17380-42-6

Basic information

• Product Name: 3-[2-(dimethylamino)ethyl]-1H-indole-5-carbonitrile
• CAS NO: 17380-42-6
• Molecular Formula: C₁₃H₁₅N₃
• Molecular Weight: 213.2783
• Mol File: 17380-42-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 403.5°C at 760 mmHg
• Flash Point: 197.8°C
• Density: 1.14g/cm³
• Vapor Pressure: 1.01E-06mmHg at 25°C
• Refractive Index: 1.619
• CAS DataBase Reference: 3-[2-(dimethylamino)ethyl]-1H-indole-5-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[2-(dimethylamino)ethyl]-1H-indole-5-carbonitrile(17380-42-6)
• EPA Substance Registry System: 3-[2-(dimethylamino)ethyl]-1H-indole-5-carbonitrile(17380-42-6)

Safety Data

• Hazardous Substances Data: 17380-42-6(Hazardous Substances Data)

Upstream product

• 50-00-0 formaldehyd 
• 101831-71-4 3-(2-aminoethyl)-5-cyano-1H-indole hydrochloride 
• 17274-65-6 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole 
• 22120-38-3 2-(5-iodo-1H-indol-3-yl)-N,N-dimethylethanamine 
• 544-92-3 copper(I) cyanide 
• 557-21-1 dicyanozinc 

Relevant articles and documents

Substituted indole compounds having NOS inhibitory activity

The present invention features inhibitors of nitric oxide synthase (NOS), particularly those that selectively inhibit neuronal nitric oxide synthase (nNOS) in preference to other NOS isoforms. The NOS inhibitors of the invention, alone or in combination w

SYNTHESIS OF AMINES AND INTERMEDIATES FOR THE SYNTHESIS THEREOF

The invention relates in a first embodiment to a method for the manufacture of esters of the formula (I), or especially of amides of the formula (II), wherein the symbols have the meanings given in the specification, as well as other intermediates and compounds useful in the synthesis of tryptamines and other substances mentioned in the title. The synthesis methods and intermediates are useful in the synthesis of pharmaceuticals.

N-arylsulfonylindole derivatives as serotonin 5-HT6 receptor ligands

A series of N1-arylsulfonyltryptamines were found to be potent ligands of the human serotonin 5-HT6 receptor with the 5-methoxy-1-benzenesulfonyl analogue (19) having the highest affinity. Additionally, it was discovered that a group such as 3-(3-methoxybenzyl)-1,2,4-oxadiazol-5-yl in the 2-position of the indole ring (43) can replace the arylsulfonyl substituent in the 1-position with no loss of affinity. This suggested that the binding conformation of the aminoethyl side chain at this receptor was toward the 4-position of the indole ring and was supported by the fact that the 4-(aminoethyl)indoles (45) also displayed high affinity, as did the conformationally rigid 1,3,4,5-tetrahydrobenz[c,d]indole (49). Molecular modeling showed that 19, 43, and 45 all had low-energy conformers that overlaid well onto 49. Both 19 and 49 had good selectivity over other serotonin receptors tested, with 49 also showing excellent selectivity over all dopamine receptors. In a functional adenylate cyclase stimulation assay, 19 and 49 had no agonist activity, whereas 45 behaved as a partial agonist. Finally, it was shown that 19 had good activity in the 5-HT2A centrally mediated mescaline-induced head twitch assay, which implies that it is brain-penetrant.