Cristian Caprari , Elena Ferri , Martin G. Schmid , Loretta L. Del Mercato , Cinzia Citti , Giuseppe Cannazza
{"title":"Δ9-Tetrahydrocannabiphorol: Identification and quantification in recreational products","authors":"Cristian Caprari , Elena Ferri , Martin G. Schmid , Loretta L. Del Mercato , Cinzia Citti , Giuseppe Cannazza","doi":"10.1016/j.forc.2024.100595","DOIUrl":null,"url":null,"abstract":"<div><p>Δ<sup>9</sup>-Tetrahydrocannabinol (Δ<sup>9</sup>-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 Δ<sup>9</sup>-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.</p><p>As a result, new semi-synthetic natural and pseudo natural cannabinoids related to the most famous Δ<sup>9</sup>-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.</p><p>Some of these products (gummies, cannabis flower and a vape cartridge), all declared to contain the most potent among all the known cannabinoids, Δ<sup>9</sup>-Tetrahydrocannabiphorol (Δ<sup>9</sup>-THCP), were bought from an online shop and tested through LC-HRMS to determine the effective amount of Δ<sup>9</sup>-THCP and of other cannabinoids.</p><p>All the three samples were found to contain Δ<sup>9</sup>-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.</p></div>","PeriodicalId":324,"journal":{"name":"Forensic Chemistry","volume":"40 ","pages":"Article 100595"},"PeriodicalIF":2.6000,"publicationDate":"2024-06-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Forensic Chemistry","FirstCategoryId":"3","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S246817092400047X","RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ANALYTICAL","Score":null,"Total":0}
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.
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.