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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:40:50 UTC
Update Date2019-07-23 14:38:54 UTC
HMDB IDHMDB0240236
Secondary Accession NumbersNone
Metabolite Identification
Common NameQuifenadine
DescriptionQuifenadine belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Quifenadine is a very strong basic compound (based on its pKa). In humans, quifenadine is involved in quifenadine h1-antihistamine action. Quifenadine (Russian: хифенадин, trade name: Phencarol, Фенкарол) is a 2nd generation antihistamine drug, marketed mainly in post-Soviet countries.
Structure
Data?1563892734
Synonyms
ValueSource
Α,α-diphenyl-3-quinuclidinemethanolHMDB
alpha,alpha-Diphenyl-3-quinuclidinemethanolHMDB
Diphenyl-3-quinuclidylcarbinolHMDB
QuifenadineHMDB
Chemical FormulaC20H23NO
Average Molecular Weight293.41
Monoisotopic Molecular Weight293.177964365
IUPAC Name{1-azabicyclo[2.2.2]octan-2-yl}diphenylmethanol
Traditional Name1-azabicyclo[2.2.2]octan-2-yldiphenylmethanol
CAS Registry Number10447-39-9
SMILES
OC(C1CC2CCN1CC2)(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C20H23NO/c22-20(17-7-3-1-4-8-17,18-9-5-2-6-10-18)19-15-16-11-13-21(19)14-12-16/h1-10,16,19,22H,11-15H2
InChI KeyJNZMANQLHCNXTA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Quinuclidine
  • Aralkylamine
  • Piperidine
  • Tertiary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • 1,2-aminoalcohol
  • Organoheterocyclic compound
  • Azacycle
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.77ALOGPS
logP3.52ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)12.87ChemAxon
pKa (Strongest Basic)9.36ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity89.9 m³·mol⁻¹ChemAxon
Polarizability33.29 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0190000000-256fa29ee83a48fb7eebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0036-0980000000-b7e02cfd3848711fd415Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fr-3900000000-6776e6b0e1ea3161e72cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-0ae6164e56a923d4a348Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1190000000-683090136635d8db9f23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08i0-4930000000-bb3852505004a55484e5Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2308316
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkQuifenadine
METLIN IDNot Available
PubChem Compound3045613
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Makarov L, Balykova L, Soldatova O, Komolyatova V, Serebruany V: The antiarrhythmic properties of quifenadine, H1-histamine receptor blocker in children with premature beats: a randomized controlled pilot trial. Am J Ther. 2010 Jul-Aug;17(4):396-401. doi: 10.1097/MJT.0b013e3181a86987. [PubMed:19487925 ]