[2-[[[1,1'-Bicyclohexyl]-1-ylcarbonyl]oxy]ethyl]diethylammoniumchlorid

Bezeichnung:[2-[[[1,1'-Bicyclohexyl]-1-ylcarbonyl]oxy]ethyl]diethylammoniumchlorid

CAS-Nr67-92-5

Englisch Name:DICYCLOMINE HYDROCHLORIDE

CBNumberCB2285591

SummenformelC19H36ClNO2

Molgewicht345.95

MOL-Datei67-92-5.mol

Synonyma

[2-[[[1,1'-Bicyclohexyl]-1-ylcarbonyl]oxy]ethyl]diethylammoniumchlorid

[2-[[[1,1'-Bicyclohexyl]-1-ylcarbonyl]oxy]ethyl]diethylammoniumchlorid physikalisch-chemischer Eigenschaften

Schmelzpunkt	164-166°C
storage temp.	-20°C Freezer
Löslichkeit	H₂O: 50 mg/mL
Aggregatzustand	powder
Farbe	off-white
BCS Class	2/4
EPA chemische Informationen	2-Diethylaminoethyl bicyclohexyl-1-carboxylate hydrochloride (67-92-5)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/37/38
S-Sätze:	26-36
WGK Germany	3
RTECS-Nr.	DT7350000
HS Code	2922199695
Toxizität	LD50 orl-rat: 1290 mg/kg DRUGAY 6,317,82

Gefahreninformationscode (GHS)

DICYCLOMINE HYDROCHLORIDE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
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.
Chemische Eigenschaften
White Crystalline Powder
Originator
Bentyl ,Merrell National ,US,1950
Verwenden
Dicyclomine Hydrochloride can be used as medication to treat gastric diseases.
Verwenden
anticholinergic
Verwenden
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.
Trademarks
Bentyl (Axcan Scandipharm).
Therapeutic Function
Spasmolytic
Allgemeine Beschreibung
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.
Sicherheitsprofil
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.

DICYCLOMINE HYDROCHLORIDE Upstream-Materialien And Downstream Produkte

[2-[[[1,1'-Bicyclohexyl]-1-ylcarbonyl]oxy]ethyl]diethylammoniumchlorid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

67-92-5, DICYCLOMINE HYDROCHLORIDE Verwandte Suche:

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