57477-39-1

57477-39-1 structure

Name: BRL-54443
Chemical Name: 3-(1-methylpiperidin-4-yl)-1H-indol-5-ol
CAS Number: 57477-39-1
Molecular Formula: C₁₄H₁₈N₂O
Molecular Weight: 230.305
Catalog: Biochemical Inhibitor Neuronal Signaling 5-HT Receptor Agonist
Create Date: 2018-07-24 18:50:40
Modify Date: 2024-01-02 19:20:52
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].

Name	3-(1-methylpiperidin-4-yl)-1H-indol-5-ol
Synonyms	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

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.

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	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

Hazard Codes	Xi
Risk Phrases	36/37/38
Safety Phrases	26-36
WGK Germany	3
HS Code	2933990090

111963-87-2

~85%

57477-39-1

Literature: Eli Lilly and Company Patent: US6358972 B1, 2002 ; US 6358972 B1

1953-54-4

57477-39-1

Literature: Medicinal Chemistry Research, , vol. 5, # 9 p. 680 - 689

Precursor 2
111963-87-2 1953-54-4
DownStream 0

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%

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