Oxymetazoline (CHEM017582)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:28:32 UTC
Update Date2016-11-09 01:15:37 UTC
Accession NumberCHEM017582
Identification
Common NameOxymetazoline
ClassSmall Molecule
DescriptionA direct acting sympathomimetic used as a vasoconstrictor to relieve nasal congestion. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1251)
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(4-Tert-butyl-2,6-dimethyl-3-hydroxybenzyl)-2-imidazolineChEBI
3-[(4,5-Dihydro-1H-imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethylphenolChEBI
6-t-Butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenolChEBI
6-Tert-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenolChEBI
OxymetazolinaChEBI
OxymetazolinumChEBI
AfrinKegg
OperilKegg
OximetazolinumHMDB
Oxymetazoline hydrochloride crystallineHMDB
OxymethazolineHMDB
OxymetozolineHMDB
Hydrochloride, oxymetazolineHMDB
Oxymetazoline hydrochlorideHMDB
Chemical FormulaC16H24N2O
Average Molecular Mass260.375 g/mol
Monoisotopic Mass260.189 g/mol
CAS Registry Number1491-59-4
IUPAC Name6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol
Traditional Nameoxymetazoline
SMILESCC1=CC(=C(O)C(C)=C1CC1=NCCN1)C(C)(C)C
InChI IdentifierInChI=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)
InChI KeyWYWIFABBXFUGLM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as xylenols. These are aromatic compounds that contain a xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups, and at least one hydroxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassXylenes
Direct ParentXylenols
Alternative Parents
Substituents
  • Xylenol
  • Phenylpropane
  • M-xylene
  • O-cresol
  • P-cresol
  • Phenol
  • Imidolactam
  • 2-imidazoline
  • Amidine
  • Carboxylic acid amidine
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.052 g/LALOGPS
logP3.7ALOGPS
logP3.03ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)10.91ChemAxon
pKa (Strongest Basic)10.15ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area44.62 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.8 m³·mol⁻¹ChemAxon
Polarizability30.64 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004m-3970000000-ee2ec321a55bc78173e1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01di-9847000000-0444f6bbf25ec5a41405Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-c488f3b0f9552a4b7dfcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1290000000-a18cdab404c55b4e4497Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-7960000000-1c8f2a11df7638b325dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-fd2fa239fe46b8ca41c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1090000000-0e91b1578606ee50752fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01r6-4890000000-3e6c50f85057e4ad43d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0190000000-d99fec2889c2b1f7a321Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-1970000000-c0fcd30c275a95baee23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-6910000000-b96b7ef48bcbbf6173b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-7c4aa654b272455d2904Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-0970000000-1e55ae3560aa333e78faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ac-0930000000-4066d357ff89a3ee1206Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00935
HMDB IDHMDB0015070
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkOxymetazoline
Chemspider ID4475
ChEBI ID7862
PubChem Compound ID4636
Kegg Compound IDC07363
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10487000
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21177487
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23679077
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23988443
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=4003266