158942-04-2

Basic information

• Product Name: 5-METHYL-1-(3-PYRIDYLCARBAMOYL)-1,2,3,5-TETRAHYDROPYRROLO [2,3-F]INDOLE
• Synonyms: 3,5-DIHYDRO-5-METHYL-N-3-PYRIDINYLBENZO[1,2-B:4,5-B']DIPYRROLE-1(2H)-CARBOXAMIDE HYDROCHLORIDE;5-METHYL-1-(3-PYRIDYLCARBAMOYL)-1,2,3,5-TETRAHYDROPYRROLO [2,3-F]INDOLE;SB 206553;SB 206553 HYDROCHLORIDE;N-3-PYRIDINYL-3,5-DIHYDRO-5-METHYL-BENZO[1,2-B:4,5-B']DIPYRROLE-1(2H)-CARBOXAMIDE HYDROCHLORIDE;SB 206553 HCL;5-METHYL-3,5-DIHYDRO-2H-PYRROLO[2,3-F]INDOLE-1-CARBOXYLIC ACID PYRIDIN-3-YLAMIDE;5-methyl-1-(3-pyridylcarbamoyl)-1,2,3,5-tetrahydropyrrolo[2,3-f]indole hydrochloride
• CAS NO: 158942-04-2
• Molecular Formula: C₁₇H₁₆N₄O
• Molecular Weight: 292.34
• Product Categories: pharmacetical;Serotonin receptor
• Mol File: 158942-04-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 575.4 °C at 760 mmHg
• Flash Point: 301.8 °C
• Appearance: brown/solid
• Density: 1.33 g/cm³
• Vapor Pressure: 3.04E-13mmHg at 25°C
• Storage Temp.: Desiccate at RT
• Solubility: H2O: 30 mg/mL
• PKA: 13.50±0.20(Predicted)
• CAS DataBase Reference: 5-METHYL-1-(3-PYRIDYLCARBAMOYL)-1,2,3,5-TETRAHYDROPYRROLO [2,3-F]INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYL-1-(3-PYRIDYLCARBAMOYL)-1,2,3,5-TETRAHYDROPYRROLO [2,3-F]INDOLE(158942-04-2)
• EPA Substance Registry System: 5-METHYL-1-(3-PYRIDYLCARBAMOYL)-1,2,3,5-TETRAHYDROPYRROLO [2,3-F]INDOLE(158942-04-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 158942-04-2(Hazardous Substances Data)

Usage

Uses

SB 206553 Hydrochloride is a 5-HT2 antagonist.

Biological Activity

Potent and selective 5-HT 2B /5-HT 2C receptor antagonist (rat 5-HT 2B pA 2 = 8.89, human 5-HT 2C pK i = 7.92). Displays > 80-fold selectivity over all other 5-HT receptor subtypes and a variety of other receptors (pK i < 6). Centrally active following oral administration in vivo .

InChI:InChI=1/C17H16N4O.ClH/c1-20-7-4-12-10-16-13(9-15(12)20)5-8-21(16)17(22)19-14-3-2-6-18-11-14;/h2-4,6-7,9-11H,5,8H2,1H3,(H,19,22);1H

Upstream product

• 40995-78-6 1-acetyl-1,2,3,5-tetrahydropyrrolo<2,3-f>indole 
• 166413-85-0 N-(1-acetyl-5-indolinyl)-2,2-dimethoxyethylamine 
• 158942-38-2 1-acetyl-5-methyl-1,2,3,5-tetrahydropyrrolo<2,3-f>indole 
• 137601-29-7 1-acetyl-5-(trifluoroacetyl)-1,2,3,5-tetrahydropyrrolo<2,3-f>indole 
• 4993-96-8 1-(5-aminoindolin-1-yl)ethanone 
• 15268-31-2 3-Pyridyl isocyanate 
• 158942-39-3 5-methyl-1,2,3,5-tetrahydropyrrolo<2,3-f>indole 

Relevant articles and documents

Model studies on a synthetically facile series of N-substituted phenyl-N'-pyridin-3-yl ureas leading to 1-(3-pyridylcarbamoyl) indolines that are potent and selective 5-HT(2C/2B) receptor antagonists

A model series of 5-HT(2C) antagonists have been prepared by rapid parallel synthesis. These N-substituted phenyl-N'-pyridin-3-yl ureas were found to have a range of 5-HT(2C) receptor affinities and selectivities over the closely related 5-HT(2A) receptor. Extrapolation of simple SAR, derived from this set of compounds, to the more active but synthetically more complex 1-(3-pyridyl-carbamoyl)indoline series allowed us to target optimal substitution patterns and identify potent and selective 5-HT(2C/2B) antagonists. Copyright (C) 1999 Elsevier Science Ltd.