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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:41:47 UTC
Update Date2022-03-07 03:18:14 UTC
HMDB IDHMDB0240238
Secondary Accession NumbersNone
Metabolite Identification
Common NameTolpropamine
DescriptionTolpropamine, also known as pragman, 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. In humans, tolpropamine is involved in the tolpropamine h1-antihistamine action pathway. Tolpropamine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Tolpropamine.
Structure
Data?1563892734
Synonyms
ValueSource
N,N-4-Trimethyl-gamma-phenylbenzenepropanMeSH
N,N-Dimethyl-3-phenyl-3-(p-tolyl)propylamineMeSH
PragmanMeSH
Tolpropamine hydrochlorideMeSH
TolpropamineHMDB
Chemical FormulaC18H23N
Average Molecular Weight253.389
Monoisotopic Molecular Weight253.183049745
IUPAC Namedimethyl[3-(4-methylphenyl)-3-phenylpropyl]amine
Traditional Namepragman
CAS Registry Number5632-44-0
SMILES
CN(C)CCC(C1=CC=CC=C1)C1=CC=C(C)C=C1
InChI Identifier
InChI=1S/C18H23N/c1-15-9-11-17(12-10-15)18(13-14-19(2)3)16-7-5-4-6-8-16/h4-12,18H,13-14H2,1-3H3
InChI KeyCINROOONPHQHPO-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
  • Monoterpenoid
  • Monocyclic monoterpenoid
  • Aromatic monoterpenoid
  • P-cymene
  • Aralkylamine
  • Toluene
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
Process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP4.09ALOGPS
logP4.58ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)9.65ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity83.64 m³·mol⁻¹ChemAxon
Polarizability31.24 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M-H]-169.32631661259
AllCCS[M+H]+158.74131661259
DeepCCS[M+H]+165.96530932474
DeepCCS[M-H]-163.60730932474
DeepCCS[M-2H]-196.49330932474
DeepCCS[M+Na]+172.05830932474
AllCCS[M+H]+158.732859911
AllCCS[M+H-H2O]+154.832859911
AllCCS[M+NH4]+162.432859911
AllCCS[M+Na]+163.432859911
AllCCS[M-H]-169.332859911
AllCCS[M+Na-2H]-169.332859911
AllCCS[M+HCOO]-169.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TolpropamineCN(C)CCC(C1=CC=CC=C1)C1=CC=C(C)C=C12459.8Standard polar33892256
TolpropamineCN(C)CCC(C1=CC=CC=C1)C1=CC=C(C)C=C11927.2Standard non polar33892256
TolpropamineCN(C)CCC(C1=CC=CC=C1)C1=CC=C(C)C=C11877.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tolpropamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-7920000000-074dc79b1052dd0931e72017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tolpropamine 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 - Tolpropamine 10V, Positive-QTOFsplash10-0udi-0090000000-20595ab35a506ecfe0902017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolpropamine 20V, Positive-QTOFsplash10-0zfr-0390000000-9599381daf54c96d5a9d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolpropamine 40V, Positive-QTOFsplash10-0as0-2940000000-dfe2f5f1a9e8d0ba09de2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolpropamine 10V, Negative-QTOFsplash10-0udi-0090000000-79b01f2515ae8fd302692017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolpropamine 20V, Negative-QTOFsplash10-0udi-1090000000-f4ae73472da1c75ed5692017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolpropamine 40V, Negative-QTOFsplash10-054o-9650000000-2f9f305607425f11d0fa2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolpropamine 10V, Positive-QTOFsplash10-0zfr-0090000000-801df037a10f4e3a6c492021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolpropamine 20V, Positive-QTOFsplash10-0a4i-1590000000-fc42a496cced028107b62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolpropamine 40V, Positive-QTOFsplash10-069u-3900000000-47e33e53c43a75628e312021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolpropamine 10V, Negative-QTOFsplash10-0udi-0090000000-29f321564479847420fe2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolpropamine 20V, Negative-QTOFsplash10-0udl-8590000000-6abeda0a0ffd179829402021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolpropamine 40V, Negative-QTOFsplash10-0fc3-5910000000-b4ffcf73120a5957f2c72021-09-24Wishart LabView Spectrum
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 IDDB13305
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID65115
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTolpropamine
METLIN IDNot Available
PubChem Compound72141
PDB IDNot Available
ChEBI IDNot Available
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. Montgomery LC, Deuster PA: Effects of antihistamine medications on exercise performance. Implications for sportspeople. Sports Med. 1993 Mar;15(3):179-95. [PubMed:7680815 ]