Diphenylpyraline (CHEM022245)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:25:26 UTC
Update Date2016-11-09 01:17:27 UTC
Accession NumberCHEM022245
Identification
Common NameDiphenylpyraline
ClassSmall Molecule
DescriptionDiphenylpyraline is an antihistamine. Antihistamines used in the treatment of allergy act by competing with histamine for H 1-receptor sites on effector cells. Antihistamines prevent, but do not reverse, responses mediated by histamine alone. Antihistamines antagonize, in varying degrees, most of the pharmacological effects of histamine, including urticaria and pruritus.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Methyl-4-hydroxypiperidine benzhydryl etherChEBI
1-Methyl-4-piperidyl benzhydryl etherChEBI
4-(Benzhydryloxy)-1-methylpiperidineChEBI
4-(Benzhydryloxy)-N-methylpiperidineChEBI
DifenilpiralinaChEBI
DiphenylpyralamineChEBI
DiphenylpyralinumChEBI
DiphenylpyrileneHMDB
4-Diphenylmethoxy-1-methylpiperidineHMDB
Diphenylpyraline maleate (2:1)HMDB
Diphenylpyraline hydrochlorideHMDB
LergobineHMDB
Chemical FormulaC19H23NO
Average Molecular Mass281.392 g/mol
Monoisotopic Mass281.178 g/mol
CAS Registry Number147-20-6
IUPAC Name4-(diphenylmethoxy)-1-methylpiperidine
Traditional Namediphenylpyraline
SMILESCN1CCC(CC1)OC(C1=CC=CC=C1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C19H23NO/c1-20-14-12-18(13-15-20)21-19(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-19H,12-15H2,1H3
InChI KeyOWQUZNMMYNAXSL-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
  • Benzylether
  • Piperidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen 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 Solubility0.019 g/LALOGPS
logP3.82ALOGPS
logP3.66ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)8.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity87.36 m³·mol⁻¹ChemAxon
Polarizability32.97 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9500000000-c0c4dde4b9a2e2daa726Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9500000000-c0c4dde4b9a2e2daa726Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-9710000000-a770606b36046ca8a4aeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-2090000000-f121f756a940c93c3c82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ls-6590000000-13f8de940c2071abfbe5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01b9-9200000000-9ffe64cee5b5f40c2ec1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1190000000-602133655b9c8911993aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1490000000-3becf8ff3d41f41e70dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9600000000-8ed7a3e501298037b71bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0390000000-e5129a83970231fe41feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0910000000-798a31f1be1c1e43f403Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9300000000-a4f815502c5ef2b7c10fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-a2d4cba31dc9278eeca1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0890000000-33c92852c81f3c229784Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2910000000-3458648a46e7b108c7afSpectrum
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 IDDB01146
HMDB IDHMDB0015277
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDiphenylpyraline
Chemspider ID2992
ChEBI ID59788
PubChem Compound ID3103
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Puhakka H, Rantanen T, Virolainen E: Diphenylpyraline (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis. J Int Med Res. 1977;5(1):37-41.
2. Ohno T, Kobayashi S, Hayashi M, Sakurai M, Kanazawa I: Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients. J Neurol Sci. 2001 Jan 1;182(2):95-7.
3. Lapa GB, Mathews TA, Harp J, Budygin EA, Jones SR: Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties. Eur J Pharmacol. 2005 Jan 4;506(3):237-40. Epub 2004 Dec 8.
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=14039
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15627433
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22445882