MEPENZOLATE BROMIDE Property

Melting point:

228-229°C dec.

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly)

color 

White to Off-White

Safety

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

36

WGK Germany 

3

RTECS 

TN5710000

Toxicity

LD50 orally in rats: 742±47 mg/kg (Goldenthal)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

MEPENZOLATE BROMIDE Chemical Properties,Usage,Production

Chemical Properties

Crystalline Solid

Originator

Cantil,Merrell National,US,1956

Uses

Used as an anticholinergic

Definition

ChEBI: Mepenzolate bromide is a diarylmethane.

Manufacturing Process

A mixture containing 8 g (0.06 mol) of N-methyl-3-chloro-piperidine and 13.6 g (0.06 mol) of benzilic acid in 50 cc of anhydrous isopropyl alcohol was refluxed for 3 days; the isopropyl alcohol was removed by distillation in vacuo, the residue treated with dilute aqueous hydrochloric acid and the aqueous acid mixture extracted repeatedly with ether. The aqueous phase was separated, made strongly alkaline with 20% aqueous sodium hydroxide and extracted with ether. The ether extracts were dried with potassium carbonate and distilled; the product was collected at 175° to 176°C (0.03 mm), yield 11.5 g (59 %).The ester base thus prepared was then dissolved in 75 cc of isopropyl alcohol and 3.4 g (0.037 mol) methyl bromide added. The reaction mixture was allowed to stand at 30°C for 2 days and the product isolated by filtration, yield, 13 g (87%), MP 228° to 229°C dec.

Therapeutic Function

Spasmolytic

General Description

Mepenzolate bromide, 3-hydroxy-1,1-dimethylpiperidinium bromide benzilate (Cantil),has an activity about one half that of atropine in reducingACh-induced spasms of the guinea pig ileum. The selectiveaction on colonic hypermotility is said to relieve pain, cramps,and bloating and to help curb diarrhea.

Pharmacology

Mepenzolate inhibits muscarinic action of acetylcholine on postganglionic parasympathetic effector regions. It is used in place of other drugs for treating stomach ulcers and inflammation of the intestine. Synonyms of this drug are cantil and eftoron.

Synthesis

Mepenzolate, 3-[(hydroxydiphenylacetyl)oxy]-1,1-dimethyl piperidinium bromide (14.1.13), is synthesized by esterification of benzilic acid with 1-methyl-3- chloropiperidine and subsequent reaction of the resulting ester (14.1.12) with methyl bromide [14,15].