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cycrimine

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cycrimine Basic information

Product Name:
cycrimine
Synonyms:
  • 1-cyclopentyl-1-phenyl-3-piperidin-1-ylpropan-1-ol
  • 1-cyclopentyl-1-phenyl-3-piperidino-propan-1-ol
  • 1-Piperidinepropanol, a-cyclopentyl-a-phenyl-
  • cycrimine
  • 1-Phenyl-1-cyclopentyl-3-piperidino-1-propanol
  • α-Cyclopentyl-α-phenyl-1-piperidine-1-propanol
  • 1-cyclopentyl-1-phenyl-3-piperidin-1-yl-propan-1-ol
  • cycrimine USP/EP/BP
CAS:
77-39-4
MF:
C19H29NO
MW:
287.444
EINECS:
201-024-6
Mol File:
77-39-4.mol
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cycrimine Chemical Properties

Melting point:
90-92°C
Boiling point:
125-135 °C(Press: 0.02 Torr)
Density 
1.057±0.06 g/cm3(Predicted)
storage temp. 
-20°C Freezer, Under inert atmosphere
solubility 
Chloroform (Slightly), Ethyl Acetate, Methanol (Slightly)
form 
Solid
pka
14.40±0.29(Predicted)
color 
Off-White to Pale Yellow
Stability:
Stable under recommended storage conditions., Stable Under Recommended Storage C
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cycrimine Usage And Synthesis

Originator

Pagitane,Lilly,US,1953

Uses

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

Definition

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.

Manufacturing Process

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.

brand name

Pagitane (Lilly).

Therapeutic Function

Muscle relaxant, Antiparkinsonian

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