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

• ChemBase ID: 73045
• Molecular Formular: C16H25ClN2O
• Molecular Mass: 296.8355
• Monoisotopic Mass: 296.16554111
• SMILES: c1(c(c(c(c(c1)C)CC1=NCCN1)C)O)C(C)(C)C.Cl
• Canonical SMILES: Cc1cc(c(c(c1CC1=NCCN1)C)O)C(C)(C)C.Cl
• InChI: InChI=1S/C16H24N2O.ClH/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);1H
• InChIKey: BEEDODBODQVSIM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol hydrochloride; 6-tert-butyl-3-[(4,5-dihydro-1H-imidazol-2-yl)methyl]-2,4-dimethylphenol hydrochloride
• IUPAC Traditional name: oxymetazoline hydrochloride
• Synonyms: Oxymetazoline; 3-[(4,5-Dihydro-1H-imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethylphenol Hydrochloride; 2-(4-tert-Butyl-2,6-dimethyl-3-hydroxybenzyl)-2-imidazoline Hydrochloride; 6-tert-Butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol Hydrochloride; Hazol; Navasin; Navisin; Nezeril; Oxylazine; Rhinofrenol; Rhinolitan; Sinerol; 2-(3-hydroxy-2,6-dimethyl-4-tert-butylbenzyl)-2-imidazoline hydrochloride; 2-(3-Hydroxy-2,6-dimethyl-4-t-butylbenzyl)-2-imidazoline hydrochloride; Oxymetazoline hydrochloride; 2-[3-Hydroxy-2,6-dimethyl-4-t-butyl-benzyl]-2-imidazoline; OXYMETAZOLINE HYDROCHLORIDE

Database IDs

• CAS Number: 2315-02-8; 1491-59-4; 151615
• EC Number: 219-015-0; 216-079-1
• MDL Number: MFCD00058147
• PubChem SID: 24277792; 162037965
• PubChem CID: 66259

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: alcohol: soluble; DMSO; H2O: soluble; Methanol; Water
• Apperance: Off-White Solid; solid
• Melting Point: >270°C (dec.)

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: SK1050000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1; I
• Australian Hazchem: 2XE
• Risk Statements: 28; R:28
• Safety Statements: 22-28-36/37/39-45; S:28-29-36/37/39-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• RID/ADR: UN 2811 6.1/PG 1

Pharmacology Properties

• Gene Information: human ... ADRA2A(150), HTR1A(3350), HTR1B(3351), HTR1D(3352)

Product Information

• Purity: ≥99%; 98%
• Salt Data: hydrochloride

DETAILS

MP Biomedicals - 02190255

Hydrochloride
Crystalline
Adrenergic compound

Selleck Chemicals - S2495

Research Area: Cardiovascular Disease
Biological Activity:
Oxymetazoline hydrochloride is an α1 and α2 adrenergic receptor agonist. It is available over-the-counter as a topical decongestant in nasal sprays. The action of oxymetazoline results in vasoconstriction. In addition, the local application of the drug also results in vasoconstriction due to its action on endothelial postsynaptic α2 receptors; systemic application of α2 agonists, in contrast, causes vasodilation because of centrally-mediated inhibition of sympathetic tone via presynaptic α2 receptors. [1]

Sigma Aldrich - O2378

Biochem/physiol Actions
Oxymetazoline hydrochloride is a partial α2A-adrenoceptor agonist; agonist at 5-HT1A, 5-HT1B, and 5-HT1D serotonin receptors. It is a mixed agonist-antagonist at 5-HT1C serotonin receptors.

Toronto Research Chemicals - O876470

Vasoconstrictor, used as a nasal decongestant. An ingredient of Drixin.

REFERENCES

• http://en.wikipedia.org/wiki/Oxymetazoline
• Huang, X., et al.: Mol. Pharmacol., 76, 710 (2009)
• Kurko, D., et al.: Neurochem. Int., 55, 467 (2009)
• Chen, Q., et al.: Anal. Bioanal. Chem., 398, 937 (2009)