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互联网上售卖的合成大麻素的核磁共振光谱参考数据。

NMR Spectroscopic Reference Data of Synthetic Cannabinoids Sold on the Internet.

作者信息

Hubner Eva-Maria, Schmid Martin G, Manojlovic Verina, Gattringer Daniela, Pferschy-Wenzig Eva-Maria, Kunert Olaf

机构信息

Institute of Pharmaceutical Sciences, Department of Pharmaceutical Chemistry, University of Graz, Graz, Austria.

Institute of Pharmaceutical Sciences, Department of Pharmacognosy, University of Graz, Graz, Austria.

出版信息

Magn Reson Chem. 2025 Mar;63(3):241-255. doi: 10.1002/mrc.5498. Epub 2025 Jan 1.

DOI:10.1002/mrc.5498
PMID:39743737
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11788098/
Abstract

Besides classic illegal drugs, numerous designer drugs, also called new psychoactive substances (NPSs), are available on the global drug market. One of the biggest and fastest-growing substance classes comprises the synthetic cannabinoids. According to the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA), 254 out of 950 monitored substances belong to this group of NPS, with 9 new cannabinoids registered for the first time in 2023. For their purchase, it is not necessary to use the dark web. Due to the structural differences compared to the illegal Δ-THC (delta-9-tetrahydrocannabinol), the legal status changes and the synthetic cannabinoids are available via clear web pages. They come as powders or dissolved and sprayed onto non-psychoactive layers such as cannabidiol hemp, industrial hemp or also on other plant material like herbal tea mixtures or dried flowers. These adulterated plant parts can be smoked as a substitute to the psychoactive and in many countries illegal Δ-THC-containing hemp. The main task of this project was to check the identity of online available synthetic cannabinoid samples and to generate experimental data using a combination of gas and liquid chromatography with mass spectrometric detection and NMR-based structure elucidation. In total, 25 substances in solid state were bought from various online shops. They turned out to be 21 synthetic cannabinoids after analysis, including 13 with no or incomplete experimental NMR data available in the literature and one, CH-PIATA, which has not been mentioned in literature yet. More than 50% of the acquired substances were falsely declared.

摘要

除了传统的非法药物外,全球毒品市场上还存在大量所谓的“策划药”,即新型精神活性物质(NPS)。其中规模最大且增长最快的一类物质是合成大麻素。据欧洲毒品和毒瘾监测中心(EMCDDA)称,在950种受监测物质中,有254种属于这类新型精神活性物质,2023年首次登记了9种新型大麻素。购买这些物质无需通过暗网。由于与非法的Δ-THC(9-四氢大麻酚)结构不同,其法律地位有所变化,合成大麻素可通过普通网页获取。它们呈粉末状,或溶解后喷洒在非精神活性物质层上,如大麻二酚大麻、工业大麻,也可喷洒在其他植物材料上,如花草茶混合物或干花。这些掺杂了合成大麻素的植物部分可作为含精神活性成分且在许多国家非法的含Δ-THC大麻的替代品进行吸食。本项目的主要任务是鉴定在线可得的合成大麻素样品的身份,并结合气相色谱、液相色谱与质谱检测以及基于核磁共振的结构解析来生成实验数据。总共从不同的在线商店购买了25种固态物质。经分析,它们中有21种是合成大麻素,其中13种在文献中没有或只有不完整的核磁共振实验数据,还有一种CH-PIATA在文献中尚未被提及。超过50%的所购物质存在虚假申报情况。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1920/11788098/06aa3d6b6a68/MRC-63-241-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1920/11788098/ebf5ce9f59cd/MRC-63-241-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1920/11788098/d8585244a573/MRC-63-241-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1920/11788098/feb250fb61dd/MRC-63-241-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1920/11788098/06aa3d6b6a68/MRC-63-241-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1920/11788098/ebf5ce9f59cd/MRC-63-241-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1920/11788098/d8585244a573/MRC-63-241-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1920/11788098/feb250fb61dd/MRC-63-241-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1920/11788098/06aa3d6b6a68/MRC-63-241-g004.jpg

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本文引用的文献

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Acute Liver Ischemia Caused by Vasculitis Due to the Use of Synthetic Cannabinoids.使用合成大麻素导致血管炎引起的急性肝缺血
J Belg Soc Radiol. 2024 Apr 29;108(1):46. doi: 10.5334/jbsr.3556. eCollection 2024.
2
Catatonia Induced by First-Time Use of Synthetic Cannabinoids: A Case Report.首次使用合成大麻素诱发的紧张症:一例报告
Cureus. 2024 Jan 31;16(1):e53324. doi: 10.7759/cureus.53324. eCollection 2024 Jan.
3
The synthetic cannabinoids menace: a review of health risks and toxicity.合成大麻素的威胁:健康风险和毒性综述。
Eur J Med Res. 2024 Jan 12;29(1):49. doi: 10.1186/s40001-023-01443-6.
4
Fatal Overdose with the Cannabinoid Receptor Agonists MDMB-4en-PINACA and 4F-ABUTINACA: A Case Report and Review of the Literature.大麻素受体激动剂MDMB - 4en - PINACA和4F - ABUTINACA导致的致命过量用药:一例报告及文献综述
Toxics. 2023 Aug 5;11(8):673. doi: 10.3390/toxics11080673.
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From Euphoria to Emergency: Exploring the Role of K2/Spice in Diffuse Alveolar Hemorrhage.从欣快到紧急情况:探索K2/香料在弥漫性肺泡出血中的作用
Cureus. 2023 Jul 14;15(7):e41887. doi: 10.7759/cureus.41887. eCollection 2023 Jul.
6
"Spice"-related deaths in and around Munich, Germany: A retrospective look at the role of synthetic cannabinoid receptor agonists in our post-mortem cases over a seven-year period (2014-2020).德国慕尼黑及其周边地区与“香料”相关的死亡事件:回顾过去七年(2014-2020 年)我们在尸检案例中合成大麻素受体激动剂的作用。
Int J Legal Med. 2023 Jul;137(4):1059-1069. doi: 10.1007/s00414-023-02995-2. Epub 2023 Apr 19.
7
Persistent Coagulopathy After Synthetic Cannabinoid Use.使用合成大麻素后出现持续性凝血障碍。
Cureus. 2023 Mar 14;15(3):e36156. doi: 10.7759/cureus.36156. eCollection 2023 Mar.
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Drug Test Anal. 2023 Mar;15(3):368-373. doi: 10.1002/dta.3401. Epub 2022 Nov 22.
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