Xylometazoline hydrochloride

Xylometazoline hydrochloride Basic information
Product Name:Xylometazoline hydrochloride
Synonyms:2-(4-tert-butyl-2,6-dimethylbenzyl)-2-imidazolinmonohydrochloride;2-[[4-(1,1-dimethylethyl)-2,6-dimethylphenyl]methyl]-4,5-dihydro-1h-imidazol;Galazolin;Neo-Rinoleina;Neo-Synephrine II;Novorin;Olynth;Therapin
CAS:1218-35-5
MF:C16H25ClN2
MW:280.84
EINECS:214-936-4
Product Categories:API;ALBENZA;Miscellaneous Natural Products;Adrenoceptor;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:1218-35-5.mol
Xylometazoline hydrochloride Structure
Xylometazoline hydrochloride Chemical Properties
Melting point 131-133 C
storage temp. 2-8°C
solubility Freely soluble in water, in ethanol (96 per cent) and in methanol.
form neat
color Crystals
Merck 14,10086
CAS DataBase Reference1218-35-5(CAS DataBase Reference)
EPA Substance Registry System1H-Imidazole, 2-[[4-(1,1-dimethylethyl)-2,6-dimethylphenyl]methyl]-4,5-dihydro-, monohydrochloride (1218-35-5)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38
Safety Statements 36-26
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS NJ2390000
HazardClass 6.1
PackingGroup III
HS Code 29332900
ToxicityLD50 orl-rat: 230 mg/kg KSRNAM 5,555,71
MSDS Information
ProviderLanguage
SigmaAldrich English
Xylometazoline hydrochloride Usage And Synthesis
Chemical PropertiesXylometazoline hydrochloride is white or almost white, crystalline powder.
OriginatorOtrivin,Geigy,US,1959
UsesXylometazoline hydrochloride may be used as a reference standard in determining the xylometazoline hydrochloride content in samples of nasal drops using high performance liquid chromatography (HPLC).
UsesXylometazoline hydrochloride is used as a nasal decongestant.
Usesanthelmintic
Manufacturing Process62 grams of para-tertiany-butyl-ortho,ortho'-dimethyl-phenyl-acetonitrile [obtainable, for example, by the method of Buu-Hoi and P. Cagniant, Bulletin de la Societe Chimique de France, volume 9, page 891 (1942)], 20.6 grams of ethylenediamine of 96% purity and 1.55 cc of carbon disulfide are heated together in a distillation flask with the exclusion of moisture for 48 hours on a boiling water bath. Ammonia is evolved. Upon cooling the reaction product solidifies and is then dissolved in benzene, the solution is filtered while hot with the addition of animal charcoal and petroleum ether is added. The mixture is filtered to remove the impurities that are first precipitated and by the further addition of petroleum ether 2-(para-tertiary-butyl-ortho,ortho'- dimethyl-phenyl-methyl)-imidazoline is caused to crystallize out.
The product melts at 131° to 133°C after being recrystallized from a mixture of benzene and petroleum ether. It can be converted into its hydrochloride as follows:
189 grams of 2-(para-tertiary-butyl-ortho,ortho'-dimethyl-phenyl-methyl)- imidazoline are dissolved in 400 cc of absolute ethanol, the solution is rendered acid by the addition of 104 cc of an ethanolic solution of hydrochloric acid of 30% strength, the mixture is filtered with the addition of animal charcoal, and dry ethyl acetate and absolute ether are added until crystallization sets in. After cooling the mixture, the salt is filtered off with suction and crystallized several times from absolute ethanol with the use of animal charcoal and the addition of dry mixture of ethyl acetate and ether. The hydrochloride so obtained melts at 327° to 329°C (with decomposition).
Brand nameNeo-Synephrine II (Sterling Winthrop); Otrivin Hydrochloride (Ciba-Geigy).
Therapeutic FunctionAdrenergic (vasopressor)
General DescriptionXylometazoline hydrochloride is a derivative of imidazole, and a representative of the class of α1 agonists. It is commonly used in nasal decongestants, which works on the principle of constricting the blood vessels in the mucous membranes.
Biochem/physiol Actionsα-adrenoceptor agonist; imidazoline binding site ligand.
Safety ProfilePoison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx and HCl.
Xylometazoline hydrochloride Preparation Products And Raw materials
Raw materialsHydrochloric acid-->Ethylenediamine
Dimethylbenzylcarbinyl acetate 2-(4-TERT-BUTYL-2,6-DIMETHYL-BENZYL)-4,5-DIHYDRO-1H-IMIDAZOLE 2-Tetralin-1-yl-4,5-dihydro-1H-imidazole hydrochloride Cyhalofop-butyl Benzyl chloride Benzyltriethylammonium chloride tert-Butyl acetate Cefazolin tert-Butyldimethylsilyl chloride Buprofezin tert-Butanol tert-Butyl peroxyacetate Diethylene glycol monobutyl ether Butyl acrylate Benzyldimethylcarbinyl butyrate Butyl acetate Oxymetazoline hydrochloride Cefazolin sodium salt

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