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首页> 外文期刊>Journal of mass spectrometry: JMS >Isomerization of delta-9-THC to delta-8-THC when tested as trifluoroacetyl-, pentafluoropropionyl-, or heptafluorobutyryl-derivatives
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Isomerization of delta-9-THC to delta-8-THC when tested as trifluoroacetyl-, pentafluoropropionyl-, or heptafluorobutyryl-derivatives

机译：作为三氟乙酰基，五氟丙酰基或七氟丁酰基衍生物测试时，δ9-THC的异构化为δ8-THC

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For GC-MS analysis of delta-9-tetrahydrocannabinol (delta-9-THC), perfluoroacid anhydrides in combination with perfluoroalcohols are commonly used for derivatization. This reagent mixture is preferred because it allows simultaneous derivatization of delta-9-THC and its acid metabolite, 11-nor-delta-9-THC-9-carboxylic acid present in biological samples. When delta-9-THC was derivatized by trifluoroacetic anhydride/hexafluoroisopropanol (TFAA/HFIPOH) and analyzed by GC-MS using full scan mode (50-550 amu), two peaks (P1 and P2) with an identical molecular mass of 410 amu were observed. On the basis of the total ion chromatogram (TIC), P1 with a shorter retention time (RT) was the major peak (TIC 84%). To identify the peaks, delta-8-THC was also tested under the same conditions. The RT and spectra of the major peak (TIC 95%) were identical with that of Pi for delta-9-THC. A minor peak (5%) present also correlated well with the latter peak (P2) for the delta-9-THC derivative. The fragmentation pathway of P1 was primarily demethylation followed by retro Diels-Alder fragmentation (M - 15-68, base peak 100%) indicating P1 as a delta-8-THC-trifluoroacetyl compound. This indicated that delta-9-THC isomerized to delta-8-THC during derivatization with TFAA/HFIPOH. Similar results were also observed when delta-9-THC was derivatized with pentafluoropropionic anhydride/pentafluoropropanol or heptafluorobutyric anhydride/heptafluorobutanol. No isomerization was observed when chloroform was used in derivatization with TFAA. In this reaction, the peaks of delta-8-THC-TFA and delta-9-THC-TFA had retention times and mass spectra matching with P1 and P2, respectively. Because of isomerization, perfluoroacid anhydrides/perfluoroalcohols are not suitable derivatizing agents for analysis of delta-9-THC; whereas the TFAA in chloroform is suitable for the analysis.
机译：为了对delta-9-四氢大麻酚（delta-9-THC）进行GC-MS分析，通常将全氟酸酐与全氟醇结合使用进行衍生化。该试剂混合物是优选的，因为它可以同时衍生生物样品中存在的delta-9-THC及其酸代谢物11-nor-delta-9-THC-9-羧酸。用三氟乙酸酐/六氟异丙醇（TFAA / HFIPOH）衍生delta-9-THC并通过使用全扫描模式（50-550 amu）的GC-MS分析时，两个峰（P1和P2）具有相同的分子量410 amu被观察。根据总离子色谱图（TIC），保留时间（RT）较短的P1是主要峰（TIC 84％）。为了鉴定峰，还在相同条件下测试了delta-8-THC。主峰（TIC 95％）的RT和光谱与δ-9-THC的Pi相同。对于delta-9-THC衍生物，次要峰（5％）也与后一个峰（P2）很好相关。 P1的片段化途径主要是去甲基化，然后是逆狄尔斯-阿尔德片段化（M-15-68，基峰为100％），表明P1为delta-8-THC-三氟乙酰基化合物。这表明在用TFAA / HFIPOH衍生化期间，Δ9-THC异构化为Δ8-THC。当将δ-9-THC用五氟丙酸酐/五氟丙醇或七氟丁酸酐/七氟丁醇衍生化时，也观察到类似的结果。当将氯仿用于TFAA衍生化时，未观察到异构化。在该反应中，δ8-THC-TFA和δ-9-THC-TFA的峰的保留时间和质谱分别与P1和P2匹配。由于异构化，全氟酸酐/全氟醇不适合用于δ9-THC分析。氯仿中的TFAA适合分析。

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