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。

IF 2.7 3区 医学 Q2 BIOCHEMICAL RESEARCH METHODS
Rie Tanaka, Maiko Kawamura, Michiho Ito, Ruri Kikura-Hanajiri
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引用次数: 0

摘要

自2021年左右以来,声称含有四氢大麻酚(THC)类似物的电子烟液体烟管、草药产品和软糖产品等产品已经在互联网上出售。最近,声称含有其他四氢大麻酚衍生物的产品出现了。在这项研究中,我们确定了在互联网上销售的产品中声称含有四氢大麻酚衍生物的成分。本研究分析的电子烟烟筒产品于2024年9月从日本获得。取1毫克油品,用1毫升乙腈超声处理。所得溶液分别用于气相色谱-质谱(GC-MS)和液相色谱-光电二极管阵列-质谱(LC-PDA-MS)测定。从产物中分离纯化未知成分后,通过1H、13C核磁共振(NMR)和各种二维核磁共振(COSY、HMQC、HMBC和NOESY)以及混合四极飞行时间质谱(LC)进行结构分析。分析表明,氯化hhc(即(9R)-2-氯- hhc、(9S)-2-氯- hhc、(9R)-4-氯- hhc、(9R)-2,4-二氯- hhc和(9S)-2,4-二氯- hhc)是主要成分;和氯化二氢异thc(即10-氯-二氢异thc、8-氯-二氢异thc和8,10-二氯异thc)是从产品中分离鉴定的次要成分。此外,还检测到Δ9-THCB-O-butanoate,其中Δ9THCB的C1位羟基被丁烷化的化合物。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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.

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来源期刊
Drug Testing and Analysis
Drug Testing and Analysis BIOCHEMICAL RESEARCH METHODS-CHEMISTRY, ANALYTICAL
CiteScore
5.90
自引率
24.10%
发文量
191
审稿时长
2.3 months
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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