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UB-165
Systematic (IUPAC) name
(1R,6R)-5-(6-chloropyridin-3-yl)-9-azabicyclo[4.2.1]non-4-ene
Identifiers
CAS number 200432-86-6
ATC code  ?
PubChem 5310970
Chemical data
Formula C13H15ClN2 
Mol. mass 234.724
SMILES eMolecules & PubChem
Therapeutic considerations
Pregnancy cat.  ?
Legal status

UB-165 is a drug which acts as an agonist at neural nicotinic acetylcholine receptors being a full agonist at α3β2 and a partial agonist for the α4β2* isoform. It is used to study the role of this receptor subtype in the release of dopamine and noradrenaline in the brain,[1][2] and has also been used as a lead compound to derive a number of other selective nicotinic receptor ligands.[3][4][5][6]

References

  1. ^ Sharples, CG; Kaiser; Soliakov; Marks; Collins; Washburn; Wright; Spencer et al. (2000). "UB-165: a novel nicotinic agonist with subtype selectivity implicates the alpha4beta2* subtype in the modulation of dopamine release from rat striatal synaptosomes". The Journal of neuroscience : the official journal of the Society for Neuroscience 20 (8): 2783–91. PMID 10751429.  edit
  2. ^ Cao, Y.; Surowy, C.; Puttfarcken, P. (2005). "Nicotinic acetylcholine receptor-mediated 3Hdopamine release from hippocampus". The Journal of pharmacology and experimental therapeutics 312 (3): 1298–1304. doi:10.1124/jpet.104.076794. PMID 15542623.  edit
  3. ^ Gohlke, H; Gündisch; Schwarz; Seitz; Tilotta; Wegge (2002). "Synthesis and nicotinic binding studies on enantiopure diazine analogues of the novel (2-chloro-5-pyridyl)-9-azabicyclo4.2.1non-2-ene UB-165". Journal of medicinal chemistry 45 (5): 1064–72. doi:10.1021/jm010936y. PMID 11855986.  edit
  4. ^ Sharples, CG; Karig; Simpson; Spencer; Wright; Millar; Wonnacott; Gallagher (2002). "Synthesis and pharmacological characterization of novel analogues of the nicotinic acetylcholine receptor agonist (+/-)-UB-165". Journal of medicinal chemistry 45 (15): 3235–45. doi:10.1021/jm020814l. PMID 12109907.  edit
  5. ^ Sutherland, A.; Gallagher, T.; Sharples, C.; Wonnacott, S. (2003). "Synthesis of two fluoro analogues of the nicotinic acetylcholine receptor agonist UB-165". The Journal of organic chemistry 68 (6): 2475–2478. doi:10.1021/jo026698b. PMID 12636420.  edit
  6. ^ Karig, G; Large; Sharples; Sutherland; Gallagher; Wonnacott (2003). "Synthesis and nicotinic binding of novel phenyl derivatives of UB-165. Identifying factors associated with alpha7 selectivity". Bioorganic & medicinal chemistry letters 13 (17): 2825–8. doi:10.1016/S0960-894X(03)00594-8. PMID 14611837.  edit
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