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;
CompTox Dashboard (EPA)	DTXSID0047323 ;
Chemical and physical data
Formula	C22H19F3N4O2
Molar mass	428.41 g/mol 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;

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

^ Wood, M. D.; Reavill, C.; Trail, B.; Wilson, A.; Stean, T.; Kennett, G. A.; Lightowler, S.; Blackburn, T. P.; Thomas, D.; Gager, T. L.; Riley, G.; Holland, V.; Bromidge, S. M.; Forbes, I. T.; Middlemiss, D. N. (2001). "SB-243213; a selective 5-HT2C receptor inverse agonist with improved anxiolytic profile: Lack of tolerance and withdrawal anxiety". Neuropharmacology. 41 (2): 186–199. doi:10.1016/S0028-3908(01)00054-5. PMID 11489455.
^ Blackburn, T. P.; Minabe, Y.; Middlemiss, D. N.; Shirayama, Y.; Hashimoto, K.; Ashby Jr, C. R. (2002). "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): 129–139. doi:10.1002/syn.10116. PMID 12325040.
^ Di Matteo, V.; Pierucci, M.; Esposito, E. (2004). "Selective stimulation of serotonin2Creceptors blocks the enhancement of striatal and accumbal dopamine release induced by nicotine administration". Journal of Neurochemistry. 89 (2): 418–429. doi:10.1111/j.1471-4159.2004.02337.x. PMID 15056285.
^ Millan, M. J.; Brocco, M.; Gobert, A.; Dekeyne, A. (2004). "Anxiolytic properties of agomelatine, an antidepressant with melatoninergic and serotonergic properties: Role of 5-HT2C receptor blockade". Psychopharmacology. 177 (4): 448–458. doi:10.1007/s00213-004-1962-z. PMID 15289999.
^ Berg, K. A.; Navailles, S.; Sanchez, T. A.; Silva, Y. M.; Wood, M. D.; Spampinato, U.; Clarke, W. P. (2006). "Differential effects of 5-methyl-1-2-(2-methyl-3-pyridyl)oxyl-5-pyridylcarbamoyl-6-trifluoromethylindone (SB 243213) on 5-hydroxytryptamine(2C) receptor-mediated responses". Journal of Pharmacology and Experimental Therapeutics. 319 (1): 260–268. doi:10.1124/jpet.106.104448. PMID 16807362.
^ Monti, J. M.; Jantos, H. C. (2006). "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): 163–170. doi:10.1016/j.ejphar.2006.09.027. PMID 17059817.
^ Leggio, G. M.; Cathala, A.; Moison, D.; Cunningham, K. A.; Piazza, P. V.; Spampinato, U. (2009). "Serotonin2C receptors in the medial prefrontal cortex facilitate cocaine-induced dopamine release in the rat nucleus accumbens". Neuropharmacology. 56 (2): 507–513. doi:10.1016/j.neuropharm.2008.10.005. PMC 3130963. PMID 18977370.
^ Kadiri, N.; Lagière, M. L.; Le Moine, C.; Millan, M. J.; De Deurwaerdère, P.; Navailles, S. (2012). "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. doi:10.1016/j.ejphar.2012.05.022. PMID 22643326.

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[1] Wood, M. D.; Reavill, C.; Trail, B.; Wilson, A.; Stean, T.; Kennett, G. A.; Lightowler, S.; Blackburn, T. P.; Thomas, D.; Gager, T. L.; Riley, G.; Holland, V.; Bromidge, S. M.; Forbes, I. T.; Middlemiss, D. N. (2001). "SB-243213; a selective 5-HT2C receptor inverse agonist with improved anxiolytic profile: Lack of tolerance and withdrawal anxiety". Neuropharmacology. 41 (2): 186–199. doi:10.1016/S0028-3908(01)00054-5. PMID 11489455.

[2] Blackburn, T. P.; Minabe, Y.; Middlemiss, D. N.; Shirayama, Y.; Hashimoto, K.; Ashby Jr, C. R. (2002). "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): 129–139. doi:10.1002/syn.10116. PMID 12325040.

[3] Di Matteo, V.; Pierucci, M.; Esposito, E. (2004). "Selective stimulation of serotonin2Creceptors blocks the enhancement of striatal and accumbal dopamine release induced by nicotine administration". Journal of Neurochemistry. 89 (2): 418–429. doi:10.1111/j.1471-4159.2004.02337.x. PMID 15056285.

[4] Millan, M. J.; Brocco, M.; Gobert, A.; Dekeyne, A. (2004). "Anxiolytic properties of agomelatine, an antidepressant with melatoninergic and serotonergic properties: Role of 5-HT2C receptor blockade". Psychopharmacology. 177 (4): 448–458. doi:10.1007/s00213-004-1962-z. PMID 15289999.

[5] Berg, K. A.; Navailles, S.; Sanchez, T. A.; Silva, Y. M.; Wood, M. D.; Spampinato, U.; Clarke, W. P. (2006). "Differential effects of 5-methyl-1-2-(2-methyl-3-pyridyl)oxyl-5-pyridylcarbamoyl-6-trifluoromethylindone (SB 243213) on 5-hydroxytryptamine(2C) receptor-mediated responses". Journal of Pharmacology and Experimental Therapeutics. 319 (1): 260–268. doi:10.1124/jpet.106.104448. PMID 16807362.

[6] Monti, J. M.; Jantos, H. C. (2006). "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): 163–170. doi:10.1016/j.ejphar.2006.09.027. PMID 17059817.

[7] Leggio, G. M.; Cathala, A.; Moison, D.; Cunningham, K. A.; Piazza, P. V.; Spampinato, U. (2009). "Serotonin2C receptors in the medial prefrontal cortex facilitate cocaine-induced dopamine release in the rat nucleus accumbens". Neuropharmacology. 56 (2): 507–513. doi:10.1016/j.neuropharm.2008.10.005. PMC 3130963. PMID 18977370.

[8] Kadiri, N.; Lagière, M. L.; Le Moine, C.; Millan, M. J.; De Deurwaerdère, P.; Navailles, S. (2012). "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. doi:10.1016/j.ejphar.2012.05.022. PMID 22643326.

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See also

References