Background
Hemp crop is a widely grown cash crop, in addition to textile, food, building materials and other common uses, its active functional ingredients in the field of biomedicine, agriculture and other fields also have a wide range of research and applications. Cannabis belongs to the genus Cannabis in the family Cannabaceae and has a long history of cultivation and widespread use as an annual herb. The medicinal and economic value of cannabis is constantly being developed, and pharmacological studies have shown that cannabis has analgesic, antitumor, antibacterial, and anti-inflammatory effects.
Cannabis is rich in phytocannabinoids, of which there are over 500 known, with tetrahydrocannabinol (THC) being one of the most common. Δ9-tetrahydrocannabinol is the main psychoactive substance in cannabis and a key component in cannabis addiction. Δ8-tetrahydrocannabinol is its double-bonded isomer. THC has a terpene-phenolic skeleton with functional groups including a benzene ring, a secondary alcohol, 3 methyl groups, and an oxacyclohexane ring. Various synthetic cannabinoids have also been developed in recent years based on the chemical structure of THC. Based on the medicinal value of cannabis, initial research on THC focused on its sedative and analgesic effects. Subsequently, it was found that THC also had a certain effect on the central nervous system, producing euphoria after use, with hallucinogenic, euphoric and addictive properties. Chronic intake of THC can make the body dependent and impair cognitive memory, induce psychotic symptoms and anxiety, lead to neurocognitive disorders, and also cause neuroinflammation.
Figure 1. The structures of the cannabinoids
(Source: Tagen M, et al. 2022)
The endocannabinoid system (ECS) consists of the endocannabinoids (ECBs), their biosynthetic and catabolic enzymes, and their corresponding receptors. The ECS is involved in the regulation of a wide range of physiological and pathological processes at multiple sites including the central and peripheral nervous systems and peripheral organs. THC can interact with the endocannabinoid system, specifically with cannabinoid receptor 1 (CB1R) and cannabinoid receptor 2 (CB2R), resulting in a euphoric effect on the CNS. Long-term use can lead to addiction, causing cognitive and behavioral effects that lead to problems with sensory, emotional, motor, and cognitive abilities, and at high doses can lead to hallucinations, delusions, and psychosis. In addition, researchers have begun to focus on the effects of THC on the physiological functions of other systems, such as the reproductive, cardiovascular, immune, and digestive systems.
Alternative Names
Tetrahydrocannabinol Delta 8
References
- 1. Tagen M, et al. Review of delta-8-tetrahydrocannabinol (Δ8 -THC): Comparative pharmacology with Δ9 -THC. Br J Pharmacol. 2022 Aug;179(15):3915-3933.
- 2. Pagano C, et al. Cannabinoids: Therapeutic Use in Clinical Practice. Int J Mol Sci. 2022 Mar 19;23(6):3344.
References
Cannabinol (CBN) Cross-Reacts with Two Urine Immunoassays Designed to Detect Tetrahydrocannabinol (THC) Metabolite
JOURNAL OF APPLIED LABORATORY MEDICINE
Authors: Kroner, Grace M.; Johnson-Davis, Kamisha L.; Doyle, Kelly; McMillin, Gwendolyn A.
Abstract
Background: The psychoactive component of cannabis, tetrahydrocannabinol (THC), is one of many cannabinoids present in the plant. Since cannabinoids have extensive structural similarity, it is important to be aware of potential cross-reactivity with immunoassays designed to detect THC metabolite. This is especially important as cannabinoid products are increasingly marketed as legal supplements. The objective of this study was to assess the cross-reactivity of 2 commercial immunoassays designed to detect THC metabolite with 4 cannabinoids: cannabidiol, cannabinol, cannabichromene, and cannabigerol. Methods: Deidentified residual patient urine samples that tested negative for THC metabolite on initial testing were pooled and fortified with the above compounds to detect cross-reactivity. We next tested a range of CBN concentrations to determine what concentration of CBN was required to trigger a positive immunoassay result. Finally, we tested whether CBN has an additive effect with THC in the immunoassay by adding CBN to 21 samples weakly positive for THC by a mass spectrometry method but negative by the EMIT II Plus immunoassay. Results: Both the EMIT II Plus assay and the Microgenics MultiGent assay demonstrated cross-reactivity with CBN. For the EMIT II Plus assay, about 5-fold more CBN than THC metabolite was required to produce an assay signal equivalent to the cutoff concentration, and CBN displayed an additive effect with THC metabolite. For the Microgenics assay, 20-fold more CBN than THC metabolite was required to cross the cutoff concentration. Conclusions: These data may help guide the need for confirmatory testing when results of THC metabolite testing by immunoassay are inconsistent with expectations.
Identifying and Quantifying Cannabinoids in Biological Matrices in the Medical and Legal Cannabis Era
CLINICAL CHEMISTRY
Authors: Karschner, Erin L.; Swortwood-Gates, Madeleine J.; Huestis, Marilyn A.
Abstract
BACKGROUND: Cannabinoid analyses generally included, until recently, the primary psychoactive cannabis compound, D9-tetrahydrocannabinol (THC), and/or its inactive metabolite, 11-nor-9-carboxy-THC, in blood, plasma, and urine. Technological advances revolutionized the analyses of major and minor phytocannabinoids in diverse biological fluids and tissues. An extensive literature search was conducted in PubMed for articles on cannabinoid analyses from 2000 through 2019. References in acquired manuscripts were also searched for additional articles. CONTENT: This article summarizes analytical methodologies for identification and quantification of multiple phytocannabinoids (including THC, cannabidiol, cannabigerol, and cannabichromene) and their precursors and/or metabolites in blood, plasma, serum, urine, oral fluid, hair, breath, sweat, dried blood spots, postmortem matrices, breast milk, meconium, and umbilical cord since the year 2000. Tables of nearly 200 studies outline parameters including analytes, specimen volume, instrumentation, and limits of quantification. Important diagnostic and interpretative challenges of cannabinoid analyses are also described. Medicalization and legalization of cannabis and the 2018 Agricultural Improvement Act increased demand for cannabinoid analyses for therapeutic drug monitoring, emergency toxicology, workplace and pain-management drug testing programs, and clinical and forensic toxicology applications. This demand is expected to intensify in the near future, with advances in instrumentation performance, increasing LC-MS/MS availability in clinical and forensic toxicology laboratories, and the ever-expanding knowledge of the potential therapeutic use and toxicity of phytocannabinoids. SUMMARY: Cannabinoid analyses and data interpretation are complex; however, major and minor phytocannabinoid detection windows and expected concentration ranges in diverse biological matrices improve the interpretation of cannabinoid test results.
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