BRL-54443

Names

[ Name ]:
BRL-54443

[Synonym ]:
1H-Indol-5-ol, 3-(1-methyl-4-piperidinyl)-
5-hydroxy-3-(1-methylpiperidin-4-yl)indole
UNII-Q2DH1CHI0Y
3-(1-methyl-piperidin-4-yl)-indol-5-ol
3-(1-Methylpiperidin-4-yl)-1H-indol-5-ol
BRL-54443
BRL 54443
Tocris-1129
3-(1-Methyl-4-piperidinyl)-1H-indol-5-ol
Lopac-B-173
3-(1-methylpiperidin-4-yl)1H-indol-5-ol

Biological Activity

[Description]:

BRL 54443 is a potent 5-HT1E/1F receptor agonist (pKi values are 8.7 and 8.9 respectively); displays > 30-fold selectivity over other 5-HT and dopamine receptors.IC50 value: 8.7(pKi, 5-HT1E); 8.9 (pKi, 5-HT1F) Target: 5-HT1E/1F receptorin vitro: BRL 54443 is a potent 5-ht1E/1F receptor agonist (pEC50 values are 8.5 and 8.6 respectively). Displays > 30-fold selectivity over other 5-HT and dopamine receptors (pKi values are 8.7. 8.9, 7.2, 6.9, 7.2, 5.9, 7.0, 6.5, < 6, < 6, 6.3 and 6.2 for human 5-HT1E, 1F, 1A, 1B, 1D, 2A, 2B, 2C, 4, 7, D2 and D3 receptors respectively). Induces 5-HT2A receptor-mediated mouse aortic contraction in vitro (pEC50 = 6.52). Active in vivo. In DG membranes, BRL54443, a 5-ht(1E) /5-HT(1F) agonist, selectively stimulated 5-ht(1E) receptors and potently inhibited forskolin-dependent cAMP production (IC50 = 14 nM) [2]. The 5-HT(1E/1F) receptor agonist BRL 54443 also induced contraction (-log EC(50) = 6.52) [1].in vivo: Reduction of flinching was considered as antinociception. Ipsilateral, but not contralateral, peripheral administration of BRL54443 (5-HT(1E/1F); 3-300 microg/paw) significantly reduced formalin-induced flinching in rats [3].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

Research Areas >> Cardiovascular Disease

[References]

[1]. Klein MT, et al. Toward selective drug development for the human 5-hydroxytryptamine 1E receptor: a comparison of 5-hydroxytryptamine 1E and 1F receptor structure-affinity relationships. J Pharmacol Exp Ther. 2011 Jun;337(3):860-867.

[2]. McKune CM, et al. Characterization of the serotonin receptor mediating contraction in the mouse thoracic aorta and signal pathway coupling. J Pharmacol Exp Ther. 2001 Apr;297(1):88-95.

[3]. Klein MT, et al. Distribution of 5-ht(1E) receptors in the mammalian brain and cerebral vasculature: an immunohistochemical and pharmacological study. Br J Pharmacol. 2012 Jun;166(4):1290-302.

[4]. Granados-Soto V, et al. The role of peripheral 5-HT1A, 5-HT1B, 5-HT1D, 5-HT1E and 5-HT1F serotonergic receptors in the reduction of nociception in rats. Neuroscience. 2010 Jan 20;165(2):561-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
431.5±45.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₄H₁₈N₂O

[ Molecular Weight ]:
230.305

[ Flash Point ]:
214.8±28.7 °C

[ Exact Mass ]:
230.141907

[ PSA ]:
39.26000

[ LogP ]:
1.16

[ Appearance of Characters ]:
solid | white

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.646

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
H2O: 50 mg/mL

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-36

[ WGK Germany ]:
3

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%