2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]-4,5-dihydro-1H-imidazole

• ChemBase ID: 4432
• Molecular Formular: C16H24N2
• Molecular Mass: 244.37516
• Monoisotopic Mass: 244.19394878
• SMILES: Cc1cc(cc(C)c1CC1=NCCN1)C(C)(C)C
• Canonical SMILES: Cc1cc(cc(c1CC1=NCCN1)C)C(C)(C)C
• InChI: InChI=1S/C16H24N2/c1-11-8-13(16(3,4)5)9-12(2)14(11)10-15-17-6-7-18-15/h8-9H,6-7,10H2,1-5H3,(H,17,18)
• InChIKey: HUCJFAOMUPXHDK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]-4,5-dihydro-1H-imidazole
• IUPAC Traditional name: stas; xylometazoline
• Brand Name: Otrivine; Otriven; Otrivin; Otrix
• Synonyms: Xylomethazoline; Xylometazoline; 2-(4-tert-Butyl-2,6-dimethyl-benzyl)-4,5-dihydro-1H-imidazole; 2-(4-tert-butyl-2,6-dimethylbenzyl)-4,5-dihydro-1h-imidazole

Database IDs

• CAS Number: 526-36-3
• MDL Number: MFCD00242956
• PubChem SID: 99443248; 160967864
• PubChem CID: 5709

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.3619118
• LogD (pH = 7.4): 1.48564
• Log P: 3.7755392
• Molar Refractivity: 77.8176 cm^3
• Polarizability: 29.674038 Å^3
• Polar Surface Area: 24.39 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.68
• LOG S: -4.44
• Solubility (Water): 8.93e-03 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.2; 5.376

Product Information

• Purity: 95%; 96%

DETAILS

DrugBank - DB06694

• Drug Groups: approved
• Description: A nasal vasoconstricting decongestant drug which acts by binding to the same receptors as adrenaline. It is applied as a spray or as drops into the nose to ease inflammation and congestion of the nasal passageways. It binds alpha-adrenergic receptors to activate the adrenal system which causes systemic vasoconstriction, thereby easing nasal congestion.
• Indication: It is used for treating nasal congestion and minor inflammation due to allergies or colds.
• Pharmacology: Xylometazoline is a direct acting sympathomimetic adrenergic alpha-agonist used to induce systemic vasoconstriction, thereby decreasing nasal congestion. The sympathomimetic action of xylometazoline constricts the smaller arterioles of the nasal passages, producing a prolonged (8-12 hours) decongesting effect.
• References: Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2009 Dec 17. [Pubmed]
• External Links: Wikipedia; RxList

REFERENCES

• Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2009 Dec 17. Pubmed