DICYCLOMINE HYDROCHLORIDE Chemical Properties

Melting point:

164-166°C

storage temp. 

-20°C Freezer

solubility 

H₂O: 50 mg/mL

form 

powder

color 

off-white

BCS Class

2/4

EPA Substance Registry System

2-Diethylaminoethyl bicyclohexyl-1-carboxylate hydrochloride (67-92-5)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

DT7350000

HS Code 

2922199695

Toxicity

LD50 orl-rat: 1290 mg/kg DRUGAY 6,317,82

MSDS

• Language:English Provider:SigmaAldrich

DICYCLOMINE HYDROCHLORIDE Usage And Synthesis

Description

Dicyclomine is an M₁ and M₂ muscarinic acetylcholine receptor antagonist (K_is = 3.16 and 44.7 nM, respectively). It inhibits inositol phosphate accumulation induced by the non-selective acetylcholine agonist carbamoylcholine (carbachol; ) in guinea pig cortex (K_i = 12 nM; pA₂ = 7.88). Dicyclomine (10 mg/kg, i.v.) inhibits potassium-induced contraction of ileum, colon, and duodenum in anesthetized rats by 21.85, 30.81, and 37.86%, respectively. Formulations containing dicyclomine have been used to treat functional and irritable bowel syndrome and to relieve muscle spasms in the gastrointestinal tract.

Chemical Properties

White Crystalline Powder

Originator

Bentyl ,Merrell National ,US,1950

Uses

Dicyclomine Hydrochloride can be used as medication to treat gastric diseases.

Uses

anticholinergic

Uses

Used as a gastrointestinal antispasmodic antacid

Definition

ChEBI: The hydrochloride salt of dicyclomine. An anticholinergic, it is used to treat or prevent spasm in the muscles of the gastrointestinal tract, particularly that associated with irritable bowel syndrome.

Manufacturing Process

155 grams of 1-phenylcyclohexanecyanide, 350 cc of concentrated sulfuric acid and 1,130 cc of ethyl alcohol are refluxed vigorously for 48 hours. The remaining alcohol is then removed by vacuum distillation and the residue is poured into 1 liter of ice water. An oil separates which is extracted 3 times with 200 cc portions of petroleum ether, the extracts are combined and heated on a steam bath to remove the ether. The resulting crude ester may be used directly for the reesterification operation or it may be distilled to purify it first. A mixture of the ester so obtained, 155 grams of βdiethylaminoethanol and 800 cc of dry xylene are placed in a reaction vessel with about 2 grams of sodium. The vessel is heated in an oil bath at 150°- 160°C. A xylene-ethanol azeotrope distills over at about 78°-82°C over a period of 2 to 3 hours. The distillate is cooled and shaken with about 3 times its volume of water, the decrease in volume of the distillate being considered a measure of the amount of alcohol formed. When 80-90% of the theoretical amount of alcohol is obtained in the distillate the reaction mixture is subjected to vacuum distillation to remove most of the xylene and unreacted diethylaminoethanol. The residue is poured into 500 cc of benzene which is then extracted 3 times with 500 cc portions of water.
The washed benzene layer is diluted with an equal volume of ether and alcoholic hydrochloric acid is added until the mixture is acid to Congo red. A white crystalline solid forms which is dissolved in 300-400 cc of alcohol and diluted with ether to the point where precipitation starts. A few drops of butanone are added, the solution is cooled to -10°C, and filtered to recover the crystals which separate. The product is obtained in the form of white needles melting at 159°-160°C, in good yield.
13 parts of β-diethylaminoethyl 1-phenylcyclohexanecarboxylate hydrochloride, 125 parts of glacial acetic acid and 0.3 part of Adams' catalyst are heated to 70°C and shaken with hydrogen at 50 lb pressure until 90- 100% of the theoretical hydrogen is absorbed. The acetic acid is then removed by distillation and the residue recrystallized from butanone, giving the above product as a crystalline hydrochloride melting at 165°-166°C, in good yields. This product may also be prepared by reacting cyclohexyl bromide with cyclohexyl cyanide with the use of sodium amide followed by alcoholysis and reesterification.

brand name

Bentyl (Axcan Scandipharm).

Therapeutic Function

Spasmolytic

General Description

Dicyclomine hydrochloride,2-(diethylamino)ethyl bicyclohexyl-1-carboxylatehydrochloride (Bentyl), has some muscarinic receptorsubtype selectivity. It binds more firmly to M1 and M3 thanto M2 and M4 receptors.76Dicyclomine hydrochloride has one eighth of the neurotropicactivity of atropine and approximately twice themusculotropic activity of papaverine. This preparation, firstintroduced in 1950, has minimized the adverse effects associatedwith the atropine-type compounds.

Clinical Use

Dicyclomine Hydrochloride is used for itsspasmolytic effect on various smooth muscle spasms, particularlythose associated with the GI tract. It is also usefulin dysmenorrhea, pylorospasm, and biliary dysfunction.

Safety Profile

Poison by intravenous route.Moderately toxic by ingestion. Human systemic effects byingestion: rigidity, dyspnea, cyanosis. When heated todecomposition it emits very toxic fumes of HCl and NOx.

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