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HomeProduct name listXylometazoline hydrochloride

Xylometazoline hydrochloride

Synonym(s):2-(4-tert-Butyl-2,6-dimethylbenzyl)-2-imidazoline hydrochloride;Xylometazoline hydrochloride

  • CAS NO.:1218-35-5
  • Empirical Formula: C16H25ClN2
  • Molecular Weight: 280.84
  • MDL number: MFCD00238707
  • EINECS: 214-936-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-07-02 08:55:06
Xylometazoline hydrochloride  Structural

What is Xylometazoline hydrochloride ?

Chemical properties

Xylometazoline hydrochloride is white or almost white, crystalline powder.

Originator

Otrivin,Geigy,US,1959

The Uses of Xylometazoline hydrochloride

Xylometazoline hydrochloride is used as a nasal decongestant.

The Uses of Xylometazoline hydrochloride

anthelmintic

The Uses of Xylometazoline hydrochloride

Xylometazoline 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).

What are the applications of Application

Xylometazoline hydrochloride is α-adrenoceptor agonist

Manufacturing Process

62 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 name

Neo-Synephrine II (Sterling Winthrop); Otrivin Hydrochloride (Ciba-Geigy).

Therapeutic Function

Adrenergic (vasopressor)

General Description

Xylometazoline 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 Actions

α-adrenoceptor agonist; imidazoline binding site ligand.

Safety Profile

Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx and HCl.

Properties of Xylometazoline hydrochloride

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
form  Solid
color  Crystals
Merck  14,10086
CAS DataBase Reference 1218-35-5(CAS DataBase Reference)
EPA Substance Registry System 1H-Imidazole, 2-[[4-(1,1-dimethylethyl)-2,6-dimethylphenyl]methyl]-4,5-dihydro-, monohydrochloride (1218-35-5)

Safety information for Xylometazoline hydrochloride

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
GHS Hazard Statements H301:Acute toxicity,oral
Precautionary Statement Codes P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

Computed Descriptors for Xylometazoline hydrochloride

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