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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:51 UTC
HMDB IDHMDB0015070
Secondary Accession Numbers
  • HMDB15070
Metabolite Identification
Common NameOxymetazoline
DescriptionOxymetazoline is only found in individuals that have used or taken this drug. It is a direct acting sympathomimetic used as a vasoconstrictor to relieve nasal congestion. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1251)Oxymetazoline is a direct acting sympathomimetic amine, which acts on alpha-adrenergic receptors in the arterioles of the conjunctiva and nasal mucosa. It produces vasoconstriction, resulting in decreased conjunctival congestion in ophthalmic. In nasal it produces constriction, resulting in decreased blood flow and decreased nasal congestion.
Structure
Data?1582753255
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 Weight260.3746
Monoisotopic Molecular Weight260.1888634
IUPAC Name6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol
Traditional Nameoxymetazoline
CAS Registry Number1491-59-4
SMILES
CC1=CC(=C(O)C(C)=C1CC1=NCCN1)C(C)(C)C
InChI Identifier
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)
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
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point182 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.052 g/LNot Available
LogP3.4Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available169.894http://allccs.zhulab.cn/database/detail?ID=AllCCS00000752
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+163.78331661259
DarkChem[M-H]-160.74631661259
DeepCCS[M+H]+165.5230932474
DeepCCS[M-H]-163.16230932474
DeepCCS[M-2H]-196.04830932474
DeepCCS[M+Na]+171.61430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OxymetazolineCC1=CC(=C(O)C(C)=C1CC1=NCCN1)C(C)(C)C2892.6Standard polar33892256
OxymetazolineCC1=CC(=C(O)C(C)=C1CC1=NCCN1)C(C)(C)C2208.5Standard non polar33892256
OxymetazolineCC1=CC(=C(O)C(C)=C1CC1=NCCN1)C(C)(C)C2302.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oxymetazoline,1TMS,isomer #1CC1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C(C)=C1CC1=NCCN12273.3Semi standard non polar33892256
Oxymetazoline,1TMS,isomer #2CC1=CC(C(C)(C)C)=C(O)C(C)=C1CC1=NCCN1[Si](C)(C)C2253.1Semi standard non polar33892256
Oxymetazoline,2TMS,isomer #1CC1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C(C)=C1CC1=NCCN1[Si](C)(C)C2306.3Semi standard non polar33892256
Oxymetazoline,2TMS,isomer #1CC1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C(C)=C1CC1=NCCN1[Si](C)(C)C2353.1Standard non polar33892256
Oxymetazoline,2TMS,isomer #1CC1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C(C)=C1CC1=NCCN1[Si](C)(C)C2969.1Standard polar33892256
Oxymetazoline,1TBDMS,isomer #1CC1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C)=C1CC1=NCCN12474.5Semi standard non polar33892256
Oxymetazoline,1TBDMS,isomer #2CC1=CC(C(C)(C)C)=C(O)C(C)=C1CC1=NCCN1[Si](C)(C)C(C)(C)C2501.8Semi standard non polar33892256
Oxymetazoline,2TBDMS,isomer #1CC1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C)=C1CC1=NCCN1[Si](C)(C)C(C)(C)C2704.2Semi standard non polar33892256
Oxymetazoline,2TBDMS,isomer #1CC1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C)=C1CC1=NCCN1[Si](C)(C)C(C)(C)C2790.0Standard non polar33892256
