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07-SEPTEMBER-2008 03:17:44 - 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 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, is a 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.78 It is also a neuroprotective antioxidant.9 Contents 1 Medicinal use 2 Pharmacology 3 Chemistry 4 References 5 See also 6 External links 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.10 Recently it was found to be an antagonist at the putative new cannabinoid receptor, GPR55, a GPCR expressed in the caudate nucleus and putamen.11 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.12 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.13 In strongly basic medium and the presence of air it is oxidized to a quinone.14 Under acidic conditions it cyclizes to THC.15 The synthesis of cannabidiol has been accomplished by several research groups.161718 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. ^ 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. ^ 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. doi:10.1097/01.jcp.0000125688.05091.8f. 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. doi:10.1073/pnas.180314297. PMID 10931962. ^ 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. ^ 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. ^ 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. ^ Article on BBC site ^ Cannabidiol and -Δ9-tetrahydrocannabinol are neuroprotective antioxidants, A. J. Hampson, M. Grimaldi, J. Axelrod, and D. Wink, Proc Natl Acad Sci U S A. 1998 July 7; 9514: 8268-8273. ^ 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. British Journal of Pharmacology 152: 1092. doi:10.1038/sj.bjp.0707460. PMID 17876302. ^ 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. ^ 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:10.1016/0040-40206888159-1. ^ Gaoni Y, Mechoulam R 1966. Hashish-VII The isomerization of cannabidiol to tetrahydrocannabinols. Tetrahedron 22 4: 1481-1488. doi:10.1016/S0040-40200199446-3. ^ 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/S0040-40390098518-6. ^ 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. See also Cannabinoids Cannabinoid receptors Cannabis Health issues and the effects of cannabis Medical marijuana External links Erowid Compounds found in Cannabis sativa v d e Cannabinoids Plant cannabinoids CBD CBDV CBN CBG CBV CBL THC THC-C4 THCV Cannabinoid metabolites 11-Hydroxy-THC 11-nor-9-Carboxy-THC Endogenous cannabinoids Arachidonoyl ethanolamide Anandamide or AEA 2-Arachidonoylglycerol 2-AG 2-Arachidonyl glyceryl ether noladin ether Virodhamine N-arachidonoyl-dopamine NADA; Oleamide Synthetic cannabinoid agonists Classical cannabinoids Dibenzopyrans A-41988 Ajulemic acid AM-087 AM-411 AM-855 AM-905 AM-906 AM-919 AM-938 AM-4030 AMG-1 AMG-3 AMG-36 AMG-41 Dexanabinol HU-211 DMHP Dronabinol HU-210 JWH-051 JWH-133 JWH-139 L-759,633 L-759,656 Levonantradol Nabilone Nabitan O-806 O-823 O-1057 O-1125 O-1238 O-2545 O-2694 Parahexyl THC-O-acetate THC-O-phosphate Nonclassical cannabinoids CP 47,497 CP 55,244 CP 55,940 HU-308 2-Isopropyl-5-methyl-1-2,6-dihydroxy-4-nonylphenylcyclohex-1-ene Aminoalkylindoles AM-630 AM-1241 JWH-015 JWH-018 JWH-073 JWH-081 JWH-200 L-768,242 Pravadoline WIN 55,212-2 Aminoalkylpyrroles JWH-030 JWH-147 JWH-307 Eicosanoids AM-883 Arachidonyl-2'-chloroethylamide Arachidonylcyclopropylamide Methanandamide O-585 O-689 O-1812 O-1860 O-1861 Others BAY 38-7271 BAY 59-3074 GW 842,166X JWH-171 O-2220 Endocannabinoid activity enhancers AM-404 CAY-10401 CAY-10402 N-arachidonoyl-serotonin O-1624 PF-622 PF-750 URB-597 URB-602 URB-754 Cannabinoid antagonists and inverse agonists AM-251 AM-281 AM-630 AVE-1625 BML-190 CAY-10508 CB-25 CB-52 JTE-907 LY-320,135 MK-9470 NESS-0327 O-1184 O-2050 O-2654 Rimonabant SLV-319 SR-144,528 Surinabant Taranabant VCHSR Retrieved from http://en..org/wiki/Cannabidiol Categories: Cannabinoids | Antipsychotics | Anti-inflammatory agents Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Español Italiano Magyar Polski Português РуÑ?Ñ?кий Suomi Svenska This page was last modified on 30 July 2008, at 22:37
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