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 

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

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

Toxicity

LD50 orl-rat: 230 mg/kg KSRNAM 5,555,71

MSDS

• Language:English Provider:SigmaAldrich

Xylometazoline hydrochloride Usage And Synthesis

Chemical Properties

Xylometazoline hydrochloride is white or almost white, crystalline powder.

Originator

Otrivin,Geigy,US,1959

Uses

anthelmintic

Uses

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).

Uses

Xylometazoline hydrochloride is used as a nasal decongestant.

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.

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