NationMaster - Encyclopedia: Cannabinoids

Cannabinoids are a group of terpeno phenolic compounds present in Cannabis (Cannabis sativa L). The broader definition of cannabinoids refer to a group of substances that are structurally related to tetrahydrocannabinol (THC) or that bind to cannabinoid receptors. The chemical definition encompasses a variety of distinct chemical classes: the classical cannabinoids structurally related to THC, the nonclassical cannabinoids, the aminoalkylindoles, the eicosanoids related to the endocannabinoids, 1,5-diarylpyrazoles, quinolines and arylsulphonamides and additional compounds that do not fall into these standard classes but bind to cannabinoid receptors.^[1] The term cannabinoids also refers to a unique group of secondary metabolites found in the cannabis plant, which are responsible for the plant's peculiar pharmacological effects. Currently, there are three general types of cannabinoids: phytocannabinoids occur uniquely in the cannabis plant; endogenous cannabinoids are produced in the bodies of humans and other animals; and synthetic cannabinoids are similar compounds produced in a laboratory. Many terpenes are derived from conifer resins, here a pine. ... Phenol, also known under an older name of carbolic acid, is a colourless crystalline solid with a typical sweet tarry odor. ... Binomial name Linnaeus Subspecies L. subsp. ... THC redirects here. ... The cannabinoid receptors are a class of receptors under the G-protein coupled receptor superfamily. ... In biochemistry, eicosanoids are a class of oxygenated hydrophobic molecules that largely function as autocrine and paracrine mediators. ... Quinoline, also known as 1-azanaphthalene, 1-benzazine, or benzo[b]pyridine, is a heterocyclic aromatic organic compound. ... It has been suggested that this article or section be merged into natural product. ... This article is about the plant genus Cannabis. ... Pharmacology (in Greek: pharmakon (Ï†Î¬ÏÎ¼Î±ÎºÎ¿Î½) meaning drug, and lego (Î»ÎÎ³Ï‰) to tell (about)) is the study of how drugs interact with living organisms to produce a change in function. ... This article is about modern humans. ... For other uses, see Animal (disambiguation). ...

Cannabinoid receptors

Main article: cannabinoid receptor

Before the 1980's, 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. There are currently two known types of cannabinoid receptors, termed CB1 and CB2. The cannabinoid receptors are a class of receptors under the G-protein coupled receptor superfamily. ... In biochemistry, a receptor is a protein on the cell membrane or within the cytoplasm or cell nucleus that binds to a specific molecule (a ligand), such as a neurotransmitter, hormone, or other substance, and initiates the cellular response to the ligand. ... Subclasses & Infraclasses Subclass â€ Allotheria* Subclass Prototheria Subclass Theria Infraclass â€ Trituberculata Infraclass Metatheria Infraclass Eutheria Mammals (class Mammalia) are warm-blooded, vertebrate animals characterized by the presence of sweat glands, including milk producing sweat glands, and by the presence of: hair, three middle ear bones used in hearing, and a neocortex... For other uses, see Bird (disambiguation). ... For other uses, see Fish (disambiguation). ... Reptilia redirects here. ...

CB1 receptors are found primarily in the brain, specifically in the basal ganglia and in the limbic system, including the hippocampus. They are also found in the cerebellum and in both male and female reproductive systems. CB1 receptors are essentially absent in the medulla oblongata, the part of the brain stem that is responsible for respiratory and cardiovascular functions. Thus, there is not a risk of respiratory or cardiovascular failure as there is with many other drugs. CB1 receptors appear to be responsible for the euphoric and anticonvulsive effects of cannabis.

CB2 receptors are almost exclusively found in the immune system, with the greatest density in the spleen. While generally found only in the peripheral nervous system, a report does indicate that CB2 is expressed by a subpopulation of microglia in the human cerebellum ^[2]. CB2 receptors appear to be responsible for the anti-inflammatory and possibly other therapeutic effects of cannabis.

Human brain In animals, the brain (enkephale) (Greek for in the skull), is the control center of the central nervous system, responsible for behavior. ... The basal ganglia (or basal nuclei) are a group of nuclei in the brain interconnected with the cerebral cortex, thalamus and brainstem. ... The limbic system is a historically defined set of brain structures that support a variety of functions including emotion and memory. ... For other uses, see Hippocampus (disambiguation). ... The cerebellum (Latin: little brain) is a region of the brain that plays an important role in the integration of sensory perception and motor control. ... A pictorial illustration of the human female reproductive system. ... The medulla oblongata is the lower portion of the brainstem. ... The brain stem is the lower part of the brain, adjoining and structurally continuous with the spinal cord. ... A scanning electron microscope image of a single neutrophil (yellow), engulfing anthrax bacteria (orange). ... The spleen is an organ located in the abdomen, where it functions in the destruction of old red blood cells and holding a reservoir of blood. ... Microglia cells positive for lectins Microglia are a type of glial cell that act as the immune cells of the Central nervous system (CNS). ... The cerebellum (Latin: little brain) is a region of the brain that plays an important role in the integration of sensory perception and motor control. ...

Phytocannabinoids

Type	Skeleton	Cyclization
Cannabigerol-type CBG
Cannabichromene-type CBC
Cannabidiol-type CBD
Tetrahydrocannabinol- and Cannabinol-type THC, CBN
Cannabielsoin-type CBE
iso- Tetrahydrocannabinol- type iso-THC
Cannabicyclol-type CBL
Cannabicitran-type CBT
Main classes of natural cannabinoids

