11-Hydroxycannabinol
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11-Hydroxycannabinol
11-Hydroxycannabinol (11-OH-CBN) is the main active metabolite of cannabinol (CBN), one of the active components of cannabis, and has also been isolated from cannabis itself. It is more potent than CBN itself, acting as an agonist of CB1 with around the same potency as THC, but is a weak antagonist at CB2. See also * 11-Hydroxyhexahydrocannabinol * 11-Hydroxy-THC * 11-Hydroxy-Delta-8-THC * Cannabinodiol References Cannabinoids Benzochromenes {{cannabinoid-stub ...
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Cannabinol
Cannabinol (CBN) is a mildly psychoactive cannabinoid that acts as a low affinity partial agonist at both CB1 and CB2 receptors. This activity at CB1 and CB2 receptors constitutes interaction of CBN with the endocannabinoid system (ECS). CBN was the first cannabis compound to be isolated from cannabis extract in the late 1800s. Its structure and chemical synthesis were achieved by 1940, followed by some of the first basic research studies to determine the effects of individual cannabis-derived compounds in vivo. Although CBN shares the same mechanism of action as other phytocannabinoids (e.g., delta-9 tetrahydrocannabinol or D9THC), it has a lower affinity for CB1 receptors, meaning that much higher doses of CBN are required in order to experience effects, such as mild sedation. Chemical structure Cannabinoid receptor agonists are categorized into four groups based on chemical structure. CBN, as one of the many phytocannabinoids derived from Cannabis Sativa L, is considered ...
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11-Hydroxyhexahydrocannabinol
11-Hydroxyhexahydrocannabinol (11-OH-9α-HHC and 11-OH-9β-HHC, or alternatively 7-OH-HHC under the benzopyran numbering system) is an active metabolite of tetrahydrocannabinol (THC) and the major metabolite of the trace cannabinoid hexahydrocannabinol (HHC). In a pathway that parallels the metabolism of the THC family of cannabinoids, following ingestion HHC undergoes hepatic metabolism by cytochrome p450 (predominantly the CYP3A4 isozyme, with some contribution from CYP2C9 and CYP2C19) to a multitude of oxygenated derivatives, including 8-OH-HHC and 11-OH-HHC. C11-oxidation is the major pathway of THC and HHC metabolism. Like other 11-OH cannabinoid metabolites, 11-OH-9β-HHC retains activity comparable to HHC itself while the 9α-isomer is significantly less active. However, upon formation it is rapidly metabolized further to the inactive 11-carboxylates, producing a shortened half-life within the body and lowering its bioavailability considerably through first-pass metab ...
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Cannabis
''Cannabis'' () is a genus of flowering plants in the family Cannabaceae. The number of species within the genus is disputed. Three species may be recognized: ''Cannabis sativa'', '' C. indica'', and '' C. ruderalis''. Alternatively, ''C. ruderalis'' may be included within ''C. sativa'', all three may be treated as subspecies of ''C. sativa'', or ''C. sativa'' may be accepted as a single undivided species. The genus is widely accepted as being indigenous to and originating from Asia. The plant is also known as hemp, although this term is often used to refer only to varieties of ''Cannabis'' cultivated for non-drug use. Cannabis has long been used for hemp fibre, hemp seeds and their oils, hemp leaves for use as vegetables and as juice, medicinal purposes, and as a recreational drug. Industrial hemp products are made from cannabis plants selected to produce an abundance of fibre. Various cannabis strains have been bred, often selectively to pro ...
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Tetrahydrocannabinol
Tetrahydrocannabinol (THC) is the principal psychoactive constituent of cannabis and one of at least 113 total cannabinoids identified on the plant. Although the chemical formula for THC (C21H30O2) describes multiple isomers, the term ''THC'' usually refers to the Delta-9-THC isomer with chemical name (−)-''trans''-Δ9-tetrahydrocannabinol. THC is a lipid found in cannabis and, like most pharmacologically active secondary metabolites of plants, it is assumed to be involved in the plant's evolutionary adaptation, putatively against insect predation, ultraviolet light, and environmental stress. THC was first discovered and isolated by Israeli chemist Raphael Mechoulam in Israel in 1964. It was found that, when smoked, THC is absorbed into the bloodstream and travels to the brain, attaching itself to endocannabinoid receptors located in the cerebral cortex, cerebellum, and basal ganglia. These are the parts of the brain responsible for thinking, memory, pleasure, coordination a ...
