PD-168,077

PD-168,077
Identifiers
	IUPAC name N-([4-(2-cyanophenyl)piperazin-1-yl]methyl)-3-methylbenzamide;
CAS Number	190383-31-4;
PubChem CID	3645619;
IUPHAR/BPS	975;
ChemSpider	2879553 ;
ChEMBL	ChEMBL45244 ;
CompTox Dashboard (EPA)	DTXSID7044007 ;
Chemical and physical data
Formula	C20H22N4O
Molar mass	334.423 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Cc2cc(ccc2)C(=O)NCN(CC3)CCN3c1ccccc1C#N;
	InChI InChI=1S/C20H22N4O/c1-16-5-4-7-17(13-16)20(25)22-15-23-9-11-24(12-10-23)19-8-3-2-6-18(19)14-21/h2-8,13H,9-12,15H2,1H3,(H,22,25) ; Key:DNULYRGWTFLJQL-UHFFFAOYSA-N ;
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PD-168,077 is a drug which acts as a dopamine agonist selective for the D₄ subtype,^[1]^[2] which is used for researching the role of D₄ receptors in the brain,^[3]^[4]^[5] particularly relating to learning and memory.^[6] It also induces penile erections in rats.^[7]

References

^ Clifford JJ, Waddington JL (May 2000). "Topographically based search for an "Ethogram" among a series of novel D(4) dopamine receptor agonists and antagonists". Neuropsychopharmacology. 22 (5): 538–544. doi:10.1016/S0893-133X(99)00141-4. PMID 10731629.
^ Matulenko MA, Hakeem AA, Kolasa T, Nakane M, Terranova MA, Uchic ME, et al. (July 2004). "Synthesis and functional activity of (2-aryl-1-piperazinyl)-N-(3-methylphenyl)acetamides: selective dopamine D4 receptor agonists". Bioorganic & Medicinal Chemistry. 12 (13): 3471–3483. doi:10.1016/j.bmc.2004.04.035. PMID 15186832.
^ Wang X, Zhong P, Gu Z, Yan Z (October 2003). "Regulation of NMDA receptors by dopamine D4 signaling in prefrontal cortex". The Journal of Neuroscience. 23 (30): 9852–9861. doi:10.1523/JNEUROSCI.23-30-09852.2003. PMC 6740894. PMID 14586014.
^ Melis MR, Succu S, Sanna F, Melis T, Mascia MS, Enguehard-Gueiffier C, et al. (October 2006). "PIP3EA and PD-168077, two selective dopamine D4 receptor agonists, induce penile erection in male rats: site and mechanism of action in the brain". The European Journal of Neuroscience. 24 (7): 2021–2030. doi:10.1111/j.1460-9568.2006.05043.x. PMID 17067298. S2CID 36871301.
^ Succu S, Sanna F, Melis T, Boi A, Argiolas A, Melis MR (March 2007). "Stimulation of dopamine receptors in the paraventricular nucleus of the hypothalamus of male rats induces penile erection and increases extra-cellular dopamine in the nucleus accumbens: Involvement of central oxytocin". Neuropharmacology. 52 (3): 1034–1043. doi:10.1016/j.neuropharm.2006.10.019. PMID 17164075. S2CID 36595888.
^ Bernaerts P, Tirelli E (June 2003). "Facilitatory effect of the dopamine D4 receptor agonist PD168,077 on memory consolidation of an inhibitory avoidance learned response in C57BL/6J mice". Behavioural Brain Research. 142 (1–2): 41–52. doi:10.1016/S0166-4328(02)00371-6. PMID 12798264. S2CID 21960608.
^ Melis MR, Succu S, Sanna F, Melis T, Mascia MS, Enguehard-Gueiffier C, et al. (October 2006). "PIP3EA and PD-168077, two selective dopamine D4 receptor agonists, induce penile erection in male rats: site and mechanism of action in the brain". The European Journal of Neuroscience. 24 (7): 2021–2030. doi:10.1111/j.1460-9568.2006.05043.x. PMID 17067298. S2CID 36871301.

