A rapid preparation method for the analysis of the urine from a cannabis user was established. Generally, 11-nor-9-carboxy-∆⁹-tetrahydrocannabinol (THC-COOH), which is one of the main metabolites of ∆⁹-tetrahydorocannabinol (THC), must be detected from a user’s urine to verify cannabis use. However, existing preparation methods are usually multistep and time-consuming processes. Before the analysis by liquid-chromatography tandem mass spectrometry (LC-MS/MS), deconjugation by treatment with β-glucuronidase or alkaline solution, liquid-liquid extraction or solid-phase extraction (SPE), and evaporation are generally performed. In addition, subsequent derivatization (silylation or methylation) are certainly necessary for gas-chromatography mass spectrometry (GC/MS) analysis. Here, we focused on the phenylboronic-acid (PBA) SPE, which selectively binds compounds with a cis-diol moiety. THC-COOH is metabolized as a glucuronide conjugate (THC-COOGlu) which has cis-diol moieties, therefore, we investigated the conditions of its retention and elution to reduce the operating time. We developed four elution conditions, which afford the following derivatives: acidic elution for THC-COOGlu, alkaline elution for THC-COOH, methanolysis elution for the THC-COOH methyl ester (THC-COOMe), and methanolysis elution and following methyl etherification for O-methyl-THC-COOMe (O-Me-THC-COOMe). All repeatability and recovery rates were evaluated by LC-MS/MS in this study. As a result, these four pathways required short times (within 10–25 min) and exhibited good repeatability and recovery rates. Detection limits of pathway I-IV were 10.8, 1.7, 18.9, and 13.8 ng mL^-1, respectively. Lower limits of quantification were 62.5, 31.25, 57.3, and 62.5 ng mL^-1, respectively. When proof of cannabis use is required, any elution condition can be selected to match the possessing reference standards and analytical instruments. To our knowledge, this is the first report of using PBA SPE for the preparation of the urine samples containing cannabis and achieving partial derivatization when eluting from a PBA carrier. Our method can provide a new and practical solution for the preparation of the urine samples from cannabis users. Although the PBA SPE method cannot recover THC-COOH in urine because of its lack of a 1,2-diol moiety, this method has technological advantages for simplifying the process and reducing the operating time, thereby avoiding human errors.

建立了一种用于分析大麻使用者尿液的快速制备方法。一般来说，必须从使用者的尿液中检测11-正-9-羧基-Δ ^{9 -四氢大麻酚 (THC-COOH)，它是 Δ 9 -}四氢大麻酚 (THC)的主要代谢物之一，以验证大麻的使用情况。然而，现有的制备方法通常是多步骤且耗时的过程。在进行液相色谱串联质谱（LC-MS/MS）分析之前，通常进行用β-葡萄糖醛酸酶或碱性溶液处理解偶联、液-液萃取或固相萃取（SPE）以及蒸发。此外，随后的衍生化（甲硅烷基化或甲基化）对于气相色谱质谱（GC/MS）分析来说肯定是必要的。在这里，我们重点关注苯基硼酸 (PBA) SPE，它选择性地结合具有顺式二醇部分的化合物。THC-COOH 被代谢为具有顺式二醇部分的葡萄糖醛酸结合物 (THC-COOGlu)，因此，我们研究了其保留和洗脱条件以减少操作时间。我们开发了四种洗脱条件，提供以下衍生物：THC-COOGlu的酸性洗脱、THC-COOH的碱性洗脱、THC-COOH甲酯(THC-COOMe)的甲醇解洗脱以及O的甲醇解洗脱和随后的甲基醚化-甲基-THC-COOMe ( O -Me-THC-COOMe)。本研究中所有重复性和回收率均通过 LC-MS/MS 进行评估。因此，这四种途径所需时间短（10-25 分钟内），并且表现出良好的重复性和回收率。途径I-IV的检测限分别为10.8、1.7、18.9和13.8 ng mL ^-1。定量下限分别为62.5、31.25、57.3和62.5 ng mL ^-1。当需要大麻使用证明时，可以选择任何洗脱条件以匹配所拥有的参考标准和分析仪器。据我们所知，这是首次使用 PBA SPE 制备含有大麻的尿液样品，并在从 PBA 载体上洗脱时实现部分衍生化。我们的方法可以为大麻使用者尿液样本的制备提供一种新的实用解决方案。尽管PBA SPE方​​法由于缺少1,2-二醇部分而无法回收尿液中的THC-COOH，但该方法具有简化流程、减少操作时间、从而避免人为错误的技术优势。