286943-21-3

Basic information

• Product Name: 2,5-Diazabicyclo[2.2.1]heptane,2-(6-methyl-3-pyridinyl)-,(1S,4S)-(9CI)
• Synonyms: 2,5-Diazabicyclo[2.2.1]heptane,2-(6-methyl-3-pyridinyl)-,(1S,4S)-(9CI)
• CAS NO: 286943-21-3
• Molecular Formula: C11H15N3
• Molecular Weight: 0
• Product Categories: PIPERIDINE
• Mol File: 286943-21-3.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,5-Diazabicyclo[2.2.1]heptane,2-(6-methyl-3-pyridinyl)-,(1S,4S)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Diazabicyclo[2.2.1]heptane,2-(6-methyl-3-pyridinyl)-,(1S,4S)-(9CI)(286943-21-3)
• EPA Substance Registry System: 2,5-Diazabicyclo[2.2.1]heptane,2-(6-methyl-3-pyridinyl)-,(1S,4S)-(9CI)(286943-21-3)

Safety Data

• Hazardous Substances Data: 286943-21-3(Hazardous Substances Data)

Usage

Molecular structure

2,5-Diazabicyclo[2.2.1]heptane, 2-(6-methyl-3-pyridinyl)is a bicyclic amine that contains a pyridine ring and a diaza ring.

Stereochemistry

The (1S,4S) stereochemistry indicates the absolute configurations of the two chiral centers in the molecule.

Use as a catalyst

It is often used as a catalyst in organic synthesis due to its basic properties and ability to accelerate various chemical reactions.

Applications

It has been employed in the pharmaceutical industry for the synthesis of various drugs, as well as in the manufacturing of polymers and other industrial chemicals. It has also been investigated for its potential application in asymmetric synthesis and catalysis.

Upstream product

• 113451-59-5 (1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester 
• 286946-48-3 tert-butyl (1S,4S)-5-(6-methyl-3-pyridinyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate 
• 3430-13-5 5-bromo-2-methylpyridine 

Relevant articles and documents

Structure-activity studies and analgesic efficacy of N-(3-pyridinyl)- bridged bicyclic diamines, exceptionally potent agonists at nicotinic acetylcholine receptors

A series of exceptionally potent agonists at neuronal nicotinic acetylcholine receptors (nAChRs) has been investigated. Several N-(3-pyridinyl) derivatives of bridged bicyclic diamines exhibit double-digit-picomolar binding affinities for the α4β2 subtype, placing them with epibatidine among the most potent nAChR ligands described to date. Structure-activity studies have revealed that substitutions, particularly hydrophilic groups in the pyridine 5-position, differentially modulate the agonist activity at ganglionic vs central nAChR subtypes, so that improved subtype selectivity can be demonstrated in vitro. Analgesic efficacy has been achieved across a broad range of pain states, including rodent models of acute thermal nociception, persistent pain, and neuropathic allodynia. Unfortunately, the hydrophilic pyridine substituents that were shown to enhance agonist selectivity for central nAChRs in vitro tend to limit CNS penetration in vivo, so that analgesic efficacy with an improved therapeutic window was not realized with those compounds.