Oxymetazoline

Title: Oxymetazoline
CAS Registry Number: 1491-59-4
CAS Name: 3-[(4,5-Dihydro-1H-imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethylphenol
Additional Names: 6-tert-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol; 2-(4-tert-butyl-2,6-dimethyl-3-hydroxybenzyl)-2-imidazoline
Manufacturers' Codes: H-990
Trademarks: Navisin; Hazol; Rhinofrenol; Rhinolitan (3M Pharma); Sinerol; Nezeril (Draco)
Molecular Formula: C16H24N2O
Molecular Weight: 260.37
Percent Composition: C 73.81%, H 9.29%, N 10.76%, O 6.14%
Literature References: Prepd from (4-tert-butyl-2,6-dimethyl-3-hydroxyphenyl)acetonitrile and ethylenediamine: Fruhstorfer, Mueller-Calgan, DE 1117588 (1961 to E. Merck), C.A. 57, 4674a (1962). Toxicity data: Hotovy et al., Arzneim.-Forsch. 11, 1016 (1961).
Properties: Crystals from benzene, mp 181-183°.
Melting point: mp 181-183°
Derivative Type: Hydrochloride
CAS Registry Number: 2315-02-8
Trademarks: Afrazine (Schering-Plough); Afrin (Schering-Plough); Iliadin (Meda); Nafrine; Nasivin (Merck KGaA); Oxilin (Allergan); Sinex (LaChartre)
Molecular Formula: C16H24N2O.HCl
Molecular Weight: 296.84
Percent Composition: C 64.74%, H 8.49%, N 9.44%, O 5.39%, Cl 11.94%
Properties: Crystals, dec 300-303°. Freely sol in water, alcohol. Practically insol in ether, chloroform, benzene. LD50 orally in mice: 10 mg/kg (Hotovy).
Toxicity data: LD50 orally in mice: 10 mg/kg (Hotovy)
NOTE: Ingredient of Drixin.
Therap-Cat: Adrenergic (vasoconstrictor); nasal decongestant.
Keywords: a-Adrenergic Agonist; Decongestant.
Oxymethurea Oxypendyl Oxypertine Oxyphenbutazone Oxyphencyclimine

Oxymetazoline
Oxymetazoline.svg
Oxymetazoline 3d.gif
Systematic (IUPAC) name
3-(4,5-dihydro-1H-imidazol-2-ylmethyl)- 2,4-dimethyl-6-tert-butyl-phenol
Clinical data
Trade names Afrin, Ocuclear, Drixine
AHFS/Drugs.com monograph
Pregnancy cat. C
Legal status GSL (UK) OTC (US)
Pharmacokinetic data
Half-life 5-6 hours
Identifiers
CAS number 1491-59-4 YesY
ATC code R01AA05
R01AB07 (combinations), S01GA04
PubChem CID 4636
IUPHAR ligand 124
DrugBank DB00935
ChemSpider 4475 YesY
UNII 8VLN5B44ZY YesY
KEGG D08322 YesY
ChEMBL CHEMBL762 YesY
Chemical data
Formula C16H24N2O 
Mol. mass 260.375 g·mol−1
Physical data
Melt. point 301.5 °C (575 °F)
 YesY (what is this?)  (verify)

Oxymetazoline is a selective alpha-1 agonist and partial alpha-2 agonist topical decongestant, used in the form of Oxymetazoline hydrochloride, in products such as Afrin, Dristan, Nasivin, Logicin, Vicks Sinex, Visine L.R., Sudafed OM, Zicam and SinuFrin. It was developed from xylometazoline at E. Merck Darmstadt by Fruhstorfer in 1961. Oxymetazoline is generally available as a nasal spray.