Watanabe Shimpei, Murakami Takaya, Muratsu Seiji, Fujiwara Hiroyuki, Nakanishi Toshio, Seto Yasuo
Forensic Science Group, Photon Science Research Division, RIKEN SPring-8 Center, Sayo, Japan.
Forensic Science Laboratory, Ishikawa Prefectural Police Headquarters, Kanazawa, Japan.
Drug Test Anal. 2025 May;17(5):694-700. doi: 10.1002/dta.3777. Epub 2024 Jul 22.
A number of synthetic cannabinoids have been appearing in the recreational drug market for more than a decade. Recent additions are so-called semi-synthetic cannabinoids, and they structurally closely resemble the main psychoactive component of cannabis, Δ-tetrahydrocannabinol. Knowledge of new (semi-)synthetic cannabinoids is essential to help identify them in authentic forensic case samples. Therefore, the aim of the study was to examine two commercially available electronic cigarette liquid products claiming to contain cannabinoids and characterize the structures of the main compounds. The liquid products were analyzed by gas chromatography-mass spectrometry (GC-MS), GC-quadrupole time-of-flight mass spectrometry (GC-QTOF-MS), and liquid chromatography-high-resolution mass spectrometry (LC-HRMS). In product A, typical cannabinoids (cannabidiol, cannabigerol, and cannabinol) and terpenes (α-caryophyllene and β-caryophyllene) were identified by comparison with reference materials. An unknown peak was isolated by semi-preparative high-performance LC, analyzed by nuclear magnetic resonance (NMR) spectroscopy, and identified to be Δ-tetrahydrocannabihexol acetate (Δ-THCH-O). To the authors' knowledge, this is the first report of the identification of Δ-THCH-O in commercially available products. Another compound estimated as cannabihexol acetate was also detected. In product B, cannabidiol, cannabinol, α-caryophyllene, and β-caryophyllene were identified, while two unknown peaks were estimated as tetrahydrocannabidiol isomers. Despite products A and B being labeled to contain "60% HHCPM" and "80% 10-OH-HHC," respectively, no such compounds were detected. The findings of this study could help detect Δ-THCH-O in case samples and highlight the need to keep monitoring commercial products to identify new drugs, while warning that the package labels cannot be trusted.
十多年来，多种合成大麻素一直在娱乐性毒品市场上出现。最近出现的是所谓的半合成大麻素，它们在结构上与大麻的主要精神活性成分Δ-四氢大麻酚极为相似。了解新型（半）合成大麻素对于在真实法医案件样本中识别它们至关重要。因此，本研究的目的是检测两种声称含有大麻素的市售电子烟液产品，并对主要化合物的结构进行表征。通过气相色谱-质谱联用仪（GC-MS）、气相色谱-四极杆飞行时间质谱联用仪（GC-QTOF-MS）和液相色谱-高分辨率质谱联用仪（LC-HRMS）对液体产品进行分析。在产品A中，通过与参考物质比较，鉴定出了典型的大麻素（大麻二酚、大麻萜酚和大麻酚）和萜类化合物（α-石竹烯和β-石竹烯）。通过半制备高效液相色谱分离出一个未知峰，经核磁共振（NMR）光谱分析，鉴定为醋酸Δ-四氢大麻己醇（Δ-THCH-O）。据作者所知，这是在市售产品中鉴定出Δ-THCH-O的首次报告。还检测到了另一种估计为醋酸大麻己醇的化合物。在产品B中，鉴定出了大麻二酚、大麻酚、α-石竹烯和β-石竹烯，但有两个未知峰估计为四氢大麻二酚异构体。尽管产品A和B分别标注含有“60% HHCPM”和“80% 10-OH-HHC”，但未检测到此类化合物。本研究结果有助于在案件样本中检测出Δ-THCH-O，并强调需要持续监测商业产品以识别新毒品，同时警告不能轻信包装标签。