Phytocannabinoids, also called natural cannabinoids, herbal cannabinoids, and classical cannabinoids, are only known to occur naturally in significant quantity in the cannabis plant, and are concentrated in a viscous resin that is produced in glandular structures known as trichomes. In addition to cannabinoids, the resin is rich in terpenes, which are largely responsible for the odour of the cannabis plant. Image File history File links Size of this preview: 800 Ã— 420 pixelsFull resolution (3066 Ã— 1611 pixel, file size: 30 KB, MIME type: image/png) Description: chemical structure of a CBG-type cannabinoid Author: Cacycle Date of creation: 9 January 2006 (UTC) Source: selfmade Copyright: GNU Free Documentation License (GFDL) Creative... Image File history File links Size of this preview: 800 Ã— 455 pixelsFull resolution (2829 Ã— 1608 pixel, file size: 25 KB, MIME type: image/png) Description: chemical structure of the CBG-type cyclization of cannabinoids Author: Cacycle Date of creation: 9 January 2006 (UTC) Source: selfmade Copyright: GNU Free Documentation License... Image File history File links Size of this preview: 800 Ã— 352 pixelsFull resolution (3326 Ã— 1465 pixel, file size: 29 KB, MIME type: image/png) Description: chemical structure of a CBC-type cannabinoid Author: Cacycle Date of creation: 9 January 2006 (UTC) Source: selfmade Copyright: GNU Free Documentation License (GFDL) Creative... Image File history File links Size of this preview: 800 Ã— 455 pixelsFull resolution (2829 Ã— 1608 pixel, file size: 26 KB, MIME type: image/png) Description: chemical structure of the CBC-type cyclization of cannabinoids Author: Cacycle Date of creation: 9 January 2006 (UTC) Source: selfmade Copyright: GNU Free Documentation License... Image File history File links Size of this preview: 800 Ã— 484 pixelsFull resolution (3029 Ã— 1834 pixel, file size: 35 KB, MIME type: image/png) Description: chemical structure of a CBD-type cannabinoid Author: Cacycle Date of creation: 9 January 2006 (UTC) Source: selfmade Copyright: GNU Free Documentation License (GFDL) Creative... Image File history File links Size of this preview: 800 Ã— 455 pixelsFull resolution (2829 Ã— 1609 pixel, file size: 26 KB, MIME type: image/png) Description: chemical structure of the CBD-type cyclization of cannabinoids Author: Cacycle Date of creation: 9 January 2006 (UTC) Source: selfmade Copyright: GNU Free Documentation License... Image File history File links Size of this preview: 800 Ã— 464 pixelsFull resolution (2838 Ã— 1646 pixel, file size: 33 KB, MIME type: image/png) Description: chemical structure of a CBN-type cannabinoid Author: Cacycle Date of creation: 9 January 2006 (UTC) Source: selfmade Copyright: GNU Free Documentation License (GFDL) Creative... Image File history File links Size of this preview: 800 Ã— 455 pixelsFull resolution (2829 Ã— 1609 pixel, file size: 27 KB, MIME type: image/png) Description: chemical structure of the CBN-type cyclization of cannabinoids Author: Cacycle Date of creation: 9 January 2006 (UTC) Source: selfmade Copyright: GNU Free Documentation License... Image File history File links Size of this preview: 800 Ã— 516 pixelsFull resolution (2962 Ã— 1911 pixel, file size: 37 KB, MIME type: image/png) Description: chemical structure of a CBE-type cannabinoid Author: Cacycle Date of creation: 9 January 2006 (UTC) Source: selfmade Copyright: GNU Free Documentation License (GFDL) Creative... Image File history File links Size of this preview: 800 Ã— 455 pixelsFull resolution (2829 Ã— 1608 pixel, file size: 26 KB, MIME type: image/png) Description: chemical structure of the CBE-type cyclization of cannabinoids Author: Cacycle Date of creation: 9 January 2006 (UTC) Source: selfmade Copyright: GNU Free Documentation License... Image File history File links Size of this preview: 800 Ã— 460 pixelsFull resolution (3197 Ã— 1839 pixel, file size: 34 KB, MIME type: image/png) Description: chemical structure of a iso-CBN-type cannabinoid Author: Cacycle Date of creation: 9 January 2006 (UTC) Source: selfmade Copyright: GNU Free Documentation License (GFDL... Image File history File links Size of this preview: 800 Ã— 455 pixelsFull resolution (2829 Ã— 1609 pixel, file size: 27 KB, MIME type: image/png) Description: chemical structure of the iso-CBN-type cyclization of cannabinoids Author: Cacycle Date of creation: 9 January 2006 (UTC) Source: selfmade Copyright: GNU Free Documentation... Image File history File links Size of this preview: 800 Ã— 464 pixelsFull resolution (2687 Ã— 1557 pixel, file size: 32 KB, MIME type: image/png) Description: chemical structure of a CBL-type cannabinoid Author: Cacycle Date of creation: 9 January 2006 (UTC) Source: selfmade Copyright: GNU Free Documentation License (GFDL) Creative... Image File history File links Size of this preview: 800 Ã— 455 pixelsFull resolution (2829 Ã— 1609 pixel, file size: 29 KB, MIME type: image/png) Description: chemical structure of the CBL-type cyclization of cannabinoids Author: Cacycle Date of creation: 9 January 2006 (UTC) Source: selfmade Copyright: GNU Free Documentation License... Image File history File links Size of this preview: 800 Ã— 464 pixelsFull resolution (2837 Ã— 1647 pixel, file size: 27 KB, MIME type: image/png) Description: chemical structure of a CBT-type cannabinoid Author: Cacycle Date of creation: 9 January 2006 (UTC) Source: selfmade Copyright: GNU Free Documentation License (GFDL) Creative... Image File history File links Size of this preview: 800 Ã— 455 pixelsFull resolution (2829 Ã— 1609 pixel, file size: 27 KB, MIME type: image/png) Description: chemical structure of the CBT-type cyclization of cannabinoids Author: Cacycle Date of creation: 9 January 2006 (UTC) Source: selfmade Copyright: GNU Free Documentation License... This article is about the plant genus Cannabis. ... This article does not cite any references or sources. ... Trichomes, from the Greek meaning growth of hair, are fine outgrowths or appendages on plants and protists. ... Many terpenes are derived from conifer resins, here a pine. ...

Phytocannabinoids are nearly insoluble in water but are soluble in lipids, alcohols, and other non-polar organic solvents. However, as phenols they form more water-soluble phenolate salts under strongly alkaline conditions. Some common lipids. ... This article does not cite any references or sources. ... A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ... In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl group (-O H) attached to an aromatic hydrocarbon group. ... The phenolate anion C6H5O- is the conjugate base and anion of phenol. ... This article is about common table salt. ... The common (Arrhenius) definition of a base is a chemical compound that either donates hydroxide ions or absorbs hydrogen ions when dissolved in water. ...

All natural cannabinoids are derived from their respective 2-carboxylic acids (2-COOH) by decarboxylation (catalyzed by heat, light, or alkaline conditions). Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted... A Decarboxylation is any chemical reaction in which a carboxyl group (-COOH) is split off from a compound as carbon dioxide (CO2). ... The common (Arrhenius) definition of a base is a chemical compound that either donates hydroxide ions or absorbs hydrogen ions when dissolved in water. ...

Types

At least 66 cannabinoids have been isolated from the cannabis plant^[3] To the right the main classes of natural cannabinoids are shown. All classes derive from cannabigerol-type compounds and differ mainly in the way this precursor is cyclized.

Tetrahydrocannabinol (THC), cannabidiol (CBD) and cannabinol (CBN) are the most prevalent natural cannabinoids and have received the most study. Other common ones are listed below: THC redirects here. ... Cannabidiol, also known as CBD, is an antipsychotic cannabinoid found in the hemp plant Cannabis sativa. ... Cannabinol, also known as CBN, is a non_psychoactive cannabinoid found in the hemp plant Cannabis sativa. ...

