137730-52-0

Basic information

• Product Name: L-693,403 MALEATE
• Synonyms: N-1'-BENZYL-3,4-DIHYDROSPIRO[1H-INDENE-1,4'-PIPERIDINE] MALEATE;L-693,403 MALEATE;2,3-dihydro-1'-(phenylmethyl)-spiro[1H-indene-1,4'-pieridine]
• CAS NO: 137730-52-0
• Molecular Formula: C₂₀H₂₃N
• Molecular Weight: 393.48
• Mol File: 137730-52-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 595.5°Cat760mmHg
• Flash Point: 314°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 4.98E-15mmHg at 25°C
• Storage Temp.: Desiccate at -20°C
• PKA: 9.09±0.20(Predicted)
• CAS DataBase Reference: L-693,403 MALEATE(CAS DataBase Reference)
• NIST Chemistry Reference: L-693,403 MALEATE(137730-52-0)
• EPA Substance Registry System: L-693,403 MALEATE(137730-52-0)

Safety Data

• Hazardous Substances Data: 137730-52-0(Hazardous Substances Data)

Usage

Description

L-693,403 MALEATE is a sigma receptor-binding compound that has been identified for its potential therapeutic applications, particularly in the management of pain associated with diabetes.

Uses

Used in Pharmaceutical Industry:
L-693,403 MALEATE is used as a therapeutic agent for the treatment of diabetes-associated pain. Its interaction with sigma receptors aids in alleviating the discomfort and pain experienced by patients suffering from this condition.

Biological Activity

High affinity σ ligand with excellent selectivity over the dopamine D 2 receptor.

InChI:InChI=1/C20H23N.C4H4O4/c1-2-6-17(7-3-1)16-21-14-12-20(13-15-21)11-10-18-8-4-5-9-19(18)20;5-3(6)1-2-4(7)8/h1-9H,10-16H2;1-2H,(H,5,6)(H,7,8)/b;2-1-

Upstream product

• 38025-43-3 1-benzyl-4-(2-phenylethyl)-1,2,3,6-tetrahydropyridine 
• 428-38-6 2,3-dihydrospiro[1H-indene-1,4'-piperidine] 
• 100-39-0 benzyl bromide 
• 2116-64-5 4-(2-phenylethyl)pyridine 
• 100-44-7 benzyl chloride 

Relevant articles and documents

Spiroindene and spiroindane compounds

A compound of the formula (I): wherein Z, A, B, C, R1, R2, X1, X2, Q and n are as disclosed herein.

Spirovesamicols: Conformationally restricted analogs of 2-(4- phenylpiperidino)cyclohexanol (vesamicol, AH5183) as potential modulators of presynaptic cholinergic function

In an effort to develop selective inhibitors of vesicular acetylcholine storage, we have synthesized a series of semirigid vesamicol receptor ligands based on the structure of 2-(4-phenylpiperidino)-cyclohexanol (vesamicol, AH5183, 1). In these compounds, the planes of the phenyl and piperidyl moieties of the parent ligand 1 are held at right angles by vinyl, ethylene, and propylene bridges to form N-substituted derivatives of spiro[indene- 1,4'-piperidine], 2,3-dihydrospiro[indene-1,4'-piperidine], and 3,4- dihydrospiro[naphthalene-1(2H),4'-piperidine], respectively. Preliminary evaluation of these compounds in electric organ synaptic vesicles revealed several potent vesamicol receptor ligands, such as 1'-(2-hydroxy-1,2,3,4- tetrahydronaphth-3-yl)spiro[1H-indene-1,4'-piperidine] (11b) and 1'-(2- hydroxy-1,2,3,4-tetrahydronaphth-3-yl)spiro[2-bromo-1H-indene-1,4'- piperidine] (14), which display subnanomolar affinity for this receptor. In general, the vinyl and ethylene bridges yielded the most potent analogs while the propylene-bridged analogs were among the least potent compounds. The increased rigidity of these spiro-fused compounds, relative to the corresponding simple 4-phenylpiperidine derivatives of vesamicol, is expected to confer greater selectivity for the vesamicol receptor.

Spiropiperidines as high-affinity, selective σ ligands

A variety of achiral conformationally restricted spirocyclic piperidines have been prepared in an attempt to investigate the functional role of the central σ recognition site. All the compounds possessed a lipophilic N- substituent incorporating either a tetralin, indan, or benzocycloheptane skeleton. Their in vitro affinity at the σ site was assessed in radioligand displacement experiments with guinea pig cerebellum homogenates using the σ- specific radioligand [3H]-N,N'-di-o-tolylguanidine ([3H]-DTG, [3H]-6). A study of the structure-activity relationships identified the N-butyl and N- dimethylallyl substituents as the optimum groups for high affinity and selectivity at the σ site (e.g., 3,4-dihydro-1'-(3-methylbut-2- enyl)spiro[1H-indene-1,4'-piperidine] (48), pIC50 = 8.9 vs [3H]-6 and greater than 10 000-fold selective over the dopamine D2 receptor). Such compounds are amongst the highest affinity σ ligands reported to date, with excellent selectivity over the dopamine D2 receptor, and may serve as a useful tool for exploring the physiological role of the σ site.