102597-03-5

Basic information

• Product Name: 2-(1-methylpyrrolidin-2-yl)ethyl diphenylacetate
• CAS NO: 102597-03-5
• Molecular Formula: C₂₁H₂₅NO₂
• Molecular Weight: 323.4287
• Mol File: 102597-03-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 429.3°C at 760 mmHg
• Flash Point: 134.4°C
• Density: 1.083g/cm³
• Vapor Pressure: 1.41E-07mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: 2-(1-methylpyrrolidin-2-yl)ethyl diphenylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1-methylpyrrolidin-2-yl)ethyl diphenylacetate(102597-03-5)
• EPA Substance Registry System: 2-(1-methylpyrrolidin-2-yl)ethyl diphenylacetate(102597-03-5)

Safety Data

• Hazardous Substances Data: 102597-03-5(Hazardous Substances Data)

Upstream product

• 67004-64-2 2-(1-methyl-2-pyrrolidine)ethanol 
• 1871-76-7 diphenylacetic acid chloride 

Relevant articles and documents

Synthesis of novel nicotinic ligands with multimodal action: Targeting Acetylcholine α4β2, Dopamine and Serotonin Transporters

Nicotinic acetylcholine receptors (nAChRs), serotonin transporters (SERT) and dopamine transporters (DAT) represent targets for the development of novel nicotinic derivatives acting as multiligands associated with different health conditions, such as depressive, anxiety and addiction disorders. In the present work, a series of functionalized esters structurally related to acetylcholine and nicotine were synthesized and pharmacologically assayed with respect to these targets. The synthesized compounds were studied in radioligand binding assays at α4β2 nAChR, h-SERT and h-DAT. SERT experiments showed not radioligand [3H]-paroxetine displacement, but rather an increase in the radioligand binding percentage at the central binding site was observed. Compound 20 showed Ki values of 1.008 ± 0.230 μM for h-DAT and 0.031 ± 0.006 μM for α4β2 nAChR, and [3H]-paroxetine binding of 191.50% in h-SERT displacement studies, being the only compound displaying triple affinity. Compound 21 displayed Ki values of 0.113 ± 0.037 μM for α4β2 nAChR and 0.075 ± 0.009 μM for h-DAT acting as a dual ligand. Molecular docking studies on homology models of α4β2 nAChR, h-DAT and h-SERT suggested potential interactions among the compounds and agonist binding site at the α4/β2 subunit interfaces of α4β2 nAChR, central binding site of h-DAT and allosteric modulator effect in h-SERT.