{"title":"四氢大麻酚及其类似物的乙酰基、丙基和丁基衍生物及其在油和草药产品中的合成副产物的鉴定。","authors":"Rie Tanaka, Michiho Ito, Ruri Kikura-Hanajiri","doi":"10.1002/dta.3883","DOIUrl":null,"url":null,"abstract":"<p><p>Since 2021, products claiming to contain Δ<sup>9</sup>-tetrahydrocannabinol (Δ<sup>9</sup>-THC) analogs have been distributed online and in physical stores, including liquid cartridges for electronic cigarettes, herbal products, and gummy products. This study identified the ingredients in products claiming to contain THC analogs distributed online. Seven oil products and one herbal product were analyzed via gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-photodiode array-mass spectrometry (LC-PDA-MS). After isolating and purifying the unknown components from the products, structural analysis was performed by measuring <sup>1</sup>H and <sup>13</sup>C nuclear magnetic resonance (NMR) spectroscopy and various two-dimensional NMR (COSY, HMQC, HMBC, and NOESY). The analysis revealed the presence of Δ<sup>8</sup>-tetrahydrocannabinol acetate (Δ<sup>8</sup>-THC-O), Δ<sup>9</sup>-tetrahydrocannabinol acetate (Δ<sup>9</sup>-THC-O), Δ<sup>4(8)</sup>-iso-THC-O-acetate, Δ<sup>9</sup>-tetrahydrocannabihexol acetate (Δ<sup>9</sup>-THCH-O), Δ<sup>9</sup>-tetrahydrocannabiphorol acetate (Δ<sup>9</sup>-THCP-O), Δ<sup>8</sup>-THC-O-propionate, Δ<sup>9</sup>-THC-O-propionate, Δ<sup>4(8)</sup>-iso-THC-O-propionate, Δ<sup>9</sup>-THCB-O-butanoate, and Δ<sup>9</sup>-THCP-O-butanoate in these products.</p>","PeriodicalId":160,"journal":{"name":"Drug Testing and Analysis","volume":" ","pages":""},"PeriodicalIF":2.6000,"publicationDate":"2025-03-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Identification of Acetyl, Propionyl, and Butanoyl Derivatives of THC and Its Analogs, and Their Synthetic By-Products in Oils and a Herbal Product.\",\"authors\":\"Rie Tanaka, Michiho Ito, Ruri Kikura-Hanajiri\",\"doi\":\"10.1002/dta.3883\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Since 2021, products claiming to contain Δ<sup>9</sup>-tetrahydrocannabinol (Δ<sup>9</sup>-THC) analogs have been distributed online and in physical stores, including liquid cartridges for electronic cigarettes, herbal products, and gummy products. This study identified the ingredients in products claiming to contain THC analogs distributed online. Seven oil products and one herbal product were analyzed via gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-photodiode array-mass spectrometry (LC-PDA-MS). After isolating and purifying the unknown components from the products, structural analysis was performed by measuring <sup>1</sup>H and <sup>13</sup>C nuclear magnetic resonance (NMR) spectroscopy and various two-dimensional NMR (COSY, HMQC, HMBC, and NOESY). The analysis revealed the presence of Δ<sup>8</sup>-tetrahydrocannabinol acetate (Δ<sup>8</sup>-THC-O), Δ<sup>9</sup>-tetrahydrocannabinol acetate (Δ<sup>9</sup>-THC-O), Δ<sup>4(8)</sup>-iso-THC-O-acetate, Δ<sup>9</sup>-tetrahydrocannabihexol acetate (Δ<sup>9</sup>-THCH-O), Δ<sup>9</sup>-tetrahydrocannabiphorol acetate (Δ<sup>9</sup>-THCP-O), Δ<sup>8</sup>-THC-O-propionate, Δ<sup>9</sup>-THC-O-propionate, Δ<sup>4(8)</sup>-iso-THC-O-propionate, Δ<sup>9</sup>-THCB-O-butanoate, and Δ<sup>9</sup>-THCP-O-butanoate in these products.</p>\",\"PeriodicalId\":160,\"journal\":{\"name\":\"Drug Testing and Analysis\",\"volume\":\" \",\"pages\":\"\"},\"PeriodicalIF\":2.6000,\"publicationDate\":\"2025-03-12\",\"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.3883\",\"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.3883","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 Acetyl, Propionyl, and Butanoyl Derivatives of THC and Its Analogs, and Their Synthetic By-Products in Oils and a Herbal Product.
Since 2021, products claiming to contain Δ9-tetrahydrocannabinol (Δ9-THC) analogs have been distributed online and in physical stores, including liquid cartridges for electronic cigarettes, herbal products, and gummy products. This study identified the ingredients in products claiming to contain THC analogs distributed online. Seven oil products and one herbal product were analyzed via gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-photodiode array-mass spectrometry (LC-PDA-MS). After isolating and purifying the unknown components from the products, structural analysis was performed by measuring 1H and 13C nuclear magnetic resonance (NMR) spectroscopy and various two-dimensional NMR (COSY, HMQC, HMBC, and NOESY). The analysis revealed the presence of Δ8-tetrahydrocannabinol acetate (Δ8-THC-O), Δ9-tetrahydrocannabinol acetate (Δ9-THC-O), Δ4(8)-iso-THC-O-acetate, Δ9-tetrahydrocannabihexol acetate (Δ9-THCH-O), Δ9-tetrahydrocannabiphorol acetate (Δ9-THCP-O), Δ8-THC-O-propionate, Δ9-THC-O-propionate, Δ4(8)-iso-THC-O-propionate, Δ9-THCB-O-butanoate, and Δ9-THCP-O-butanoate in these products.
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.
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