Abnormalni kanabidiol
IUPAC ime | |
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4-[(1S,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol | |
Identifikatori | |
CAS broj | 78216-32-7 Y |
ATC kod | none |
PubChem | CID 3060519 |
ChemSpider | 2321442 Y |
Hemijski podaci | |
Formula | C21H30O2 |
Molarna masa | 314,46 |
SMILES
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InChI
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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]
Vidi još
Literatura
- ^ 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.
- ^ 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 . PMID 20346144. doi:10.1186/1471-2202-11-44.
- ^ 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 . PMID 10570211. doi:10.1073/pnas.96.24.14136.
- ^ 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 . PMID 20346144. doi:10.1186/1471-2202-11-44. Сукоб URL—викивеза (помоћ)
- ^ 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.
- ^ 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.
- ^ 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 . PMID 16467152. doi:10.1073/pnas.0510676103.
- ^ 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.
- ^ 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 . PMID 17876302. doi:10.1038/sj.bjp.0707460.
- ^ 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 . PMID 19723626. doi:10.1074/jbc.M109.050187.
- ^ 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.
- ^ Brown AJ (2007). „Novel cannabinoid receptors”. British Journal of Pharmacology. 152 (5): 567—75. PMC 2190013 . PMID 17906678. doi:10.1038/sj.bjp.0707481.
- ^ 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 . PMID 17704827. doi:10.1038/sj.bjp.0707419.
- ^ 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.
- ^ 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.
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agonisti receptora
Klasični kanabinoidi (Dibenzopirani) | A-40174 • A-41988 • A-42574 • Ajulemska kiselina • AM-087 • AM-411 • AM-855 • AM-905 • AM-906 • AM-919 • AM-926 • AM-938 • AM-2389 • AM-4030 • AMG-1 • AMG-3 • AMG-36 • AMG-41 • Deksanabinol (HU-211) • DMHP • Dronabinol • HHC • HU-210 • JWH-051 • JWH-133 • JWH-139 • JWH-161 • JWH-229 • JWH-359 • KM-233 • L-759,633 • L-759,656 • Levonantradol (CP 50,5561) • Menabitan • Nabazenil • Nabidroks (Kanbisol) • Nabilon • Nabitan • Naboktat • O-224 • O-581 • O-774 • O-806 • O-823 • O-1057 • O-1125 • O-1191 • O-1238 • O-2048 • O-2113 • O-2365 • O-2372 • O-2373 • O-2383 • O-2426 • O-2484 • O-2545 • O-2694 • O-2715 • O-2716 • O-3223 • O-3226 • Paraheksil • Perotetinen • Pirnabin • THC-O-acetat • THC-O-fosfat |
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Neklasični kanabinoidi | |
Benzoilindoli | 1-Butil-3-(2-metoksibenzoil)indol • 1-Butil-3-(4-metoksibenzoil)indol • 1-Pentil-3-(2-metoksibenzoil)indol • AM-630 • AM-679 • AM-694 • AM-1241 • AM-2233 • GW-405,833 (L-768,242) • Pravadolin • RCS-4 • WIN 54,461 |
Naftoilindoli | |
Naftilmetilindoli | JWH-175 • JWH-184 • JWH-185 • JWH-192 • JWH-194 • JWH-195 • JWH-196 • JWH-197 • JWH-199 |
Fenilacetilindoli | |
Naftoilpiroli | |
Eikozanoidi | AM-883 • AM-1346 • Arahidonil-2'-hloroetilamid (ACEA) • Arahidonilciklopropilamid (ACPA) • Metanandamid (AM-356) • O-585 • O-689 • O-1812 • O-1860 • O-1861 |
Drugi | N-(S)-Fenhil-1-(2-morfolinoetil)-7-metoksindol-3-karboksamid • A-796,260 • A-834,735 • A-836,339 • A-955,840 • Abnormalni kanabidiol • AB-001 • AKB48 • AM-1248 • AZ-11713908 • BAY 38-7271 • BAY 59-3074 • CB-13 • CB-86 • CBS-0550 • GW-842,166X • JWH-176 • JTE 7-31 • LASSBio-881 • LBP-1 • Lilamin • MDA-7 • MDA-19 • NMP-7 • O-889 • O-1269 • O-1270 • O-1399 • O-1918 • O-2220 • Org 28312 • Org 28611 • PF-03550096 • S-444,823 • Tedalinab • UR-144 • URB-447 • SER-601 • VSN-16 • WIN 56,098 • XLR-11 |
kanabinoidnih receptora
pojačivači aktivnosti
kanabinoidnog receptora