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
Klinički podaci
Identifikatori
CAS broj 78216-32-7
ATC kod nije dodeljen
PubChem[1][2] 3060519
ChemSpider[3] 2321442
Hemijski podaci
Formula C21H30O2 
Mol. masa 314,46
SMILES eMolekuli & PubHem
InChI
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 DaY
Key: YWEZXUNAYVCODW-OALUTQOASA-N DaY
Farmakoinformacioni podaci
Trudnoća ?
Pravni status

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.[4][5]

Bilo je pokazano da akcije abnormalnog kanabidiola nisu posredovane kroz CB1 i CB2 receptore.[5][6] Abnormalni kanabidiol i O-1602 deluju na receptor čiji endogeni ligandi su: anandamid (AEA), N-arahidonoil glicin (NAGly) i N-arahidonoil L-serin.[7][8][9][10] Višestruke linije dokaza idu u podršku predlogu da je GPR18 receptor za te ligande.[5] Jedan drugi, kontroverzniji biološki cilj abnormalnog kanabidiola je GPR55, koji je zadobio mnogo pažnje jer se smatralo da je kanabinoidni receptor.[11][12] Međutim, sve je više dokaza da je lizofosfatidilinozitol (LPI) endogeni ligand za GPR55.[13][14] Dalja istraživanja su dovela do zaključka da postoji još nekoliko kanabinoidnih receptora.[15][16][17][18]

Vidi još

Literatura

  1. ↑ 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. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519.  edit
  2. ↑ 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. 
  3. ↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846.  edit
  4. ↑ 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. 
  5. ↑ 5,0 5,1 5,2 McHugh D, Hu SS, Rimmerman N, Juknat A, Vogil Z, Walker JM, Bradshaw HB (March 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. DOI:10.1186/1471-2202-11-44. PMC 2865488. PMID 20346144. 
  6. ↑ Járai, Z; Wagner, JA; Varga, K; Lake, KD; Compton, DR; Martin, BR; Zimmer, AM; Bonner, TI i dr.. (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. DOI:10.1073/pnas.96.24.14136. PMC 24203. PMID 10570211. 
  7. ↑ McHugh D, Hu SS, Rimmerman N, Juknat A, Vogil Z, Walker JM, Bradshaw HB (March 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. DOI:10.1186/1471-2202-11-44. PMC 2865488. PMID 20346144. 
  8. ↑ 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. 
  9. ↑ Offertáler, L; Mo, FM; Bátkai, S; Liu, J; Begg, M; Razdan, RK; Martin, BR; Bukoski, RD i dr.. (2003). „Selective ligands and cellular effectors of a G protein-coupled endothelial cannabinoid receptor.”. Molecular pharmacology 63 (3): 699–705. PMID 12606780. 
  10. ↑ Milman, G; Maor, Y; Abu-Lafi, S; Horowitz, M; Gallily, R; Batkai, S; Mo, FM; Offertaler, L i dr.. (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. DOI:10.1073/pnas.0510676103. PMC 1413724. PMID 16467152. 
  11. ↑ 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. DOI:10.1124/jpet.106.117549. PMID 17379772. 
  12. ↑ Ryberg, E; Larsson, N; Sjögren, S; Hjorth, S; Hermansson, NO; Leonova, J; Elebring, T; Nilsson, K i dr.. (2007). „The orphan receptor GPR55 is a novel cannabinoid receptor.”. British journal of pharmacology 152 (7): 1092–101. DOI:10.1038/sj.bjp.0707460. PMC 2095107. PMID 17876302. 
  13. ↑ 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. DOI:10.1074/jbc.M109.050187. PMC 2785612. PMID 19723626. 
  14. ↑ 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. DOI:10.1096/fj.08-108670. PMID 18757503. 
  15. ↑ Brown AJ (November 2007). „Novel cannabinoid receptors”. British Journal of Pharmacology 152 (5): 567–75. DOI:10.1038/sj.bjp.0707481. PMC 2190013. PMID 17906678. 
  16. ↑ Johns, DG; Behm, DJ; Walker, DJ; Ao, Z; Shapland, EM; Daniels, DA; Riddick, M; Dowell, S i dr.. (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. DOI:10.1038/sj.bjp.0707419. PMC 2190033. PMID 17704827. 
  17. ↑ 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. DOI:10.1124/mol.107.041863. PMID 17965195. 
  18. ↑ 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. DOI:10.1002/glia.20756. PMID 18837048. 
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Fitokanabinoidi
Kariofilen  • CBCV • CBC • CBD • CBDV • CBGM • CBGV • CBN • CBG • CBV • CBL • THC • THCA • THC-C4 • THCV
Kanabinoidni metaboliti
8,11-DiOH-THC • 11-COOH-THC • 11-OH-THC
Endogeni kanabinoid
Arahidonoil etanolamid (Anandamid ili AEA) • 2-Arahidonoilglicerol (2-AG) • 2-Arahidonil gliceril etar (noladin etar) • Virodhamin • N--Arahidonoil dopamin (NADA) • Oleamid • RVD-Hpα
Sintetički kanabinoid
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
Neklasični kanabinoidi
Kanabicikloheksanol • CP 47,497 • CP 55,244 • CP 55,940 • HU-308 • HU-320 • HU-331 • HU-336 • HU-345 • HU-910  • Nonabin • O-1376 • O-1422 • O-1601 • O-1656 • O-1657 • O-1660 • O-1871 • SPA-229  • Tinabinol • 2-Izopropil-5-metil-1-(2,6-dihidroksi-4-nonilfenil)ciklohesk-1-en
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
AM-1220 • AM-1221 • AM-1235 • AM-2201 • AM-2232 • JWH-007 • JWH-015 • JWH-018 • JWH-019 • JWH-073 • JWH-081 • JWH-098 • JWH-116 • JWH-122 • JWH-149 • JWH-164 • JWH-182 • JWH-193 • JWH-198 • JWH-200 • JWH-210 • JWH-398 • JWH-424 • MAM-2201 • WIN 55,212-2
Naftilmetilindoli
JWH-175 • JWH-184 • JWH-185 • JWH-192 • JWH-194 • JWH-195 • JWH-196 • JWH-197 • JWH-199
Fenilacetilindoli
Naftoilpiroli
JWH-030 • JWH-147 • JWH-307 • JWH-369 • JWH-370
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
Alosterni modulatori
kanabinoidnih receptora
Org 27569 • Org 27759 • Org 29647 • RTI-371
Endokanabinoidni
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
Antagonisti i inverzni agonisti
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