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O-1918

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
O-1918
Identifiers
  • 1,3-dimethoxy-5-methyl-2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]benzene
CAS Number
PubChemCID
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC19H26O2
Molar mass286.415 g·mol−1
3D model (JSmol)
  • CC1=C[C@@H](C2=C(OC)C=C(C)C=C2OC)[C@H](C(C)=C)CC1

O-1918 is a synthetic compound related tocannabidiol, which is an antagonist at two formerorphan receptorsGPR18 andGPR55, that appear to be related to the cannabinoid receptors. O-1918 is used in the study of these receptors, which have been found to be targets for a number of endogenous and synthetic cannabinoid compounds, and are thought to be responsible for most of the non-CB1, non-CB2 mediated effects that have become evident in the course of cannabinoid research.[1][2][3][4][5]

Subsequent research by using electrophysiological approach has shown that O-1918 is a potent BKCa channel inhibitor.[6][7][8]

See also

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References

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  1. ^Offertáler L, Mo FM, Bátkai S, Liu J, Begg M, Razdan RK, et al. (March 2003). "Selective ligands and cellular effectors of a G protein-coupled endothelial cannabinoid receptor".Molecular Pharmacology.63 (3):699–705.doi:10.1124/mol.63.3.699.PMID 12606780.
  2. ^Zakrzeska A, Schlicker E, Baranowska M, Kozłowska H, Kwolek G, Malinowska B (June 2010)."A cannabinoid receptor, sensitive to O-1918, is involved in the delayed hypotension induced by anandamide in anaesthetized rats".British Journal of Pharmacology.160 (3):574–84.doi:10.1111/j.1476-5381.2009.00579.x.PMC 2931558.PMID 20105178.
  3. ^Schuelert N, McDougall JJ (August 2011). "The abnormal cannabidiol analogue O-1602 reduces nociception in a rat model of acute arthritis via the putative cannabinoid receptor GPR55".Neuroscience Letters.500 (1):72–6.doi:10.1016/j.neulet.2011.06.004.PMID 21683763.S2CID 3410391.
  4. ^Szczesniak AM, Maor Y, Robertson H, Hung O, Kelly ME (October 2011). "Nonpsychotropic cannabinoids, abnormal cannabidiol and canabigerol-dimethyl heptyl, act at novel cannabinoid receptors to reduce intraocular pressure".Journal of Ocular Pharmacology and Therapeutics.27 (5):427–35.doi:10.1089/jop.2011.0041.PMID 21770780.
  5. ^Caldwell MD, Hu SS, Viswanathan S, Bradshaw H, Kelly ME, Straiker A (June 2013)."A GPR18-based signalling system regulates IOP in murine eye".British Journal of Pharmacology.169 (4):834–43.doi:10.1111/bph.12136.PMC 3687663.PMID 23461720.
  6. ^Godlewski G, Offertáler L, Osei-Hyiaman D, Mo FM, Harvey-White J, Liu J, et al. (January 2009)."The endogenous brain constituent N-arachidonoyl L-serine is an activator of large conductance Ca2+-activated K+ channels".The Journal of Pharmacology and Experimental Therapeutics.328 (1):351–361.doi:10.1124/jpet.108.144717.PMC 2605781.PMID 18923087.
  7. ^Bondarenko AI, Panasiuk O, Drachuk K, Montecucco F, Brandt KJ, Mach F (March 2018)."The quest for endothelial atypical cannabinoid receptor: BKCa channels act as cellular sensors for cannabinoids in in vitro and in situ endothelial cells".Vascular Pharmacology.102:44–55.doi:10.1016/j.vph.2018.01.004.PMC 6481560.PMID 29355732.
  8. ^Bondarenko AI, Panasiuk O, Okhai I, Montecucco F, Brandt KJ, Mach F (June 2017)."Direct activation of Ca2+ and voltage-gated potassium channels of large conductance by anandamide in endothelial cells does not support the presence of endothelial atypical cannabinoid receptor".European Journal of Pharmacology.805:14–24.doi:10.1016/j.ejphar.2017.03.038.PMC 6520242.PMID 28327344.
Phytocannabinoids
(comparison)
Cannabibutols
Cannabichromenes
Cannabicyclols
Cannabidiols
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AllostericCBRTooltip Cannabinoid receptorligands
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enhancers

(inactivation inhibitors)
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(
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  • Others:2-PG(directly potentiates activity of 2-AG at CB1 receptor)
  • ARN-272(FAAH-like anandamide transporter inhibitor)
See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)
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