CBG Cannabigerol
CBC Cannabichromene
CBL Cannabicyclol
CBV Cannabivarin
THCV Tetrahydrocannabivarin
CBDV Cannabidivarin
CBCV Cannabichromevarin
CBGV Cannabigerovarin
CBGM Cannabigerol Monoethyl Ether

Cannabigerol, also known as CBG, is a non-phychoactive Cannabinoid found in the Cannabis strain of plants. ... Cannabicyclol, also known as CBL, is a non-psychedelic cannabinoids found in the Cannabis species. ... Cannabivarin, also known as cannabivarol or CBV, is a non-psychoactive cannabinoid found in minor amounts in the hemp plant Cannabis sativa. ... Tetrahydrocannabivarin, also known as tetrahydrocannabivarol, THCV, or THV, is a psychoactive cannabinoid found in minor amounts in the hemp plant Cannabis sativa. ... Cannabidivarine, also known as cannabidivarol or CBDV, is a non_psychoactive cannabinoid found in minor amounts in the hemp plant Cannabis sativa. ...

Tetrahydrocannabinol

Main article: Tetrahydrocannabinol

THC is the primary psychoactive component of the plant. Medically, it appears to ease moderate pain (analgetic) and to be neuroprotective. THC has approximately equal affinity for the CB1 and CB2 receptors.^[4] Its effects are perceived to be more cerebral.^{[citation needed]} THC redirects here. ... For other uses of painkiller, see painkiller (disambiguation) An analgesic (colloquially known as painkiller) is any member of the diverse group of drugs used to relieve pain. ... Serving to protect neurons from injury or degeneration. ... Wikipedia does not yet have an article with this exact name. ...

delta-9-Tetrahydrocannabinol (Δ⁹-THC, THC) and delta-8-tetrahydrocannabinol (Δ⁸-THC), mimic the action of anandamide, a neurotransmitter produced naturally in the body. The THCs produce the high associated with cannabis by binding to the CB₁ cannabinoid receptors in the brain. THC redirects here. ... Anandamide, also known as arachidonoylethanolamine or AEA, is a naturally occurring endogenous cannabinoid neurotransmitter found in the brain of animals, as well as other organs. ... Chemical structure of D-aspartic acid, a common amino acid neurotransmitter. ... Cannabis, also known as marijuana[1] or ganja (Hindi: à¤—à¤¾à¤‚à¤œà¤¾),[2] is a psychoactive product of the plant Cannabis sativa. ...

Cannabidiol

Main article: cannabidiol

CBD is not psychoactive, and neither does it affect the psychoactivity of THC^[5]. Cannabidiol, also known as CBD, is an antipsychotic cannabinoid found in the hemp plant Cannabis sativa. ... A psychoactive drug or psychotropic substance is a chemical that alters brain function, resulting in temporary changes in perception, mood, consciousness, or behaviour. ...

Medically, it appears to relieve convulsion, inflammation, anxiety, and nausea.^{[citation needed]} CBD has a greater affinity for the CB2 receptor than for the CB1 receptor. It is perceived to have more effect on the body.^{[citation needed]}

CBD shares a precursor with THC and is the main cannabinoid in low-THC Cannabis strains.

Cannabinol

Main article: cannabinol

CBN is the primary product of THC degradation, and there is usually little of it in a fresh plant. CBN content increases as THC degrades in storage, and with exposure to light and air. It is only mildly psychoactive. Cannabinol, also known as CBN, is a non_psychoactive cannabinoid found in the hemp plant Cannabis sativa. ...

Tetrahydrocannabivarin

Main article: Tetrahydrocannabivarin

Tetrahydrocannabivarin (THCV) is prevalent in certain South African and Southeast Asian strains of Cannabis. It is an antagonist of THC at CB₁ receptors and attenuates the psychoactive effects of THC.^[6] Tetrahydrocannabivarin, also known as tetrahydrocannabivarol, THCV, or THV, is a psychoactive cannabinoid found in minor amounts in the hemp plant Cannabis sativa. ... For other uses, see Antagonist (disambiguation). ...

Cannabichromene

Main article: Cannabichromene

Cannabichromene (CBC) is non-psychoactive and does not affect the psychoactivity of THC,^[5] a precursor of CBD and THC.

Double bond position

In addition, each of the compounds above may be in different forms depending on the position of the double bond in the alicyclic carbon ring. There is potential for confusion because there are different numbering systems used to describe the position of this double bond. Under the dibenzopyran numbering system widely used today, the major form of THC is called delta-9-THC, while the minor form is called delta-8-THC. Under the alternate terpene numbering system, these same compounds are called delta-1-THC and delta-6-THC, respectively. Cyclopropane is the smallest alicyclic compound. ... Many terpenes are derived from conifer resins, here a pine. ...

Length

Most herbal cannabinoid compounds are 21 carbon compounds. However, some do not follow this rule, primarily because of variation in the length of the side chain attached to the aromatic ring. In THC, CBD, and CBN, this side chain is a pentyl (5 carbon) chain. In the most common homologue, the pentyl chain is replaced with a propyl (3 carbon) chain. Cannabinoids with the propyl side chain are named using the suffix "varin", and are designated, for example, THCV, CBDV, or CBNV. It appears that shorter chains increase the intensity and decrease the duration of the activity of the chemicals. The term Side chain can have different meanings depending on the context: In chemistry and biochemistry a side chain is a part of a molecule attached to a core structure. ... An aromatic hydrocarbon (abbreviated as AH) or arene [1] is a hydrocarbon, the molecular structure of which incorporates one or more planar sets of six carbon atoms that are connected by delocalised electrons numbering the same as if they consisted of alternating single and double covalent bonds. ...

Plant profile

Cannabis plants can exhibit wide variation in the quantity and type of cannabinoids they produce. The mixture of cannabinoids produced by a plant is known as the plant's cannabinoid profile. Selective breeding has been used to control the genetics of plants and modify the cannabinoid profile. For example, strains which are used as fiber (commonly called hemp), are bred such that they are low in psychoactive chemicals like THC. Strains used in medicine are often bred for high CBD content, and strains used for recreational purposes are usually bred for high THC content, or for a specific chemical balance. Some strains of more than 20% THC have been created.^{[citation needed]} Selective breeding in domesticated animals is the process of developing a cultivated breed over time. ... U.S. Marihuana production permit. ... This article does not cite its references or sources. ...

