Abnormalni kanabidiol

Abnormalni kanabidiol
IUPAC ime
4-[(1S,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol
Identifikatori
CAS broj78216-32-7 ДаY
ATC kodnone
PubChemCID 3060519
ChemSpider2321442 ДаY
Hemijski podaci
FormulaC21H30O2
Molarna masa314,46
  • CCCCCC1=CC(=CC(=C1[C@H]2C=C(CC[C@H]2C(=C)C)C)O)O
  • InChI=1S/C21H30O2/c1-5-6-7-8-16-12-17(22)13-20(23)21(16)19-11-15(4)9-10-18(19)14(2)3/h11-13,18-19,22-23H,2,5-10H2,1,3-4H3/t18-,19-/m0/s1 ДаY
  • Key:YWEZXUNAYVCODW-OALUTQOASA-N ДаY

Abnormalni kanabidiol (abn-cbd) je sintetički regioizomer kanabidiola, koji za razliku od većine drugih kanabinoida proizvodi vazodilatorne efekte, snižava krvni pritisak, i podstiče ćelijsku migracija, ćelijsku proliferaciju i aktivira mitogenom-aktivirane proteinske kinaze kod mikroglija, ali ne proizvodi psihoaktivne efekte.[1][2]

Bilo je pokazano da akcije abnormalnog kanabidiola nisu posredovane kroz CB1 i CB2 receptore.[2][3] Abnormalni kanabidiol i O-1602 deluju na receptor čiji endogeni ligandi su: anandamid (AEA), N-arahidonoil glicin (NAGly) i N-arahidonoil L-serin.[4][5][6][7] Višestruke linije dokaza idu u podršku predlogu da je GPR18 receptor za te ligande.[2] Jedan drugi, kontroverzniji biološki cilj abnormalnog kanabidiola je GPR55, koji je zadobio mnogo pažnje jer se smatralo da je kanabinoidni receptor.[8][9] Međutim, sve je više dokaza da je lizofosfatidilinozitol (LPI) endogeni ligand za GPR55.[10][11] Dalja istraživanja su dovela do zaključka da postoji još nekoliko kanabinoidnih receptora.[12][13][14][15]

