100752-88-3

Usage

InChI:InChI=1/C8H13NO/c1-7(10)8-3-5-9(2)6-4-8/h3H,4-6H2,1-2H3

Upstream product

• 54238-21-0 1-methyl-1,2,3,6-tetrahydropyridine-4-carboxylic acid hydrochloride 
• 7630-04-8 1-methyl-4-acetylpyridinium iodide 
• 60553-34-6 1-methyl-4-(2-methyl-1,3-dioxolan-2-yl)pyridinium iodide 
• 60553-32-4 1-methyl-4-(2-methyl-1,3-dioxolan-2-yl)-1,2,3,6-tetrahydropyridine 
• 112654-70-3 1-methyl-4-(2-hydroxyethyl)-1,2,3,6-tetrahydropyridine 
• 676-58-4 methylmagnesium chloride 
• 132335-05-8 N-Methoxy-1,N-dimethyl-1,2,3,6-tetrahydro-4-pyridinecarboxamide 

Relevant academic research and scientific papers

Synthesis, pharmacology, and molecular modeling studies of semirigid, nicotinic agonists

Eight nicotinic agonists were synthesized, and their potencies were estimated by contracture of the frog rectus abdominis muscle. The most potent, 1-methyl-4-acetyl-1,2,3,6-tetrahydropyridine methiodide (3b), 50 times as potent as carbamylcholine, served as a template for the rest. Although all of the agonists could easily conform to the putative nicotinic pharmacophore, their potencies spanned a nearly 10,000-fold range. This pharmacophore, therefore, may be necessary but deficient. Computer-assisted molecular modeling studies helped to delineate additional factors that may contribute to potency. The factors are (1) the ground-state conformation, (2) superimposability of the hydrogen bond acceptor and the cationic head onto the template, (3) electrostatic potential at the cationic head and at the hydrogen bond acceptor site, and (4) the presence of a methyl group bonded to the carbon atom that bears the hydrogen bond acceptor. A new program, ARCHEM, was used to calculate and to visualize electrostatic potentials at the van der Waals surfaces of the agonists.

An Improved Synthesis of 1-(1,2,3,6-Tetrahydro-1-methyl-4- Pyridinyl)ethanone, Isoarecolone

A convenient synthesis of 1-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)ethanone, isoarecolone, starting with 4-acetylpyridine is presented. 4-Acetylpyridine was protected as the ketal followed by reaction with iodomethane to give the quaterary salt. The quaterary salt was reduced with sodium borohydride followed by deprotection to give isoarecolone in 80% overall yield.

O-substituted tetrahydropyridine oxime cholinergic agents

Certain O-substituted 1-(1,2,3,6-tetrahydro-1-methyl-3-pyridinyl)ketone oximes and O-substituted 1-(1,2,3,6-tetrahydro-4-pyridinyl)ketone oximes are useful as analgesic agents or agents for the treatment or amelioration of the symptoms of cerebral insufficiency characterized by decreased central acetylcholine production or release. Pharmaceutical compositions containing the compounds and methods of using the compositions in a pharmaceutical method are also disclosed.