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11-Hydroxy-THC
11-Hydroxy-Δ9-tetrahydrocannabinol (11-OH-Δ9-THC, alternatively numbered as 7-OH-Δ1-THC), usually referred to as 11-hydroxy-THC, is the main active metabolite of tetrahydrocannabinol (THC), which is formed in the body after THC is consumed. After cannabis consumption, THC is metabolized inside the body by cytochrome P450 enzymes such as CYP2C9 and CYP3A4 into 11-hydroxy-THC and then further metabolized by the dehydrogenase and CYP2C9 enzyme to form 11-nor-9-carboxy-THC (THC-COOH) which is inactive at the CB1 receptors; and further glucuronidated to form 11-nor-delta-9-tetrahydrocannabinol-9-carboxylic acid glucuronide (delta-9-THC-COOH-glu) where it is excreted in both feces and urine. Both compounds, along with THC, can be assayed in drug tests. 11-hydroxy-THC can be formed after consumption of THC from inhalation (vaping, smoking) and oral (by mouth, edible, sublingual) use, although levels of 11-hydroxy-THC are typically higher when eaten compared to inhalation. Pharmaco ...
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11-Hydroxy-Delta-8-THC
11-Hydroxy-Delta-8-tetrahydrocannabinol (11-OH-Δ8-THC, alternatively numbered as 7-OH-Δ6-THC) is an active metabolite of Delta-8-THC (Δ8-THC), a psychoactive cannabinoid found in small amounts in cannabis. It is an isomer of 11-OH-Δ9-THC, and is produced via the same metabolic pathway. It was the first cannabinoid metabolite discovered in 1970. It retains psychoactive effects in animal studies with higher potency than Δ8-THC but lower potency than 11-OH-Δ9-THC. With widespread legal use of semi-synthetic Δ8-THC in jurisdictions where Δ9-THC remains illegal, 11-OH-Δ8-THC is now an important metabolite for distinguishing between use of legal Δ8-THC and illegal Δ9-THC. See also * 3'-Hydroxy-THC * 7-Hydroxycannabidiol * 8,11-Dihydroxytetrahydrocannabinol * 9-OH-HHC * 11-OH-HHC * 11-OH-CBN * 11-Nor-9-carboxy-THC * Delta-6-Cannabidiol Delta-6-cannabidiol (∆6-CBD) is a positional isomer of cannabidiol, found in only trace amounts in natural cannabis plants b ...
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Cannabinodiol
Cannabinodiol (CBND), also known as cannabidinodiol, cannabinoid that is present in the plant '' Cannabis sativa'' at low concentrations. It is the fully aromatized derivative of cannabidiol (CBD) and can occur as a product of the photochemical conversion of cannabinol (CBN). See also * Cannabidiol * Cannabinol * Cannabichromene Cannabichromene (CBC), also called cannabichrome, cannanbichromene, pentylcannabichromene or cannabinochromene, is an anti-inflammatory which may contribute to the pain-killing effect of cannabis. It is one of the hundreds of cannabinoids found i ... * Cannabimovone * Delta-6-CBD * Dimethylheptylpyran * HU-210 * Nabilone * Parahexyl * Tetrahydrocannabivarin References Cannabinoids Natural phenols 2,6-Dihydroxybiphenyls Alkyl-substituted benzenes {{cannabinoid-stub ...
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Cannabinoids
Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tetrahydrocannabinol (THC) (delta-9-THC), the primary intoxicating compound in cannabis. Cannabidiol (CBD) is a major constituent of temperate Cannabis plants and a minor constituent in tropical varieties. At least 113 distinct phytocannabinoids have been isolated from cannabis, although only four (i.e., THCA, CBDA, CBCA and their common precursor CBGA) have been demonstrated to have a biogenetic origin. It was reported in 2020 that phytocannabinoids can be found in other plants such as rhododendron, licorice and liverwort, and earlier in Echinacea. Phytocannabinoids are multi-ring phenolic compounds structurally related to THC, but endocannabinoids are fatty acid derivatives. Nonclassical synthetic cannabinoids (cannabimimetics) include amin ...
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