77-39-4

Pagitane,Lilly,US,1953

Cycrimine is a cholinolytic anti-Parkinson drug which can cause neuromuscular blockades in isolated rat diaphragms.

ChEBI: A member of the class of piperidines that is 3-(piperidin-1-yl)propan-1-ol in which one of the hydrogen atoms at the 1-position is substituted by cyclopentyl, and the other is substituted by phenyl. A central anticholinergic, it is used as its hydrochlorid salt in the management and treatment of Parkinson's disease.

The manufacture of the cyclohexyl analog is as follows. Phenyl magnesium bromide was prepared from 48.5 g (0.308 mol) of bromobenzene, 7 g (0.29 mol) of magnesium, and 125 ml of dry ether. To it was added at 5°C over a period of ? hour 40 g (0.18 mol) of cyclohexyl β-(N-piperidyl)-ethyl ketone (BP 115° to 117°C/1 mm) in 125 ml of dry ether. The mixture was allowed slowly to come to room temperature, refluxed for one hour, and then poured into ice containing 80 ml of concentrated hydrochloric acid. Ammonium chloride (100 g) and 200 ml of concentrated ammonium hydroxide were added and the organic layer was separated. After drying and removing the solvent, the residue was distilled under reduced pressure. The base distilled at 158° to 170°C (1 mm) and solidified. Upon recrystallization from methanol it melted at 112° to 113°C.

Pagitane (Lilly).

Muscle relaxant, Antiparkinsonian