Chemistry:SB-243213

SB-243213
Identifiers
	IUPAC name 5-methyl-N-(6-[(2-methylpyridin-3-yl)oxy]pyridin-3-yl)-6-(trifluoromethyl)indoline-1-carboxamide;
CAS Number	200940-23-4;
PubChem CID	443391;
ChemSpider	391620;
UNII	PA86JD65ZJ;
Chemical and physical data
Formula	C22H19F3N4O2
Molar mass	428.415 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=C(C(F)(F)F)C=C(N(C(NC2=CN=C(OC3=C(C)N=CC=C3)C=C2)=O)CC4)C4=C1;
	InChI InChI=1S/C22H19F3N4O2/c1-13-10-15-7-9-29(18(15)11-17(13)22(23,24)25)21(30)28-16-5-6-20(27-12-16)31-19-4-3-8-26-14(19)2/h3-6,8,10-12H,7,9H2,1-2H3,(H,28,30); Key:ZETBBVYSBABLHL-UHFFFAOYSA-N;

Short description: Chemical compound

SB-243213 is a research chemical which acts as a selective inverse agonist for the 5HT_2C receptor and has anxiolytic effects. It has better than 100x selectivity for 5-HT_2C over all other receptor subtypes tested, and a longer duration of action compared to older 5-HT_2C antagonist ligands.^[1]^[2]^[3]^[4]^[5]^[6]^[7]^[8]

References

↑ "SB-243213; a selective 5-HT2C receptor inverse agonist with improved anxiolytic profile: lack of tolerance and withdrawal anxiety". Neuropharmacology 41 (2): 186–99. August 2001. doi:10.1016/S0028-3908(01)00054-5. PMID 11489455.
↑ "Effect of acute and chronic administration of the selective 5-HT2C receptor antagonist SB-243213 on midbrain dopamine neurons in the rat: an in vivo extracellular single cell study". Synapse 46 (3): 129–39. December 2002. doi:10.1002/syn.10116. PMID 12325040.
↑ "Selective stimulation of serotonin2c receptors blocks the enhancement of striatal and accumbal dopamine release induced by nicotine administration". Journal of Neurochemistry 89 (2): 418–29. April 2004. doi:10.1111/j.1471-4159.2004.02337.x. PMID 15056285.
↑ "Anxiolytic properties of agomelatine, an antidepressant with melatoninergic and serotonergic properties: role of 5-HT2C receptor blockade". Psychopharmacology 177 (4): 448–58. February 2005. doi:10.1007/s00213-004-1962-z. PMID 15289999.
↑ "Differential effects of 5-methyl-1-2-[(2-methyl-3-pyridyl)oxyl]-5-pyridyl]carbamoyl]-6-trifluoromethylindone (SB 243213) on 5-hydroxytryptamine(2C) receptor-mediated responses". The Journal of Pharmacology and Experimental Therapeutics 319 (1): 260–8. October 2006. doi:10.1124/jpet.106.104448. PMID 16807362.
↑ "Effects of the serotonin 5-HT2A/2C receptor agonist DOI and of the selective 5-HT2A or 5-HT2C receptor antagonists EMD 281014 and SB-243213, respectively, on sleep and waking in the rat". European Journal of Pharmacology 553 (1–3): 163–70. December 2006. doi:10.1016/j.ejphar.2006.09.027. PMID 17059817.
↑ "Serotonin2C receptors in the medial prefrontal cortex facilitate cocaine-induced dopamine release in the rat nucleus accumbens". Neuropharmacology 56 (2): 507–13. February 2009. doi:10.1016/j.neuropharm.2008.10.005. PMID 18977370.
↑ "Diverse effects of 5-HT2C receptor blocking agents on c-Fos expression in the rat basal ganglia". European Journal of Pharmacology 689 (1–3): 8–16. August 2012. doi:10.1016/j.ejphar.2012.05.022. PMID 22643326.

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Original source: https://en.wikipedia.org/wiki/SB-243213. Read more

[1] "SB-243213; a selective 5-HT2C receptor inverse agonist with improved anxiolytic profile: lack of tolerance and withdrawal anxiety". Neuropharmacology 41 (2): 186–99. August 2001. doi:10.1016/S0028-3908(01)00054-5. PMID 11489455.

[2] "Effect of acute and chronic administration of the selective 5-HT2C receptor antagonist SB-243213 on midbrain dopamine neurons in the rat: an in vivo extracellular single cell study". Synapse 46 (3): 129–39. December 2002. doi:10.1002/syn.10116. PMID 12325040.

[3] "Selective stimulation of serotonin2c receptors blocks the enhancement of striatal and accumbal dopamine release induced by nicotine administration". Journal of Neurochemistry 89 (2): 418–29. April 2004. doi:10.1111/j.1471-4159.2004.02337.x. PMID 15056285.

[4] "Anxiolytic properties of agomelatine, an antidepressant with melatoninergic and serotonergic properties: role of 5-HT2C receptor blockade". Psychopharmacology 177 (4): 448–58. February 2005. doi:10.1007/s00213-004-1962-z. PMID 15289999.

[5] "Differential effects of 5-methyl-1-2-[(2-methyl-3-pyridyl)oxyl]-5-pyridyl]carbamoyl]-6-trifluoromethylindone (SB 243213) on 5-hydroxytryptamine(2C) receptor-mediated responses". The Journal of Pharmacology and Experimental Therapeutics 319 (1): 260–8. October 2006. doi:10.1124/jpet.106.104448. PMID 16807362.

[6] "Effects of the serotonin 5-HT2A/2C receptor agonist DOI and of the selective 5-HT2A or 5-HT2C receptor antagonists EMD 281014 and SB-243213, respectively, on sleep and waking in the rat". European Journal of Pharmacology 553 (1–3): 163–70. December 2006. doi:10.1016/j.ejphar.2006.09.027. PMID 17059817.

[7] "Serotonin2C receptors in the medial prefrontal cortex facilitate cocaine-induced dopamine release in the rat nucleus accumbens". Neuropharmacology 56 (2): 507–13. February 2009. doi:10.1016/j.neuropharm.2008.10.005. PMID 18977370.

[8] "Diverse effects of 5-HT2C receptor blocking agents on c-Fos expression in the rat basal ganglia". European Journal of Pharmacology 689 (1–3): 8–16. August 2012. doi:10.1016/j.ejphar.2012.05.022. PMID 22643326.

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Identifiers

IUPAC name 5-methyl-N-(6-[(2-methylpyridin-3-yl)oxy]pyridin-3-yl)-6-(trifluoromethyl)indoline-1-carboxamide
CAS Number	200940-23-4
PubChem CID	443391
ChemSpider	391620
UNII	PA86JD65ZJ
Chemical and physical data
Formula	C₂₂H₁₉F₃N₄O₂
Molar mass	428.415 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC1=C(C(F)(F)F)C=C(N(C(NC2=CN=C(OC3=C(C)N=CC=C3)C=C2)=O)CC4)C4=C1
InChI InChI=1S/C22H19F3N4O2/c1-13-10-15-7-9-29(18(15)11-17(13)22(23,24)25)21(30)28-16-5-6-20(27-12-16)31-19-4-3-8-26-14(19)2/h3-6,8,10-12H,7,9H2,1-2H3,(H,28,30) Key:ZETBBVYSBABLHL-UHFFFAOYSA-N

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