ChemicalBook--->CAS DataBase List--->71-81-8

71-81-8

71-81-8 Structure

71-81-8 Structure
IdentificationBack Directory
[Name]

ISOPROPAMIDE IODIDE
[CAS]

71-81-8
[Synonyms]

r79
isamid
5579md
darbid
skf4740
Tyrimide
dipramid
sanulcin
priamide
marygin-m
dipramide
piaccamide
priazimide
ISOPROPAMIDE
ISOPROPAMIDE IODIDE
LABOTEST-BB LT00772055
ISOPROPAMIDEIODIDE,USP
Isopropamide Iodide (200 mg)
2,2-diphenyl-4-diisopropylaminobutyramidemethiodide
(3-carbamoyl-3,3-diphenylpropyl)diisopropylmethyl-ammoniuiodide
(3-carbamoyl-3,3-diphenylpropyl)diisopropylmethylammoniumiodide
(4-amino-4-oxo-3,3-diphenylbutyl)-methyl-di(propan-2-yl)azanium:iodide
4-Amino-N,N-diisopropyl-N-methyl-4-oxo-3,3-diphenyl-1-butanaminium Iodide
Benzenepropanaminium, .gamma.-(aminocarbonyl)-N-methyl-N,N-bis(1-methylethyl)-.gamma.-phenyl-, iodide
[EINECS(EC#)]

200-766-8
[Molecular Formula]

C23H33IN2O
[MDL Number]

MFCD00063513
[MOL File]

71-81-8.mol
[Molecular Weight]

480.43
Chemical PropertiesBack Directory
[Melting point ]

199℃ (Decomposition)
[density ]

1.2711 (estimate)
[storage temp. ]

Store at -20°C
[solubility ]

DMSO: 250 mg/mL (520.37 mM)
[Water Solubility ]

Practically insoluble in water
[form ]

powder to crystal
[color ]

White to Almost white
[Merck ]

14,5202
[Major Application]

pharmaceutical (small molecule)
[InChI]

1S/C23H33N2O.HI/c1-18(2)25(5,19(3)4)17-16-23(22(24)26,20-12-8-6-9-13-20)21-14-10-7-11-15-21;/h6-15,18-19H,16-17H2,1-5H3,(H2,24,26);1H
[InChIKey]

ZTDSVARXIUOODA-UHFFFAOYSA-N
[SMILES]

I.CC(C)[N](C)(CCC(C(N)=O)(c1ccccc1)c2ccccc2)C(C)C
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26-36
[WGK Germany ]

2
[RTECS ]

BP0693200
[HS Code ]

2924296000
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
[Toxicity]

LD50 oral in rat: > 10gm/kg
Hazard InformationBack Directory
[Originator]

Darbid,SKF,US,1957
[Uses]

anticholinergic
[Definition]

ChEBI: Isopropamide iodide is a diarylmethane.
[Manufacturing Process]

γ-Diisopropylamino-α,α-diphenylbutyronitrile (60 g) was added in several portions to a mixture of sulfuric acid (150 ml) and water (15 ml) and the solution was heated 3% hours on the steam bath and then poured on ice and made basic with NH4OH. The γ-diisopropylamino-α,α-diphenylbutyramide precipitated as a solid, which was taken up in methylene chloride from an aqueous slurry. The methylene chloride was separated and dried by filtering through anhydrous K2CO3. The solvent was removed by distillation, leaving the amide which was crystallized from Skellysolve B five times and found then to have MP 87.0° to 88.5°C.
γ-Diisopropylamino-α,α-diphenylbutyramide in propanol was refluxed 4 hours in the presence of excess methyl iodide. Upon dilution of the solution with ethyl acetate (100 ml per 50 ml isopropyl alcohol) and cooling γ- diisopropylamino-α,α-diphenylbutyramide methiodide precipitated, was collected by filtration and recrystallized (9.0 g) by dissolving in a hot mixtureof 100 ml isopropyl alcohol and 10 ml methanol and then diluting with 90 ml Skellysolve B, to give 8.3 g recrystallized product, MP 182° to 184°C.
[Brand name]

Darbid (GlaxoSmithKline).
[Therapeutic Function]

Spasmolytic
[General Description]

Isopropamide iodide, 3-carbamoyl-3,3-diphenylpropyl)diisopropylmethylammoniumiodide (Darbid), occurs as a bitter, white to pale yellow, crystallinepowder that is only sparingly soluble in water butfreely soluble in chloroform and alcohol.
This drug, introduced in 1957, is a potent anticholinergic,producing atropine-like effects peripherally. Even with itsquaternary nature, it does not cause sympathetic blockade atthe ganglionic level except at high dosages. Its principal distinguishingfeature is its long duration of action. A singledose can provide antispasmodic and antisecretory effects foras long as 12 hours.
[Clinical Use]

ISOPROPAMIDE IODIDE is used as adjunctive therapy in the treatment of pepticulcer and other conditions of the GI tract associated withhypermotility and hyperacidity. It has the usual side effectsof anticholinergics (dryness of mouth, mydriasis, difficulturination) and is contraindicated in glaucoma, prostatic hypertrophy,etc.
[Synthesis]

Isopropamide, (3-carbamoyl-3,3-diphenylpropyl)di-iso-propylmethyl ammonium iodide (14.1.25), is synthesized by alkylating diphenylacetonitrile with di-isopropylaminoethylchloride in the presence of sodium amide, and the subsequent hydrolysis of the nitrile group of the resulting compound (14.1.23) to an amide group (14.1.24). Alkylation of this compound with methyliodide gives isopropamide (14.1.25) [19¨C22].

Synthesis_71-81-8

[storage]

Store at -20°C
Spectrum DetailBack Directory
[Spectrum Detail]

ISOPROPAMIDE IODIDE(71-81-8)1HNMR
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