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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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Delta-8-THC
Delta-8-tetrahydrocannabinol (delta-8-THC, Δ8-THC) is a psychoactive cannabinoid found in the Cannabis plant. It is an isomer of delta-9-tetrahydrocannabinol (delta-9-THC, Δ9-THC), the compound commonly known as THC. ∆8-THC is under preliminary research for its biological properties. Effects ∆8-THC is moderately less potent than Δ9-THC. This essentially means that it has properties similar to those of ∆9-THC, although to a lesser degree per milligram of material consumed. Delta-8-THC and delta-9-THC both contain a double bond in their molecular structure, but the location is different. Delta-8-THC has the bond in the eighth carbon while delta-9 contains it in the 9th carbon. Although ∆8-THC functions similarly to Δ9-THC in many ways, it appears to be only two-thirds as psychoactive. This may be because it binds differently to CB1, the cannabinoid receptor that regulates much of THC’s mind-altering effect. ∆8-THC may cause increased heart rate, reddening of ...
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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. Pha ...
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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-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, ... * 11-Nor-9-carboxy-THC References Cannabinoids Benzochromenes {{cannabinoid-stub ...
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8,11-Dihydroxytetrahydrocannabinol
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-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, ... * 11-Nor-9-carboxy-THC * Cannabitriol References Benzochromenes Cannabinoids {{cannabinoid-stub ...
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9-OH-HHC
9-Hydroxyhexahydrocannabinol (9-OH-HHC) is a semi-synthetic derivative of tetrahydrocannabinol. It is formed as an impurity in the synthesis of Delta-8-THC, and retains activity in animal studies though with only around 1/10 the potency of Δ9-THC, with the 9α- and 9β- enantiomers having around the same potency. See also * 9-Nor-9β-hydroxyhexahydrocannabinol * 11-Hydroxyhexahydrocannabinol * 11-Hydroxy-THC * 11-Hydroxy-Delta-8-THC * Cannabicitran * Cannabitriol * Delta-10-THC * Hexahydrocannabinol Hexahydrocannabinol (HHC) is a hydrogenated derivative of tetrahydrocannabinol. It is a naturally occurring phytocannabinoid that has rarely been identified as a trace component in ''Cannabis sativa'', but can also be produced synthetically by h ... References Cannabinoids Benzochromenes Phenols {{cannabinoid-stub ...
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11-OH-CBN
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 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 photochemica ... References Cannabinoids Benzochromenes {{cannabinoid-stub ...
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HU-210
HU-210 is a synthetic cannabinoid that was first synthesized in 1988 from (1R,5S)-myrtenol by a group led by Raphael Mechoulam at the Hebrew University. HU-210 is 100 to 800 times more potent than natural THC from cannabis and has an extended duration of action. HU-210 has a binding affinity of 0.061nM at CB1 and 0.52nM at CB2 in cloned human cannabinoid receptors. Compared to Delta-9-THC of 40.7nM at CB1. HU-210 is the (–)-1,1-dimethylheptyl analog of 11-hydroxy- Δ8- tetrahydrocannabinol; in some references it is called 1,1-dimethylheptyl- 11-hydroxytetrahydrocannabinol. The abbreviation "HU" stands for Hebrew University. Effects and research HU-210, the (–) enantiomer of 11-OH-D8-THC-DMH, has almost all of the cannabinoid activity, while the (+) enantiomer, known as HU-211, is inactive as a cannabinoid and instead acts as an NMDA antagonist having neuroprotective effects. HU-210 promotes proliferation, but not differentiation, of cultured embryonic hippocampal ...
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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 design ...
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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 selecti ...
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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-OH-HHC
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 metabol ...
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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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