Aceclidine

Therapeutic Function Miotic, cholinomimetic Chemical Name 1 -Azabicyclo[2.2.2] octan-3-ol acetate Common Name 3-Qulnuclidlnol Acetate 

A mixture of 274 g of methyl Isonicotinate, 367 g of ethyl bromoacetate and 125 cc of ethyl alcohol was stirred without heating for 4 hours in a flask equipped with a reflux condenser. (The reaction was exothermic and precautions were taken to keep the temperature below 70°C.) The reaction mixture was then left for 15 hours at room temperature. 

The reaction product (1-carbethoxymethyl-4-carbomethoxy-pyridinium bromide) was obtained in crystalline form. (It formed prisms melting at 166°-169°C after recrystallization from a mixture of isopropanoi and acetone.) It was not necessary to isolate it. For the following reduction step, the reaction mixture was brought into solution by the addition of about 1 liter of warm ethyl alcohol. It was then hydrogenated at about 30 atm pressure In the presence of 2 g of platinum oxide. The temperature rose during this reaction to about 40°C. 

After the calculated amount of hydrogen had been absorbed, the catalyst was filtered off, the solution was concentrated in vacuo, and the residual syrup was dissolved in ice water. Benzene was added and the mixture was made alkaline with an excess of concentrated ice cold potassium carbonate solution. The temperature was kept low by continuous addition of ice, and the benzene layer was separated and dried with sodium sulfate. The dried benzene solution was concentrated in vacuo and the residual oil was distilled in vacuo. BP 30 mm = 175°-182°C, 

A solution of 50 g of the above ketone-hydrochloride in 30 cc of water was made alkaline by the addition of 30 g of potassium hydroxide. After the alkali was dissolved, 35 g of granular potassium carbonate were added. The free basic ketone was then extracted from the viscous mixture by shaking with 4 portions of hot benzene (300 cc in each portion). The benzene extracts were decanted, filtered over sodium sulfate in order to remove any suspended alkali, and concentrated in vacuo. The residual 1-azabicyclo[2.2.2]-3-octanone was purified by sublimation (50°-70 C/0.5 mm Hg) it can also be purified by recrystallization from petroleum ether. It formed feathery crystals melting at 147°-148 C. 

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Azatadine maleate Chlorprothixene Cyproheptadine iphenidol Flupentixol Heptabarbitol Mepivacaine Methadone HCI Methallenestril Methohexital sodium Oxitropium bromide Pipethanate ethobromide Pyrithyidione Ethyl bromoacetate Aceclidine... 

Muscarinic agonists and antagonists are used for the treatment of a variety of pathophysiological conditions. For example, muscarinic agonists (pilocarpine, carba-chol, or aceclidine) reduce intraocular pressure when... 

C7H13NO 1619-34-7) see Aceclidine Clidinium bromide (lo,3p,5a)-3-hydroxyspiro[8-azoniabicyclo[3.2.1]octane-8,r-pyrroUdlnium] chloride... 

Bisoxatin Acetate Choleretic Piprozolin Cholinergic Agent Aceclidine Coccidiostats Oxyphenisatin Acetate... 

In contrast to the enantiomers of (145), both enantiomers of 3-acetoxyquinuclidine (aceclidine, 149) are potent muscarinics, and the S-enantiomer is only approximately one order cf magnitude less potent than acetylcholine. 

Thiadiazole ether analogs (213,214) of vedaclidine (212) have also been viewed as being analogs of the potent muscarinic agonist aceclidine (149) (248). These ether analogs are... 

This field has been explored exclusively by Russian chemists and biologists under the leadership of M. V. Rubtsov and M. D. Mashkovsky. The following drugs have been developed Aceclidine (47), Aprolidine (48), Oxylidine (49), Diochine (50), and Qualidile (51). 

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