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. The species was first classified by Carl Linnaeus in 1753. The specific epithet sativa means 'cultivated'. Indigenous to Eastern Asia, the plant is now of cosmopolitan distribution due to widespread cultivation. It has been cultivated throughout recorded history and used as a source of industrial fiber, seed oil, food, and medicine. It is also used as a recreational drug and for religious and spiritual purposes.
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).
Cannabigerol (CBG) is one of more than 120 identified cannabinoid compounds found in the plant genus Cannabis. Cannabigerol is the decarboxylated form of cannabigerolic acid, the parent molecule from which other cannabinoids are synthesized.
N-Arachidonyl glycine receptor, also known as G protein-coupled receptor 18 (GPR18), is a protein that in humans is encoded by the GPR18 gene. Along with the other previously "orphan" receptors GPR55 and GPR119, GPR18 has been found to be a receptor for endogenous lipid neurotransmitters, several of which also bind to cannabinoid receptors. It has been found to be involved in the regulation of intraocular pressure.
Δ9-Tetrahydrocannabutol is a phytocannabinoid found in cannabis that is a homologue of tetrahydrocannabinol (THC), the main active component of Cannabis. Structurally, they are only different by the pentyl side chain being replaced by a butyl side chain. THCB was studied by Roger Adams as early as 1942
Cannabichromene (CBC), also called cannabichrome, cannanbichromene, pentylcannabichromene or cannabinochromene, exhibits anti-inflammatory properties in vitro, which may, theoretically, contribute to cannabis analgesic effects. It is a phytocannabinoid, one of the hundreds of cannabinoids found in the Cannabis plant. It bears structural similarity to the other natural cannabinoids, including tetrahydrocannabinol (THC), tetrahydrocannabivarin (THCV), cannabidiol (CBD), and cannabinol (CBN), among others. CBC and cannabinols are present in cannabis. It is not scheduled by the Convention on Psychotropic Substances.
Tetrahydrocannabinolic acid is a precursor of tetrahydrocannabinol (THC), an active component of cannabis.
Tetrahydrocannabiphorol (THCP) is a potent phytocannabinoid, a CB1 and CB2 agonist which was known as a synthetic homologue of THC, but for the first time in 2019 was isolated as a natural product in trace amounts from Cannabis sativa. It is structurally similar to Δ9-THC, the main active component of cannabis, but with the pentyl side chain extended to heptyl. Since it has a longer side chain, its cannabinoid effects are "far higher than Δ9-THC itself." Tetrahydrocannabiphorol has a reported binding affinity of 1.2 nM at CB1, approximately 33 times that of Δ9-THC (40 nM at CB1).
Cannabigerolic acid (CBGA) is the acidic form of cannabigerol (CBG). It is a dihydroxybenzoic acid and olivetolic acid in which the hydrogen at position 3 is substituted by a geranyl group. It is a biosynthetic precursor to Delta-9-tetrahydrocannabinol, which is the principal psychoactive constituent of the Cannabis plant. It is also a meroterpenoid, a member of resorcinols and a phytocannabinoid. It derives from an olivetolic acid. It is a conjugate acid of a cannabigerolate.
Δ9-Tetrahydrocannabiorcol (Δ9-THCC, (C1)-Δ9-THC) is a phytocannabinoid found in Cannabis pollen. It is a homologue of THC and THCV with the alkyl side chain replaced by a smaller methyl group. Unlike THC and THCV, THCC has negligible affinity for the CB1 and CB2 cannabinoid receptors because of the smaller methyl group and does not have psychoactive effects as a result, but conversely it is significantly more potent than THC or THCV as an activator of the TRPA1 calcium channel which plays an important role in pain perception, and it has been shown to produce analgesic effects via activation of spinal TRPA1 channels. THCC was studied by Roger Adams as early as 1942.
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 firstly acid cyclization of cannabidiol and then hydrogenation of tetrahydrocannabinol. The synthesis and bioactivity of HHC was first reported in 1940 by Roger Adams.
7,8-Dihydrocannabinol (7,8-DHC) is a trace component of cannabis. Despite its structural similarity to active cannabinoids such as tetrahydrocannabinol and cannabinol, its pharmacology has not been studied.
Cannabitriol ((+)-CBT, (S,S)-9,10-Dihydroxy-Δ6a(10a)-THC) is a phytocannabinoid first isolated in 1966, an oxidation product of tetrahydrocannabinol which has been identified both as a trace component of cannabis and as a metabolite in cannabis users. Its pharmacology has been little studied, though it has been found to act as an antiestrogen and aromatase inhibitor.
Tetrahydrocannabihexol is a phytocannabinoid, the hexyl homologue of tetrahydrocannabinol (THC) which was first isolated from Cannabis plant material in 2020 along with the corresponding hexyl homologue of cannabidiol, though it had been known for several decades prior to this as an isomer of the synthetic cannabinoid parahexyl. Another isomer Δ8-THCH is also known as a synthetic cannabinoid under the code number JWH-124, though it is unclear whether this occurs naturally in Cannabis, but likely is due to Δ8-THC itself being a degraded form of Δ9-THC. THC-Hexyl can be synthesized from 4-hexylresorcinol and was studied by Roger Adams as early as 1942.
Cannabimovone (CBM) is a phytocannabinoid first isolated from a non-psychoactive strain of Cannabis sativa in 2010, which is thought to be a rearrangement product of cannabidiol. It lacks affinity for cannabinoid receptors, but acts as an agonist at both TRPV1 and PPARγ.
Cannabinoids are compounds found in the cannabis plant or synthetic compounds that can interact with the endocannabinoid system. The most notable cannabinoid is the phytocannabinoid tetrahydrocannabinol (THC) (Delta-9-THC), the primary intoxicating compound in cannabis. Cannabidiol (CBD) is another major constituent of some cannabis plants. CBD heated to 250–300 °C may partially be converted into THC.
Cannabiripsol is a minor phytocannabinoid with a hexahydrocannabinol backbone, found in trace amounts in the cannabis plant. While it lacks activity at cannabinoid receptors, its activity at other targets has not been studied.
Isotetrahydrocannabinol (iso-THC) is a phytocannabinoid similar in structure to cannabicitran which has been identified as a trace component of Cannabis, but is more commonly found as an impurity in synthetic THC which has been made from cannabidiol. iso-THC is present with other isomers with the double bond in a different position and the saturated dihydro derivative. iso-THC can be described as the upper cyclization product of CBD, while THC is the lower cyclization product of CBD. Its pharmacology has not been studied, though it is commonly found as a trace impurity in commercially marketed Δ8-THC products.
THC valine hemisuccinate is a synthetic prodrug of tetrahydrocannabinol, developed at the University of Mississippi as a stabilised formulation for ophthalmic administration, for use in the treatment of glaucoma and other eye conditions requiring reduction in intraocular pressure.
