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3'-Hydroxy-THC
3'-Hydroxy-THC (3'-OH-Δ9-THC) is a minor active metabolite of THC, the main psychoactive component of cannabis. It is one of a number of metabolites of THC hydroxylated on the pentyl side chain, but while the other side-chain hydroxyl isomers are much weaker or inactive, the ''S'' enantiomer of 3'-OH-THC is several times more potent than THC itself, and while it is produced in smaller amounts than other active metabolites such as 11-Hydroxy-THC and 8,11-Dihydroxy-THC, it is thought to contribute to the overall pharmacological profile of cannabis. See also * 7-Hydroxycannabidiol * 11-Hydroxy-Delta-8-THC * 11-Nor-9-carboxy-THC 11-Nor-9-carboxy-Δ9-tetrahydrocannabinol (11-COOH-THC or THC-COOH), often referred to as 11-nor-9-carboxy-THC or THC-11-oic acid, is the main secondary metabolite of tetrahydrocannabinol (THC) which is formed in the body after cannabis is consu ... References Cannabinoids Benzochromenes {{cannabinoid-stub ...
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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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8,11-Dihydroxy-THC
8,11-Dihydroxytetrahydrocannabinol (8β,11-diOH-Δ9-THC) is an active metabolite of THC, the main active component of cannabis. The 8β enantiomer retains psychoactive effects in animal studies with only slightly lower potency than THC, while the 8α enantiomer is much weaker. Both enantiomers have a shorter half-life in the body than 11-Hydroxy-THC, making 8,11-dihydroxy-THC potentially useful for drug testing to distinguish between recent cannabis use and use longer in the past. See also * 3'-Hydroxy-THC * 7-Hydroxycannabidiol * 11-Hydroxy-Delta-8-THC * 11-Nor-9-carboxy-THC 11-Nor-9-carboxy-Δ9-tetrahydrocannabinol (11-COOH-THC or THC-COOH), often referred to as 11-nor-9-carboxy-THC or THC-11-oic acid, is the main secondary metabolite of tetrahydrocannabinol (THC) which is formed in the body after cannabis is consu ... * Cannabitriol References Benzochromenes Cannabinoids {{cannabinoid-stub ...
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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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Active Metabolite
An active metabolite is an active form of a drug after it has been processed by the body. Metabolites of drugs An active metabolite results when a drug is metabolized by the body into a modified form which continues to produce effects in the body. Usually these effects are similar to those of the parent drug but weaker, although they can still be significant (see e.g. 11-hydroxy-THC, morphine-6-glucuronide). Certain drugs such as codeine and tramadol have metabolites (morphine and ''O''-desmethyltramadol respectively) that are stronger than the parent drug and in these cases the metabolite may be responsible for much of the therapeutic action of the parent drug. Sometimes, however, metabolites may produce toxic effects and patients must be monitored carefully to ensure they do not build up in the body. This is an issue with some well-known drugs, such as pethidine (meperidine) and dextropropoxyphene. Prodrugs Sometimes drugs are formulated in an inactive form that is designe ...
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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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7-Hydroxycannabidiol
7-Hydroxycannabidiol (7-OH-CBD) is an active metabolite of cannabidiol, generated in the body from cannabidiol by the action of the enzyme CYP2C19. While methods have been developed for its synthetic production, and measurement of levels in the body following consumption of cannabidiol, its pharmacology has been relatively little studied, though it has been found to possess similar anticonvulsant effects to cannabidiol itself, as well as lowering blood triglyceride levels. Like its precursor CBD, it is not known to exhibit any psychoactive effects on the body and is known to counter the psychoactive effects of THC if it is present at the same time. This mode of action in 2015 was discovered to be at least contributing in part by being a non competitive negative allosteric modulator of the Cannabinoid receptor type 1. See also * 4'-Fluorocannabidiol * 8,9-Dihydrocannabidiol * 8,11-Dihydroxytetrahydrocannabinol * 11-Hydroxy-THC * Cannabidiolic acid * Cannabidiol dimethyl ether * ...
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11-Nor-9-carboxy-THC
11-Nor-9-carboxy-Δ9-tetrahydrocannabinol (11-COOH-THC or THC-COOH), often referred to as 11-nor-9-carboxy-THC or THC-11-oic acid, is the main secondary metabolite of tetrahydrocannabinol (THC) which is formed in the body after cannabis is consumed. Metabolism and detection 11-COOH-THC is formed in the body by oxidation of the active metabolite 11-hydroxy-THC (11-OH-THC) by liver enzymes. It is then metabolized further by conjugation with glucuronide, forming a water-soluble congener which can be more easily excreted by the body. 11-COOH-THC has a long half-life in the body of up to several days (or even weeks in very heavy users), making it the main metabolite tested for blood or urine testing for cannabis use. More selective tests are able to distinguish between 11-OH-THC and 11-COOH-THC, which can help determine how recently cannabis was consumed; if only 11-COOH-THC is present then cannabis was used some time ago and any impairment in cognitive ability or motor function wi ...
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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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