Quantitative analysis of a plant's cannabinoid profile is usually determined by gas chromatography (GC), or more reliably by gas chromatography combined with mass spectrometry (GC/MS). Liquid chromatography (LC) techniques are also possible, although these are often only semi-quantitative or qualitative. There have been systematic attempts to monitor the cannabinoid profile of cannabis over time, but their accuracy is impeded by the illegal status of the plant in many countries. Quantitative analysis has different meanings in different contexts. ... Gas-liquid chromatography (GLC), or simply gas chromatography (GC) is a type of chromatography in which the mobile phase is a carrier gas, usually an inert gas such as helium or nitrogen, and the stationary phase is a microscopic layer of liquid on an inert solid support. ... Mass spectrometry (previously called mass spectroscopy (deprecated) or informally, mass-spec and MS) is an analytical technique that measures the mass-to-charge ratio of ions. ... Chromatography is a family of analytical chemistry techniques for the separation of mixtures. ...

Pharmacology

Cannabinoids can be administered by smoking, vaporizing, oral ingestion, transdermal patch, intravenous injection, sublingual absorption, or rectal suppository. Once in the body, most cannabinoids are metabolized in the liver, especially by cytochrome P450 mixed-function oxidases, mainly CYP 2C9. Thus supplementing with CYP 2C9 inhibitors leads to extended intoxication. For the bird, see Liver bird. ... Cytochrome P450 Oxidase (CYP2E1) Cytochrome P450 oxidase (commonly abbreviated CYP) is a generic term for a large number of related, but distinct, oxidative enzymes (EC 1. ...

Some is also stored in fat in addition to being metabolized in liver. Delta-9-THC is metabolized to 11-hydroxy-delta-9-THC, which is then metabolized to 9-carboxy-THC. Some cannabis metabolites can be detected in the body after several weeks. For other uses, see FAT. Fats consist of a wide group of compounds that are generally soluble in organic solvents and largely insoluble in water. ... A metabolite is the product of metabolism. ...

Production

Production of cannabinoids include both the synthesis in the plant, and separation of certain types from this material.

Plant synthesis

Cannabinoid production starts when an enzyme causes geranyl pyrophosphate and olivetolic acid to combine and form CBG. Next, CBG is independently converted to either CBD or CBC by two separate synthase enzymes. CBC is then enzymatically cyclized to THC. For the propyl homologues (THCV, CBDV and CBNV), there is a similar pathway that is based on CBGV. Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... Chemical structure of geranyl pyrophosphate. ... In biochemistry, a synthase is an enzyme which catalyzes a synthesis process. ...

Separation

Cannabinoids can be separated from the plant by extraction with organic solvents. Hydrocarbons and alcohols are often used as solvents. However, these solvents are flammable and many are toxic. Supercritical solvent extraction with carbon dioxide is an alternative technique. Although this process requires high pressures, there is minimal risk of fire or toxicity, solvent removal is simple and efficient, and extract quality can be well-controlled. Once extracted, cannabinoid blends can be separated into individual components using wiped film vacuum distillation or other distillation techniques. However, to produce high purity cannabinoids, chemical synthesis or semisynthesis is generally required. In chemistry, liquid-liquid extraction (or more briefly, solvent extraction) is a useful method to separate components (compounds) of a mixture. ... For other uses, see Solvent (disambiguation). ... Look up Hydrocarbon in Wiktionary, the free dictionary. ... This article does not cite any references or sources. ... Carbon dioxide is a chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom. ... Laboratory distillation set-up: 1: Heat source 2: Still pot 3: Still head 4: Thermometer/Boiling point temperature 5: Condenser 6: Cooling water in 7: Cooling water out 8: Distillate/receiving flask 9: Vacuum/gas inlet 10: Still receiver 11: Heat control 12: Stirrer speed control 13: Stirrer/heat plate... In chemistry, chemical synthesis is purposeful execution of chemical reactions in order to get a product, or several products. ... Semisynthesis or partial chemical synthesis is a type of chemical synthesis that uses compounds isolated from natural sources (e. ...

History

Cannabinoids were first discovered in the 1940s, when CBD and CBN were identified. The structure of THC was first determined in 1964.

Due to molecular similarity and ease of synthetic conversion, it was originally believed that CBD was a natural precursor to THC. However, it is now known that CBD and THC are produced independently in the cannabis plant.

Endocannabinoids

For more details on the roles and regulation of the endocannabinoids, see Endocannabinoid system.

Anandamide, an endogenous ligand of CB1 and CB2

Endocannabinoids are substances produced from within the body which activate cannabinoid receptors. After the discovery of the first cannabinoid receptor in 1988, scientists began searching for an endogenous ligand for the receptor. The endocannabinoid system (also endogenous cannabinoid system) consists of two transmembrane cannabinoid receptors, endogenous cannabinoids, a transporter protein (anandamide transporter), and the metabolic enzymes inactivating the endocannabinoids (MGL and FAAH). ... Image File history File links No higher resolution available. ... Anandamide, also known as arachidonoylethanolamine or AEA, is a naturally occurring endogenous cannabinoid neurotransmitter found in the brain of animals, as well as other organs. ... In chemistry, a ligand is an atom, ion, or molecule (see also: functional group) that generally donates one or more of its electrons through a coordinate covalent bond to, or shares its electrons through a covalent bond with, one or more central atoms or ions (these ligands act as a... The cannabinoid receptors are a class of receptors under the G-protein coupled receptor superfamily. ... In chemistry, a ligand is an atom, ion, or molecule (see also: functional group) that generally donates one or more of its electrons through a coordinate covalent bond to, or shares its electrons through a covalent bond with, one or more central atoms or ions (these ligands act as a...

Types of endocannabinoid ligands

Arachidonoyl ethanolamide (Anandamide or AEA)

In 1992, the first such compound was identified as arachidonoyl ethanolamide and named anandamide, a name derived from the Sanskrit word for bliss and -amide. Anandamide is derived from the essential fatty acid arachidonic acid. It has a pharmacology similar to THC, although its chemical structure is different. Anandamide binds to the central (CB1) and, to a lesser extent, peripheral (CB2) cannabinoid receptors, where it acts as a partial agonist. Anandamide is about as potent as THC at the CB1 receptor.^[7] It is found in nearly all tissues in a wide range of animals.^{[citation needed]} Anandamide, also known as arachidonoylethanolamide or AEA, is an endogenous cannabinoid neurotransmitter found in animal and human organs, especially in the brain. ... Anandamide, also known as arachidonoylethanolamine or AEA, is a naturally occurring endogenous cannabinoid neurotransmitter found in the brain of animals, as well as other organs. ... Sanskrit ( , for short ) is a classical language of India, a liturgical language of Hinduism, Buddhism, Sikhism, and Jainism, and one of the 23 official languages of India. ... Amide functional group Amides possess a conjugated system spread over the O, C and N atoms, consisting of molecular orbitals occupied by delocalized electrons. ... Essential fatty acids, or EFAs, are fatty acids that cannot be constructed within an organism from other components (generally all references are to humans) by any known chemical pathways; and therefore must be obtained from the diet. ... Arachidonic acid (AA) is an omega-6 fatty acid 20:4(Ï‰-6). ... THC redirects here. ...

