Oxymetazoline Chemical Properties

Melting point:

182 °C

Boiling point:

403.63°C (rough estimate)

Density 

0.9822 (rough estimate)

refractive index 

1.5800 (estimate)

pka

11.93±0.28(Predicted)

color 

Crystals from C6H6

CAS DataBase Reference

1491-59-4(CAS DataBase Reference)

NIST Chemistry Reference

Oxymetazoline(1491-59-4)

Safety Information

RIDADR 

3249

HazardClass 

6.1(a)

PackingGroup 

II

Hazardous Substances Data

1491-59-4(Hazardous Substances Data)

Toxicity

LD50 orl-rat: 800 mg/kg TXAPA9 18,185,71

MSDS

• Language:English Provider:Oxymetazoline

Oxymetazoline Usage And Synthesis

Originator

Nasivin,Merck,W. Germany ,1961

Uses

Vasoconstrictor, used as a nasal decongestant.

Uses

Oxymetazoline is used for the same indications as naphazoline, primarily for rhinitis.

Definition

ChEBI: Oxymetazoline is a member of the class of phenols that is 2,4-dimethylphenol which is substituted at positions 3 and 6 by 4,5-dihydro-1H-imidazol-2-ylmethyl and tert-butyl groups, respectively. A direct-acting sympathomimetic with marked alpha-adrenergic activity, it is a vasoconstrictor that is used (generally as the hydrochloride salt) to relieve nasal congestion. It has a role as an alpha-adrenergic agonist, a sympathomimetic agent, a nasal decongestant and a vasoconstrictor agent. It is a member of phenols, a carboxamidine and a member of imidazolines. It is a conjugate base of an oxymetazoline(1+).

Manufacturing Process

10 grams 2,6-dimethyl-3-hydroxy-4-tertiary butylbenzylcyanide (produced by chloromethylation of 2,4-dimethyl-6-tertiary butyl-phenol with formaldehyde and HCl and conversion of the substituted benzyl chloride with NaCN; crystals, from alcohol, melting at 135° to 137°C) and 10.7 grams ethylenediaminemono-p-toluenesulfonate are heated in an oil bath to approximately 235°C for 1? hours, whereby ammonia is evolved. The free base is obtained from the p-toluene-sulfonic acid imidazoline salt which is difficultly soluble in water, by conversion with 50 cc of a 10% NaOH solution. Said base is recrystallized from benzene, and 7.5 grams (62% of the theoretical yield) 2-(2',6'-dimethyl3'-hydroxy-4'-tertiary butylbenzyl)-2-imidazoline, MP 180° to 182°C, are obtained.
By dissolving the free base in an ethyl alcohol solution of hydrochloric acid and adding ether, the hydrochloride can be produced in the usual manner. Said hydrochloride melts, when recrystallized from alcoholic ether, at 300° to 303°C and is decomposed

brand name

Ocuclear (Schering-Plough); Visine (Pfizer).

Therapeutic Function

Nasal decongestant

Safety Profile

Poison by ingestion and subcutaneous routes. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.

Synthesis

Oxymetazoline, 6-tert-butyl-3(2-imidazolin-2-ilmethyl)-2,4-dimethylphenol (11.1.39), is synthesized by chloromethylation of 6-tert-butyl-2,4-dimethylphenol and the further transformation of the resulting chloromethyl derivative (11.1.37) into a nitrile (11.1.38). The reaction of this with ethylendiamine gives oxymetazoline (11.1.39) [41,42].

Enzyme inhibitor

This vasoconstrictor and nasal decongestant (FW = 260.38 g/mol; CAS 1491-59-4), systematically named as 6-t-butyl-3-(4,5-dihydro-1H-imidazol- 2-ylmethyl)-2,4-dimethylphenol, is a partial a2A-adrenergic agonist as well as a 5-HT1A, 5-HT1B, and 5-HT1D serotonin receptor agonist. It is an overthe-counter drug that is most often used topically to treat rhinitis and sinusitis. Oxymetazoline exerts a dose-dependent inhibitory effect on total iNOS activity, as indicated by nitrite/nitrate formation, and this effect is attributable to inhibition of enzyme induction rather than direct inhibition of the enzyme itself.

Oxymetazoline(1491-59-4)Related Product Information

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