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UB-165

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From Wikipedia, the free encyclopedia

Pharmaceutical drug

Pharmaceutical compound

UB-165
Identifiers

IUPAC name (1R,6R)-5-(6-chloropyridin-3-yl)-9-azabicyclo[4.2.1]non-4-ene
CAS Number	200432-86-6^Y
PubChemCID	5310970
CompTox Dashboard(EPA)	DTXSID401028829
Chemical and physical data
Formula	C₁₃H₁₅ClN₂
Molar mass	234.73 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c2nc(Cl)ccc2C1=CCCC3CCC1N3
(verify)

UB-165 is adrug which acts as anagonist atneuronal nicotinic acetylcholine receptors being afull agonist of theα3β2 isoform and apartial agonist of theα4β2* isoform. It is used to study the role of this receptor subtype in the release ofdopamine andnoradrenaline in the brain,^[1]^[2] and has also been used as alead compound to derive a number of other selective nicotinic receptor ligands.^[3]^[4]^[5]^[6]

References

[edit]

^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.
^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.
^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.
^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.
^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.
^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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ATC code:N06B

Nicotinic acetylcholine receptor modulators

nAChRsTooltip Nicotinic acetylcholine receptors

Agonists
(and PAMsTooltip positive allosteric modulators)

Antagonists
(and NAMsTooltip negative allosteric modulators)

Precursors
(andprodrugs)

See also: Receptor/signaling modulators; Muscarinic acetylcholine receptor modulators; Acetylcholine metabolism/transport modulators

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