Institute of Pharmaceutical Biology, Technische Universität Braunschweig, Braunschweig, Germany.
Anal Bioanal Chem. 2012 Jul;404(1):157-71. doi: 10.1007/s00216-012-6122-4. Epub 2012 Jun 19.
In this study, seven commercial "spice-like" products available on the German market were analyzed. They all contained significant amounts of synthetic cannabinoids and had distinctly different compositions of these adulterants. All synthetic cannabinoids were extracted and purified by different chromatographic techniques from the respective product. The structures of all compounds were elucidated by nuclear magnetic resonance spectroscopy and further characterized by mass spectrometry (MS) and ultraviolet and infrared spectroscopy to generate a full data set of each compound. Altogether, eight compounds were identified, and one deuterium-labeled cannabinoid was used as internal standard. Four products contained only one individual compound, while three products contained mixtures of two compounds. Among the eight isolated compounds, six were already known from recent publications (JWH-081, JWH-210, JWH-122, AM2201, RCS-4, and JWH-203), but the published data were not always complete. In addition, two unknown compounds (AM2201-pMe, RCS-4-(N-Me)) were isolated. Overall, compounds from three distinct classes of synthetic cannabinoids could be identified, characterized, and compared. The MS data of the different subclasses allowed the postulation of some general key fragmentations to distinguish between these subclasses. In addition, we established a general method using an isotopically labeled internal standard (JWH-018-D(3)) to quantify synthetic cannabinoids in herbal mixtures. The total content of the synthetic cannabinoids ranged from 77.5 to 202 mg/g, while individual compounds were detected from 19.3 to 202 mg/g in these products. The spectroscopic data for all compounds mentioned here were collected and added en bloc as Electronic supplementary material to this manuscript.
在这项研究中，分析了在德国市场上可买到的七种商业“香料样”产品。它们都含有大量的合成大麻素，并且这些掺杂物的组成明显不同。所有合成大麻素均通过不同的色谱技术从相应的产品中提取和纯化。所有化合物的结构均通过核磁共振波谱法阐明，并通过质谱（MS）和紫外及红外光谱法进一步表征，以生成每个化合物的完整数据集。总共鉴定出八种化合物，并用一种氘标记的大麻素作为内标。四种产品仅含有一种单一化合物，而三种产品则含有两种化合物的混合物。在所分离的八种化合物中，有六种是从最近的出版物中已知的（JWH-081、JWH-210、JWH-122、AM2201、RCS-4 和 JWH-203），但已发表的数据并不总是完整的。此外，还分离出两种未知化合物（AM2201-pMe、RCS-4-（N-Me））。总体而言，可鉴定、表征和比较来自三种不同类别的合成大麻素的化合物。不同子类别的 MS 数据允许假设一些一般的关键碎裂，以区分这些子类。此外，我们建立了一种使用同位素标记内标（JWH-018-D(3)）的通用方法，以定量草药混合物中的合成大麻素。合成大麻素的总含量范围为 77.5 至 202mg/g，而在这些产品中，个别化合物的含量从 19.3 至 202mg/g 不等。本文提到的所有化合物的光谱数据均已收集并作为电子补充材料整块添加到本文稿中。
