RS-67,333

RS-67,333
Identifiers
	IUPAC name 1-(4-amino-5-chloro-2-methoxyphenyl)-3-(1-butyl-4-piperidinyl)-1-propanone;
CAS Number	160845-95-4 ;
PubChem CID	183782;
ChemSpider	159808 ;
UNII	39N8XG5C9A;
CompTox Dashboard (EPA)	DTXSID90167010 ;
Chemical and physical data
Formula	C19H29ClN2O2
Molar mass	352.90 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C(CCC1CCN(CC1)CCCC)(=O)c1c(cc(c(c1)Cl)N)OC;
	InChI InChI=1S/C19H29ClN2O2/c1-3-4-9-22-10-7-14(8-11-22)5-6-18(23)15-12-16(20)17(21)13-19(15)24-2/h12-14H,3-11,21H2,1-2H3 ; Key:JBHLYIVFFLNISJ-UHFFFAOYSA-N ;
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RS-67,333 is a drug which has been investigated as a potential rapid-acting antidepressant,^[1] nootropic,^[2] and treatment for Alzheimer's disease.^[3] It is a high-affinity 5-HT4 receptor partial agonist, as well as a sigma receptor ligand of both subtypes to a lesser extent.^[4]

References

^ Lucas G, Rymar VV, Du J, Mnie-Filali O, Bisgaard C, Manta S, Lambas-Senas L, Wiborg O, Haddjeri N, Piñeyro G, Sadikot AF, Debonnel G (2007). "Serotonin(4) (5-HT(4)) Receptor Agonists Are Putative Antidepressants with a Rapid Onset of Action". Neuron. 55 (5): 712–25. doi:10.1016/j.neuron.2007.07.041. PMID 17785179. S2CID 14558104.
^ Lamirault L, Simon H (2001). "Enhancement of place and object recognition memory in young adult and old rats by RS 67333, a partial agonist of 5-HT4 receptors". Neuropharmacology. 41 (7): 844–53. doi:10.1016/S0028-3908(01)00123-X. PMID 11684148. S2CID 31707593.
^ Cho S, Hu Y (2007). "Activation of 5-HT4 receptors inhibits secretion of beta-amyloid peptides and increases neuronal survival". Experimental Neurology. 203 (1): 274–8. doi:10.1016/j.expneurol.2006.07.021. PMID 16978609. S2CID 41975593.
^ Eglen RM, Bonhaus DW, Johnson LG, Leung E, Clark RD (August 1995). "Pharmacological characterization of two novel and potent 5-HT4 receptor agonists, RS 67333 and RS 67506, in vitro and in vivo". Br. J. Pharmacol. 115 (8): 1387–92. doi:10.1111/j.1476-5381.1995.tb16628.x. PMC 1908873. PMID 8564196.

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Identifiers

IUPAC name 1-(4-amino-5-chloro-2-methoxyphenyl)-3-(1-butyl-4-piperidinyl)-1-propanone
CAS Number	160845-95-4^Y
PubChem CID	183782
ChemSpider	159808^N
UNII	39N8XG5C9A
CompTox Dashboard (EPA)	DTXSID90167010
Chemical and physical data
Formula	C₁₉H₂₉ClN₂O₂
Molar mass	352.90 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C(CCC1CCN(CC1)CCCC)(=O)c1c(cc(c(c1)Cl)N)OC
InChI InChI=1S/C19H29ClN2O2/c1-3-4-9-22-10-7-14(8-11-22)5-6-18(23)15-12-16(20)17(21)13-19(15)24-2/h12-14H,3-11,21H2,1-2H3^N Key:JBHLYIVFFLNISJ-UHFFFAOYSA-N^N
^NY (what is this?) (verify)