Two analogs of anandamide, 7,10,13,16-docosatetraenoylethanolamide and homo-γ-linolenoylethanolamide, have similar pharmacology. All of these are members of a family of signalling lipids called N-acylethanolamides, which also includes the noncannabimimetic palmitoylethanolamide and oleoylethanolamide which possess anti-inflammatory and orexigenic effects, respectively. Many N-acylethanolamides have also been identified in plant seeds^[8] and in molluscs.^[9] Pharmacology (in Greek: pharmakon (Ï†Î¬ÏÎ¼Î±ÎºÎ¿Î½) meaning drug, and lego (Î»ÎÎ³Ï‰) to tell (about)) is the study of how drugs interact with living organisms to produce a change in function. ... Anti-inflammatory refers to the property of a substance or treatment that reduces inflammation. ...

2-arachidonoyl glycerol (2-AG)

Another endocannabinoid, 2-arachidonoyl glycerol, binds to both the CB1 and CB2 receptors with similar affinity, acting as a full agonist at both.^[7] 2-AG is present at significantly higher concentrations in the brain than anandamide^[10], and there is some controversy over whether 2-AG rather than anandamide is chiefly responsible for endocannabinoid signalling in vivo^[11]. In particular, one in vitro study suggests that 2-AG is capable of stimulating higher G-protein activation than anandamide, although the physiological implications of this finding are not yet known.^[12] 2-Arachidonoylglycerol (2-AG) is an endocannabinoid, an endogenous agonist of the CB1 receptor. ... 2-Arachidonoylglycerol (2-AG) is an endocannabinoid, an endogenous agonist of the CB1 receptor. ... G-proteins, short for guanine nucleotide binding proteins, are a family of proteins involved in second messenger cascades. ...

2-arachidonyl glyceryl ether (noladin ether)

In 2001 a third, ether-type endocannabinoid, 2-arachidonyl glyceryl ether (noladin ether), was isolated from porcine brain. ^[13] Prior to this discovery, it had been synthesized as a stable analog of 2-AG; indeed, some controversy remains over its classification as an endocannabinoid, as another group failed to detect the substance at "any appreciable amount" in the brains of several different mammalian species.^[14] It binds to the CB1 cannabinoid receptor (K_i = 21.2 nmol/L) and causes sedation, hypothermia, intestinal immobility, and mild antinociception in mice. It binds primarily to the CB1 receptor, and only weakly to the CB2 receptor.^[7] 2-Arachidonyl glyceryl ether (2-AGE, Noladin ether) is a putative endocannabinoid discovered by LumÃr HanuÅ¡ at the Hebrew University of Jerusalem, Israel. ... This article is about a general class of chemical compounds. ...

N-arachidonoyl-dopamine (NADA)

Discovered in 2000, NADA preferentially binds to the CB1 receptor.^[15] Like anandamide, NADA is also an agonist for the vanilloid receptor subtype 1 (TRPV1), a member of the vanilloid receptor family.^[16]^[17] The vanilloid receptor subtype 1 (TRPV1) is a nonselective ligand-gated cation channel that may be activated by a wide variety of exogenous and endogenous stimuli, including heat greater than 43Â°C, low pH, anandamide, and capsaicin. ...

Virodhamine (OAE)

A fifth endocannabinoid, virodhamine, or O-arachidonoyl-ethanolamine (OAE) was discovered in June 2002. Although it is a full agonist at CB2 and a partial agonist at CB1, it behaves as a CB1 antagonist in vivo. In rats, virodhamine was found to be present at comparable or slightly lower concentrations than anandamide in the brain, but 2- to 9-fold higher concentrations peripherally.^[18] Virodhamine (O-arachidonoyl ethanolamine) is an endocannibinoid and a nonclassic eicosanoid, derived from arachidonic acid. ... Agonists An agonist is a substance that binds to a receptor and triggers a response in the cell. ... Agonists An agonist is a substance that binds to a receptor and triggers a response in the cell. ... Species 50 species; see text *Several subfamilies of Muroids include animals called rats. ... Human brain In animals, the brain (enkephale) (Greek for in the skull), is the control center of the central nervous system, responsible for behavior. ...

Function

Endocannabinoids serve as intercellular 'lipid messengers', signaling molecules that are released from one cell and activate the cannabinoid receptors present on other nearby cells. Although in this intercellular signaling role they are similar to the well-known monoamine neurotransmitters, such as acetylcholine, GABA or dopamine, endocannabinoids differ in numerous ways from them. For instance, they use retrograde signaling. Furthermore, endocannabinoids are lipophilic molecules that are not very soluble in water. They are not stored in vesicles, and exist as integral constituents of the membrane bilayers that make up cells. They are believed to be synthesized 'on-demand' rather than made and stored for later use. The mechanisms and enzymes underlying the biosynthesis of endocannabinoids remain elusive and continue to be an area of active research. Lipid signaling refers to a number of cellular signal transduction pathways that use cell membrane lipids as second messengers. ... In biochemistry, monoamines are a group of organic compounds containing only one amino group. ... Chemical structure of D-aspartic acid, a common amino acid neurotransmitter. ... The chemical compound acetylcholine, often abbreviated as ACh, was the first neurotransmitter to be identified. ... Gaba may refer to: GabÃ¢ or gabaa (Philippines), the concept of negative karma of the Cebuano people GABA, the gamma-amino-butyric acid neurotransmitter GABA receptor, in biology, receptors with GABA as their endogenous ligand Gaba 1 to 1, an English conversational school in Japan Marianne Gaba, a US model... For other uses, see Dopamine (disambiguation). ... In neuroscience, retrograde signaling is a phenomenon in which a signal travels from a postsynaptic neuron to a presynaptic one. ...

The endocannabinoid 2-AG has been found in bovine and human maternal milk.^[19] ...

Retrograde signal

Conventional neurotransmitters are released from a ‘presynaptic’ cell and activate appropriate receptors on a ‘postsynaptic’ cell, where presynaptic and postsynaptic designate the sending and receiving sides of a synapse, respectively. Endocannabinoids, on the other hand, are described as retrograde transmitters because they most commonly travel ‘backwards’ against the usual synaptic transmitter flow. They are in effect released from the postsynaptic cell and act on the presynaptic cell, where the target receptors are densely concentrated on axonal terminals in the zones from which conventional neurotransmitters are released. Activation of cannabinoid receptors temporarily reduces the amount of conventional neurotransmitter released. This endocannabinoid mediated system permits the postsynaptic cell to control its own incoming synaptic traffic. The ultimate effect on the endocannabinoid releasing cell depends on the nature of the conventional transmitter that is being controlled. For instance, when the release of the inhibitory transmitter, GABA, is reduced, the net effect is an increase in the excitability of the endocannabinoid-releasing cell. Conversely, when release of the excitatory neurotransmitter, glutamate, is reduced, the net effect is a decrease in the excitability of the endocannabinoid-releasing cell. In neuroscience, retrograde signaling is a phenomenon in which a signal travels from a postsynaptic neuron to a presynaptic one. ...

