UB-165
Identifiers
  • (1R,6R)-5-(6-chloropyridin-3-yl)-9-azabicyclo[4.2.1]non-4-ene
CAS Number
PubChem CID
Chemical and physical data
FormulaC13H15ClN2
Molar mass234.724 g·mol−1
3D model (JSmol)
  • c2nc(Cl)ccc2C1=CCCC3CCC1N3
  (verify)

UB-165 is a drug which acts as an agonist at neuronal nicotinic acetylcholine receptors being a full agonist of the α3β2 isoform and a partial agonist of 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 S, Soliakov L, Marks MJ, Collins AC, Washburn M, et al. (April 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. 20 (8): 2783–91. doi:10.1523/JNEUROSCI.20-08-02783.2000. PMC 6772190. PMID 10751429.
  2. ↑ Cao YJ, Surowy CS, Puttfarcken PS (March 2005). "Nicotinic acetylcholine receptor-mediated [3H]dopamine release from hippocampus". The Journal of Pharmacology and Experimental Therapeutics. 312 (3): 1298–304. doi:10.1124/jpet.104.076794. PMID 15542623. S2CID 20437091.
  3. ↑ Gohlke H, Gündisch D, Schwarz S, Seitz G, Tilotta MC, Wegge T (February 2002). "Synthesis and nicotinic binding studies on enantiopure diazine analogues of the novel (2-chloro-5-pyridyl)-9-azabicyclo[4.2.1]non-2-ene UB-165". Journal of Medicinal Chemistry. 45 (5): 1064–72. doi:10.1021/jm010936y. PMID 11855986.
  4. ↑ Sharples CG, Karig G, Simpson GL, Spencer JA, Wright E, Millar NS, et al. (July 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.
  5. ↑ Sutherland A, Gallagher T, Sharples CG, Wonnacott S (March 2003). "Synthesis of two fluoro analogues of the nicotinic acetylcholine receptor agonist UB-165". The Journal of Organic Chemistry. 68 (6): 2475–8. doi:10.1021/jo026698b. PMID 12636420.
  6. ↑ Karig G, Large JM, Sharples CG, Sutherland A, Gallagher T, Wonnacott S (September 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.
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