143682-52-4

Basic information

• Product Name: 3-[4-(4-phenyl-1-piperidyl)-butyl]-indole
• CAS NO: 143682-52-4
• Molecular Weight: 332.489
• Mol File: 143682-52-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-[4-(4-phenyl-1-piperidyl)-butyl]-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[4-(4-phenyl-1-piperidyl)-butyl]-indole(143682-52-4)
• EPA Substance Registry System: 3-[4-(4-phenyl-1-piperidyl)-butyl]-indole(143682-52-4)

Safety Data

• Hazardous Substances Data: 143682-52-4(Hazardous Substances Data)

Upstream product

• 7440-06-4 platinum 
• 43064-12-6 1,2,3,6-tetrahydro-4-phenylpyridine hydrochloride 
• 133-32-4 4-indol-3-yl-butyric acid 
• 15591-70-5 methyl 4-(1H-indol-3-yl)butanoate 
• 3364-37-2 4-(1H-indol-3-yl)butan-1-ol 
• 771-99-3 4-phenylpiperidine 
• 163630-96-4 4-(1H-indol-3-yl)-1-butanol methanesulfonate ester 
• 73966-54-8 1-<4-(3-indolyl)butanoyl>-1,2,3,6-tetrahydro-4-phenylpyridine 

Relevant articles and documents

σ Ligands with subnanomolar affinity and preference for the σ2 binding site. 1. 3-(ω-Aminoalkyl)-1H-indoles

A series of 4-(1H-indol-3-yl)-1-butyl-substituted 4-phenylpiperidines, 4- phenyl-1,2,3,6-terrahydropyridines, and 4-phenylpiperazines was synthesized. The phenyl group was optionally substituted with 4-fluoro or 2-methoxy substituents. High affinity for both σ1 and σ1 binding sites was achieved with these compounds. Additionally, these compounds had relatively high affinity for serotonin 5-HT(1A) and 5-HT(2A), dopamine D2, and adrenergic α1 receptors. Introduction of a 4-fluorophenyl substituent at the indole nitrogen atom rendered very selective σ2 ligands with subnanomolar affinity for the σ2 binding site. The prototype of such a compound was 1-(4- fluorophenyl)-3-[4-[4-(4-fluorophenyl)-1-piperidinyl]-1-butyl]-1H-indole, 11a (code no. Lu 29-253). This compound had the following binding affinities: IC50 (σ1) = 16 nM, IC50 (σ2) = 0.27 riM, IC50 (5-HT(1A)) = 22 000 nM, IC50 (5-HT(2A)) = 270 nM, IC50 (D2) = 4200 nM, IC50 (α1) = 220nM. Spiro-joining of the phenyl and the piperidine rings into a spiro[isobenzofuran-1(3H),4'-piperidinel ring system resulted in even more selective compounds. Variations of the 1-substituent at the indole and of the chain length of the alkylene spacer group were studied. The optimal compound was the spiro analogue of compound 11a. This compound is 1'-14-[1(4- fluorophenyl)-1H-indol-3-yl]-1-butyl]spiro[isobenzofuran-1(3H),4'- piperidine], 14f (code no. Lu 28-179), with the binding affinities: IC50 (σ1) = 17 nM, IC50 (σ2) = 0.12 nM, IC50 (5-HT(1A)) = 21 000 nM, IC50 (5-HT(2A)) = 2000 nM, IC50 (D2) = 800 nM, IC50 (α1) = 330 nM. However, the most selective σ2 versus σ1 ligand was the tropane derivative 1-(4-fluorophenyl)-3-[4-[3-(4-fluorophenyl)-8- azabicyclo[3.2.1]oct-2-en-8-yl]-1-butyl]-1H-indole, 15a. This compound had the following binding affinities: IC50 (σ1) = 1200 nM, IC50 (σ2) = 2.5 nM. Potent anxiolytic activity in the black/white box exploration test in rats was found with the two most prominent σ2 ligands Lu 29-253 and Lu 28- 179. Good penetration into the CNS was documented both after subcutaneous and peroral administration of Lu 28-179 by ex vivo binding studies. Long duration of action was demonstrated both in ex vivo binding (T(1/2) ~ 20 h) and in the black/white box exploration test.

Indolealkylamines and processes for their preparation

Indolealkylamines of the formula STR1 wherein Ind is 1-R4 -2-R5 -indol-3-yl or the corresponding group in which the benzene ring is monosubstituted to trisubstituted by alkyl, O-alkyl, S-alkyl, OH, F, Cl, Br, CF3 or CN; A