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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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4'-Fluorocannabidiol
4'-Fluorocannabidiol (also known as PECS-101 and 4'-F-CBD, and formerly as HUF-101 and HU-474) is a fluorinated cannabidiol derivative that has more potent anxiolytic, antidepressant, antipsychotic and anti-compulsive activity in mice compared to its parent compound. It was first synthesized in 2016, alongside 10-fluorocannabidiol diacetate and 8,9-dihydro-7-fluorocannabidiol, which showed much weaker activity. Synthesis 4'-Fluorocannabidiol has been synthesized from isolated cannabidiol by putting it in dry dichloromethane and adding 1-fluoropyridinium triflate. See also * 7-Hydroxycannabidiol * 8,9-Dihydrocannabidiol * Abnormal cannabidiol * Cannabinoids * Cannabinoid receptors * HU-331 * KLS-13019 KLS-13019 is a cannabidiol derivative that has been modified on the side chain to improve solubility and tissue penetration properties. It was developed and patented by Neuropathix subsidiary Kannalife and found to be 50x more potent than cann ... * O-1602 * O-1918 ...
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8,9-Dihydrocannabidiol
8,9-Dihydrocannabidiol (also known as H2CBD, DiHydroCBD, Delta-1-H2CBD, or Delta-1-DiHydroCBD) is a synthetic cannabinoid that is closely related to cannabidiol (CBD) itself. Pharmacology It may have certain advantages over CBD, in that it is fully synthetic, inexpensive to produce, and it is not a scheduled drug (cannabis extracts are controlled substances in most parts of the world). In addition, there is no path to synthesize the psychoactive substance tetrahydrocannabinol (THC) from H2CBD. CBD has been shown to convert to some extent to THC in the gastric tract, and the deliberate laboratory conversion of CBD to THC is straightforward. H2CBD has therefore been studied for its potential use as an alternative to CBD in terms of its lack of abuse liability and absence of psychotropic effects. It was shown to have anti-seizure activity essentially identical to that of CBD in tests with rats. In 2006 it was reported that 8,9-Dihydrocannabidiol binds very weakly to the CB1 rec ...
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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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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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Cannabidiol Dimethyl Ether
Cannabidiol dimethyl ether (CBDD) is a trace component of cannabis which can also be made synthetically. It is a potent and selective inhibitor of the enzyme 15-lipoxygenase and inhibits oxygenation of linoleic acid, a process involved in the development of atherosclerosis. See also * 4'-Fluorocannabidiol * 7-Hydroxycannabidiol * 8,9-Dihydrocannabidiol * Cannabicitran * Delta-6-Cannabidiol * KLS-13019 KLS-13019 is a cannabidiol derivative that has been modified on the side chain to improve solubility and tissue penetration properties. It was developed and patented by Neuropathix subsidiary Kannalife and found to be 50x more potent than cann ... * O-1918 References Cannabinoids Methoxy compounds {{cannabinoid-stub ...
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Delta-6-Cannabidiol
Delta-6-cannabidiol (∆6-CBD) is a positional isomer of cannabidiol, found in only trace amounts in natural cannabis plants but readily synthesised from cannabidiol by base-catalysed migration of the double bond. See also * 4'-Fluorocannabidiol * 7-Hydroxycannabidiol * 8,9-Dihydrocannabidiol * Abnormal cannabidiol * Cannabidiolic acid * Cannabidiol dimethyl ether * Cannabidiphorol * Cannabigerol * Cannabinodiol * Cannabidivarin * Cannabimovone * 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 pr ... * Delta-10-THC References Cannabinoids {{cannabinoid-stub ...
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HU-320
HU-320 (7-nor-7-carboxy-CBD-1,1-DMH) is a drug related to cannabidiol, which has strong antiinflammatory and immunosuppressive properties while demonstrating no psychoactive effects. See also * 7-Hydroxycannabidiol * Ajulemic acid * 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 d ... * HU-308 * HU-331 References HU cannabinoids Cyclohexenes 2,6-Dihydroxybiphenyls {{pharmacology-stub ...
