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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.
13 articles
Newest firstZevaquenabant (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 ↗(-)-Cannabidiol (CBD) is a nonpsychotropic phytocannabinoid found in Cannabis strains with well-established pharmacological applications. Conversely, (+)-cannabidiol (ent-CBD), the non-natural enantiomer of CBD, has been involved in a limited number of pharmacological studies. Therefore, CBD and ent-CBD are synthesized using (R)-(-)- and (S)-(+)-carvone as starting materials, respectively, via a highly diastereose…
New psychoactive substances (NPSs) are emerging narcotics or psychotropics that pose a public health risk. The most commonly reported NPSs are synthetic cannabinoids and synthetic cathinones. Synthetic cannabinoids mimic the effects of Δ9-tetrahydrocannabinol (Δ9-THC), often with greater potency, while synthetic cathinones act as stimulants, frequently serving as cheaper alternatives to amphetamines, 3,4-methylene…
Objective Cannabis sativa L. is renowned for its medicinal and recreational uses. With the increasing global legalization of C. sativa L.-based products for medicinal purposes, there is a growing need for well-characterized products. While the stability of cannabinoids such as tetrahydrocannabinol and cannabidiol is well understood, information on the chemical and enantiomeric stability of terpenes remains scarce.…
Open article record in new tab ↗Developmental epilepsy syndromes are characterized by recurrent seizures and developmental delays. Current anticonvulsants target γ-aminobutyric acid type A receptor signaling to decrease neuronal excitability, however, there are adverse effects for the developing brain, and many patients are refractory. The major non-psychotropic phytocannabinoid cannabidiol (CBD) has emerged as an anti-seizure medication effecti…
Until recently, chirality has not been a major focus in the study of cannabinoids, as most cannabinoids of interest, such as cannabidiol and tetrahydrocannabinol, exist as a single isomer from natural sources. However, this is changing as more cannabinoids are identified, and compounds such as cannabichromene and cannabicyclol are emerging as potential investigatory candidates for varying indications. Because thes…
Open article record in new tab ↗Synthesis planning programs trained on chemical reaction data can design efficient routes to new molecules of interest, but are limited in their ability to leverage rare chemical transformations. This challenge is acute for enzymatic reactions, which are valuable due to their selectivity and sustainability but are few in number. We report a retrosynthetic search algorithm using two neural network models for retros…
Open article record in new tab ↗In vitro pharmacokinetic studies were conducted on enantiomer pairs of twelve valinate or tert-leucinate indole and indazole-3-carboxamide synthetic cannabinoid receptor agonists (SCRAs) detected on the illicit drug market to investigate their physicochemical parameters and structure-metabolism relationships (SMRs). Experimentally derived Log D7.4 ranged from 2.81 (AB-FUBINACA) to 4.95 (MDMB-4en-PINACA) and all SC…
Alcohol consumption is associated with gut dysbiosis, increased intestinal permeability, endotoxemia, and a cascade that leads to persistent systemic inflammation, alcoholic liver disease, and other ailments. Craving for alcohol and its consequences depends, among other things, on the endocannabinoid system. We have analyzed the relative role of central vs. peripheral cannabinoid CB1 receptors (CB1R) using a "two-…
The two most important and studied phytocannabinoids present in Cannabis sativa L. are undoubtedly cannabidiol (CBD), a non-psychotropic compound, but with other pharmacological properties, and Δ9-tetrahydrocannabinol (Δ9-THC), which instead possesses psychotropic activity and is responsible for the recreative use of hemp. Recently, the homolog series of both CBDs and THCs has been expanded by the isolation in a m…
A small series of indol-3-yl-oxoacetamides was synthesized starting from the literature known N-(adamantan-1-yl)-2-(5-(furan-2-yl)-1-pentyl-1H-indol-3-yl)-2-oxoacetamide (5) by substituting the 1-pentyl-1H-indole subunit. Our preliminary biological evaluation showed that the fluorinated derivative 8 is a potent and selective CB₂ ligand with Ki = 6.2 nM.
A 3D-QSAR (CoMFA) study was performed in an extensive series of aminoalkylindoles derivatives with affinity for the cannabinoid receptors CB1 and CB2. The aim of the present work was to obtain structure-activity relationships of the aminoalkylindole family in order to explain the affinity and selectivity of the molecules for these receptors. Major differences in both, steric and electrostatic fields were found in…