6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol

• ChemBase ID: 811
• Molecular Formular: C16H24N2O
• Molecular Mass: 260.37456
• Monoisotopic Mass: 260.1888634
• SMILES: Oc1c(C(C)(C)C)cc(c(c1C)CC1=NCCN1)C
• Canonical SMILES: Cc1cc(c(c(c1CC1=NCCN1)C)O)C(C)(C)C
• InChI: InChI=1S/C16H24N2O/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14/h8,19H,6-7,9H2,1-5H3,(H,17,18)
• InChIKey: WYWIFABBXFUGLM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol; 6-tert-butyl-3-[(4,5-dihydro-1H-imidazol-2-yl)methyl]-2,4-dimethylphenol
• IUPAC Traditional name: oxymetazoline
• Brand Name: Afrin; Afrin Cherry 12 Hour Nasal Spray; Afrin Extra Moisturizing 12 Hour Nasal Spray; Afrin Original 12 Hour Nasal Spray; Afrin Original 12 Hour Nose Drops; Afrin Original 12 Hour Pump Mist; Afrin Sinus 12 Hour Nasal Spray; Dristan Long Lasting Mentholated Nasal Spray; Dristan Long Lasting Nasal Mist; Drixoral Nasal Solution; Duramist Plus Up To 12 Hour Nasal Decongestant Spray; Duration 12 Hour Nasal Spray; Genasal Nasal Spray Up to 12 Hour Relief; Hazol; Iliadin; Nafrine; Nasal Relief 12 Hour Nasal Spray; Nasivine; Navasin; Navisin; Neo-Synephrine 12 Hour Spray; Nezeril; Nostrilla 12 Hour Nasal Decongestant; OcuClear; Oxylazine; Rhinofrenol; Rhinolitan; Sinerol; Vicks Sinex 12 Hour Nasal Spray; Vicks Sinex 12 Hour Ultra Fine Mist for Sinus Relief; Visine L.R; Visine L.R.; Afrin, Dristan12-hrnasalspray, Ocuclear, Drixine
• Synonyms: oxymetazoline hydrochloride crystalline; Oxymethazoline; Oxymetozoline; Oximetazolinum; Oxymetazoline; 2-(3-hydroxy-2,6-dimethyl-4-tert-butylbenzyl)-2-imidazoline

Database IDs

• CAS Number: 1491-59-4
• PubChem SID: 160964274; 46505622
• PubChem CID: 4636
• ATC CODE: R01AB07; S01GA04; R01AA05
• CHEMBL: 762
• Chemspider ID: 4475
• DrugBank ID: DB00935
• IUPHAR ligand ID: 124
• KEGG ID: D08322
• Unique Ingredient Identifier: 8VLN5B44ZY
• Wikipedia Title: Oxymetazoline

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.906928
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.0586748
• LogD (pH = 7.4): 1.2011817
• Log P: 3.0323153
• Molar Refractivity: 79.7985 cm^3
• Polarizability: 30.251978 Å^3
• Polar Surface Area: 44.62 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.7
• LOG S: -3.7
• Solubility (Water): 5.15e-02 g/l

PROPERTIES

Physical Property

• Melting Point: 301.5°C (574.7°F)
• Hydrophobicity(logP): 3.4

Pharmacology Properties

• Half Life: 5-6 hours
• Legal Status: GSL (UK); OTC (US)
• Pregnancy Category: C

Product Information

• Purity: 97%

DETAILS

DrugBank - DB00935

• Drug Groups: approved
• Description: A direct acting sympathomimetic used as a vasoconstrictor to relieve nasal congestion. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1251)
• Indication: For treatment of nasal congestion and redness associated with minor irritations of the eye
• Pharmacology: Oxymetazoline a adrenergic alpha-agonists, direct acting sympathomimetic used as a vasoconstrictor to relieve nasal congestion The sympathomimetic action of oxymetazoline constricts the smaller arterioles of the nasal passages, producing a prolonged (up to 12 hours), gentle and decongesting effect. Oxymetazoline elicits relief of conjunctival hyperemia by causing vasoconstriction of superficial conjunctival blood vessels. The drug's action has been demonstrated in acute allergic conjunctivitis and in chemical (chloride) conjunctivitis.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia; Drugs.com