Caramiphen edisylate
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Caramiphen edisylate
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CAS No:
125-86-0
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Formula:
C18H27NO2.1/2C2H6O6S2
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Chemical Name:
Caramiphen edisylate
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Synonyms:
Cyclopentanecarboxylic acid,1-phenyl-,2-(diethylamino)ethyl ester,1,2-ethanedisulfonate (2:1);Cyclopentanecarboxylic acid,1-phenyl-,2-(diethylamino)ethyl ester,1,2-ethanedisulfonate;1,2-Ethanedisulfonic acid,compd. with 2-(diethylamino)ethyl 1-phenylcyclopentanecarboxylate (1:2);Bis[1-(carbo-β-diethylaminoethoxy)-1-phenylcyclopentane]ethanedisulfonate;Bis[1-(2-diethylaminoethoxycarbonyl)-1-phenylcyclopentane]ethanedisulfonate;Diethylaminoethyl 1-phenylcyclopentane-1-carboxylate ethanedisulfonate;1-Phenylcyclopentanecarboxylic acid 2-diethylaminoethyl ester 1,2-ethanedisulfonate;Taoryl;Toryn;Caramiphen edisylate;Caramiphen ethanedisulfonate;Alcopon;SKF 769-J2;Tosivia;Tussoryl;6209-22-9
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CAS No:
Characteristics
185
7.69040
115-116 °C
392.1ºC at 760 mmHg
124.8ºC
2.35E-06mmHg at 25°C
Oral-rat LDL0: 1400 mg/kg; Oral-Mouse LD50: 485 mg/kg
Thermal decomposition emits toxic nitrogen oxides and sulfur oxide fumes
Safety Information
GY3850000
The warehouse is low-temperature, ventilated and dry; stored separately from food materials
P264, P270, P301+P312, P330, P501
H302
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.
Caramiphen edisylate Use and Manufacturing
It is obtained by bromination, cyclization, hydrolysis, acidification, chlorination, esterification, neutralization and salt formation of tetrahydrofuran. In the presence of sulfuric acid, tetrahydrofuran reacts with hydrobromic acid to produce 1, 4-dibromobutane, and then in the presence of sodium hydroxide, 1, 4-dibromobutane is cyclized with benzyl cyanide to obtain 1-phenyl- 1-cyanocyclopentane. It is heated and reacted with sodium hydroxide and water for 5h, hydrolyzed to generate sodium 1-phenyl-cyclopentane carboxylate, and acidified to pH 3 by adding concentrated hydrochloric acid to obtain 1-phenyl cyclopentane carboxylic acid. 1-Phenylcyclopentane carboxylic acid, chlorinated with phosphorus trichloride, heated at reflux for 5h, to generate 1-phenylcyclopentanecarboxylic acid chloride, the chlorinated product is distilled under reduced pressure, solvent benzene is recovered, and the relative density of the residual liquid It is 1.12-1.17, which is 1-phenylcyclopentanecarboxylic acid chloride. It was stirred and cooled to 10-15°C, and diethylaminoethanol was added dropwise. Obtain 1-phenylcyclopentanecarboxylic acid-β-diethylamino ethyl ester hydrochloride. Add sodium carbonate to neutralize to obtain the caramifen base (C18H27NO2, [77-22-5]. Finally, using acetone as a solvent, the resulting caramifen base and ethane disulfonic acid are salted to obtain the crude product. Calamifen is obtained by refining with acetone and absolute ethanol.
Used as an antitussive.
Computed Properties
Molecular Weight:769.0
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:19
Exact Mass:768.36893846
Monoisotopic Mass:768.36893846
Topological Polar Surface Area:185
Heavy Atom Count:52
Complexity:552
Covalently-Bonded Unit Count:3
Compound Is Canonicalized:Yes