2-Arahidonilgliceril etar
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Nazivi | |
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IUPAC nazivs 2-[(5Z,8Z,11Z,14Z)-5,8,11,14- Ikosatetraen- 1-iloksi]-1,3-propanediol | |
Drugi nazivi 2-AGE, 2-arahidonilgliceril etar, Noladin etar, Noladin | |
Identifikacija | |
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3D model (Jmol) |
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ChemSpider |
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PubChem[1][2] C ID |
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SMILES
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Svojstva | |
C23H40O3 | |
Molarna masa | 364,56 g/mol |
Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje materijala (na 25 °C [77 °F], 100 kPa). | |
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Reference infokutije | |
2-Arahidonilgliceril etar (2-AGE, Noladinski etar) je endokanabinoid. Njegova izolacija iz svinjskog mozga, strukturno određivanje i sinteza su opisani 2001.[3]
Farmakologija
2-AGE se vezuje sa Ki od 21 nM za CB1 receptor[3] i 480 nM za CB2 receptor.[4] On je agonist na oba receptora i parcijalni agonist za TRPV1 kanal.[5] Nakon vezivanja CB2 receptora on inhibira adenilat ciklazu i stimuliše ERK-MAPK.[6] U poređenju sa 2-arahidonoilglicerolom, noladin je metabolički stabilniji, te ima duži poluživot.[7] On snižava intraokularni pritisak,[7] povišava stepen GABA preuzimanja u globus pallidus pacova[8] i ima neuroprotektivno dejstvo.[9]
Reference
- ^ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today. 15 (23-24): 1052—7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди
- ^ Evan E. Bolton; Yanli Wang; Paul A. Thiessen; Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry. 4: 217—241. doi:10.1016/S1574-1400(08)00012-1.
- ^ а б Hanus, L.; Abu-Lafi, S.; Fride, E.; Breuer, A.; Vogel, Z.; Shalev, D.; Kustanovich, I.; Mechoulam, R. (2001). „2-Arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor”. Proceedings of the National Academy of Sciences. 98 (7): 3662—3665. PMC 31108
. PMID 11259648. doi:10.1073/pnas.061029898.
- ^ Shoemaker JL, Joseph BK, Ruckle MB, Mayeux PR, Prather PL (2005). „The endocannabinoid noladin ether acts as a full agonist at human CB2 cannabinoid receptors”. J. Pharmacol. Exp. Ther. 314 (2): 868—75. PMID 15901805. doi:10.1124/jpet.105.085282.
- ^ Duncan M, Millns P, Smart D, Wright JE, Kendall DA, Ralevic V (2004). „Noladin ether, a putative endocannabinoid, attenuates sensory neurotransmission in the rat isolated mesenteric arterial bed via a non-CB1/CB2 Gi/o linked receptor”. Br. J. Pharmacol. 142 (3): 509—18. PMC 1574960
. PMID 15148262. doi:10.1038/sj.bjp.0705789.
- ^ Shoemaker JL, Ruckle MB, Mayeux PR, Prather PL (2005). „Agonist-directed trafficking of response by endocannabinoids acting at CB2 receptors”. J. Pharmacol. Exp. Ther. 315 (2): 828—38. PMID 16081674. doi:10.1124/jpet.105.089474.
- ^ а б Laine K, Järvinen K, Mechoulam R, Breuer A, Järvinen T (2002). „Comparison of the enzymatic stability and intraocular pressure effects of 2-arachidonylglycerol and noladin ether, a novel putative endocannabinoid”. Invest. Ophthalmol. Vis. Sci. 43 (10): 3216—22. PMID 12356827.
- ^ Venderova K, Brown TM, Brotchie JM (2005). „Differential effects of endocannabinoids on [(3)H]-GABA uptake in the rat globus pallidus”. Exp. Neurol. 194 (1): 284—7. PMID 15899265. doi:10.1016/j.expneurol.2005.02.012.
- ^ Sun Y; Alexander SP; Garle MJ; et al. (2007). „Cannabinoid activation of PPARα; a novel neuroprotective mechanism”. Br. J. Pharmacol. 152 (5): 734—43. PMC 2190030
. PMID 17906680. doi:10.1038/sj.bjp.0707478.
Vidi još
Spoljašnje veze
- Commercial supplier of Noladin ether
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- r
- u
8,11-DiOH-THC • 11-COOH-THC • 11-OH-THC
Arahidonoil etanolamid (Anandamid ili AEA) • 2-Arahidonoilglicerol (2-AG) • 2-Arahidonil gliceril etar (noladin etar) • Virodhamin • N-Arahidonoil dopamin (NADA) • Oleamid • RVD-Hpα
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
AM-404 • Arahidonoil serotonin • Arvanil • Biohanin A • CAY-10401 • CAY-10429 • JNJ 1661010 • JZL184 • JZL195 • Genistein • Kaempferol • LY-2183240 • O-1624 • O-2093 • Oleoiletanolamid (OEA) • Olvanil • Palmitoiletanolamid (PEA) • PF-04457845 • PF-622 • PF-750 • PF-3845 • PHOP • URB-447 • URB-597 • URB-602 • URB-754
kanabinoidnog receptora
AM-251 • AM-281 • AM-630 • AM-1387 • AM-4113 • AM-6527 • AM-6545 • BML-190 • CAY-10508 • CB-25 • CB-52 • CB-86 • CP-945,598 • Drinabant (AVE1625) • Hemopresin • Ibipinabant (SLV319) • JTE-907 • LH-21 • LY-320,135 • MDA-77 • MJ-15 • MK-9470 • NESS-0327 • NIDA-41020 • O-606 • O-1184 • O-1248 • O-2050 • O-2654 • Otenabant • PF-514273 • Rimonabant (SR141716) • Rosonabant (E-6776) • SR144528 • Surinabant (SR147778) • Taranabant (MK-0364) • TM-38837 • VCHSR