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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[antidepressant-Lucas-1] 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.

[nootropic-Lamirault-2] 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.

[alzheimers-Cho-3] 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.

[pmid8564196-4] 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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v t e Sigma receptor modulators
σ₁	Agonists: 3-PPP 4-PPBP 5-MeO-DMT Alazocine (SKF-10047) Amantadine Arketamine BD-737 BD-1052 Blarcamesine Captodiame Citalopram CGRPTooltip Calcitonin gene-related peptide Cloperastine Cocaine Cutamesine (SA-4503) Cyclazocine Dehydroepiandrosterone (DHEA) (prasterone) Dehydroepiandrosterone sulfate (DHEA-S) (prasterone sulfate) Dextrallorphan Dextromethorphan (DXM) Dextrorphan (DXO) Dimemorfan Dimethyltryptamine (DMT) Ditolylguanidine (DTG) Donepezil Eliprodil Escitalopram Fabomotizole (afobazole) Fluoxetine Fluvoxamine Ifenprodil Igmesine (JO-1784) IPAB Ketamine L-687384 MDMA (midomafetamine) Memantine Methamphetamine Methoxetamine Methylphenidate Nepinalone Neuropeptide Y Noscapine OPC-14523 Opipramol Pentazocine Pentoxyverine (carbetapentane) PRE-084 Pregnenolone Pregnenolone sulfate Pridopidine Racemethorphan (methorphan) Racemorphan (morphanol) UMB-23 UMB-82 Antagonists: 3-PPP AC-927 BD-1008 BD-1031 BD-1047 BD-1060 BD-1063 BD-1067 BMY-14802 (BMS-181100) CM-156 Dup-734 E-5842 E-52862 (S1RA) Haloperidol LR-132 LR-172 MS-377 NE-100 NPC-16377 Panamesine (EMD-57455) PD-144418 Pentazocine Progesterone Rimcazole (BW-234U) Sertraline SR-31742A Allosteric modulators: Phenytoin; Positive: Methylphenylpiracetam SOMCL-668 Unknown/unsorted: 3-Methoxydextrallorphan 3-MeO-PCP 4C-T-2 4-IBP 4-IPBS 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Amitriptyline Azidopamil Chlorpromazine Clemastine Clomipramine Clorgiline D-Deprenyl DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Imipramine KCR-12-83.1 Nemonapride Noribogaine RHL-033 RS-67,333 RTI-55 Saffron Safinamide Selegiline Spipethiane Trifluoperazine W-18 YKP10A
σ₂	Agonists: 3-PPP Arketamine BD-1047 BD1063 Ditolylguanidine (DTG) DKR-1005 DKR-1051 Haloperidol Ifenprodil Ketamine MDMA (midomafetamine) Methamphetamine OPC-14523 Opipramol PB-28 Phencyclidine Siramesine (Lu 28-179) UKH-1114 Antagonists: AC-927 BD-1008 BD-1067 CM-156 CT-1812 LR-172 MIN-101 Panamesine (EMD-57455) SAS-0132 Unknown/unsorted: 3-Methoxydextrallorphan 3-MeO-PCE 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Clemastine DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Lu 29-252 Nemonapride Nepinalone Noribogaine Pentazocine RS-67,333 Safinamide TMATooltip 3,4,5-Trimethoxyamphetamine UMB-23 UMB-82 W-18
Unsorted	Agonists: Berberine Ethylketazocine Fourphit Metaphit Naluzotan Tapentadol Tenocyclidine Antagonists: AHD1 AZ66 Lamotrigine Naloxone SM-21 UMB-100 UMB-101 UMB-103 UMB-116 YZ-011 YZ-069 YZ-185 Allosteric modulators: SKF-83959 Unknown/unsorted: 18-Methoxycoronaridine BMY-13980 Butaclamol Caramiphen Carvotroline Chlorphenamine (chlorpheniramine) Chlorpromazine Cinnarizine Cinuperone Clocapramine Dezocine EMD-59983 Hypericin (St. John's wort) Fluphenazine Gevotroline (WY-47384) Mepyramine (pyrilamine) Molindone Perphenazine Pimozide Proadifen Promethazine Propranolol Quinidine Remoxipride SL 82.0715 SR-31747A Tiospirone (BMY-13859) Venlafaxine
See also: Receptor/signaling modulators