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Readable research linked to original sources
Browse normalized, publication-ready research with direct links to its evidence and source.
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Readable research linked to original sources
Browse normalized, publication-ready research with direct links to its evidence and source.
51 articles
Newest firstDeveloping synthetic methods that allow controllable homologation to quickly access new chemical space is vital yet remains challenging for studying biological pathways. Utilizing underexplored elements as biological probes offers promising platforms to reveal uncharted aspects of G-protein-coupled receptor (GPCR) pharmacology. Here we report the development of an expeditious, sustainable platform for the scalable…
Open article record in new tab ↗Nine previously undescribed meroterpenoid glucosides, named nemophilosides A-I, were isolated from the whole plant extract of Nemophila menziesii. Their molecular structures were determined from their NMR and MS spectra, and the absolute configurations were confirmed using ECD spectroscopy by comparing the experimental data with calculated data. The meroterpenoids consist of monoterpenoids and hydroquinone moietie…
Zevaquenabant (S-MRI-1867) is a clinical-stage agent that is a peripherally restricted, potent antagonist of CB1R and an inhibitor of inducible nitric oxide synthase. A novel synthetic route to this highly selective active pharmaceutical agent is described in this paper. This route makes use of rationally installed chiral thio-substituted leaving group derived from a Bunte-salt reaction approach to yield diastereo…
Open article record in new tab ↗Hexahydrocannabinol (HHC), a hydrogenated derivative of Δ9-tetrahydrocannabinol (Δ9-THC), is a semi-synthetic cannabinoid marketed as an alternative to Δ9-THC. Its hydroxylated metabolite, 8-hydroxyhexahydrocannabinol (8-OH-HHC), exists as four stereoisomers: (6aR,8R,9R,10aR), (6aR,8S,9S,10aR), (6aR,8S,9R,10aR), and (6aR,8R,9S,10aR). However, the lack of reference standards has hindered pharmacokinetic and forensi…
Open article record in new tab ↗MDMB-5'Br-PINACA is a recently identified brominated synthetic cannabinoid that was detected in herbal materials seized in Brazil in 2025, raising concerns regarding further potential intoxication cases. In this sense, the evaluation of physicochemical properties and metabolic fate may improve its analytical detectability. Therefore, an integrated in silico and in vitro approach was employed to investigate the phy…
Monoacylglycerol lipase (MAGL) is a key enzyme for signal termination in the endocannabinoid system (ECS). MAGL inhibition results in indirect activation of the cannabinoid receptors, which offers unique advantages for the treatment of, e.g., multiple sclerosis, epilepsy, and other neurological disorders. Molecular imaging techniques are valuable tools to overcome the current poor understanding of MAGL's distribut…
We report the first isolation of a previously unknown cannabinoid, cannabizetol (CBGD, 7), from Cannabis sativa extracts, representing the third member of the rare class of methylene-bridged dimeric cannabinoids. The availability of a chemically synthesized standard was crucial for its unequivocal identification, thus confirming the natural occurrence of this new compound. In addition to this structural discovery,…
Open article record in new tab ↗The rapid structural evolution and extensive metabolism of synthetic cannabinoid receptor agonists (SCRAs) following consumption makes their detection in biological samples challenging, especially in urine. In vitro metabolite identification studies are an essential tool for identifying analytical targets to confirm SCRA consumption in clinical and forensic toxicology casework. Systematic studies on structurally r…
Cannabinoid molecules are the family of molecules that bind to the cannabinoid receptors (CB1 and CB2) of the human body and cause changes in numerous biological functions including motor coordination, emotion, and pain reception. Cannabinoids occur either naturally in the Cannabis Sativa plant or can be produced synthetically in the laboratory. The need for accurate analytical methods for analyzing cannabinoid mo…
Open article record in new tab ↗Oxidative byproducts of cannabidiol (CBD) are known to be cytotoxic. However, CBD susceptibility to oxidation and resulting toxicity dissolved in two common solvents, ethanol (EtOH) and dimethyl sulfoxide (DMSO), is seldom discussed. Furthermore, CBD products contain a wide range of concentrations, making it challenging to link general health risks associated with CBD cytotoxicity. Here, we report on the effect of…
