ChemicalBook--->CAS DataBase List--->3485-62-9

3485-62-9

3485-62-9 Structure

3485-62-9 Structure
IdentificationMore
[Name]

Clidinium bromide
[CAS]

3485-62-9
[Synonyms]

3-HYDROXY-1-METHYLQUINUCLIDINIUM BROMIDE BENZILATE
3-[(HYDROXYPHENYLACETYL)OXY]-1-METHYL-1-AZONIABICYCLO[2,2,2]OCTANE BROMIDE
CLIDINIUM BROMIDE
QUARZAN
RO-2-3773
1-methyl-3-benzil-oxyloxy-quinuclidiniumbromide
3-((hydroxydiphenylacetyl)oxy)-1-methyl-1-azoniabicyclo(2.2.2)octanbromi
3-(2,2-diphenyl-2-hydroxyethanoyloxy)-quinuclidiniumbromide
3-(benziloyloxy)-1-methylquinuclidiniumbromide
benzilicacid,esterwith3-hydroxy-1-methylquinuclidinium
quarzanbromide
quinuclidinium,3-hydroxy-1-methyl-,bromide,benzilate
quinuclidinolmethylbromide,benzilate
3-[(Hydroxyphenylacetyl)oxy]-1-methyl-1-azoniabicyclo[2,2,2]octane Bromide, Ro-2-3773, Quarzan
Clidinium
(1-Methyl-1-azoniabicyclo[2.2.2]octan-8-yl) 2-hydroxy-2,2-diphenylacetate bromide
1-Azoniabicyclo[2.2.2]octane, 3-[(hydroxydiphenylacetyl)oxy]-1-methyl-, bromide
3-[(Hydroxydiphenylacetyl)oxy]-1-methyl-1-azoniabicyclo[2.2.2]octane bromide
Ro-3773
3-[(Hydroxydiphenylacetyl)oxy]-1-methyl-1-azoniabicyclo[2.2.2]octane
[EINECS(EC#)]

222-471-3
[Molecular Formula]

C22H26BrNO3
[MDL Number]

MFCD00078996
[Molecular Weight]

432.35
[MOL File]

3485-62-9.mol
Chemical PropertiesBack Directory
[Appearance]

White Crystalline Solid
[Melting point ]

240-241°C
[storage temp. ]

Inert atmosphere,Room Temperature
[solubility ]

DMSO (Slightly), Methanol (Slightly, Sonicated), Water (Slightly)
[form ]

neat
[color ]

White to Off-White
[Usage]

An anticholinergic. Used as an antispasmodic
[CAS DataBase Reference]

3485-62-9(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

R22:Harmful if swallowed.
[Safety Statements ]

S36:Wear suitable protective clothing .
[RIDADR ]

3249
[WGK Germany ]

3
[RTECS ]

VD6125000
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[HS Code ]

2933399090
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

(1-Methyl-1-azoniabicyclo[2.2.2]octan-8-yl) 2-hydroxy-2,2-diphenylacetate bromide(3485-62-9).msds
Hazard InformationBack Directory
[Description]

Clidinium is a gastrointestinal muscarinic receptor antagonist (Ki = 3 nM against [3H]quinuclidinyl benzilate binding in rat colonic enterocytes). Administration of clidinium, at a dose of 1 mg/kg, slows intestinal transit and induces constipation in mice. This clidinium-induced constipation induces serum hyperammonemia and decreases clonic, myoclonic, and tonic seizure thresholds in a murine pentylenetetrazole-induced epilepsy model.
[Chemical Properties]

White Crystalline Solid
[Originator]

Librax,Roche,US,1961
[Uses]

An anticholinergic. Used as an antispasmodic
[Uses]

An anticholinergic. Used as an antispasmodic.
[Definition]

ChEBI: The bromide salt of clinidium. It is used for the symptomatic treatment of peptic ulcer disease and also to help relieve abdominal or stomach spasms or cramps due to colicky abdominal pain, diverticulitis, and irritable bowel syndrome.
[Manufacturing Process]

5.12 g of 1-azabicyclo[2.2.2]-3-octanol were refluxed with a suspension of 0.92 g of finely divided sodium in 50 cc of toluene, until most of the sodium had reacted (about 4 hours). The thus obtained suspension of the white amorphous alcoholate was cooled with ice, and reacted with 10.16 g of diphenylchloroacetyl chloride, which was added in form of a solution in approximately 40 cc of toluene. The mixture was stirred for 1 hour at room temperature. Small amounts of unreacted sodium were destroyed with isopropanol, and 120 cc of 1 N hydrochloric acid were then added, The mixture was refluxed for 1/2 hour, in order to convert the first formed product, diphenylchloroacetic acid ester of 1-azabicyclo[2.2.2]-3-octanol, into the corresponding benzilic acid ester.
The toluene phase was separated and discarded. The aqueous phase, together with a precipitated water- and toluene-insoluble oil, was made alkaline and extracted repeatedly with chloroform. The chloroform solution was concentrated in vacuo. The residue was recrystallized from a mixture of acetone and ether (alternatively, from chloroform and ether), and formed needles melting at 164° to 165°C. It was identified as 3-benziloyloxy-1- azabicyclo[2.2.2]octane.
3-Benziloyloxy-1-azabicyclo[2.2.2]octane methobromide was prepared by adding 20 cc of a 30% solution of methyl bromide in ether to a solution of 2.5 g of 3-benziloyloxy-1-azabicyclo[2.2.2]octane in 20 cc of chloroform. After standing for 3 hours at room temperature and 15 hours at +5°C, a crystalline precipitate had formed. This was filtered off and recrystallized from a mixture of methanol, acetone, and ether; prisms melting at 240° to 241°C.
[Brand name]

Quarzan (Roche).
[Therapeutic Function]

Anticholinergic, Antiulcer
[General Description]

Clidinium bromide, 3-hydroxy-1-methylquinuclidinium bromide benzilate (Quarzan),is a white or nearly white, almost odorless, crystalline powderthat is optically inactive. It is soluble in water and alcohol butonly very slightly soluble in ether and benzene.
[Clinical Use]

This anticholinergic agent is marketed alone and in combinationwith the minor tranquilizer chlordiazepoxide (Librium)in a product known as Librax. The rationale of the combinationfor the treatment of GI complaints is the use of an anxiety-reducing agent together with an anticholinergic agent,based on the recognized contribution of anxiety to the developmentof the diseased condition. It is suggested for pepticulcer, hyperchlorhydria, ulcerative or spastic colon, anxietystates with GI manifestations, nervous stomach, irritable orspastic colon, and others. Clidinium bromide is contraindicatedin glaucoma and other conditions that may be aggravatedby the parasympatholytic action, such as prostatic hypertrophyin elderly men, which could lead to urinary retention.
[Synthesis]

Clidinium, 3-benzyloyloxy-1-methylcynuclidinium bromide (14.1.19), is synthesized by reacting 3-hydroxycynuclidine (14.1.17) with the of benzilic acid chloride producing the ester (14.1.18), which if further alkylated at the nitrogen atom by methylbromide, giving clidinium (14.1.19) [16].

Synthesis_3485-62-9

Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

3485-62-9(sigmaaldrich)
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