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Abnormal cannabidiol
Systematic (IUPAC) name
4-[(1S,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol
Identifiers
CAS number 78216-32-7
ATC code  ?
PubChem 3060519
Chemical data
Formula C 21H30O2  
Mol. mass 314.46
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?

Abnormal cannabidiol (abn-cbd) is a cannabinoid derivative found in marijuana,[1] which unlike most other cannabinoids produces vasodilator effects and lowers blood pressure, but without producing any psychoactive effects.[2] It has been shown that the vasodilator actions of abnormal cannabidiol are mediated through a site separate from the CB1 and CB2 receptors,[3] which responds to abnormal cannabidiol and the endogenous ligands anandamide and N-arachidonoyl L-serine.[4][5][6] This novel target has subsequently been identified as the previously orphan receptor GPR55, which has consequently been suggested as the previously anticipated CB3 receptor,[7][8] although further research suggests there may be one or more additional cannabinoid receptors beyond the three already identified.[9][10][11][12]

See also

References

  1. ^ Anday JK, Mercier RW. Gene ancestry of the cannabinoid receptor family. Pharmacological Research. 2005 Dec;52(6):463-6. PMID 16118055
  2. ^ Adams MD, Earnhardt JT, Martin BR, Harris LS, Dewey WL, Razdan RK. A cannabinoid with cardiovascular activity but no overt behavioral effects. Experientia. 1977 Sep 15;33(9):1204-5.PMID 891878
  3. ^ Járai Z, Wagner JA, Varga K, Lake KD, Compton DR, Martin BR, Zimmer AM, Bonner TI, Buckley NE, Mezey E, Razdan RK, Zimmer A, Kunos G. Cannabinoid-induced mesenteric vasodilation through an endothelial site distinct from CB1 or CB2 receptors. Proceedings of the National Academy of Sciences USA. 1999 Nov 23;96(24):14136-41. PMID 10570211
  4. ^ Walter L, Franklin A, Witting A, Wade C, Xie Y, Kunos G, Mackie K, Stella N. Nonpsychotropic cannabinoid receptors regulate microglial cell migration. Journal of Neuroscience. 2003 Feb 15;23(4):1398-405. PMID 12598628
  5. ^ Offertáler L, Mo FM, Bátkai S, Liu J, Begg M, Razdan RK, Martin BR, Bukoski RD, Kunos G. Selective ligands and cellular effectors of a G protein-coupled endothelial cannabinoid receptor. Molecular Pharmacology. 2003 Mar;63(3):699-705. PMID 12606780
  6. ^ Milman G, Maor Y, Abu-Lafi S, Horowitz M, Gallily R, Batkai S, Mo FM, Offertaler L, Pacher P, Kunos G, Mechoulam R. N-arachidonoyl L-serine, an endocannabinoid-like brain constituent with vasodilatory properties. Proceedings of the National Academy of Sciences USA. 2006 Feb 14;103(7):2428-33. PMID 16467152
  7. ^ McCollum L, Howlett AC, Mukhopadhyay S. Anandamide-mediated CB1/CB2 cannabinoid receptor--independent nitric oxide production in rabbit aortic endothelial cells. Journal of Pharmacology and Experimental Therapeutics. 2007 Jun;321(3):930-7. PMID 17379772
  8. ^ Ryberg E, Larsson N, Sjögren S, Hjorth S, Hermansson NO, Leonova J, Elebring T, Nilsson K, Drmota T, Greasley PJ. The orphan receptor GPR55 is a novel cannabinoid receptor. British Journal of Pharmacology. 2007 Dec;152(7):1092-101. PMID 17876302
  9. ^ Brown AJ (November 2007). "Novel cannabinoid receptors". British Journal of Pharmacology 152 (5): 567–75. doi:10.1038/sj.bjp.0707481. PMID 17906678.  
  10. ^ Johns DG, Behm DJ, Walker DJ, Ao Z, Shapland EM, Daniels DA, Riddick M, Dowell S, Staton PC, Green P, Shabon U, Bao W, Aiyar N, Yue TL, Brown AJ, Morrison AD, Douglas SA. The novel endocannabinoid receptor GPR55 is activated by atypical cannabinoids but does not mediate their vasodilator effects. British Journal of Pharmacology. 2007 Nov;152(5):825-31. PMID 17704827
  11. ^ McHugh D, Tanner C, Mechoulam R, Pertwee RG, Ross RA. Inhibition of human neutrophil chemotaxis by endogenous cannabinoids and phytocannabinoids: evidence for a site distinct from CB1 and CB2. Molecular Pharmacology. 2008 Feb;73(2):441-50. PMID 17965195
  12. ^ Kreutz S, Koch M, Böttger C, Ghadban C, Korf HW, Dehghani F. 2-Arachidonoylglycerol elicits neuroprotective effects on excitotoxically lesioned dentate gyrus granule cells via abnormal-cannabidiol-sensitive receptors on microglial cells. Glia. 2009 Feb;57(3):286-94. PMID 18837048
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