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Encyclopedia > Cannabidiol
Cannabidiol
Systematic (IUPAC) name
2-((1S,6S)-3-methyl-6-(prop-1-en-2-yl)
cyclohex-2-enyl)-5-pentylbenzene-1,3-diol
Identifiers
CAS number 13956-29-1
ATC code noentry
PubChem 644019
DrugBank none
Chemical data
Formula C21H30O2 
Mol. mass 314.46
SMILES search in eMolecules, PubChem
Physical data
Melt. point 66 °C (151 °F)
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

? Image File history File links Download high-resolution version (3030x1799, 30 KB) Description: chemical structure of cannabidiol Author: Cacycle Date of creation: 8 January 2006 (UTC) Source: selfmade Copyright: GNU Free Documentation License (GFDL) Creative Commons License (attribution, sharealike, 2. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The biological half-life of a substance is the time required for half of that substance to be removed from an organism by either a physical or a chemical process. ... The kidneys are important excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status
Routes  ?

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] “THC” 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. ...

Contents

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 tō 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. ... “THC” redirects here. ...


References

  1. ^ Grlie, L (1976). "A comparative study on some chemical and biological characteristics of various samples of cannabis resin.". Bulletin on Narcotics 14: 37-46. 
  2. ^ 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. 
  3. ^ Straus, Stephen E. (15 August 2000). "Immunoactive cannabinoids: Therapeutic prospects for marijuana constituents". Proc Natl Acad Sci U S A. 97 (17): 9363–9364. 
  4. ^ 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. 
  5. ^ 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. 
  6. ^ 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. 
  7. ^ 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. 
  8. ^ 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. 
  9. ^ Jones PG, Falvello L, Kennard O, Sheldrick GM Mechoulam R (1977). "Cannabidiol". Acta Cryst. B33: 3211-3214. doi:10.1107/S0567740877010577. 
  10. ^ 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. 
  11. ^ 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. 
  12. ^ 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. 
  13. ^ 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. 
  14. ^ 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. 

ISSN, or International Standard Serial Number, is the unique eight-digit number applied to a periodical publication including electronic serials. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 123rd day of the year (124th in leap years) in the Gregorian calendar. ... 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. ... ISSN, or International Standard Serial Number, is the unique eight-digit number applied to a periodical publication including electronic serials. ... 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. ... 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. ... 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. ... 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. ... 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. ... 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. ... 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. ... 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. ... 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. ...

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

  • Erowid Compounds found in Cannabis sativa

  Results from FactBites:
 
Cannabidiol: The Wonder Drug of the 21st Century? (803 words)
Cannabidiol, CBD, a non-psychoactive cannabinoid of Marijuana, was given to 5 patients with dystonia disorders.
Cannabidiol reported having slept significantly more than those receiving placebo; seven out of eight epileptics receiving Cannabidiol had improvement of their disease state.
Cannabidiol (CBD) which is not psychoactive, is very high in fiber-type hemp but low in drug-type marijuana.
Cannabidiol - Wikipedia, the free encyclopedia (189 words)
Cannabidiol, also known as CBD, is a non-psychoactive cannabinoid found in the hemp plant Cannabis sativa.
CBD alone is not psychoactive, but it appears to reduce the euphoric effect of THC (which is an isomer of cannabidiol) and add a sedative quality.
It may decrease the rate of THC clearance from the body, perhaps by interfering with the metabolism of THC in the liver.
  More results at FactBites »

 
 

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