Range

Endocannabinoids are hydrophobic molecules. They cannot travel unaided for long distances in the aqueous medium surrounding the cells from which they are released, and therefore act locally on nearby target cells. Hence, although emanating diffusely from their source cells, they have much more restricted spheres of influence than do hormones, which can affect cells throughout the body.

Other thoughts

Endocannabinoids constitute a versatile system for affecting neuronal network properties in the nervous system.

Scientific American published an article in December of 2004, entitled "The Brain's Own Marijuana" discussing the endogenous cannabinoid system. ^[20] There are very few or no other articles that link to this one. ...

The current understanding recognizes the role that endocannabinoids play in almost every major life function in the human body.^{[citation needed]} Cannabinoids act as a bioregulatory mechanism for most life processes, which reveals why medical cannabis has been cited as treatments for many diseases and ailments in anecdotal reports and scientific literature. Some of these ailments include: pain, arthritic conditions, migraine headaches, anxiety, epileptic seizures, insomnia, loss of appetite, GERD (chronic heartburn), nausea, glaucoma, AIDS wasting syndrome, depression, bipolar disorder (particularly depression-manic-normal), multiple sclerosis, menstrual cramps, Parkinson's, trigeminal neuralgia (tic douloureux), high blood pressure, irritable bowel syndrome, and bladder incontinence.

Synthetic & Patented Cannabinoids

Historically, laboratory synthesis of cannabinoids were often based on the structure of herbal cannabinoids and a large number of analogs have been produced and tested, especially in a group led by Roger Adams as early as 1941 and later in a group led by Raphael Mechoulam. Newer compounds are no longer related to natural cannabinoids or are based on the structure of the endogenous cannabinoids. Roger Adams (1889â€“1971) was an American organic chemist. ...

Synthetic cannabinoids are particularly useful in experiments to determine the relationship between the structure and activity of cannabinoid compounds, by making systematic, incremental modifications of cannabinoid molecules.

Medications containing natural or synthetic cannabinoids or cannabinoid analogs:

Dronabinol (Marinol), is Δ9-tetrahydrocannabinol (THC), used as an appetite stimulant, anti-emetic and analgesic.
Nabilone (Cesamet), a synthetic cannabinoid and an analog of Marinol. It is Schedule II unlike Marinol which is Schedule III.
Sativex, a cannabinoid extract oral spray containing THC, CBD, and other cannabinoids used for neuropathic pain and spasticity in Canada and Spain. Sativex develops whole plant cannabinoid medicines.
Rimonabant (SR141716), a selective cannabinoid (CB1) receptor antagonist used as an anti-obesity drug under the proprietary name, Acomplia. It is also used for smoking cessation.

Other notable synthetic cannabinoids include:
Tetrahydrocannabinol, also known as THC, Δ9-THC, Δ9-tetrahydrocannabinol, Δ1-tetrahydrocannabinol (using an older numbering scheme), or dronabinol, is the main psychoactive substance found in the hemp plant Cannabis sativa. ... THC redirects here. ... An antiemetic is a drug that is effective against vomiting and nausea. ... An analgesic (colloquially known as a painkiller) is any member of the diverse group of drugs used to relieve pain (achieve analgesia). ... Nabilone is a cannabinoid with therapeutic use as an antiemetic. ... This box: The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ... This box: The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ... Sativex is an oromucosal (mouth) spray developed by the UK company GW Pharmaceuticals for multiple sclerosis patients, who can use it to alleviate neuropathic pain and spasticity. ... Cannabidiol, also known as CBD, is an antipsychotic cannabinoid found in the hemp plant Cannabis sativa. ... Rimonabant (SR141716) is an anorectic anti-obesity drug. ... For other uses, see Antagonist (disambiguation). ... Anti-obesity drugs include all pharmacological treatments intended to reduce or control weight. ...

CP-55940, produced in 1974, this synthetic cannabinoid receptor agonist is many times more potent than THC
Dimethylheptylpyran
HU-210, about 100 times as potent as THC^[21].
SR144528, a CB2 receptor antagonists
WIN 55,212-2, a potent cannabinoid receptor agonist
JWH-133, a potent selective CB2 receptor agonist.
Levonantradol (Nantrodolum), an anti-emetic and analgesic but not currently in use in medicine.

Created by Pfizer in 1974, CP-55940 is a cannabinoid which mimics the effects of naturally occurring THC (The psychoactive compound found in marijuana). ... Dimethylheptylpyran (DMHP, 1,2-dimethylheptyl-Î”3THC) is a synthetic analogue of THC, which was invented in 1949 during attempts to elucidate the structure of Î”9-THC, the active component of cannabis. ... HU-210 HU-210 (CAS# 112830-95-2) is a synthetic cannabinoid that was discovered around 1988 in the group of Dr Raphael Mechoulam at the Hebrew University. ... WIN 55,212-2 is a chemical agent in the Cannabinoid family. ... Agonists An agonist is a substance that binds to a receptor and triggers a response in the cell. ... JWH-133 is a potent selective CB2 receptor agonist. ... Levonantradol is a synthetic cannabinoid analog of dronabinol (Marinol). ...

Table of natural cannabinoids

External links

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Please improve this article by removing excessive or inappropriate external links.

