WAY-181187

WAY-181187
Clinical data
ATC code	none;
Identifiers
	IUPAC name 2-(1-{6-Chloroimidazo[2,1-b][1,3]thiazole-5-sulfonyl}-1H-indol-3-yl)ethan-1-amine;
CAS Number	554403-49-5;
PubChem CID	10150497;
IUPHAR/BPS	3240;
ChemSpider	8326005;
UNII	WXE3H7W295;
ChEMBL	ChEMBL392760 ;
CompTox Dashboard (EPA)	DTXSID50204011 ;
Chemical and physical data
Formula	C15H13ClN4O2S2
Molar mass	380.87 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES NCCc1cn(c2ccccc12)S(=O)(=O)c1c(Cl)nc2sccn12;
	InChI InChI=1S/C15H13ClN4O2S2/c16-13-14(19-7-8-23-15(19)18-13)24(21,22)20-9-10(5-6-17)11-3-1-2-4-12(11)20/h1-4,7-9H,5-6,17H2; Key:RYBOXBBYCVOYNO-UHFFFAOYSA-N;

WAY-181187 is a high affinity and selective 5-HT₆ receptor full agonist.^[1]^[2] It induces robust increases in extracellular GABA levels in the frontal cortex, hippocampus, striatum, and amygdala of rats without affecting concentrations in the nucleus accumbens or thalamus, and has modest to no effects on norepinephrine, serotonin, dopamine, or glutamate levels in these areas.^[1]^[3] WAY-181187 has demonstrated preclinical efficacy in rodent models of depression, anxiety, and notably obsessive-compulsive disorder,^[1]^[4] though it has also been shown to impair cognition and memory.^[3]^[5]

References

^ ^a ^b ^c Schechter LE, Lin Q, Smith DL, et al. (May 2008). "Neuropharmacological profile of novel and selective 5-HT6 receptor agonists: WAY-181187 and WAY-208466". Neuropsychopharmacology. 33 (6): 1323–35. doi:10.1038/sj.npp.1301503. PMID 17625499.
^ Cole DC, Stock JR, Lennox WJ, et al. (November 2007). "Discovery of N1-(6-chloroimidazo[2,1-b][1,3]thiazole-5-sulfonyl)tryptamine as a potent, selective, and orally active 5-HT(6) receptor agonist". Journal of Medicinal Chemistry. 50 (23): 5535–8. doi:10.1021/jm070521y. PMID 17948978.
^ ^a ^b West PJ, Marcy VR, Marino MJ, Schaffhauser H (December 2009). "Activation of the 5-HT(6) receptor attenuates long-term potentiation and facilitates GABAergic neurotransmission in rat hippocampus". Neuroscience. 164 (2): 692–701. doi:10.1016/j.neuroscience.2009.07.061. PMID 19660530. S2CID 207246603.
^ Carr GV, Schechter LE, Lucki I (March 2010). "Antidepressant and anxiolytic effects of selective 5-HT(6) receptor agonists in rats". Psychopharmacology. 213 (2–3): 499–507. doi:10.1007/s00213-010-1798-7. PMC 2910165. PMID 20217056.
^ Loiseau F, Dekeyne A, Millan MJ (January 2008). "Pro-cognitive effects of 5-HT6 receptor antagonists in the social recognition procedure in rats: implication of the frontal cortex". Psychopharmacology. 196 (1): 93–104. doi:10.1007/s00213-007-0934-5. PMID 17922111. S2CID 35795618.

Clinical data

ATC code	none
Identifiers
IUPAC name 2-(1-{6-Chloroimidazo[2,1-b][1,3]thiazole-5-sulfonyl}-1H-indol-3-yl)ethan-1-amine
CAS Number	554403-49-5
PubChem CID	10150497
IUPHAR/BPS	3240
ChemSpider	8326005
UNII	WXE3H7W295
ChEMBL	ChEMBL392760^Y
CompTox Dashboard (EPA)	DTXSID50204011
Chemical and physical data
Formula	C₁₅H₁₃ClN₄O₂S₂
Molar mass	380.87 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES NCCc1cn(c2ccccc12)S(=O)(=O)c1c(Cl)nc2sccn12
InChI InChI=1S/C15H13ClN4O2S2/c16-13-14(19-7-8-23-15(19)18-13)24(21,22)20-9-10(5-6-17)11-3-1-2-4-12(11)20/h1-4,7-9H,5-6,17H2 Key:RYBOXBBYCVOYNO-UHFFFAOYSA-N