"name":"Drug Testing and Analysis","volume":" ","pages":""},"PeriodicalIF":2.7000,"publicationDate":"2025-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Identification of Novel THC Analogs: Chloro Derivatives of Hexahydrocannabinol and Tetrahydrocannabibutol Butanoate in an Oil Product Obtained in Japan.\",\"authors\":\"Rie Tanaka, Maiko Kawamura, Michiho Ito, Ruri Kikura-Hanajiri\",\"doi\":\"10.1002/dta.3927\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Since around 2021, products such as e-cigarette 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-cigarette cartridge product analyzed in this study was obtained from Japan in September 2024. One milligram of the oil product was treated with 1 mL of acetonitrile under ultrasonication. The resulting solutions were used for gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-photodiode array-mass spectrometry (LC-PDA-MS) measurements. After isolating and purifying unknown components from the product, structural analysis was performed by measuring <sup>1</sup>H, <sup>13</sup>C nuclear magnetic resonance (NMR) and various two-dimensional NMR (COSY, HMQC, HMBC, and NOESY) and LC with hybrid quadrupole time-of-flight MS. The analysis revealed that chlorinated HHCs (i.e., (9R)-2-chloro-HHC, (9S)-2-chloro-HHC, (9R)-4-chloro-HHC, (9S)-4-chloro-HHC, (9R)-2,4-dichloro-HHC, and (9S)-2,4-dichloro-HHC) were the major components, and chlorinated dihydro-iso-THCs (i.e., 10-chloro-dihydro-iso-THC, 8-chloro-dihydro-iso-THC, and 8,10-dichloro-iso-THC) were the minor components isolated and identified from the product. Furthermore, Δ<sup>9</sup>-THCB-O-butanoate, a compound in which the hydroxyl group at the C1 position of Δ<sup>9</sup>THCB was butanoylated, was detected.</p>\",\"PeriodicalId\":160,\"journal\":{\"name\":\"Drug Testing and Analysis\",\"volume\":\" \",\"pages\":\"\"},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2025-07-14\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Drug Testing and Analysis\",\"FirstCategoryId\":\"3\",\"ListUrlMain\":\"https://doi.org/10.1002/dta.3927\",\"RegionNum\":3,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"BIOCHEMICAL RESEARCH METHODS\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Drug Testing and Analysis","FirstCategoryId":"3","ListUrlMain":"https://doi.org/10.1002/dta.3927","RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMICAL RESEARCH METHODS","Score":null,"Total":0}
Identification of Novel THC Analogs: Chloro Derivatives of Hexahydrocannabinol and Tetrahydrocannabibutol Butanoate in an Oil Product Obtained in Japan.
Since around 2021, products such as e-cigarette 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-cigarette cartridge product analyzed in this study was obtained from Japan in September 2024. One milligram of the oil product was treated with 1 mL of acetonitrile under ultrasonication. The resulting solutions were used for gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-photodiode array-mass spectrometry (LC-PDA-MS) measurements. After isolating and purifying unknown components from the product, structural analysis was performed by measuring 1H, 13C nuclear magnetic resonance (NMR) and various two-dimensional NMR (COSY, HMQC, HMBC, and NOESY) and LC with hybrid quadrupole time-of-flight MS. The analysis revealed that chlorinated HHCs (i.e., (9R)-2-chloro-HHC, (9S)-2-chloro-HHC, (9R)-4-chloro-HHC, (9S)-4-chloro-HHC, (9R)-2,4-dichloro-HHC, and (9S)-2,4-dichloro-HHC) were the major components, and chlorinated dihydro-iso-THCs (i.e., 10-chloro-dihydro-iso-THC, 8-chloro-dihydro-iso-THC, and 8,10-dichloro-iso-THC) were the minor components isolated and identified from the product. Furthermore, Δ9-THCB-O-butanoate, a compound in which the hydroxyl group at the C1 position of Δ9THCB was butanoylated, was detected.
期刊介绍:
As the incidence of drugs escalates in 21st century living, their detection and analysis have become increasingly important. Sport, the workplace, crime investigation, homeland security, the pharmaceutical industry and the environment are just some of the high profile arenas in which analytical testing has provided an important investigative tool for uncovering the presence of extraneous substances.
In addition to the usual publishing fare of primary research articles, case reports and letters, Drug Testing and Analysis offers a unique combination of; ‘How to’ material such as ‘Tutorials’ and ‘Reviews’, Speculative pieces (‘Commentaries’ and ‘Perspectives'', providing a broader scientific and social context to the aspects of analytical testing), ‘Annual banned substance reviews’ (delivering a critical evaluation of the methods used in the characterization of established and newly outlawed compounds).
Rather than focus on the application of a single technique, Drug Testing and Analysis employs a unique multidisciplinary approach to the field of controversial compound determination. Papers discussing chromatography, mass spectrometry, immunological approaches, 1D/2D gel electrophoresis, to name just a few select methods, are welcomed where their application is related to any of the six key topics listed below.