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[pmid10731629-1] Clifford JJ, Waddington JL (May 2000). "Topographically based search for an "Ethogram" among a series of novel D(4) dopamine receptor agonists and antagonists". Neuropsychopharmacology. 22 (5): 538–544. doi:10.1016/S0893-133X(99)00141-4. PMID 10731629.

[pmid15186832-2] Matulenko MA, Hakeem AA, Kolasa T, Nakane M, Terranova MA, Uchic ME, et al. (July 2004). "Synthesis and functional activity of (2-aryl-1-piperazinyl)-N-(3-methylphenyl)acetamides: selective dopamine D4 receptor agonists". Bioorganic & Medicinal Chemistry. 12 (13): 3471–3483. doi:10.1016/j.bmc.2004.04.035. PMID 15186832.

[pmid14586014-3] Wang X, Zhong P, Gu Z, Yan Z (October 2003). "Regulation of NMDA receptors by dopamine D4 signaling in prefrontal cortex". The Journal of Neuroscience. 23 (30): 9852–9861. doi:10.1523/JNEUROSCI.23-30-09852.2003. PMC 6740894. PMID 14586014.

[pmid17067298-4] Melis MR, Succu S, Sanna F, Melis T, Mascia MS, Enguehard-Gueiffier C, et al. (October 2006). "PIP3EA and PD-168077, two selective dopamine D4 receptor agonists, induce penile erection in male rats: site and mechanism of action in the brain". The European Journal of Neuroscience. 24 (7): 2021–2030. doi:10.1111/j.1460-9568.2006.05043.x. PMID 17067298. S2CID 36871301.

[pmid17164075-5] Succu S, Sanna F, Melis T, Boi A, Argiolas A, Melis MR (March 2007). "Stimulation of dopamine receptors in the paraventricular nucleus of the hypothalamus of male rats induces penile erection and increases extra-cellular dopamine in the nucleus accumbens: Involvement of central oxytocin". Neuropharmacology. 52 (3): 1034–1043. doi:10.1016/j.neuropharm.2006.10.019. PMID 17164075. S2CID 36595888.

[pmid12798264-6] Bernaerts P, Tirelli E (June 2003). "Facilitatory effect of the dopamine D4 receptor agonist PD168,077 on memory consolidation of an inhibitory avoidance learned response in C57BL/6J mice". Behavioural Brain Research. 142 (1–2): 41–52. doi:10.1016/S0166-4328(02)00371-6. PMID 12798264. S2CID 21960608.

[MelisSuccu2006-7] Melis MR, Succu S, Sanna F, Melis T, Mascia MS, Enguehard-Gueiffier C, et al. (October 2006). "PIP3EA and PD-168077, two selective dopamine D4 receptor agonists, induce penile erection in male rats: site and mechanism of action in the brain". The European Journal of Neuroscience. 24 (7): 2021–2030. doi:10.1111/j.1460-9568.2006.05043.x. PMID 17067298. S2CID 36871301.

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Identifiers

IUPAC name N-([4-(2-cyanophenyl)piperazin-1-yl]methyl)-3-methylbenzamide
CAS Number	190383-31-4
PubChem CID	3645619
IUPHAR/BPS	975
ChemSpider	2879553^Y
ChEMBL	ChEMBL45244^N
CompTox Dashboard (EPA)	DTXSID7044007
Chemical and physical data
Formula	C₂₀H₂₂N₄O
Molar mass	334.423 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Cc2cc(ccc2)C(=O)NCN(CC3)CCN3c1ccccc1C#N
InChI InChI=1S/C20H22N4O/c1-16-5-4-7-17(13-16)20(25)22-15-23-9-11-24(12-10-23)19-8-3-2-6-18(19)14-21/h2-8,13H,9-12,15H2,1H3,(H,22,25)^N Key:DNULYRGWTFLJQL-UHFFFAOYSA-N^Y
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