TC-1698

TC-1698

Legal status
Legal status	Legal
Identifiers
IUPAC name 2-pyridin-3-yl-1-azabicyclo[3.2.2]nonane
PubChem (CID)	10130417
ChemSpider	8305933
ChEMBL	CHEMBL2151442
Chemical and physical data
Formula	C13H18N2
Molar mass	202.295
3D model (Jmol)	Interactive image
SMILES c2ncccc2C1CCC3CCN1CC3
InChI InChI=1S/C13H18N2/c1-2-12(10-14-7-1)13-4-3-11-5-8-15(13)9-6-11/h1-2,7,10-11,13H,3-6,8-9H2 Key:WIEWCOLOPGXZDJ-UHFFFAOYSA-N
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TC-1698 is a drug developed by Targacept which acts as a partial agonist for the α7 subtype of neural nicotinic acetylcholine receptors.^[1] It has neuroprotective effects in animal studies,^[2] and has been used as a lead compound to find further potent derivatives.^[3]

References

1. Romanelli, M.; Gratteri, P.; Guandalini, L.; Martini, E.; Bonaccini, C.; Gualtieri, F. (2007). "Central nicotinic receptors: structure, function, ligands, and therapeutic potential". ChemMedChem. 2 (6): 746–767. doi:10.1002/cmdc.200600207. PMID 17295372.
2. Marrero, M.; Papke, R.; Bhatti, B.; Shaw, S.; Bencherif, M. (2004). "The neuroprotective effect of 2-(3-pyridyl)-1-azabicyclo3.2.2nonane (TC-1698), a novel alpha7 ligand, is prevented through angiotensin II activation of a tyrosine phosphatase". The Journal of Pharmacology and Experimental Therapeutics. 309 (1): 16–27. doi:10.1124/jpet.103.061655. PMID 14722323.
3. Bhatti, B.; Strachan, J.; Breining, S.; Miller, C.; Tahiri, P.; Crooks, P.; Deo, N.; Day, C.; Caldwell, W. (2008). "Synthesis of 2-(Pyridin-3-yl)-1-azabicyclo[3.2.2]nonane, 2-(Pyridin-3-yl)-1-azabicyclo[2.2.2]octane, and 2-(Pyridin-3-yl)-1-azabicyclo[3.2.1]octane, a Class of Potent Nicotinic Acetylcholine Receptor-Ligands". The Journal of Organic Chemistry. 73 (9): 3497–507. doi:10.1021/jo800028q. PMID 18363376.