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KLS-13019
KLS-13019 is a cannabidiol derivative that has been modified on the side chain to improve solubility and tissue penetration properties. It was developed and patented by Neuropathix subsidiary Kannalife and found to be 50x more potent than cannabidiol as a neuroprotective agent, thought to be mediated by modulation of the sodium-calcium exchanger channel. It also had a higher therapeutic index than cannabidiol. Both KLS-13019 and cannabidiol, prevented the development of CIPN, while only KLS-13019 uniquely reversed neuropathic pain from chemotherapy. KLS-13019 binds to fewer biological targets than cannabidiol and KLS-13019 may possess the unique ability to reverse addictive behaviour, an effect not observed with cannabidiol. See also * 7-Hydroxycannabidiol * Abnormal cannabidiol * Cannabidiol dimethyl ether * Delta-6-Cannabidiol * HU-320 * HU-331 * HUF-101 * O-1602 * O-1918 O-1918 is a synthetic compound related to cannabidiol Cannabidiol (CBD) is a phytocannab ...
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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 Dextropropoxyphene is an analgesic in the opioid category, patented in 1955 a ...
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Cannabidiol
Cannabidiol (CBD) is a phytocannabinoid discovered in 1940. It is one of 113 identified cannabinoids in cannabis plants, along with tetrahydrocannabinol (THC), and accounts for up to 40% of the plant's extract. , clinical research on CBD included studies related to anxiety, cognition, movement disorders, and pain, but there is insufficient high-quality evidence that cannabidiol is effective for these conditions. Nevertheless, CBD is an herbal dietary supplement promoted with unproven claims of particular therapeutic effects. The global market size for CBD was predicted to exceed billion by 2028. Cannabidiol can be taken internally in multiple ways, including by inhaling cannabis smoke or vapor, oral, and as an aerosol spray into the cheek. It may be supplied as CBD oil containing only CBD as the active ingredient (excluding tetrahydrocannabinol HCor terpenes), CBD-dominant hemp extract oil, capsules, dried cannabis, or prescription liquid solution. CBD does not have th ...
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CYP2C19
Cytochrome P450 2C19 (abbreviated CYP2C19) is an enzyme protein. It is a member of the CYP2C subfamily of the cytochrome P450 mixed-function oxidase system. This subfamily includes enzymes that catalyze metabolism of xenobiotics, including some proton pump inhibitors and antiepileptic drugs. In humans, it is the ''CYP2C19'' gene that encodes the CYP2C19 protein. CYP2C19 is a liver enzyme that acts on at least 10% of drugs in current clinical use, most notably the antiplatelet treatment clopidogrel (Plavix), drugs that treat pain associated with ulcers, such as omeprazole, antiseizure drugs such as mephenytoin, the antimalarial proguanil, and the anxiolytic diazepam. CYP2C19 has been annotated as (R)-limonene 6-monooxygenase and (S)-limonene 6-monooxygenase in UniProt. Function The gene encodes a member of the cytochrome P450 superfamily of enzymes. Enzymes in the CYP2C subfamily, including CYP2C19, account for approximately 20% of cytochrome P450 in the adult liver. These p ...
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Anticonvulsant
Anticonvulsants (also known as antiepileptic drugs or recently as antiseizure drugs) are a diverse group of pharmacological agents used in the treatment of epileptic seizures. Anticonvulsants are also increasingly being used in the treatment of bipolar disorder and borderline personality disorder, since many seem to act as mood stabilizers, and for the treatment of neuropathic pain. Anticonvulsants suppress the excessive rapid firing of neurons during seizures. Anticonvulsants also prevent the spread of the seizure within the brain. Conventional antiepileptic drugs may block sodium channels or enhance γ-aminobutyric acid ( GABA) function. Several antiepileptic drugs have multiple or uncertain mechanisms of action. Next to the voltage-gated sodium channels and components of the GABA system, their targets include GABAA receptors, the GAT-1 GABA transporter, and GABA transaminase. Additional targets include voltage-gated calcium channels, SV2A, and α2δ. By blocking sodium or ca ...
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