Δ9-Tetrahydrocannabiphorol: Identification and quantification in recreational products

IF 2.6 3区 医学 Q2 CHEMISTRY, ANALYTICAL
Cristian Caprari , Elena Ferri , Martin G. Schmid , Loretta L. Del Mercato , Cinzia Citti , Giuseppe Cannazza
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引用次数: 0

Abstract

Δ9-Tetrahydrocannabinol (Δ9-THC) is known to be the component of the cannabis plant responsible for the psychoactive effects generated by the activation of the endocannabinoid receptor 1 (CBR1). Following extensive structure–activity relationship (SAR) studies on Δ9-THC, new molecules with increased CBR1 affinity were designed and synthesized over the last decades. The knowledge arising from the pharmacological and synthetic investigations has been extensively used in the recent past by the industry of substances for recreational use also thanks to the 2018 Farm Bill Act in the USA and the incentive for low-THC cannabis (hemp) cultivation in Europe, which have boosted the availability of hemp derived precursors.

As a result, new semi-synthetic natural and pseudo natural cannabinoids related to the most famous Δ9-THC and often not subjected to legal restrictions are now available in the online market in a broad array of retail products with no preventive study on their pharmacodynamics and pharmacokinetics.

Some of these products (gummies, cannabis flower and a vape cartridge), all declared to contain the most potent among all the known cannabinoids, Δ9-Tetrahydrocannabiphorol (Δ9-THCP), were bought from an online shop and tested through LC-HRMS to determine the effective amount of Δ9-THCP and of other cannabinoids.

All the three samples were found to contain Δ9-THCP in amounts significantly different from those declared by the producer. Moreover, the application of an untargeted metabolomics approach (cannabinomics) enabled the identification of other cannabinoids including the emerging semi-synthetic hexahydrocannabinol (HHC) and tetrahydrocannabidiol (H4-CBD) together with byproducts of synthetic origin.

Abstract Image

Δ9-四氢大麻酚:娱乐产品中的鉴定和定量
众所周知,Δ9-四氢大麻酚(Δ9-THC)是大麻植物中的一种成分,通过激活内源性大麻素受体 1(CBR1)而产生精神作用。在对Δ9-THC 进行了广泛的结构-活性关系(SAR)研究后,过去几十年中设计并合成了具有更强 CBR1 亲和力的新分子。药理学和合成研究中获得的知识最近被娱乐用物质行业广泛使用,这也要归功于美国的《2018 年农业法案》和欧洲对低四氢大麻酚大麻(大麻)种植的鼓励措施,这些措施促进了大麻衍生前体的供应。因此,与最著名的Δ9-四氢大麻酚相关的新型半合成天然大麻素和假天然大麻素,通常不受法律限制,现在可以在网上市场上买到,零售产品种类繁多,而且没有对其药效学和药代动力学进行预防性研究。我们从一家网店购买了其中的一些产品(软糖、大麻花和烟盒),并通过 LC-HRMS 进行检测,以确定 Δ9-THCP 和其他大麻素的有效含量。此外,通过应用非靶向代谢组学方法(大麻组学),还鉴定出了其他大麻素,包括新出现的半合成六氢大麻酚(HHC)和四氢大麻酚(H4-CBD)以及合成副产品。
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来源期刊
Forensic Chemistry
Forensic Chemistry CHEMISTRY, ANALYTICAL-
CiteScore
5.70
自引率
14.80%
发文量
65
审稿时长
46 days
期刊介绍: Forensic Chemistry publishes high quality manuscripts focusing on the theory, research and application of any chemical science to forensic analysis. The scope of the journal includes fundamental advancements that result in a better understanding of the evidentiary significance derived from the physical and chemical analysis of materials. The scope of Forensic Chemistry will also include the application and or development of any molecular and atomic spectrochemical technique, electrochemical techniques, sensors, surface characterization techniques, mass spectrometry, nuclear magnetic resonance, chemometrics and statistics, and separation sciences (e.g. chromatography) that provide insight into the forensic analysis of materials. Evidential topics of interest to the journal include, but are not limited to, fingerprint analysis, drug analysis, ignitable liquid residue analysis, explosives detection and analysis, the characterization and comparison of trace evidence (glass, fibers, paints and polymers, tapes, soils and other materials), ink and paper analysis, gunshot residue analysis, synthetic pathways for drugs, toxicology and the analysis and chemistry associated with the components of fingermarks. The journal is particularly interested in receiving manuscripts that report advances in the forensic interpretation of chemical evidence. Technology Readiness Level: When submitting an article to Forensic Chemistry, all authors will be asked to self-assign a Technology Readiness Level (TRL) to their article. The purpose of the TRL system is to help readers understand the level of maturity of an idea or method, to help track the evolution of readiness of a given technique or method, and to help filter published articles by the expected ease of implementation in an operation setting within a crime lab.
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