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;
UNII	810P1694K2;
ChEMBL	ChEMBL177611 ;
CompTox Dashboard (EPA)	DTXSID801017103 ;
Chemical and physical data
Formula	C14H17ClN2O
Molar mass	264.75 g·mol−1
3D model (JSmol)	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;
	(verify)

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] PNU-282987 has been shown to initiate signaling that leads to adult neurogeneis in mammals.^[6]

References

^ Hajós M, Hurst RS, Hoffmann WE, Krause M, Wall TM, Higdon NR, Groppi VE (March 2005). "The selective alpha7 nicotinic acetylcholine receptor agonist PNU-282987 [N-[(3R)-1-Azabicyclo[2.2.2]oct-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. S2CID 36149268.
^ Bodnar AL, Cortes-Burgos LA, Cook KK, Dinh DM, Groppi VE, Hajos M, et al. (February 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.
^ Hansen HH, Timmermann DB, Peters D, Walters C, Damaj MI, Mikkelsen JD (June 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. S2CID 37590479.
^ Redrobe JP, Nielsen EØ, Christensen JK, Peters D, Timmermann DB, Olsen GM (January 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.
^ Walker DP, Wishka DG, Piotrowski DW, Jia S, Reitz SC, Yates KM, et al. (December 2006). "Design, synthesis, structure-activity relationship, and in vivo activity of azabicyclic aryl amides as alpha7 nicotinic acetylcholine receptor agonists". Bioorganic & Medicinal Chemistry. 14 (24): 8219–8248. doi:10.1016/j.bmc.2006.09.019. PMID 17011782.
^ Webster MK, Cooley-Themm CA, Barnett JD, Bach HB, Vainner JM, Webster SE, Linn CL (March 2017). "Evidence of BrdU-positive retinal neurons after application of an Alpha7 nicotinic acetylcholine receptor agonist". Neuroscience. 346: 437–446. doi:10.1016/j.neuroscience.2017.01.029. PMC 5341387. PMID 28147247.

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[1] Hajós M, Hurst RS, Hoffmann WE, Krause M, Wall TM, Higdon NR, Groppi VE (March 2005). "The selective alpha7 nicotinic acetylcholine receptor agonist PNU-282987 [N-[(3R)-1-Azabicyclo[2.2.2]oct-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. S2CID 36149268.

[2] Bodnar AL, Cortes-Burgos LA, Cook KK, Dinh DM, Groppi VE, Hajos M, et al. (February 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 HH, Timmermann DB, Peters D, Walters C, Damaj MI, Mikkelsen JD (June 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. S2CID 37590479.

[4] Redrobe JP, Nielsen EØ, Christensen JK, Peters D, Timmermann DB, Olsen GM (January 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, Jia S, Reitz SC, Yates KM, et al. (December 2006). "Design, synthesis, structure-activity relationship, and in vivo activity of azabicyclic aryl amides as alpha7 nicotinic acetylcholine receptor agonists". Bioorganic & Medicinal Chemistry. 14 (24): 8219–8248. doi:10.1016/j.bmc.2006.09.019. PMID 17011782.

[6] Webster MK, Cooley-Themm CA, Barnett JD, Bach HB, Vainner JM, Webster SE, Linn CL (March 2017). "Evidence of BrdU-positive retinal neurons after application of an Alpha7 nicotinic acetylcholine receptor agonist". Neuroscience. 346: 437–446. doi:10.1016/j.neuroscience.2017.01.029. PMC 5341387. PMID 28147247.

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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
UNII	810P1694K2
ChEMBL	ChEMBL177611^Y
CompTox Dashboard (EPA)	DTXSID801017103
Chemical and physical data
Formula	C₁₄H₁₇ClN₂O
Molar mass	264.75 g·mol⁻¹
3D model (JSmol)	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
(verify)