Homepage of the ICRS - The International Cannabinoid Research Society

Pharmacokinetics and Disposition of Cannabinoids - Drugs and medical portal

Stereochemical Requirements for Cannabimimetic Activity - Drugs and medical culture

Homepage of the ECSN - The Endocannabinoid System Network

Cannabis Report (Ministry of Public Health of Belgium) - 2002 at trimbos.nl

Senate Report on Cannabis (Canada) - 2002 at Parliament of Canada

The Health and Psychological Effects of Cannabis Use (Australia - Monograph 44) - 2001 at Department of Health and Ageing (Australia)

Marijuana and Medicine - Assessing the Science Base (Institute of Medicine) - 1999 at National Academies Press

House of Lords Report - Cannabis (United Kingdom) - 1998 at Parliament of the United Kingdom

Cannabis: A Health Perspective and Research Agenda - 1997 at World Health Organization

Overview of the Endocannabinoid Signalling System at Endocannabinoid.net

Chemical Ecology of Cannabis (J. Intl. Hemp Assn. - 1994) at hempfood.com

What Every Doctor Should Know About Cannabinoids at California Cannabis Research Medical Group

Therapeutic Potential in Spotlight at Cannabinoid Researchers' Meeting at California Cannabis Research Medical Group

THC (tetrahydrocannabinol) accumulation in glands of Cannabis (Cannabaceae) at hempreport.com

Inheritance of Chemical Phenotype in Cannabis Sativa (Genetics) at Genetics Society of America

Medicinal marijuana laws, policies and news at cannabishq.com

Compounds found in Cannabis sativa at Erowid

Cannabinoids and the Brain - The most recent biomedical book on the endocannabinoid system

Image File history File links Broom_icon. ... Regions Political culture Foreign relations Other countries Atlas Politics Portal The Senate Chamber of Parliament Hill in Ottawa. ... The Department of Health and Ageing is an Australian Government department. ... National Academies Press (NAP) has lots of FREE books and is part of the United States National Academy of Sciences. ... Type Bicameral Houses House of Commons House of Lords Speaker of the House of Commons Michael Martin MP Speaker of the House of Lords HÃ©lÃ¨ne Hayman, PC Members 1377 (646 Commons, 731 Peers) Political groups Labour Party Conservative Party Liberal Democrats Scottish National Party Plaid Cymru Democratic Unionist... WHO redirects here. ... The California Cannabis Research Medical Group is a non-profit organization dedicated to educating physicians about the medical use of cannabis. ... The California Cannabis Research Medical Group is a non-profit organization dedicated to educating physicians about the medical use of cannabis. ... The Genetics Society of America is a non-exclusive association of genetics researchers and educators, and the publisher of the peer-reviewed journal Genetics. ... Erowid. ...

Cited Sources

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^ Huffman JW (2000). "The search for selective ligands for the CB2 receptor". Curr. Pharm. Des. 6 (13): 1323-37. PMID 10903395.
^ ^a ^b Behavioural Pharmacology - Abstract: Volume 16(5-6) September 2005 p 487-496 Neurophysiological and subjective profile of marijuana with varying concentrations of cannabinoids.. Retrieved on 2007-06-24.
^ British Journal of Pharmacology - Abstract of article: Evidence that the plant cannabinoid delta-9-tetrahydrocannabivarin is a cannabinoid CB1 and CB2 receptor antagonist. Retrieved on 2007-06-24.
^ ^a ^b ^c Grotenhermen F. "Cannabinoids." Current Drug Targets - CNS & Neurological Disorders. 2005 Oct;4(5):507-30. PMID 16266285
^ N-Acylethanolamines in Seeds. Quantification of Molecular Species and Their Degradation upon Imbibition -- Chapman et al. 120 (4): 1157 -- PLANT PHYSIOLOGY. Retrieved on 2007-06-24.
^ ScienceDirect - Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism : Bioactive long chain N-acylethanolamines in five species of edible bivalve molluscs: Possible implications for mollusc physiology and sea food industry. Retrieved on 2007-06-24.
^ Stella N, Schweitzer P, Piomelli D. "A second endogenous cannabinoid that modulates long-term potentiation." Nature. 1997 Aug 21; 388(6644):773-8. PMID 9285589
^ reviewed in Pacher P, Batkai S, Kunos G. "The endocannabinoid system as an emerging target of pharmacotherapy." Pharmacological Reviews. 2006 Sep;58(3):389-462. PMID 16968947
^ Savinainen JR, Jarvinen T, Laine K, Laitinen JT. "Despite substantial degradation, 2-arachidonoylglycerol is a potent full efficacy agonist mediating CB(1) receptor-dependent G-protein activation in rat cerebellar membranes." British Journal of Pharmacology. 2001 Oct; 134(3):664-72. PMID 11588122
^ Hanus L, Abu-Lafi S, Fride E, et al (2001). "2-arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor". Proc. Natl. Acad. Sci. U.S.A. 98 (7): 3662-5. doi:10.1073/pnas.061029898. PMID 11259648.
^ Oka S, Tsuchie A, Tokumura A, Muramatsu M, Suhara Y, Takayama H, Waku K, Sugiura T. "Ether-linked analogue of 2-arachidonoylglycerol (noladin ether) was not detected in the brains of various mammalian species." Journal of Neurochemistry. 2003 Jun;85(6):1374-81. PMID 12787057
^ Bisogno, T., D. Melck, M. Bobrov, N. M. Gretskaya, V. V. Bezuglov, L. De Petrocellis, V. Di Marzo. "N-acyl-dopamines: novel synthetic CB1 cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo." The Biochemical Journal. 2000 Nov 1;351 Pt 3:817-24. PMID 11042139
^ Bisogno T, Ligresti A, Di Marzo V. "The endocannabinoid signalling system: biochemical aspects." Pharmacology, Biochemistry, and Behavior. 2005 Jun;81(2):224-38. PMID 15935454
^ Ralevic V. (July 2003). "Cannabinoid modulation of peripheral autonomic and sensory neurotransmission.". European journal of pharmacology 472 (1-2): 1-21. PMID 12860468.
^ Porter AC, Sauer JM, Knierman MD, Becker GW, Berna MJ, Bao J, Nomikos GG, Carter P, Bymaster FP, Leese AB, Felder CC. (June 2002). "Characterization of a Novel Endocannabinoid, Virodhamine, with Antagonist Activity at the CB1 Receptor". The Journal of pharmacology and experimental therapeutics 301 (3): 1020-1024. PMID 12023533.
^ Fride E, Bregman T, Kirkham TC. (April 2005). "Endocannabinoids and food intake: newborn suckling and appetite regulation in adulthood.". Experimental Biology and Medicine 230 (4): 225-234. doi:10.1371/journal.pbio.0020286. PMID 15792943.
^ Nicoll RA, Alger BE (2004). "The brain's own marijuana". Sci. Am. 291 (6): 68-75. PMID 15597982.
^ http://www.marijuana.org/mydna10-12-05.htm

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References

Elsohly MA, Slade D (2005). "Chemical constituents of marijuana: the complex mixture of natural cannabinoids". Life Sci. 78 (5): 539-48. doi:10.1016/j.lfs.2005.09.011. PMID 16199061.

Hanus L (1987). "Biogenesis of cannabinoid substances in the plant". Acta Universitatis Palackianae Olomucensis Facultatis Medicae 116: 47-53. PMID 2962461.

