My watch list
my.chemeurope.com  

my.chemeurope.com

With an accout for my.chemeurope.com you can always see everything at a glance – and you can configure your own website and individual newsletter.

  • My watch list
  • My saved searches
  • My saved topics
  • My newsletter
Register free of charge
Login  
eng  
DeutschEnglishFrançaisEspañol

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.

?

Legal status
Routes  ?

Cannabidiol, also known as CBD, cannabinoid found in Cannabis. It is a major constituent of the plant, representing up to 40% in its extracts.[1]

CBD alone is not intoxicating, but it appears to moderate the euphoric effect of THC (which is an isomer of cannabidiol) and add a sedative quality.[2] Some research, however, indicates that CBD can increase alertness.[3] 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.[4]

Medically, it appears to relieve convulsion, inflammation, anxiety, and nausea, and to inhibit cancer cell growth[5]. Recent studies have shown cannabidiol to be as effective as atypical antipsychotics in treating schizophrenia.[6] In November 2007 it was reported that CBD reduces growth of aggressive human breast cancer cells in vitro and reduces their invasiveness. It thus represents the first non-toxic exogenous agent that can lead to down-regulation of tumor aggressiveness.[7][8]

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.

Pharmacology

Cannabidiol does not bind to CB1 or CB2 receptors but it does block the effects of cannabinoid agonists by an unknown indirect way[9]. Recently it was found to be an antagonist at the putative new cannabinoid receptor, GPR55, a GPCR expressed in the caudate nucleus and putamen[10].

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."[11] In November 2007, researchers at the California Pacific Medical Center reported that CBD shows promise for controlling the spread of metastatic breast cancer. In-vitro CBD downregulates the activity of the gene Id-1 which is responsible for tumor metastasis.[7]

Chemistry

Cannabidiol is insoluble in water but soluble in organic solvents. At room temperature it is a colorless crystalline solid[12]. In strongly basic medium and the presence of air it is oxidized to a quinone[13]. Under acidic conditions it cyclizes to THC[14]. The synthesis of cannabidiol has been accomplished by several research groups[15][16][17].

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. ^ Pickens JT (1981). "Sedative activity of cannabis in relation to its delta'-trans-tetrahydrocannabinol and cannabidiol content". Br. J. Pharmacol. 72 (4): 649–56. PMID 6269680.
  3. ^ 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.
  4. ^ Straus, Stephen E. (15 August 2000). "Immunoactive cannabinoids: Therapeutic prospects for marijuana constituents". Proc Natl Acad Sci U S A. 97 (17): 9363–9364.
  5. ^ Mechoulam R, Peters M, Murillo-Rodriguez E, Hanus LO (Aug. 2007). "Cannabidiol - recent advances". Chemistry & Biodiversity 4 (8): 1678–1692. doi:10.1002/cbdv.200790147. PMID 17712814.
  6. ^ 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.
  7. ^ a b McAllister SD, Christian RT, Horowitz MP, Garcia A, Desprez PY$$ (2007). "Cannabidiol as a novel inhibitor of Id-1 gene expression in aggressive breast cancer cells". Mol. Cancer Ther. 6 (11): 2921–7. doi:10.1158/1535-7163.MCT-07-0371. PMID 18025276.
  8. ^ Article on BBC site
  9. ^ 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.
  10. ^ 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.
  11. ^ 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.
  12. ^ Jones PG, Falvello L, Kennard O, Sheldrick GM Mechoulam R (1977). "Cannabidiol". Acta Cryst. B33: 3211-3214. doi:10.1107/S0567740877010577.
  13. ^ 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.
  14. ^ 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.
  15. ^ 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.
  16. ^ 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.
  17. ^ 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.

See also

v • d • e
Cannabinoids
Plant cannabinoidsCBD • CBDV • CBN • CBG • CBV • CBL • THC • THC-C4 • 11-Hydroxy-THC • THCV
Synthetic cannabinoidsAjulemic 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 cannabinoidsArachidonoyl ethanolamide (Anandamide or AEA) • 2-Arachidonoylglycerol (2-AG) • 2-Arachidonyl glyceryl ether (noladin ether) • Virodhamine • N-arachidonoyl-dopamine (NADA)
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Cannabidiol". A list of authors is available in Wikipedia.
Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE