PNU-282,987

PNU-282,987

Identifiers
IUPAC name N-[(3'R)-1'-azabicyclo[2.2.2]oct-3'-yl]-4-chlorobenzamide
CAS Number	123464-89-1
PubChem (CID)	9795278
ChemSpider	7971045
ChEMBL	CHEMBL177611
Chemical and physical data
Formula	C14H17ClN2O
Molar mass	264.750
3D model (Jmol)	Interactive image
SMILES C1CN2CCC1[C@H](C2)NC(=O)C3=CC=C(C=C3)Cl
InChI InChI=1S/C14H17ClN2O/c15-12-3-1-11(2-4-12)14(18)16-13-9-17-7-5-10(13)6-8-17/h1-4,10,13H,5-9H2,(H,16,18)/t13-/m0/s1 Key:WECKJONDRAUFDD-ZDUSSCGKSA-N
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PNU-282,987 is a drug that acts as a potent and selective agonist for the α7 subtype of neural nicotinic acetylcholine receptors.^[1][2] In animal studies, it shows nootropic effects, and derivatives may be useful in the treatment of schizophrenia,^[3][4] although PNU-282,987 is not suitable for use in humans because of excessive inhibition of the hERG antitarget.^[5]

References

1. Hajós, M.; Hurst, R.; Hoffmann, W.; Krause, M.; Wall, T.; Higdon, N.; Groppi, V. (2005). "The selective alpha7 nicotinic acetylcholine receptor agonist PNU-282987 N-(3R)-1-Azabicyclo2.2.2oct-3-yl-4-chlorobenzamide hydrochloride enhances GABAergic synaptic activity in brain slices and restores auditory gating deficits in anesthetized rats". The Journal of Pharmacology and Experimental Therapeutics. 312 (3): 1213–1222. doi:10.1124/jpet.104.076968. PMID 15523001.
2. Bodnar, A.; Cortes-Burgos, L.; Cook, K.; Dinh, D.; Groppi, V.; Hajos, M.; Higdon, N.; Hoffmann, W.; Hurst, R.; Myers, J. K.; Rogers, B. N.; Wall, T. M.; Wolfe, M. L.; Wong, E. (2005). "Discovery and structure-activity relationship of quinuclidine benzamides as agonists of alpha7 nicotinic acetylcholine receptors". Journal of Medicinal Chemistry. 48 (4): 905–908. doi:10.1021/jm049363q. PMID 15715459.
3. Hansen, H.; Timmermann, D.; Peters, D.; Walters, C.; Damaj, M.; Mikkelsen, J. (2007). "Alpha-7 nicotinic acetylcholine receptor agonists selectively activate limbic regions of the rat forebrain: an effect similar to antipsychotics". Journal of neuroscience research. 85 (8): 1810–1818. doi:10.1002/jnr.21293. PMID 17455307.
4. Redrobe, J. (2009). "Alpha7 nicotinic acetylcholine receptor activation ameliorates scopolamine-induced behavioural changes in a modified continuous Y-maze task in mice". European journal of pharmacology 602 (1): 58–65. doi:10.1016/j.ejphar.2008.09.035 PMID 18848931
5. Walker DP, Wishka DG, Piotrowski DW, et al. (2006). "Design, synthesis, structure-activity relationship, and in vivo activity of azabicyclic aryl amides as alpha7 nicotinic acetylcholine receptor agonists". Bioorg. Med. Chem. 14 (24): 8219–48. doi:10.1016/j.bmc.2006.09.019. PMID 17011782.