Oxymetazoline,2TBDMS,isomer #1CC1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C)=C1CC1=NCCN1[Si](C)(C)C(C)(C)C3097.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Oxymetazoline GC-MS (Non-derivatized) - 70eV, Positivesplash10-004m-3970000000-ee2ec321a55bc78173e12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxymetazoline GC-MS (1 TMS) - 70eV, Positivesplash10-01di-9847000000-0444f6bbf25ec5a414052017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxymetazoline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymetazoline 10V, Positive-QTOFsplash10-03di-0090000000-c488f3b0f9552a4b7dfc2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymetazoline 20V, Positive-QTOFsplash10-03di-1290000000-a18cdab404c55b4e44972016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymetazoline 40V, Positive-QTOFsplash10-0006-7960000000-1c8f2a11df7638b325df2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymetazoline 10V, Negative-QTOFsplash10-0a4i-0090000000-fd2fa239fe46b8ca41c02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymetazoline 20V, Negative-QTOFsplash10-0a4i-1090000000-0e91b1578606ee50752f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymetazoline 40V, Negative-QTOFsplash10-01r6-4890000000-3e6c50f85057e4ad43d22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymetazoline 10V, Positive-QTOFsplash10-03di-0190000000-d99fec2889c2b1f7a3212021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymetazoline 20V, Positive-QTOFsplash10-03dr-1970000000-c0fcd30c275a95baee232021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymetazoline 40V, Positive-QTOFsplash10-0596-6910000000-b96b7ef48bcbbf6173b02021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymetazoline 10V, Negative-QTOFsplash10-0a4i-0090000000-7c4aa654b272455d29042021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymetazoline 20V, Negative-QTOFsplash10-0a6r-0970000000-1e55ae3560aa333e78fa2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymetazoline 40V, Negative-QTOFsplash10-00ac-0930000000-4066d357ff89a3ee12062021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00935 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00935 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00935
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4475
KEGG Compound IDC07363
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxymetazoline
METLIN IDNot Available
PubChem Compound4636
PDB IDNot Available
ChEBI ID7862
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
References
  1. MacKinnon AC, Kilpatrick AT, Kenny BA, Spedding M, Brown CM: [3H]-RS-15385-197, a selective and high affinity radioligand for alpha 2-adrenoceptors: implications for receptor classification. Br J Pharmacol. 1992 Aug;106(4):1011-8. [PubMed:1327384 ]
  2. Mitrani P, Srinivasan M, Dodds C, Patel MS: Role of the autonomic nervous system in the development of hyperinsulinemia by high-carbohydrate formula feeding to neonatal rats. Am J Physiol Endocrinol Metab. 2007 Apr;292(4):E1069-78. Epub 2006 Dec 12. [PubMed:17164433 ]
  3. Lepretre N, Mironneau J: Alpha 2-adrenoceptors activate dihydropyridine-sensitive calcium channels via Gi-proteins and protein kinase C in rat portal vein myocytes. Pflugers Arch. 1994 Dec;429(2):253-61. [PubMed:7892112 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
References
  1. Yang HT, Endoh M: (+/-)-tamsulosin, an alpha 1A-adrenoceptor antagonist, inhibits the positive inotropic effect but not the accumulation of inositol phosphates in rabbit heart. Eur J Pharmacol. 1996 Oct 3;312(3):281-91. [PubMed:8894610 ]
  2. Deplanne V, Galzin AM: Functional characterization of alpha-1-adrenoceptor subtypes in the prostatic urethra and trigone of male rabbit. J Pharmacol Exp Ther. 1996 Aug;278(2):527-34. [PubMed:8768700 ]
  3. Shibata K, Taketani K: [Excitatory effect of noradrenaline on rat airway parasympathetic ganglion neurons]. Fukuoka Igaku Zasshi. 2001 Nov;92(11):377-83. [PubMed:11774707 ]
  4. Furukawa K, Rosario DJ, Smith DJ, Chapple CR, Uchiyama T, Chess-Williams R: Alpha 1A-adrenoceptor-mediated contractile responses of the human vas deferens. Br J Pharmacol. 1995 Sep;116(1):1605-10. [PubMed:8564226 ]
  5. Gonzalez-Espinosa C, Romero-Avila MT, Mora-Rodriguez DM, Gonzalez-Espinosa D, Garcia-Sainz JA: Molecular cloning and functional expression of the guinea pig alpha(1a)-adrenoceptor. Eur J Pharmacol. 2001 Aug 31;426(3):147-55. [PubMed:11527538 ]