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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:55 UTC
HMDB IDHMDB0015277
Secondary Accession Numbers
  • HMDB15277
Metabolite Identification
Common NameDiphenylpyraline
DescriptionDiphenylpyraline, also known as difenilpiralina or lergobine, 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. Diphenylpyraline (DPP; sold as Allergen, Arbid, Belfene, Diafen, Hispril, Histyn, Lergobine, Lyssipol, Mepiben, Neargal) is a first-generation antihistamine with anticholinergic effects of the diphenylpiperidine class. DPP has also been found to act as a dopamine reuptake inhibitor and produces hyperactivity in rodents. Diphenylpyraline is a drug which is used for use in the treatment of allergic rhinitis, hay fever, and allergic skin disorders. It has been shown to be useful in the treatment of Parkinsonism. Diphenylpyraline is a very strong basic compound (based on its pKa). In humans, diphenylpyraline is involved in diphenylpyraline h1-antihistamine action. Diphenylpyraline is a potentially toxic compound. It is marketed in Europe for the treatment of allergies.
Structure
Data?1582753278
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 Weight281.392
Monoisotopic Molecular Weight281.177964363
IUPAC Name4-(diphenylmethoxy)-1-methylpiperidine
Traditional Namediphenylpyraline
CAS Registry Number147-20-6
SMILES
CN1CCC(CC1)OC(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=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
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.019 g/LNot Available
LogP3.7Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available173.813http://allccs.zhulab.cn/database/detail?ID=AllCCS00000819
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.30731661259
DarkChem[M-H]-168.61231661259
DeepCCS[M+H]+165.98830932474
DeepCCS[M-H]-163.6330932474
DeepCCS[M-2H]-196.51630932474
DeepCCS[M+Na]+172.08130932474
AllCCS[M+H]+169.632859911
AllCCS[M+H-H2O]+166.032859911
AllCCS[M+NH4]+173.032859911
AllCCS[M+Na]+174.032859911
AllCCS[M-H]-175.732859911
AllCCS[M+Na-2H]-175.532859911
AllCCS[M+HCOO]-175.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DiphenylpyralineCN1CCC(CC1)OC(C1=CC=CC=C1)C1=CC=CC=C12866.2Standard polar33892256
DiphenylpyralineCN1CCC(CC1)OC(C1=CC=CC=C1)C1=CC=CC=C12117.5Standard non polar33892256
DiphenylpyralineCN1CCC(CC1)OC(C1=CC=CC=C1)C1=CC=CC=C12125.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Diphenylpyraline EI-B (Non-derivatized)splash10-0002-9500000000-c0c4dde4b9a2e2daa7262017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diphenylpyraline EI-B (Non-derivatized)splash10-0002-9500000000-c0c4dde4b9a2e2daa7262018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diphenylpyraline GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-9710000000-a770606b36046ca8a4ae2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diphenylpyraline 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 - Diphenylpyraline 10V, Positive-QTOFsplash10-001i-2090000000-f121f756a940c93c3c822016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenylpyraline 20V, Positive-QTOFsplash10-00ls-6590000000-13f8de940c2071abfbe52016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenylpyraline 40V, Positive-QTOFsplash10-01b9-9200000000-9ffe64cee5b5f40c2ec12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenylpyraline 10V, Negative-QTOFsplash10-001i-1190000000-602133655b9c8911993a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenylpyraline 20V, Negative-QTOFsplash10-001i-1490000000-3becf8ff3d41f41e70db2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenylpyraline 40V, Negative-QTOFsplash10-0059-9600000000-8ed7a3e501298037b71b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenylpyraline 10V, Positive-QTOFsplash10-001i-0390000000-e5129a83970231fe41fe2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenylpyraline 20V, Positive-QTOFsplash10-014i-0910000000-798a31f1be1c1e43f4032021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenylpyraline 40V, Positive-QTOFsplash10-0002-9300000000-a4f815502c5ef2b7c10f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenylpyraline 10V, Negative-QTOFsplash10-001i-0090000000-a2d4cba31dc9278eeca12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenylpyraline 20V, Negative-QTOFsplash10-001i-0890000000-33c92852c81f3c2297842021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenylpyraline 40V, Negative-QTOFsplash10-0a4i-2910000000-3458648a46e7b108c7af2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01146 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01146 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01146
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2992
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiphenylpyraline
METLIN IDNot Available
PubChem Compound3103
PDB IDNot Available
ChEBI ID59788
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 References
  1. 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. [PubMed:15627433 ]
  2. 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. [PubMed:14039 ]
  3. 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. [PubMed:11137513 ]

Enzymes

General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A3
Uniprot ID:
Q01959
Molecular weight:
68494.255
References
  1. 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. [PubMed:15627433 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Nakai T, Kitamura N, Hashimoto T, Kajimoto Y, Nishino N, Mita T, Tanaka C: Decreased histamine H1 receptors in the frontal cortex of brains from patients with chronic schizophrenia. Biol Psychiatry. 1991 Aug 15;30(4):349-56. [PubMed:1912125 ]
  4. Taniguchi K, Masuda Y, Takanaka K: Inhibitory effects of histamine H1 receptor blocking drugs on metabolic activations of neutrophils. J Pharmacobiodyn. 1991 Feb;14(2):87-93. [PubMed:1678430 ]
  5. Weis R, Schweiger K, Faist J, Rajkovic E, Kungl AJ, Fabian WM, Schunack W, Seebacher W: Antimycobacterial and H1-antihistaminic activity of 2-substituted piperidine derivatives. Bioorg Med Chem. 2008 Dec 15;16(24):10326-31. doi: 10.1016/j.bmc.2008.10.042. Epub 2008 Oct 22. [PubMed:18977145 ]
  6. 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. [PubMed:15627433 ]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]