138356-42-0

Basic information

• Product Name: N-[2-(3,4-Dichlorophenyl)ethyl]-N-methylhexahydro-1H-azepine-1-ethanamine
• Synonyms: LR-172
• CAS NO: 138356-42-0
• Molecular Formula: C₁₇H₂₆Cl₂N₂
• Molecular Weight: 329.31617
• Mol File: 138356-42-0.mol

Chemical Properties

• CAS DataBase Reference: N-[2-(3,4-Dichlorophenyl)ethyl]-N-methylhexahydro-1H-azepine-1-ethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-[2-(3,4-Dichlorophenyl)ethyl]-N-methylhexahydro-1H-azepine-1-ethanamine(138356-42-0)
• EPA Substance Registry System: N-[2-(3,4-Dichlorophenyl)ethyl]-N-methylhexahydro-1H-azepine-1-ethanamine(138356-42-0)

Safety Data

• Hazardous Substances Data: 138356-42-0(Hazardous Substances Data)

Upstream product

• 118808-13-2 N-methyl-2-(1'-homopiperidinyl)ethylamine 
• 138357-14-9 (2-Azepan-1-yl-2-oxo-ethyl)-carbamic acid tert-butyl ester 
• 138357-16-1 N-(2-Azepan-1-yl-ethyl)-2-(3,4-dichloro-phenyl)-N-methyl-acetamide 
• 111-49-9 hexamethylene imine 

Relevant articles and documents

Synthesis, characterization, and biological evaluation of a novel class of N-(arylethyl)-N-alkyl-2-(1-pyrrolidinyl)ethylamines: Structural requirements and binding affinity at the σ receptor

By synthesizing and testing a part-structure, N-[2-(3,4- dichlorophenyl)ethyl]-N-methyl-2-(1-pyrrolidinyl)ethylamine (3), derived from our previously reported high affinity σ receptor ligands (1S,2R)-(-)-N-[2- (3,4-dichlorophenyl)-ethyl]-N-methyl-2-(1-pyrrolidinyl)cyclohexylamine [(-)- 2] and (+)-2, we have identified a novel class of superpotent (subnanomolar affinity) σ ligands specific for the σ receptor labeled by [3H]-(+)-3-PPP. When 3 was tested for its capacity to displace [3H]-(+)-3-PPP from guinea pig brain membranes, it exhibited a K(i) of 0.34 nM, which is better than either of its parent compounds (-)-2 (K(i) = 1.3 nM) and (+)-2 (K(i) = 6.0 nM). Other compounds related to 3 such as N-[2-(3,4-dichlorophenyl)ethyl]-N- methyl-2-(1-homopiperidinyl)ethylamine (19) exhibited K(i) = 0.17 nM ([3H]- (+)-3-PPP). The determinants for high σ receptor affinity of 3 were examined by manipulation of this structure in a number of different ways. The high efficacy of these compounds for the σ receptor, their relative chemical simplicity and ease of synthesis, and their high degree of selectivity identifies N-[2-(3,4-dichlorophenyl)ethyl]-N-methyl-2-(1- pyrrolidinyl)ethylamine (3) and related compounds as a highly promising base for determination of the functional role of σ receptors as well as the development of novel therapeutic agents.