127424-06-0

Basic information

• Product Name: 1-azabicyclo[2.2.2]oct-3-yl methanesulfonate
• Synonyms: 1-azabicyclo[2.2.2]oct-3-yl methanesulfonate
• CAS NO: 127424-06-0
• Molecular Formula: C₈H₁₅NO₃S
• Molecular Weight: 205.2746
• Mol File: 127424-06-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-azabicyclo[2.2.2]oct-3-yl methanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-azabicyclo[2.2.2]oct-3-yl methanesulfonate(127424-06-0)
• EPA Substance Registry System: 1-azabicyclo[2.2.2]oct-3-yl methanesulfonate(127424-06-0)

Safety Data

• Hazardous Substances Data: 127424-06-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-azabicyclo[2.2.2]oct-3-yl methanesulfonate is used as an intermediate in the synthesis of azoloazabicycloalkanes, which are cholinergic agonists. These cholinergic agonists play a crucial role in the treatment of various neurological and cognitive disorders, such as Alzheimer's disease, myasthenia gravis, and glaucoma. The compound's ability to facilitate the synthesis of these agonists makes it a valuable component in the development of new therapeutic agents.
Used in Chemical Synthesis:
In the field of organic chemistry, 1-azabicyclo[2.2.2]oct-3-yl methanesulfonate is utilized as a versatile building block for the synthesis of a wide range of complex molecules. Its unique structure and reactivity enable chemists to create diverse chemical entities with potential applications in various industries, such as agrochemicals, materials science, and pharmaceuticals.
Used in Research and Development:
1-azabicyclo[2.2.2]oct-3-yl methanesulfonate is also employed in research and development settings, where it is used to explore new synthetic pathways and develop innovative methodologies for the preparation of complex organic molecules. Its unique properties make it an attractive candidate for the design and synthesis of novel compounds with potential applications in various fields.

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 1619-34-7 3-quinuclidinol 

Downstream Products

• 127424-05-9 3-(4-Methoxybenzylthio)quinuclidine 
• 852469-94-4 3-(3-benzyloxy-4-phenylpyrazol-1-yl)-1-azabicyclo[2.2.2]octane 

Relevant articles and documents

Synthesis and Muscarinic Activities of Quinuclidin-3-yltriazole and -tetrazole Derivatives

The synthesis of 15 methyl or unsubstituted 1,2,3-triazoles, 1,2,4-triazoles, and tetrazoles additionally substituted with a 1-azabicyclooctan-3-yl group is described.The potency and efficacy of these compounds as muscarinic ligands were determined in radioligand binding assays using oxotremorine and quinuclidinyl benzilate.Potency and efficacy were found in compounds in which the azole moiety was attached to the azabicyclic ring either through a carbon atom or a nitrogen atom.Electrostatic potential maps of both the C-linked and the novel N-linked series of compounds were calculated.A relationship between position and depth of the electrostatic minima relative to the azabicyclic ring and the potency and efficacy of the compounds was determined.

Substituent variation in azabicyclic triazole- and tetrazole-based muscarinic receptor ligands

The effect of variation of the 1-azabicyclic substituent on the novel 1,2,3-triazol-4-yl-, 1,2,4-triazol-1-yl-, tetrazol-5-yl-, and tetrazol-2-yl- based muscarinic receptor ligands has been studied, and the exo- azabicyclic[2.2.1]hept-3-yl substituent was found to give the most potent and efficacious compounds. In addition, variation of the second substituent on 1,2,4-triazol-1-yl- and tetrazol-2-yl-based muscarinic receptor ligands has yielded a series of novel compounds with high potencies and efficacies, ranging from full agonists to antagonists. Small lipophilic electron withdrawing substituents give potent but low efficacy compounds, while small polar electron donating substituents give potent and efficacious compounds. The activity of these compounds is described in terms of a model of the receptor involving lipophilic and hydrogen bonding interactions. These compounds provide muscarinic ligands with high potency and a range of efficacies suitable for testing as candidate drugs in the treatment of Alzheimer's disease.