PNU-120,596

PNU-120,596
Identifiers
	IUPAC name 1-(5-chloro-2,4-dimethoxyphenyl)-3-(5-methylisoxazol-3-yl)urea;
CAS Number	501925-31-1 ;
PubChem CID	311434;
IUPHAR/BPS	3991;
ChemSpider	275409 ;
UNII	9EZT3PTH2J;
ChEMBL	ChEMBL257591 ;
CompTox Dashboard (EPA)	DTXSID10964528 ;
Chemical and physical data
Formula	C13H14ClN3O4
Molar mass	311.72 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc1cc(OC)c(Cl)cc1NC(=O)Nc2noc(C)c2;
	InChI InChI=1S/C13H14ClN3O4/c1-7-4-12(17-21-7)16-13(18)15-9-5-8(14)10(19-2)6-11(9)20-3/h4-6H,1-3H3,(H2,15,16,17,18) ; Key:CEIIEALEIHQDBX-UHFFFAOYSA-N ;
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PNU-120596 is a drug that acts as a potent and selective positive allosteric modulator for the α7 subtype of neural nicotinic acetylcholine receptors.^[1]^[2] It is used in scientific research into cholinergic regulation of dopamine and glutamate release in the brain.^[3]^[4]^[5]

References

^ Hurst RS, Hajós M, Raggenbass M, Wall TM, Higdon NR, Lawson JA, et al. (April 2005). "A novel positive allosteric modulator of the alpha7 neuronal nicotinic acetylcholine receptor: in vitro and in vivo characterization". The Journal of Neuroscience. 25 (17): 4396–405. doi:10.1523/JNEUROSCI.5269-04.2005. PMC 6725110. PMID 15858066.
^ Young GT, Zwart R, Walker AS, Sher E, Millar NS (September 2008). "Potentiation of alpha7 nicotinic acetylcholine receptors via an allosteric transmembrane site". Proceedings of the National Academy of Sciences of the United States of America. 105 (38): 14686–91. Bibcode:2008PNAS..10514686Y. doi:10.1073/pnas.0804372105. PMC 2535569. PMID 18791069.
^ Livingstone PD, Srinivasan J, Kew JN, Dawson LA, Gotti C, Moretti M, et al. (February 2009). "alpha7 and non-alpha7 nicotinic acetylcholine receptors modulate dopamine release in vitro and in vivo in the rat prefrontal cortex". The European Journal of Neuroscience. 29 (3): 539–50. doi:10.1111/j.1460-9568.2009.06613.x. PMID 19187266. S2CID 13289370.
^ Barron SC, McLaughlin JT, See JA, Richards VL, Rosenberg RL (August 2009). "An allosteric modulator of alpha7 nicotinic receptors, N-(5-Chloro-2,4-dimethoxyphenyl)-N'-(5-methyl-3-isoxazolyl)-urea (PNU-120596), causes conformational changes in the extracellular ligand binding domain similar to those caused by acetylcholine". Molecular Pharmacology. 76 (2): 253–63. doi:10.1124/mol.109.056226. PMC 2713121. PMID 19411608.
^ Livingstone PD, Dickinson JA, Srinivasan J, Kew JN, Wonnacott S (January 2010). "Glutamate-dopamine crosstalk in the rat prefrontal cortex is modulated by Alpha7 nicotinic receptors and potentiated by PNU-120596". Journal of Molecular Neuroscience. 40 (1–2): 172–6. doi:10.1007/s12031-009-9232-5. PMID 19688191. S2CID 29929913.

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[1] Hurst RS, Hajós M, Raggenbass M, Wall TM, Higdon NR, Lawson JA, et al. (April 2005). "A novel positive allosteric modulator of the alpha7 neuronal nicotinic acetylcholine receptor: in vitro and in vivo characterization". The Journal of Neuroscience. 25 (17): 4396–405. doi:10.1523/JNEUROSCI.5269-04.2005. PMC 6725110. PMID 15858066.

[2] Young GT, Zwart R, Walker AS, Sher E, Millar NS (September 2008). "Potentiation of alpha7 nicotinic acetylcholine receptors via an allosteric transmembrane site". Proceedings of the National Academy of Sciences of the United States of America. 105 (38): 14686–91. Bibcode:2008PNAS..10514686Y. doi:10.1073/pnas.0804372105. PMC 2535569. PMID 18791069.

[3] Livingstone PD, Srinivasan J, Kew JN, Dawson LA, Gotti C, Moretti M, et al. (February 2009). "alpha7 and non-alpha7 nicotinic acetylcholine receptors modulate dopamine release in vitro and in vivo in the rat prefrontal cortex". The European Journal of Neuroscience. 29 (3): 539–50. doi:10.1111/j.1460-9568.2009.06613.x. PMID 19187266. S2CID 13289370.

[4] Barron SC, McLaughlin JT, See JA, Richards VL, Rosenberg RL (August 2009). "An allosteric modulator of alpha7 nicotinic receptors, N-(5-Chloro-2,4-dimethoxyphenyl)-N'-(5-methyl-3-isoxazolyl)-urea (PNU-120596), causes conformational changes in the extracellular ligand binding domain similar to those caused by acetylcholine". Molecular Pharmacology. 76 (2): 253–63. doi:10.1124/mol.109.056226. PMC 2713121. PMID 19411608.

[5] Livingstone PD, Dickinson JA, Srinivasan J, Kew JN, Wonnacott S (January 2010). "Glutamate-dopamine crosstalk in the rat prefrontal cortex is modulated by Alpha7 nicotinic receptors and potentiated by PNU-120596". Journal of Molecular Neuroscience. 40 (1–2): 172–6. doi:10.1007/s12031-009-9232-5. PMID 19688191. S2CID 29929913.

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Identifiers

IUPAC name 1-(5-chloro-2,4-dimethoxyphenyl)-3-(5-methylisoxazol-3-yl)urea
CAS Number	501925-31-1^Y
PubChem CID	311434
IUPHAR/BPS	3991
ChemSpider	275409^N
UNII	9EZT3PTH2J
ChEMBL	ChEMBL257591^N
CompTox Dashboard (EPA)	DTXSID10964528
Chemical and physical data
Formula	C₁₃H₁₄ClN₃O₄
Molar mass	311.72 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COc1cc(OC)c(Cl)cc1NC(=O)Nc2noc(C)c2
InChI InChI=1S/C13H14ClN3O4/c1-7-4-12(17-21-7)16-13(18)15-9-5-8(14)10(19-2)6-11(9)20-3/h4-6H,1-3H3,(H2,15,16,17,18)^N Key:CEIIEALEIHQDBX-UHFFFAOYSA-N^N
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