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ECHA InfoCard | 100.236.933 |
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Formula | C19H26O2 |
Molar mass | 286.415 g·mol−1 |
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Cannabidivarin (CBDV, GWP42006) is a non-intoxicating psychoactive cannabinoid found in Cannabis . It is a homolog (chemistry) of cannabidiol (CBD), with the side-chain shortened by two methylene bridges (CH2 units).
Although cannabidivarin (CBDV) is usually a minor constituent of the cannabinoid profile, enhanced levels of CBDV have been reported in feral populations of C. indica ( = C. sativa ssp. indica var. kafiristanica) from northwest India, and in hashish from Nepal. [1] = [2] [3]
CBDV demonstrated anticonvulsant in rodent models in a single published study. [4] It was identified for the first time in 1969 by Vollner et al. [5]
Similarly to CBD, it has seven double bond isomers and 30 stereoisomers (see: Cannabidiol#Isomerism). It is not scheduled by Convention on Psychotropic Substances. It is being actively developed by GW Pharmaceuticals (as GWP42006) [6] because of a demonstrated neurochemical pathway for previously observed anti-epileptic and anti-convulsive action. [7] GW has begun several Phase-2 trials for adult epilepsy, [8] for childhood epilepsy and for Prader-Willi Syndrome. [9] [10]
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.
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 terpenoid found in cannabis and, like many pharmacologically active phytochemicals, it is assumed to be involved in the plant's evolutionary adaptation 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 and movement.
Cannabinoids are several structural classes of compounds found in the cannabis plant primarily and most animal organisms or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tetrahydrocannabinol (THC) (delta-9-THC), the primary psychoactive compound in cannabis. Cannabidiol (CBD) is also 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 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.
Cannabis sativa is an annual herbaceous flowering plant indigenous to Eastern Asia, but now of cosmopolitan distribution due to widespread cultivation. It has been cultivated throughout recorded history, used as a source of industrial fiber, seed oil, food, recreation, religious and spiritual states and medicine. Each part of the plant is harvested differently, depending on the purpose of its use. The species was first classified by Carl Linnaeus in 1753. The word sativa means "things that are cultivated."
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).
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. As of 2019, 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 a herbal dietary supplement promoted with unproven claims of particular therapeutic effects.
Tetrahydrocannabivarin is a homologue of tetrahydrocannabinol (THC) having a propyl (3-carbon) side chain instead of pentyl (5-carbon), making it non-psychoactive in lower doses. It has been shown to exhibit neuroprotective activity, appetite suppression, glycemic control and reduced side effects compared to THC, making it a potential treatment for management of obesity and diabetes.
Cannabivarin (CBV), also known as cannabivarol, is considered a non-psychoactive cannabinoid — it does not produce the euphoric side effects found in THC. Minor amounts of CBV are found in the hemp plant Cannabis sativa. It is an analog of cannabinol (CBN) with the side chain shortened by two methylene bridges (-CH2-). CBV is an oxidation product of tetrahydrocannabivarin (THCV, THV).
Cannabis indica is an annual plant species in the family Cannabaceae indigenous to the Hindu Kush mountains of Southern Asia. The plant produces large amounts of tetrahydrocannabinol (THC) and tetrahydrocannabivarin (THCV) with levels up to 53.7% of total cannabinoid. It is now widely grown in China, India, Nepal, Thailand, Afghanistan, and Pakistan, as well as southern and western Africa, and is cultivated for purposes including hashish in India. The high concentrations of THC or THCV provide euphoric effects making it popular for use both as a recreational drug, alternative medicine, and a clinical research drug. And THCV for its platform for treating life-threatening diseases.
Cannabis ruderalis is a variety, subspecies, or species of Cannabis native to Central and Eastern Europe and Russia. It contains a relatively low quantity of psychoactive compound tetrahydrocannabinol (THC) Some scholars accept C. ruderalis as its own species due to its unique traits and phenotypes which distinguish it from C. indica and C. sativa; others debate whether ruderalis is a subdivision under C. sativa.
Geoffrey William Guy is a British pharmacologist, physician, businessman and academic, who co-founded GW Pharmaceuticals and has developed treatments using compounds found in cannabis, which are the first cannabis-based medicines approved by and available on the British National Health Service (NHS).
Cannabis strains are either pure or hybrid varieties of the plant genus Cannabis, which encompasses the species C. sativa, C. indica, and C. ruderalis.
The International Nonproprietary Name dronabinol, also known under the trade names Marinol, Syndros, Reduvo and Adversa, is a generic name for the molecule of delta-9-tetrahydrocannabinol in the pharmaceutical context. It has indications as an appetite stimulant, antiemetic, and sleep apnea reliever and is approved by the FDA as safe and effective for HIV/AIDS-induced anorexia and chemotherapy-induced nausea and vomiting only.
Tetrahydrocannabinolic acid is a precursor of tetrahydrocannabinol (THC), an active component of cannabis.
The entourage effect is a hypothesis that cannabis compounds other than tetrahydrocannabinol (THC) act synergistically with it to modulate the overall psychoactive effects of the plant.
Cannabidiol-dimethylheptyl (CBD-DMH or DMH-CBD) is a synthetic homologue of cannabidiol where the pentyl chain has been replaced by a dimethylheptyl chain. Several isomers of this compound are known. The most commonly used isomer in research is (−)-CBD-DMH, which has the same stereochemistry as natural cannabidiol, and a 1,1-dimethylheptyl side chain. This compound is not psychoactive and acts primarily as an anandamide reuptake inhibitor, but is more potent than cannabidiol as an anticonvulsant and has around the same potency as an antiinflammatory. Unexpectedly the “unnatural” enantiomer (+)-CBD-DMH, which has reversed stereochemistry from cannabidiol, was found to be a directly acting cannabinoid receptor agonist with a Ki of 17.4nM at CB1 and 211nM at CB2, and produces typical cannabinoid effects in animal studies, as does its 7-OH derivative.
Medical cannabis research includes any medical research on using cannabis. Different countries conduct and respond to medical cannabis research in different ways.
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.
Hexahydrocannabinol (HHC) is a hydrogenated derivative of tetrahydrocannabinol (THC). 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 hydrogenation of cannabis extracts. The synthesis and bioactivity of HHC was first reported in 1940 by Roger Adams using tetrahydrocannabinol prepared from cannabidiol.
Cannabigerovarin (CBGV), the propyl homolog of cannabigerol (CBG), is a cannabinoid present in Cannabis. There is no observation related to the psychoactive or psychotropic effects of CBGV when consumed or inhaled. The possible benefits of cannabigerovarin in human bodies are painkilling and anti-inflammatory properties to treat conditions like fibromyalgia and arthritis, the treatment and improvement of the dry-skin syndrome, cancer treatment by reducing the growth of cancer cells in patients who have leukemia. According to the pain-relieving effects of this natural cannabinoid, it can be helpful to treat patients who were undergoing drug exposure like chemotherapy or radiation therapy. In addition, cannabigerol metabolism increases and has a better absorption from the body when paired with cannabigerovarin.