Originator
Nasivin,Merck,W. Germany ,1961
Uses
Oxymetazoline is used for the same indications as naphazoline, primarily for rhinitis.
Uses
Vasoconstrictor, used as a nasal decongestant.
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.
