インターネット上で流通するオイル製品中のΔ⁸-tetrahydrocannabinol（THC）及びΔ⁹-THCのC-3位のアルキル鎖の長さが異なるTHCアナログの同定

抄録

Since around 2021, products claiming to contain a Δ⁹-tetrahydrocannabinol (THC) analog with different lengths of alkyl chain at C-3 position have been sold on the internet in Japan. Δ⁹-THC has a pentyl group derived from the precursor olivetol at the C-3 position. These products include liquid cartridges for electronic cigarettes, herbal products, and gummy products. This study analyzed and determined the ingredients in five oil products distributed on the internet from 2022 to 2023 that claim to contain THC analogs. Samples of each product were used for GC-MS and LC-MS measurements. After isolating and purifying the unknown components from the products, structural analysis was performed by measuring ¹H, ¹³C-NMR and various two-dimensional NMR [HH correlation spectroscopy (H–H COSY), heteronuclear multiple quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC), and nuclear Overhauser effect spectroscopy (NOESY)]. The analysis identified Δ⁸-tetrahydrocannabivarin (THCV), Δ⁹-THCV, Δ⁸-tetrahydrocannabutol (THCB), Δ⁹-THCB, Δ⁸-tetrahydrocannabihexol (THCH), Δ⁹-THCH, Δ⁸-3-octyl-THC (THCjd) and Δ⁹-THCjd. These compounds were Δ⁸-THC or Δ⁹-THC analogs with different lengths of alkyl chain at C-3 position. Meanwhile, Δ⁴⁽⁸⁾-iso-THCV and Δ¹¹-THCB were identified as minor components of the product, and were considered to be the reaction byproducts of the synthesis of the Δ⁸-THC or Δ⁹-THC analogs. In the future, there are concerns about the distribution of products containing new THC analogs. Therefore, continuous provision monitoring of newly detected in the products is important.