Robertson Nicholas E, Connolly Jack, Shevchenko Nikolay, Mascal Mark, Pinkerton Kent E, Nicklisch Sascha C T, Nguyen Tran B
Department of Environmental Toxicology, University of California Davis, Davis, California 95616, United States.
Department of Chemistry, University of California Davis, Davis, California 95616, United States.
Chem Res Toxicol. 2024 Dec 16;37(12):1965-1975. doi: 10.1021/acs.chemrestox.4c00326. Epub 2024 Nov 13.
Vaping cannabinoids in electronic (e)-cigarette devices is rapidly increasing in popularity, particularly among adolescents, although the chemistry affecting the composition of the vape aerosol is not well understood. This work investigates the formation of aerosol mass, bioactive hydroxyquinones, and harmful or potentially harmful carbonyls from the e-cigarette vaping of natural and synthetic cannabinoids e-liquids in propylene glycol and vegetable glycerin (PG/VG) solvent at a 50 mg/mL concentration in a commercial fourth-generation vaping device. The following cannabinoids were studied: cannabidiol (CBD), 8,9-dihydrocannabidiol (H2CBD), 1,2,8,9-tetrahydrocannabidiol (H4CBD), cannabigerol (CBG), and cannabidiolic acid (CBDA). Quantification of analytes was performed using liquid chromatography coupled to accurate mass spectrometry. The addition of cannabinoids significantly increased aerosol and carbonyl formation compared with the PG/VG solvent alone. All cannabinoids in the study formed hydroxyquinones during vaping (up to ∼1% mass conversion) except for CBDA, which primarily decarboxylated to CBD. Hydroxyquinone formation increased and carbonyl formation decreased, with a decreasing number of double bonds among CBD and its synthetic analogues (H2CBD and H4CBD). During the vaping process, ∼3-6% of the cannabinoid mass can be observed as carbonyls under the study conditions. Oxidation of the terpene moiety on the cannabinoids is proposed as a major contributor to carbonyl formation. CBD produced significantly higher concentrations of formaldehyde, acetaldehyde, acrolein, diacetyl, and methylglyoxal compared with the other cannabinoid samples. CBG produced significantly higher levels of acetone, methacrolein, and methylglyoxal. Conversion of CBD to tetrahydrocannabinol (THC) was not observed under the study conditions. The chemical mechanism basis for these observations is discussed. Compared with other modalities of use for CBD and other cannabinoids, vaping has the potential to adversely impact human health by producing harmful products during the heated aerosolization process.
在电子烟设备中吸食大麻素的现象正迅速流行起来，尤其是在青少年当中，不过影响电子烟烟雾气溶胶成分的化学过程尚未得到充分了解。本研究调查了在商用第四代电子烟设备中，以50毫克/毫升浓度溶解于丙二醇和植物甘油（PG/VG）溶剂中的天然和合成大麻素电子烟油在吸食过程中气溶胶物质、生物活性羟基醌以及有害或潜在有害羰基化合物的形成情况。研究的大麻素包括：大麻二酚（CBD）、8,9 - 二氢大麻二酚（H2CBD）、1,2,8,9 - 四氢大麻二酚（H4CBD）、大麻萜酚（CBG）和大麻二酚酸（CBDA）。使用液相色谱与精确质量质谱联用对分析物进行定量。与单独的PG/VG溶剂相比，添加大麻素显著增加了气溶胶和羰基化合物的形成。研究中的所有大麻素在吸食过程中都会形成羟基醌（质量转化率高达约1%），但CBDA除外，它主要脱羧形成CBD。随着CBD及其合成类似物（H2CBD和H4CBD）中双键数量的减少，羟基醌的形成增加，羰基化合物的形成减少。在研究条件下，吸食过程中约3 - 6%的大麻素质量会以羰基化合物的形式出现。大麻素上萜烯部分的氧化被认为是羰基化合物形成的主要原因。与其他大麻素样品相比，CBD产生的甲醛、乙醛、丙烯醛、二乙酰和甲基乙二醛浓度显著更高。CBG产生的丙酮、甲基丙烯醛和甲基乙二醛水平显著更高。在研究条件下未观察到CBD向四氢大麻酚（THC）的转化。本文讨论了这些观察结果的化学机制基础。与CBD和其他大麻素的其他使用方式相比，吸食有可能在加热雾化过程中产生有害产物，从而对人体健康产生不利影响。
