NationMaster - Encyclopedia: Cannabidiol

Cannabidiol, also known as CBD, is an antipsychotic cannabinoid found in the hemp plant Cannabis sativa. It is a major constituent of the plant, representing up to 40% in its extracts.^[1] The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... The term antipsychotic is applied to a group of drugs used to treat psychosis. ... Cannabinoids are a group of terpenophenolic compounds present in Cannabis (Cannabis sativa L). ... Look up Cannabis in Wiktionary, the free dictionary. ...

CBD alone is not intoxicating, but it appears to affect the euphoric effect of THC (which is an isomer of cannabidiol) and add a sedative quality. Some research, however, indicates that CBD can increase alertness.^[2] It may decrease the rate of THC clearance from the body, perhaps by interfering with the metabolism of THC in the liver. CBD does not appear to affect either the CB1 or CB2 receptors.^[3] â€œTHCâ€ redirects here. ... In chemistry, isomers are molecules with the same chemical formula and often with the same kinds of chemical bonds between atoms, but in which the atoms are arranged differently (analogous to a chemical anagram). ... Structure of the coenzyme adenosine triphosphate, a central intermediate in energy metabolism. ... For the bird, see Liver bird. ...

Medically, it appears to relieve convulsion, inflammation, anxiety, and nausea, as well as inhibit cancer cell growth^[4]. Recent studies have shown cannabidiol to be as effective as atypical antipsychotics in treating schizophrenia.^[5] The atypical antipsychotics (also known as second generation antipsychotics) are a class of prescription medications used to treat psychiatric conditions. ...

Medicinal use

In April 2005, Canadian authorities approved the marketing of Sativex, a mouth spray for multiple sclerosis to alleviate pain. Sativex contains tetrahydrocannabinol together with cannabidiol. It is marketed in Canada by GW Pharmaceuticals. Year 2005 (MMV) was a common year starting on Saturday (link displays full calendar) of the Gregorian calendar. ... 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 has also been shown to inhibit cancer cell growth, with low potency in non-cancer cells. Although the inhibitory mechanism is not yet fully understood, Ligresti et al suggest that "cannabidiol exerts its effects on these cells through a combination of mechanisms that include either direct or indirect activation of CB2 and TRPV1 receptors, and induction of oxidative stress, all contributing to induce apoptosis."^[6] A section of mouse liver showing an apoptotic cell indicated by an arrow Apoptosis (pronounced apo tÅ sis) is a process of suicide by a cell in a multicellular organism. ...

Pharmacology

Cannabidiol does not bind to CB1 or CB2 receptors but does block the effects of cannabinoid agonist by an unknown indirect way^[7]. Recently it was found to be an antagonist at GPR55, a GPCR expressed in the caudate nucleus and putamen^[8]. In cell biology, G-protein-coupled receptors (also known as GPCRs, seven transmembrane receptors, heptahelical receptors, or 7TM receptors) are transmembrane receptors that transduce an extracellular signal (ligand binding) into an intracellular signal (G protein activation). ... Grays Fig. ... The putamen is a structure in the middle of the brain, forming the striatum together with the caudate nucleus. ...

Chemistry

Cannabidiol is insoluble in water but soluble in organic solvents. At room temperature it is a colorless crystalline solid^[9]. In strongly basic medium and the presence of air it is oxidized to a quinone^[10]. Under acidic conditions it cyclizes to THC^[11]. The synthesis of cannabidiol has been accomplished by several research groups^[12]^[13]^[14]. A quinone (or benzoquinone) is either one of the two isomers of cyclohexadienedione or a derivative thereof. ... â€œTHCâ€ redirects here. ...