Hanuš L., Krejčí Z. Isolation of two new cannabinoid acids from Cannabis sativa L. of Czechoslovak origin. Acta Univ. Olomuc., Fac. Med. 74, 161-166 (1975)

Hanuš L., Krejčí Z., Hruban L. Isolation of cannabidiolic acid from Turkish variety of cannabis cultivated for fibre. Acta Univ. Olomuc., Fac. Med. 74, 167-172 (1975)

Turner C. E., Mole M. L., Hanuš L., ElSohly H. N. Constituents of Cannabis sativa L. XIX. Isolation and structure elucidation of cannabiglendol. A novel cannabinoid from an Indian variant. J. Nat. Prod. - Lloydia 44 (1), 27-33 (1981)

Devane WA, Hanus L, Breuer A, et al (1992). "Isolation and structure of a brain constituent that binds to the cannabinoid receptor". Science 258 (5090): 1946-9. PMID 1470919.

Hanus L, Gopher A, Almog S, Mechoulam R (1993). "Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor". J. Med. Chem. 36 (20): 3032-4. PMID 8411021.

Mechoulam R, Ben-Shabat S, Hanus L, et al (1995). "Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors". Biochem. Pharmacol. 50 (1): 83-90. PMID 7605349.

v • d • e Cannabinoids
Plant cannabinoids	CBD • CBDV • CBN • CBG • CBV • CBL • THC • THC-C4 • 11-Hydroxy-THC • THCV
Synthetic cannabinoids	Ajulemic acid • AM251 • CP 55,940 • DMHP • Dronabinol • HU-210 • JWH-133 • Levonantradol • Methanandamide • Nabilone • Nabitan • Parahexyl • Pravadoline • Rimonabant • THC-O-acetate • THC-O-phosphate • WIN 55,212-2
Endogenous cannabinoids	Arachidonoyl ethanolamide (Anandamide or AEA) • 2-Arachidonoylglycerol (2-AG) • 2-Arachidonyl glyceryl ether (noladin ether) • Virodhamine • N-arachidonoyl-dopamine (NADA)

Categories: Analgesics | Cannabinoids | Cannabis | Neurochemistry

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A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... Cannabidiol, also known as CBD, is an antipsychotic cannabinoid found in the hemp plant Cannabis sativa. ... Cannabidivarine, also known as cannabidivarol or CBDV, is a non_psychoactive cannabinoid found in minor amounts in the hemp plant Cannabis sativa. ... Cannabinol, also known as CBN, is a non_psychoactive cannabinoid found in the hemp plant Cannabis sativa. ... Cannabigerol, also known as CBG, is a non-phychoactive Cannabinoid found in the Cannabis strain of plants. ... Cannabivarin, also known as cannabivarol or CBV, is a non-psychoactive cannabinoid found in minor amounts in the hemp plant Cannabis sativa. ... Cannabicyclol, also known as CBL, is a non-psychedelic cannabinoids found in the Cannabis species. ... THC redirects here. ... 11-hydroxy-THC is the primary active Î”9-THC metabolite. ... Tetrahydrocannabivarin, also known as tetrahydrocannabivarol, THCV, or THV, is a psychoactive cannabinoid found in minor amounts in the hemp plant Cannabis sativa. ... Ajulemic acid (IP-751) is a synthetic cannabinoid derivative of the non-psychoactive THC metabolite 11-carboxy-THC which shows useful analgesic and anti-inflammatory effects without causing a subjective high.[1] It is being developed for the treatment of neuropathic pain and inflammatory conditions such as arthritis. ... AM251 is a CB1 cannabinoid receptor antagonist. ... Chemical structure of CP 55,940 CP 55,940, also written as CP55940, CP55,940, CP-55940, CP-55,940, and CP 55940, is a cannabinoid which mimics the effects of naturally occurring THC (the psychoactive compound found in marijuana). ... Dimethylheptylpyran (DMHP, 1,2-dimethylheptyl-Î”3THC) is a synthetic analogue of THC, which was invented in 1949 during attempts to elucidate the structure of Î”9-THC, the active component of cannabis. ... Tetrahydrocannabinol, also known as THC, Δ9-THC, Δ9-tetrahydrocannabinol, Δ1-tetrahydrocannabinol (using an older numbering scheme), or dronabinol, is the main psychoactive substance found in the hemp plant Cannabis sativa. ... HU-210 HU-210 (CAS# 112830-95-2) is a synthetic cannabinoid that was discovered around 1988 in the group of Dr Raphael Mechoulam at the Hebrew University. ... JWH-133 is a potent selective CB2 receptor agonist. ... Levonantradol is a synthetic cannabinoid analog of dronabinol (Marinol). ... Methanandamide [N-(2-hydroxy-1R-methylethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide] is a synthetically created stable chiral analog of anandamide. ... Nabilone is a cannabinoid with therapeutic use as an antiemetic. ... Nabitan (Nabutam, Benzopyranoperidine) is a synthetic cannabinoid analog of dronabinol (Marinol). ... Parahexyl (Synhexyl, n-hexyl-Î”3THC) is a synthetic analogue of THC, which was invented in the 1950s during attempts to elucidate the structure of Î”9THC, the active component of cannabis. ... Rimonabant (SR141716) is an anorectic anti-obesity drug. ... THC acetate ester is a derivative of THC which has been found by the DEA as an apparent controlled substance analogue of THC. It was apparently made by extracting and purifying THC from cannabis plant material followed by reaction with acetic anhydride in an analogous manner to how heroin is... THC phosphate ester is a water soluble derivative of THC, invented in 1978 in an attempt to get around the poor water solubility of THC and make it easier to inject for the purposes of animal research into its pharmacology and mechanism of action. ... WIN 55,212-2 is a chemical agent in the Cannabinoid family. ... Anandamide, also known as arachidonoylethanolamide or AEA, is an endogenous cannabinoid neurotransmitter found in animal and human organs, especially in the brain. ... 2-Arachidonoylglycerol (2-AG) is an endocannabinoid, an endogenous agonist of the CB1 receptor. ... 2-Arachidonyl glyceryl ether (2-AGE, Noladin ether) is a putative endocannabinoid discovered by LumÃr HanuÅ¡ at the Hebrew University of Jerusalem, Israel. ... Virodhamine (O-arachidonoyl ethanolamine) is an endocannibinoid and a nonclassic eicosanoid, derived from arachidonic acid. ...

Results from FactBites:

Cannabinoids - Wikipedia, the free encyclopedia (1571 words)
	Herbal cannabinoids occur naturally only in the cannabis plant, and are concentrated in a viscous resin that is produced in glandular structures known as trichomes.
	In addition to cannabinoids, the resin is rich in terpenes, which are largely responsible for the odor of the cannabis plant.
	Historically, laboratory synthesis of cannabinoids were often based on the structure of herbal cannabinoids and a large number of analogs have been produced and tested, especially in a group led by Roger Adams as early as 1941 and later in a group led by Raphael Mechoulam.

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