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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:41:47 UTC
Update Date2021-09-14 15:47:02 UTC
HMDB IDHMDB0240238
Secondary Accession NumbersNone
Metabolite Identification
Common NameTolpropamine
DescriptionTolpropamine 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. Tolpropamine is a very strong basic compound (based on its pKa). In humans, tolpropamine is involved in tolpropamine h1-antihistamine action. Tolpropamine is an antihistamine and anticholinergic used as an antipruritic.
Structure
Data?1563892734
Synonyms
ValueSource
PragmanHMDB, MeSH
TolpropamineHMDB
N,N-4-Trimethyl-gamma-phenylbenzenepropanMeSH, HMDB
N,N-Dimethyl-3-phenyl-3-(P-tolyl)propylamineMeSH, HMDB
Tolpropamine hydrochlorideMeSH, HMDB
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
Process

Naturally occurring process:

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M-H]-PredictedNot Available169.32631661259
AllCCS[M+H]+PredictedNot Available158.74131661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-7920000000-074dc79b1052dd0931e72017-08-28View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-20595ab35a506ecfe0902017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-0390000000-9599381daf54c96d5a9d2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0as0-2940000000-dfe2f5f1a9e8d0ba09de2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-79b01f2515ae8fd302692017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1090000000-f4ae73472da1c75ed5692017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-9650000000-2f9f305607425f11d0fa2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-29f321564479847420fe2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udl-8590000000-6abeda0a0ffd179829402021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fc3-5910000000-b4ffcf73120a5957f2c72021-09-08View 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTolpropamine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB 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 ]