Unit of Forensic Toxicology, Department of Anatomical, Histological, Forensic, and Orthopedic Sciences, Università la Sapienza, V. Le Regina Elena 366, 00161 Rome, Italy.
Department of Excellence of Biomedical Science and Public Health, University "Politecnica delle Marche" of Ancona, Via Tronto 10/a, 60124, Ancona, Italy.
J Pharm Biomed Anal. 2022 Oct 25;220:114987. doi: 10.1016/j.jpba.2022.114987. Epub 2022 Aug 8.
Δ9-tetrahydrocannabinol (Δ9-THC) isomers, especially Δ8-tetrahydrocannabinol (Δ8-THC), are increasing in foods, beverages, and e-cigarettes liquids. A major factor is passage of the Agriculture Improvement Act (AIA) that removed hemp containing less than 0.3 % Δ9-THC from the definition of "marijuana" or cannabis. CBD-rich hemp flooded the market resulting in excess product that could be subjected to CBD cyclization to produce Δ8-THC. This process utilizes strong acid and yields toxic byproducts that frequently are not removed prior to sale and are currently inadequately studied. Pharmacological activity is qualitatively similar for Δ8-THC and Δ9-THC, but most preclinical studies in mice, rats, and monkeys documented greater ∆9-THC potency. Both isomers caused graded dose-response effects on euphoria, blurred vision, mental confusion and lethargy, although Δ8-THC was at least 25 % less potent. The most common analytical methodologies providing baseline resolution of ∆8-THC and ∆9-THC in non-biological matrices are liquid-chromatography coupled to diode-array detection (LC-DAD or LC-PDA), while liquid chromatography coupled to mass spectrometry is preferred for biological matrices. Other available analytical methods are gas-chromatography-mass spectrometry (GC-MS) and quantitative nuclear magnetic resonance (QNMR). Current knowledge on the pharmacology of ∆8-THC and other ∆9-THC isomers are reviewed to raise awareness of the activity of these isomers in cannabis products, as well as analytical methods to discriminate ∆9-THC qualitatively, and quantitatively and ∆8-THC in biological and non-biological matrices.
Δ9-四氢大麻酚（Δ9-THC）异构体，特别是 Δ8-四氢大麻酚（Δ8-THC），在食品、饮料和电子烟液中不断增加。一个主要因素是《农业改进法案》（AIA）的通过，该法案将含Δ9-THC 低于 0.3%的大麻从“大麻”或大麻的定义中删除。富含 CBD 的大麻充斥市场，导致过剩的产品可以通过 CBD 环化生成 Δ8-THC。该过程利用强酸，并产生有毒的副产物，这些副产物在销售前通常没有被去除，目前研究不足。Δ8-THC 和 Δ9-THC 的药理学活性在质量上相似，但大多数在小鼠、大鼠和猴子中进行的临床前研究记录了更大的 ∆9-THC 效力。两种异构体都引起了快感、视力模糊、精神混乱和昏睡等程度剂量反应效应，尽管 Δ8-THC 的效力至少低 25%。最常见的分析方法是在非生物基质中提供 Δ8-THC 和 Δ9-THC 基线分辨率的液相色谱-二极管阵列检测（LC-DAD 或 LC-PDA），而液相色谱-质谱联用则更适合生物基质。其他可用的分析方法是气相色谱-质谱（GC-MS）和定量核磁共振（QNMR）。本文综述了 Δ8-THC 和其他 Δ9-THC 异构体的药理学知识，以提高对这些异构体在大麻产品中的活性的认识，以及用于定性、定量区分 Δ9-THC 和 Δ8-THC 在生物和非生物基质中的分析方法。
