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| Names | |
|---|---|
| IUPAC name (5aS,6S,9R,9aR)-6-methyl-3-pentyl-9-prop-1-en-2-yl-7,8,9,9a-tetrahydro-5aH-dibenzofuran-1,6-diol | |
Other names
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| Identifiers | |
3D model (JSmol) | |
| Abbreviations | CBE |
| ChemSpider | |
| KEGG | |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
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| Properties | |
| C21H30O3 | |
| Molar mass | 330.468 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Cannabielsoin (CBE) is a metabolite of cannabidiol, one of the major chemical components of cannabis. [2]
Cannabielsoin in scientific journals was first cited in 1973. It was concluded that cannabielsoin was formed from cannabidiol as part of the metabolic process and is non-psychoactive. [3] [ unreliable source? ]
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.
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 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 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 moods 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 binds to the cannabinoid receptors with more selectivity for CB2 over CB1 found in trace amounts from Cannabis. CBN is mostly found in cannabis that is aged and stored, and is derived from the plant's main psychoactive chemical, tetrahydrocannabinol (THC).
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 popular herbal dietary supplement, widely promoted with unproven claims of particular therapeutic benefits. The global market size for CBD was predicted to exceed US$47 billion by 2028.
Cannabidivarin (CBDV, GWP42006) is a non-psychoactive cannabinoid found in Cannabis. It is a homolog (chemistry) of cannabidiol (CBD), with the side-chain shortened by two methylene bridges (CH2 units).
11-Hydroxy-Δ9-tetrahydrocannabinol, 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.
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 in the Cannabis plant, and is therefore a phytocannabinoid. It bears structural similarity to the other natural cannabinoids, including tetrahydrocannabinol (THC), tetrahydrocannabivarin (THCV), cannabidiol (CBD), and cannabinol (CBN), among others. CBC and its derivatives are as abundant as cannabinols in cannabis. It is not scheduled by the Convention on Psychotropic Substances. It is more common in tropical cannabis varieties.
9-Nor-9β-hydroxyhexahydrocannabinol ,is a cannabinoid first discovered from early modifications to the structure of THC, in a search for the simplest compound that could still fulfill the binding requirements to produce cannabis-like activity.
The International Nonproprietary Name Dronabinol, also known as delta-9-tetrahydrocannabinol, or 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.
Cannabis in Iowa is illegal for recreational use if classified as marijuana but consumable hemp products including CBD products are legal for consumers to possess and registered retailers to sell. Possession of even small amounts of marijuana is a misdemeanor crime. The state has a medical cannabidiol program for serious medical conditions that allows for the legal possession of products containing 3% or less THC.
8,9-Dihydrocannabidiol is a synthetic cannabinoid that is closely related to cannabidiol (CBD) itself.
Cannabidiolic acid (CBDA), is a cannabinoid found in cannabis plants. It is most abundant in the glandular trichomes on the female seedless flowers or more accurately infructescence often colloquially referred to as buds. CBDA is the chemical precursor to cannabidiol (CBD). Through the process of decarboxylation cannabidol is derived via a loss of a carbon and two oxygen atoms from the 1 position of the benzoic acid ring.
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.
Cannabichromenic acid (CBCA) is minor cannabinoid and precursor of cannabichromene.
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 hydrogenation of cannabis extracts. HHC was first synthesized in 1947 by Roger Adams using natural THC found in Cannabis sativa. Several research groups have successfully synthesized (+)-HHC and (-)-HHC using citronellal and olivetol, as well as other related compounds. While similar compounds have previously been identified in cannabis, hexahydrocannabinol itself has rarely been isolated from the plant. The de Las Heras group in 2020 took lipid extract from Cannabis sativa seeds and discovered 43 cannabinoids in the crude extract; one of them being hexahydrocannabinol. It has two diastereomers at the methyl (9) position. HHC is typically made from Δ8-THC, or Δ9-THC. There are no double bonds in the cyclohexyl ring like D8/D9 have—they have been removed from the structure and hydrogens have been added to the compound. Similar structural analogs of HHC has been demonstrated to bind to the CB1 receptor and produces cannabinoid effects in animals, with the 9β-HHC enantiomer being much more active than 9α-HHC. While HHC has been shown to bind to the CB1 receptor, it binds with weaker affinity than THC, which has typically been an indication that it is not as intoxicating as typical THC. Since HHC is found naturally in the cannabis plant, humans have likely been unknowingly consuming small amounts of this cannabinoid for centuries.
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.
11-Hydroxy-Delta-8-tetrahydrocannabinol is an active metabolite of Delta-8-THC (Δ8-THC), the less predominant psychoactive component of cannabis. It retains psychoactive effects in animal studies with higher potency than Δ8-THC but lower potency than 11-OH-Δ9-THC. Historically it has been of limited interest due to the low proportion of Δ8-THC relative to Δ9-THC in cannabis, but with widespread legitimate 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.
Cannabicitran (CBTC) is a phytocannabinoid first isolated in 1974 as a trace component of Cannabis sativa, Structurally related compounds can be found in some other plants. It is not psychoactive, but was found to reduce intraocular pressure in tests on rabbits, which may reflect agonist activity at the NAGly receptor that is known to be a target of many structurally related cannabinoids.
Cannabis (/ˈkænəbɪs/) is commonly known as marijuana or hemp and has two known strains: Cannabis sativa and Cannabis indica, both of which produce chemicals to deter herbivory. The chemical composition includes specialized terpenes and cannibinoids, mainly tetrahydrocannabinol (THC), and cannabidiol (CBD). These substances play a role in defending the plant from pathogens including insects, fungi, viruses and bacteria. THC and CBD are stored mostly in the trichomes of the plant, and can cause psychological and physical impairment in the user, via the endocannabinoid system and unique receptors. THC increases dopamine levels in the brain, which attributes to the euphoric and relaxed feelings cannabis provides. As THC is a secondary metabolite, it poses no known effects towards plant development, growth, and reproduction. However, some studies show secondary metabolites such as cannabinoids, flavonoids, and terpenes are used as defense mechanisms against biotic and abiotic environmental stressors.
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