20811-26-1

Basic information

• Product Name: N,N-Dimethyl-3-(9H-carbazole-9-yl)propane-1-amine
• Synonyms: 9-[3-(Dimethylamino)propyl]-9H-carbazole;N,N-Dimethyl-3-(9H-carbazole-9-yl)propane-1-amine
• CAS NO: 20811-26-1
• Molecular Formula: C₁₇H₂₀N₂
• Molecular Weight: 252.35
• Mol File: 20811-26-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 402.6°C at 760 mmHg
• Flash Point: 197.3°C
• Appearance: /
• Density: 1.04g/cm³
• Vapor Pressure: 1.08E-06mmHg at 25°C
• Refractive Index: 1.586
• CAS DataBase Reference: N,N-Dimethyl-3-(9H-carbazole-9-yl)propane-1-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dimethyl-3-(9H-carbazole-9-yl)propane-1-amine(20811-26-1)
• EPA Substance Registry System: N,N-Dimethyl-3-(9H-carbazole-9-yl)propane-1-amine(20811-26-1)

Safety Data

• Hazardous Substances Data: 20811-26-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 5206, 1994 DOI: 10.1021/jo00097a023Synthesis, p. 29, 1984 DOI: 10.1055/s-1984-30719

InChI:InChI=1/C17H20N2/c1-18(2)12-7-13-19-16-10-5-3-8-14(16)15-9-4-6-11-17(15)19/h3-6,8-11H,7,12-13H2,1-2H3

Upstream product

• 5337-01-9 N-(2-cyanoethyl)carbazole 
• 124-40-3 dimethyl amine 
• 86-74-8 9H-carbazole 
• 109-54-6 3-(Dimethylamino)propyl chloride 
• 146041-80-7 9-<1-(Benzotriazol-1-yl)-3-(dimethylamino)propyl>carbazole 
• 908242-62-6 N-(3-dimethylaminopropyl)-N-(2-fluorophenyl)-2-iodoaniline 
• 908242-60-4 N-(3-dimethylaminopropyl)-N-(2-fluorophenyl)benzene-1,2-diamine 
• 908242-58-0 N-(3-dimethylaminopropyl)-N-(2-fluorophenyl)-2-nitroaniline 
• 88-73-3 2-Chloronitrobenzene 
• 506-59-2 N,N-dimethylammonium chloride 
• 96576-84-0 9-γ-chloropropylcarbazole 
• 5407-04-5 3-(dimethylamino)propyl chloride hydrochloride 
• 50-00-0 formaldehyd 
• 23690-10-0 3-(9H-carbazol-9-yl)propan-1-amine 

Downstream Products

• 311332-87-3 3-carbazol-9-yl-N-[2-(4-methoxyphenyl)ethyl]-N-methylpropan-1-amine 
• 311332-86-2 3-carbazol-9-yl-N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylpropan-1-amine 

Relevant articles and documents

N-Dimethylaminopropylation in a solid-liquid two phase system: Synthesis of chlorpromazine, its analogs, and related compounds

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NB 06: From a simple lysosomotropic aSMase inhibitor to tools for elucidating the role of lysosomes in signaling apoptosis and LPS-induced inflammation

Ceramide generation is involved in signal transduction of cellular stress response, in particular during stress-induced apoptosis in response to stimuli such as minimally modified Low-density lipoproteins, TNFalpha and exogenous C6-ceramide. In this paper we describe 48 diverse synthetic products and evaluate their lysosomotropic and acid sphingomyelinase inhibiting activities in macrophages. A stimuli-induced increase of C16-ceramide in macrophages can be almost completely suppressed by representative compound NB 06 providing an effective protection of macrophages against apoptosis. Compounds like NB 06 thus offer highly interesting fields of application besides prevention of apoptosis of macrophages in atherosclerotic plaques in vessel walls. Most importantly, they can be used for blocking pH-dependent lysosomal processes and enzymes in general as well as for analyzing lysosomal dependent cellular signaling. Modulation of gene expression of several prominent inflammatory messengers IL1B, IL6, IL23A, CCL4 and CCL20 further indicate potentially beneficial effects in the field of (systemic) infections involving bacterial endotoxins like LPS or infections with influenza A virus.

Carbazole inhibitors of histamine receptors for the treatment of disease

The present invention relates to carbazole compounds, pharmaceutical compositions comprising them, and methods which may be useful as inhibitors of H1R and/or H4R for the treatment or prevention of inflammatory, autoimmune, allergic, and ocular diseases.