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

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

• 50-00-0 formaldehyd 
• 23690-10-0 3-(9H-carbazol-9-yl)propan-1-amine 
• 5407-04-5 3-(dimethylamino)propyl chloride hydrochloride 
• 86-74-8 9H-carbazole 
• 53309-35-6 (2-chloro-1-methyl-ethyl)-dimethyl-amine 
• 13606-06-9 4,4'-dimethoxy-2-nitro-1,1'-biphenyl 
• 10298-80-3 2-chloro-5-methoxynitrobenzene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 55491-54-8 1-(9H-carbazol-9-yl)-N,N-dimethylpropan-2-amine 
• 506-59-2 N,N-dimethylammonium chloride 
• 84359-61-5 9-(3-bromopropyl)-9H-carbazole 
• 96576-84-0 9-γ-chloropropylcarbazole 
• 88-73-3 2-Chloronitrobenzene 
• 908242-58-0 N-(3-dimethylaminopropyl)-N-(2-fluorophenyl)-2-nitroaniline 

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

A Focused Library of Psychotropic Analogues with Neuroprotective and Neuroregenerative Potential

Overcoming the lack of effective treatments and the continuous clinical trial failures in neurodegenerative drug discovery might require a shift from the prevailing paradigm targeting pathogenesis to the one targeting simultaneously neuroprotection and neuroregeneration. In the studies reported herein, we sought to identify small molecules that might exert neuroprotective and neuroregenerative potential as tools against neurodegenerative diseases. In doing so, we started from the reported neuroprotective/neuroregenerative mechanisms of psychotropic drugs featuring a tricyclic alkylamine scaffold. Thus, we designed a focused-chemical library of 36 entries aimed at exploring the structural requirements for efficient neuroprotective/neuroregenerative cellular activity, without the manifestation of toxicity. To this aim, we developed a synthetic protocol, which overcame the limited applicability of previously reported procedures. Next, we evaluated the synthesized compounds through a phenotypic screening pipeline, based on primary neuronal systems. Phenothiazine 2Bc showed improved neuroregenerative and neuroprotective properties with respect to reference drug desipramine (2Aa). Importantly, we have also shown that 2Bc outperformed currently available drugs in cell models of Alzheimer's and Parkinson's diseases and attenuates microglial activation by reducing iNOS expression.

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The treatment of 2-fluorophenyl 2-iodophenylamines, ether, and thioether, easily prepared from commercially available products, with 3.3 equiv of t-BuLi and further reaction with selected electrophiles gives rise to functionalized carbazole, dibenzofuran, and dibenzothiophene derivatives in a direct and regioselective manner. The process involves an anionic cyclization on a benzyne-tethered aryllithium intermediate.

CALCIUM RECEPTOR MODULATING AGENTS

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