References

^ Grlie, L (1976). "A comparative study on some chemical and biological characteristics of various samples of cannabis resin.". Bulletin on Narcotics 14: 37-46.
^ Nicholson, AN; C Turner, BM Stone, and PJ Robson (June 2004). "Effect of Delta-9-tetrahydrocannabinol and cannabidiol on nocturnal sleep and early-morning behavior in young adults" (fee required). J Clin Psychopharmacol 24 (3): 305-13. ISSN 0271-0749. PMID 15118485. Retrieved on 2007-05-03.
^ Straus, Stephen E. (15 August 2000). "Immunoactive cannabinoids: Therapeutic prospects for marijuana constituents". Proc Natl Acad Sci U S A. 97 (17): 9363–9364.
^ Mechoulam R, Peters M, Murillo-Rodriguez E, Hanus LO (2007). "Cannabidiol - recent advances". Chemistry & Biodiversity 4 (8): 1678–1692. doi:10.1002/cbdv.200790147. PMID 17712814.
^ Zuardi, A.W; J.A.S. Crippa, J.E.C. Hallak, F.A. Moreira, F.S. Guimarães (2006). "Cannabidiol as an antipsychotic drug". Brazilian Journal of Medical and Biological Research 39: 421-429. ISSN 0100-879X ISSN 0100-879X.
^ Ligresti A, Moriello AS, Starowicz K, et al (2006). "Antitumor activity of plant cannabinoids with emphasis on the effect of cannabidiol on human breast carcinoma". J. Pharmacol. Exp. Ther. 318 (3): 1375–87. doi:10.1124/jpet.106.105247. PMID 16728591.
^ Thomas A, Baillie GL, Phillips AM, Razdan RK, Ross RA, Pertwee RG (2007). "Cannabidiol displays unexpectedly high potency as an antagonist of CB1 and CB2 receptor agonists in vitro". Br. J. Pharmacol. 150 (5): 613–23. doi:10.1038/sj.bjp.0707133. PMID 17245363.
^ Ryberg E, Larsson N, Sjögren S, et al (2007). "The orphan receptor GPR55 is a novel cannabinoid receptor". doi:10.1038/sj.bjp.0707460. PMID 17876302.
^ Jones PG, Falvello L, Kennard O, Sheldrick GM Mechoulam R (1977). "Cannabidiol". Acta Cryst. B33: 3211-3214. doi:10.1107/S0567740877010577.
^ Mechoulam R, Ben-Zvi Z (1968). "Hashish—XIII On the nature of the beam test". Tetrahedron 24 (16): 5615-5624. doi:10.1016/0040-4020(68)88159-1.
^ Gaoni Y, Mechoulam R (1966). "Hashish—VII The isomerization of cannabidiol to tetrahydrocannabinols". Tetrahedron 22 (4): 1481-1488. doi:10.1016/S0040-4020(01)99446-3.
^ Petrzilka T, Haefliger W, Sikemeier C, Ohloff G, Eschenmoser A (1967). "Synthese und Chiralität des (-)-Cannabidiols". Helv. Chim. Acta 50 (2): 719-723. doi:10.1002/hlca.19670500235.
^ Gaoni Y, Mechoulam R (1985). "Boron trifluoride etherate on alumuna - a modified Lewis acid reagent. An improved synthesis of cannabidiol". Tetrahedron Letters 26 (8): 1083-1086. doi:10.1016/S0040-4039(00)98518-6.
^ Kobayashi Y, Takeuchi A, Wang YG (2006). "Synthesis of cannabidiols via alkenylation of cyclohexenyl monoacetate". Org. Lett. 8 (13): 2699–2702. doi:10.1021/ol060692h. PMID 16774235.

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See also

Cannabinoids are a group of terpenophenolic compounds present in Cannabis (Cannabis sativa L). ... The cannabinoid receptors are a class of receptors under the G-protein coupled receptor superfamily. ... Look up Cannabis in Wiktionary, the free dictionary. ... This article is about health issues and the effects of cannabis. ... Cannabis sativa extract. ...

External links

Categories: Cannabinoids | Antipsychotics | Anti-inflammatory agents Cannabinoids are a group of terpenophenolic compounds present in Cannabis (Cannabis sativa L). ... 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. ... â€œTHCâ€ 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. ... 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. ... 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). ... 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. ... Nabilone is a cannabinoid with therapeutic use as an antiemetic. ... Nabitan (Nabutam, Benzopyranoperidine) is a synthetic cannabinoid analog of dronabinol (Marinol). ... Levonantradol is a synthetic cannabinoid analog of dronabinol (Marinol). ... JWH-133 is a potent selective CB2 receptor agonist. ... Rimonabant (SR141716) is an anorectic anti-obesity drug. ... AM251 is a CB1 cannabinoid receptor antagonist. ... 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. ... 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... 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. ... 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. ... 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. ... Virodhamine (O-arachidonoyl ethanolamine) is an endocannibinoid and a nonclassic eicosanoid, derived from arachidonic acid. ...

Contents

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