Cannabinoid

A cannabinoid is one of a class of diverse chemical compounds that acts on cannabinoid receptors, also known as the endocannabinoid system in cells that alter neurotransmitter release in the brain. Ligands for these receptor proteins include the endocannabinoids produced naturally in the body by animals; phytocannabinoids, found in cannabis and some other plants; and synthetic cannabinoids, manufactured artificially. The most notable cannabinoid is the phytocannabinoid tetrahydrocannabinol (THC), the primary psychoactive compound in cannabis. Cannabidiol (CBD) is another major constituent of the plant. There are at least 113 different cannabinoids isolated from cannabis, exhibiting varied effects.Cannabigerol(E)-CBG-C5Cannabigerolmonomethyl ether(E)-CBGM-C5 ACannabinerolic acid A(Z)-CBGA-C5 ACannabigerovarin(E)-CBGV-C3Cannabigerolic acid A(E)-CBGA-C5 ACannabigerolic acid Amonomethyl ether(E)-CBGAM-C5 ACannabigerovarinic acid A(E)-CBGVA-C3 A(±)-CannabichromeneCBC-C5(±)-Cannabichromenic acid ACBCA-C5 A(±)-Cannabivarichromene, (±)-CannabichromevarinCBCV-C3(±)-Cannabichromevarinicacid ACBCVA-C3 A(−)-CannabidiolCBD-C5Cannabidiolmomomethyl etherCBDM-C5Cannabidiol-C4CBD-C4(−)-CannabidivarinCBDV-C3CannabidiorcolCBD-C1Cannabidiolic acidCBDA-C5Cannabidivarinic acidCBDVA-C3CannabinodiolCBND-C5CannabinodivarinCBND-C3Δ9-TetrahydrocannabinolΔ9-THC-C5Δ9-Tetrahydrocannabinol-C4Δ9-THC-C4Δ9-TetrahydrocannabivarinΔ9-THCV-C3Δ9-TetrahydrocannabiorcolΔ9-THCO-C1Δ9-Tetrahydro-cannabinolic acid AΔ9-THCA-C5 AΔ9-Tetrahydro-cannabinolic acid BΔ9-THCA-C5 BΔ9-Tetrahydro-cannabinolic acid-C4A and/or BΔ9-THCA-C4 A and/or BΔ9-Tetrahydro-cannabivarinic acid AΔ9-THCVA-C3 AΔ9-Tetrahydro-cannabiorcolic acidA and/or BΔ9-THCOA-C1 A and/or B(−)-Δ8-trans-(6aR,10aR)-Δ8-TetrahydrocannabinolΔ8-THC-C5(−)-Δ8-trans-(6aR,10aR)-Tetrahydrocannabinolicacid AΔ8-THCA-C5 A(−)-(6aS,10aR)-Δ9-Tetrahydrocannabinol(−)-cis-Δ9-THC-C5CannabinolCBN-C5Cannabinol-C4CBN-C4CannabivarinCBN-C3Cannabinol-C2CBN-C2CannabiorcolCBN-C1Cannabinolic acid ACBNA-C5 ACannabinol methyl etherCBNM-C5(−)-(9R,10R)-trans-Cannabitriol(−)-trans-CBT-C5(+)-(9S,10S)-Cannabitriol(+)-trans-CBT-C5(±)-(9R,10S/9S,10R)-Cannabitriol(±)-cis-CBT-C5(−)-(9R,10R)-trans-10-O-Ethyl-cannabitriol(−)-trans-CBT-OEt-C5(±)-(9R,10R/9S,10S)-Cannabitriol-C3(±)-trans-CBT-C38,9-Dihydroxy-Δ6a(10a)-tetrahydrocannabinol8,9-Di-OH-CBT-C5Cannabidiolic acid Acannabitriol esterCBDA-C5 9-OH-CBT-C5 ester(−)-(6aR,9S,10S,10aR)-9,10-Dihydroxy-hexahydrocannabinol,CannabiripsolCannabiripsol-C5(−)-6a,7,10a-Trihydroxy-Δ9-tetrahydrocannabinol(−)-Cannabitetrol10-Oxo-Δ6a(10a)-tetrahydrocannabinolOTHC(5aS,6S,9R,9aR)-CannabielsoinCBE-C5(5aS,6S,9R,9aR)-C3-CannabielsoinCBE-C3(5aS,6S,9R,9aR)-Cannabielsoic acid ACBEA-C5 A(5aS,6S,9R,9aR)-Cannabielsoic acid BCBEA-C5 B(5aS,6S,9R,9aR)-C3-Cannabielsoic acid BCBEA-C3 BCannabiglendol-C3OH-iso-HHCV-C3DehydrocannabifuranDCBF-C5CannabifuranCBF-C5(−)-Δ7-trans-(1R,3R,6R)-Isotetrahydrocannabinol(±)-Δ7-1,2-cis-(1R,3R,6S/1S,3S,6R)-Isotetrahydro-cannabivarin(−)-Δ7-trans-(1R,3R,6R)-Isotetrahydrocannabivarin(±)-(1aS,3aR,8bR,8cR)-CannabicyclolCBL-C5(±)-(1aS,3aR,8bR,8cR)-Cannabicyclolic acid ACBLA-C5 A(±)-(1aS,3aR,8bR,8cR)-CannabicyclovarinCBLV-C3CannabicitranCBT-C5CannabichromanoneCBCN-C5Cannabichromanone-C3CBCN-C3CannabicoumarononeCBCON-C5 A cannabinoid is one of a class of diverse chemical compounds that acts on cannabinoid receptors, also known as the endocannabinoid system in cells that alter neurotransmitter release in the brain. Ligands for these receptor proteins include