57477-39-1

Basic information

• Product Name: BRL 54443
• Synonyms: BRL 54443;5-HYDROXY-3-(1-METHYLPIPERIDIN-4-YL)-1H-INDOLE;3-(1-Methyl-4-piperidinyl)-1H-indol-5-ol;3-(1-methylpiperidin-4-yl)-1H-indol-5-ol;1H-Indol-5-ol, 3-(1-Methyl-4-piperidinyl)-;BRL 54443 HCl;3-(1-Methyl-4-piperidinyl)-1H-indol-5-ol BRL 54443;BRL 54443, >=98%
• CAS NO: 57477-39-1
• Molecular Formula: C₁₄H₁₈N₂O
• Molecular Weight: 230.31
• Product Categories: Inhibitors
• Mol File: 57477-39-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 431.5±45.0 °C(Predicted)
• Appearance: white/solid
• Density: 1.196
• Storage Temp.: 2-8°C
• Solubility: H2O: 50 mg/mL
• PKA: 10.08±0.40(Predicted)
• CAS DataBase Reference: BRL 54443(CAS DataBase Reference)
• NIST Chemistry Reference: BRL 54443(57477-39-1)
• EPA Substance Registry System: BRL 54443(57477-39-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 57477-39-1(Hazardous Substances Data)

Usage

Uses

BRL-53443 is a potent 5-HT and dopamine receptor agonist. Neuroresearch product.

Biological Activity

A potent 5-ht 1E/1F receptor agonist (pEC 50 values are 8.5 and 8.6 respectively). Displays > 30-fold selectivity over other 5-HT and dopamine receptors (pK i 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-HT 1E , 1F , 1A , 1B , 1D , 2A , 2B , 2C , 4 , 7 , D 2 and D 3 receptors respectively). Induces 5-HT 2A receptor-mediated mouse aortic contraction in vitro (pEC 50 = 6.52). Active in vivo .

references

1. a.m. brown, k. avenell, t j. young et al. brl 54443, a potent agonist with selectivity for human cloned 5-ht1e and 5-ht1f receptors. 1998. br.j.pharmacol. 123 233p.2. s. lightowler, t. stean, n. upton et al. effect of brl 54443 (3-(1-methylpiperidin-4-yl)-1h-indol-5-ol), a 5-ht1e/1f receptor agonist, on general behaviour and maximal electroshock seizure threshold in the rat. 1998. br.j.pharmacol. 123 237p.3. mckune cm, watts sw. characterization of the serotonin receptor mediating contraction in the mouse thoracic aorta and signal pathway coupling. j pharmacol exp ther. 2001 apr;297(1):88-95.4. janssen p, tack j, sifrim d et al. influence of 5-ht1 receptor agonists on feline stomach relaxation. eur j pharmacol. 2004 may 25;492(2-3):259-67.

Upstream product

• 1953-54-4 indol-5-ol 
• 55556-41-7 5-methoxy-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole 
• 111963-87-2 5-methoxy-3-(1-methylpiperidin-4-yl)-1H-indole 

Relevant articles and documents

5-HT1F agonists

The present invention relates to a compound of formula (I): or a pharmaceutical acid addition salt thereof; which is useful for activating 5-HT1freceptors and inhibiting protein extravasation in a mammal.

Synthesis and Structure-Activity Relationships of 5-Substituted Tryptamine Derivatives of o-Tolylpiperazine as Agonists at 5-HT1D Receptors

Analogs of 1-[2-[3-(2-amino-ethyl)-1H-indol-5-yloxy]-acetyl]-4-[o-tolyl]-piperazide 1, recently reported as a novel potent 5HT1D agonist, have been prepared and tested as 5HT1A, 5HD1Dα and 5HT1Dβ ligands and eva