The cannabinoid receptor type 2 (CB2R) is overexpressed under pathological conditions. Positron emission tomography is a noninvasive imaging technique for diagnosing disease states, but requires radiotracers with high affinity and selectivity towards CB2R. Currently, there is no suitable candidate routinely used in the clinics. The naphthyridinone scaffold, a promising core structure, has been modified in the past…
Open article record in new tab ↗A series of new N,N'-diarylureas is reported as potential cannabinoid-1 (CB-1) receptor inhibitors. The synthesis of the new N,N'-diarylureas is achieved from the reaction of two substituted anilines with the aid of triphosgene. One aniline carries a pyrazol-1-yl or 1H-1,2,3-triazolyl or 2H-1,2,3-triazolyl propan-2-one group at position-3, while the other aniline is substituted by fluoro, bromo, methoxy, cyano, mo…
Although cannabis is used in a wide range of fields, including medicine and pharmacology, its use is prohibited in Japan because it contains Δ9-tetrahydrocannabinol (Δ9-THC), a compound that exhibits narcotic effects. While cannabis is primarily detected via color-based screening methods at crime scenes, the reaction products and mechanisms associated with these screening methods have not been fully elucidated. To…
Monoacylglycerol lipase (MAGL) is the pivotal catabolic enzyme responsible for signal termination in the endocannabinoid system. Inhibition of MAGL offers unique advantages over the direct activation of cannabinoid receptors in treating cancer, metabolic disorders, and inflammatory diseases. Although specific fluorescent molecular imaging probes are commonly used for the real-time analysis of the localization and…
Cannabidiol (CBD), a non-psychoactive cannabinoid, has attracted significant research interest due to its antioxidant, anti-inflammatory, and neuroprotective properties. As a versatile scaffold in drug discovery, CBD has been widely explored for developing novel therapeutics. In this study, we synthesized and evaluated the anti-tyrosinase activity of CBD-based thiosemicarbazones. Structure-activity relationship (S…
Open article record in new tab ↗Cannabicyclol ((±)-CBL), a minor phytocannabinoid, is largely unexplored, with its biological activity previously undocumented. We studied its conversion from cannabichromene (CBC) using various acidic catalysts. Montmorillonite (K30) in chloroform at room temperature had the highest yield (60%) with minimal byproducts. Key reaction conditions, such as solvent, temperature, and time, significantly impacted the yie…
Cannabichromene (CBC) is a nonpsychoactive phytocannabinoid well-known for its wide-ranging health advantages. However, there is limited knowledge regarding its human metabolism following CBC consumption. This research aimed to explore the metabolic pathways of CBC by various human liver cytochrome P450 (CYP) enzymes and support the outcomes using in vivo data from mice. The results unveiled two principal CBC meta…
Open article record in new tab ↗The synthesis of some N-(3-acyloxyacyl)glycines, an interesting class of bioactive gut microbiota metabolites, is described. This procedure involves seven reaction steps using the commercially available Meldrum's acid to obtain highly pure products, in normal or deuterated form. The key point of the synthetic strategy was the use of commendamide t-butyl ester as a synthetic intermediate, a choice that allowed the…
Open article record in new tab ↗Zebrafish (ZF; Danio rerio) larvae have become a popular in vivo model in drug metabolism studies. Here, we investigated the metabolism of methyl 2-[1-(4-fluorobutyl)-1H-indazole-3-carboxamido]-3,3-dimethylbutanoate (4F-MDMB-BINACA) in ZF larvae after direct administration of the cannabinoid via microinjection, and we visualized the spatial distributions of the parent compound and its metabolites by mass spectrome…
A series of novel cannabinoid-type derivatives were synthesized by the coupling of (1S,4R)-(+) and (1R,4S)-(-)-fenchones with various resorcinols/phenols. The fenchone-resorcinol derivatives were fluorinated using Selectfluor and demethylated using sodium ethanethiolate in dimethylformamide (DMF). The absolute configurations of four compounds were determined by X-ray single crystal diffraction. The fenchone-resorc…