the endocannabinoids produced naturally in the body by animals; phytocannabinoids, found in cannabis and some other plants; and synthetic cannabinoids, manufactured artificially. The most notable cannabinoid is the phytocannabinoid tetrahydrocannabinol (THC), the primary psychoactive compound in cannabis. Cannabidiol (CBD) is another major constituent of the plant. There are at least 113 different cannabinoids isolated from cannabis, exhibiting varied effects. Synthetic cannabinoids encompass a variety of distinct chemical classes: the classical cannabinoids structurally related to THC, the nonclassical cannabinoids (cannabimimetics) including the aminoalkylindoles, 1,5-diarylpyrazoles, quinolines, and arylsulfonamides as well as eicosanoids related to endocannabinoids. Medical uses include the treatment of nausea due to chemotherapy, spasticity, and possibly neuropathic pain. Common side effects include dizziness, sedation, confusion, dissociation and 'feeling high'. Before the 1980s, it was often speculated that cannabinoids produced their physiological and behavioral effects via nonspecific interaction with cell membranes, instead of interacting with specific membrane-bound receptors. The discovery of the first cannabinoid receptors in the 1980s helped to resolve this debate. These receptors are common in animals, and have been found in mammals, birds, fish, and reptiles. At present, there are two known types of cannabinoid receptors, termed CB1 and CB2, with mounting evidence of more. The human brain has more cannabinoid receptors than any other G protein-coupled receptor (GPCR) type. CB1 receptors are found primarily in the brain, more specifically in the basal ganglia and in the limbic system, including the hippocampus and the striatum. They are also found in the cerebellum and in both male and female reproductive systems. CB1 receptors are absent in the medulla oblongata, the part of the brain stem responsible for respiratory and cardiovascular functions. CB1 is also found in the human anterior eye and retina. CB2 receptors are predominantly found in the immune system, or immune-derived cells with the greatest density in the spleen. While found only in the peripheral nervous system, a report does indicate that CB2 is expressed by a subpopulation of microglia in the human cerebellum. CB2 receptors appear to be responsible for the anti-inflammatory and possibly other therapeutic effects of cannabis seen in animal models. The classical cannabinoids are concentrated in a viscous resin produced in structures known as glandular trichomes. At least 113 different cannabinoids have been isolated from the Cannabis plant To the right, the main classes of cannabinoids from Cannabis are shown. The best studied cannabinoids include tetrahydrocannabinol (THC), cannabidiol (CBD) and cannabinol (CBN). All classes derive from cannabigerol-type (CBG) compounds and differ mainly in the way this precursor is cyclized. The classical cannabinoids are derived from their respective 2-carboxylic acids (2-COOH) by decarboxylation (catalyzed by heat, light, or alkaline conditions). Tetrahydrocannabinol (THC) is the primary psychoactive component of the Cannabis plant. Delta-9-tetrahydrocannabinol (Δ9-THC, THC) and delta-8-tetrahydrocannabinol (Δ8-THC), through intracellular CB1 activation, induce anandamide and 2-arachidonoylglycerol synthesis produced naturally in the body and brain. These cannabinoids produce the effects associated with cannabis by binding to the CB1 cannabinoid receptors in the brain.