Abnormal cannabidiol

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Abnormal cannabidiol
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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
PubChem CID 3060519
Chemical data
Formula C21H30O2
Molar mass 314.46[[Script error: No such module "String".]]
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Abnormal cannabidiol (abn-cbd) is a synthetic regioisomer of cannabidiol, which unlike most other cannabinoids produces vasodilator effects, lowers blood pressure, and induces cell migration, cell proliferation and mitogen-activated protein kinase activation in microglia, but without producing any psychoactive effects.[1][2] It has been shown that the actions of abnormal cannabidiol are mediated through a site separate from the CB1 and CB2 receptors,[2][3] which responds to abnormal cannabidiol, O-1602, and the endogenous ligands: anandamide (AEA), N-arachidonoyl glycine (NAGly) and N-arachidonoyl L-serine.[2][4][5][6] Multiple lines of evidence support the proposed identification of this novel target in microglia as the previously "orphan" receptor GPR18.[2] Another, more controversial, target of abnormal cannabidiol is GPR55 which has received much attention as a putative cannabinoid receptor,[7][8] although a growing body of evidence points to lysophosphatidylinositol (LPI) as the endogenous ligand for GPR55. [9][10] Further research suggests there are yet more additional cannabinoid receptors.[11][12][13][14]


See also

References

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  1. ↑ 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
  2. ↑ 2.0 2.1 2.2 2.3 Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  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. ↑ Kapur A, Zhao P, Sharir H, Bai Y, Caron MG, Barak LS, Abood ME. Atypical Responsiveness of the Orphan Receptor GPR55 to Cannabinoid Ligands. The Journal of Biological Chemistry. 2009 Sep;284:29817-29827. PMID 19723626
  10. ↑ Henstridge CM, Balenga NAB, Ford LA, Ross RA, Waldhoer M, Irving AJ. The GPR55 ligand L-alpha-lysophosphatidylinositol promotes RhoA-dependent Ca2+ signaling and NFAT activtion. The FASEB Journal. 2009;23:183-193. PMID 18757503
  11. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  12. ↑ 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
  13. ↑ 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
  14. ↑ 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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