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Literatura

[уреди | уреди извор]
  1. ^ Adams, MD; Earnhardt, JT; Martin, BR; Harris, LS; Dewey, WL; Razdan, RK (1977). „A cannabinoid with cardiovascular activity but no overt behavioral effects”. Experientia. 33 (9): 1204—5. PMID 891878. 
  2. ^ а б в McHugh D, Hu SS, Rimmerman N, Juknat A, Vogil Z, Walker JM, Bradshaw HB (2010). „N-arachidonoyl glycine, an abundant endogenous lipid, potently drives directed cellular migration through GPR18, the putative abnormal cannabidiol receptor”. BMC Neuroscience. 11 (1): 44. PMC 2865488 Слободан приступ. PMID 20346144. doi:10.1186/1471-2202-11-44. 
  3. ^ Járai, Z; Wagner, JA; Varga, K; Lake, KD; Compton, DR; Martin, BR; Zimmer, AM; Bonner, TI; Buckley, NE (1999). „Cannabinoid-induced mesenteric vasodilation through an endothelial site distinct from CB1 or CB2 receptors.”. Proceedings of the National Academy of Sciences of the United States of America. 96 (24): 14136—41. PMC 24203 Слободан приступ. PMID 10570211. doi:10.1073/pnas.96.24.14136. 
  4. ^ McHugh D, Hu SS, Rimmerman N, Juknat A, Vogil Z, Walker JM, Bradshaw HB (2010). „N-arachidonoyl glycine, an abundant endogenous lipid, potently drives directed cellular migration through [[GPR18]], the putative abnormal cannabidiol receptor”. BMC Neuroscience. 11 (1): 44. PMC 2865488 Слободан приступ. PMID 20346144. doi:10.1186/1471-2202-11-44.  Сукоб URL—викивеза (помоћ)
  5. ^ Walter, L; Franklin, A; Witting, A; Wade, C; Xie, Y; Kunos, G; MacKie, K; Stella, N (2003). „Nonpsychotropic cannabinoid receptors regulate microglial cell migration.”. The Journal of neuroscience : the official journal of the Society for Neuroscience. 23 (4): 1398—405. PMID 12598628. 
  6. ^ Offertáler, L; Mo, FM; Bátkai, S; Liu, J; Begg, M; Razdan, RK; Martin, BR; Bukoski, RD; Kunos, G (2003). „Selective ligands and cellular effectors of a G protein-coupled endothelial cannabinoid receptor.”. Molecular pharmacology. 63 (3): 699—705. PMID 12606780. 
  7. ^ Milman, G; Maor, Y; Abu-Lafi, S; Horowitz, M; Gallily, R; Batkai, S; Mo, FM; Offertaler, L; Pacher, P (2006). „N-arachidonoyl L-serine, an endocannabinoid-like brain constituent with vasodilatory properties.”. Proceedings of the National Academy of Sciences of the United States of America. 103 (7): 2428—33. PMC 1413724 Слободан приступ. PMID 16467152. doi:10.1073/pnas.0510676103. 
  8. ^ McCollum, L; Howlett, AC; Mukhopadhyay, S (2007). „Anandamide-mediated CB1/CB2 cannabinoid receptor--independent nitric oxide production in rabbit aortic endothelial cells.”. The Journal of pharmacology and experimental therapeutics. 321 (3): 930—7. PMID 17379772. doi:10.1124/jpet.106.117549. 
  9. ^ Ryberg, E; Larsson, N; Sjögren, S; Hjorth, S; Hermansson, NO; Leonova, J; Elebring, T; Nilsson, K; Drmota, T (2007). „The orphan receptor GPR55 is a novel cannabinoid receptor.”. British journal of pharmacology. 152 (7): 1092—101. PMC 2095107 Слободан приступ. PMID 17876302. doi:10.1038/sj.bjp.0707460. 
  10. ^ Kapur, A; Zhao, P; Sharir, H; Bai, Y; Caron, MG; Barak, LS; Abood, ME (2009). „Atypical responsiveness of the orphan receptor GPR55 to cannabinoid ligands.”. The Journal of biological chemistry. 284 (43): 29817—27. PMC 2785612 Слободан приступ. PMID 19723626. doi:10.1074/jbc.M109.050187. 
  11. ^ Henstridge, CM; Balenga, NA; Ford, LA; Ross, RA; Waldhoer, M; Irving, AJ (2009). „The GPR55 ligand L-alpha-lysophosphatidylinositol promotes RhoA-dependent Ca2+ signaling and NFAT activation.”. The FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 23 (1): 183—93. PMID 18757503. doi:10.1096/fj.08-108670. 
  12. ^ Brown AJ (2007). „Novel cannabinoid receptors”. British Journal of Pharmacology. 152 (5): 567—75. PMC 2190013 Слободан приступ. PMID 17906678. doi:10.1038/sj.bjp.0707481. 
  13. ^ Johns, DG; Behm, DJ; Walker, DJ; Ao, Z; Shapland, EM; Daniels, DA; Riddick, M; Dowell, S; Staton, PC (2007). „The novel endocannabinoid receptor GPR55 is activated by atypical cannabinoids but does not mediate their vasodilator effects.”. British journal of pharmacology. 152 (5): 825—31. PMC 2190033 Слободан приступ. PMID 17704827. doi:10.1038/sj.bjp.0707419. 
  14. ^ McHugh, D; Tanner, C; Mechoulam, R; Pertwee, RG; Ross, RA (2008). „Inhibition of human neutrophil chemotaxis by endogenous cannabinoids and phytocannabinoids: evidence for a site distinct from CB1 and CB2.”. Molecular pharmacology. 73 (2): 441—50. PMID 17965195. doi:10.1124/mol.107.041863. 
  15. ^ Kreutz, S; Koch, M; Böttger, C; Ghadban, C; Korf, HW; Dehghani, F (2009). „2-Arachidonoylglycerol elicits neuroprotective effects on excitotoxically lesioned dentate gyrus granule cells via abnormal-cannabidiol-sensitive receptors on microglial cells.”. Glia. 57 (3): 286—94. PMID 18837048. doi:10.1002/glia.20756.