Loperamide, demethyl (CHEM045960)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 13:51:20 UTC
Update Date2016-11-09 01:23:26 UTC
Accession NumberCHEM045960
Identification
Common NameLoperamide, demethyl
ClassSmall Molecule
DescriptionA monocarboxylic acid amide that is the methylamide of 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-2,2-diphenylbutanoic acid.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Monodesmethyl loperamideChEBI
N-Desmethyl loperamideChEBI
(11C)N-Desmethyl-loperamideMeSH
(N-Methyl-11C)-desmethyl-loperamideMeSH
N-Demethyl-loperamideMeSH
N-DemethylloperamideMeSH
N-Desmethyl-loperamideMeSH
N-DesmethylloperamideMeSH
Chemical FormulaC28H31ClN2O2
Average Molecular Mass463.020 g/mol
Monoisotopic Mass462.207 g/mol
CAS Registry Number66164-07-6
IUPAC Name4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N-methyl-2,2-diphenylbutanimidic acid
Traditional Name4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N-methyl-2,2-diphenylbutanimidic acid
SMILESCN=C(O)C(CCN1CCC(O)(CC1)C1=CC=C(Cl)C=C1)(C1=CC=CC=C1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C28H31ClN2O2/c1-30-26(32)28(23-8-4-2-5-9-23,24-10-6-3-7-11-24)18-21-31-19-16-27(33,17-20-31)22-12-14-25(29)15-13-22/h2-15,33H,16-21H2,1H3,(H,30,32)
InChI KeyZMOPTLXEYOVARP-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
  • Phenylpiperidine
  • Phenylacetamide
  • Halobenzene
  • Aralkylamine
  • Chlorobenzene
  • N-acyl-amine
  • Aryl chloride
  • Piperidine
  • Aryl halide
  • Fatty amide
  • Fatty acyl
  • Tertiary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organohalogen compound
  • Organochloride
  • 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 Solubility0.00059 g/LALOGPS
logP4.93ALOGPS
logP2.69ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)-3ChemAxon
pKa (Strongest Basic)12.62ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area56.06 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity145.56 m³·mol⁻¹ChemAxon
Polarizability51.14 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ukc-4592600000-5110bdb220d9aca22d77Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0000900000-85783572a6e1d2fb7657Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gvk-0041900000-edb848068e30b129fddfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-0987300000-de4d736a445201716744Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-f65f01b38ae415ad2ce7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1102900000-ec5f39f9eea8966b0435Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-6941100000-da9b5b5c661727ac6f9eSpectrum
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 IDNot Available
HMDB IDHMDB0255118
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID7981704
ChEBI ID64043
PubChem Compound ID9805944
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18783208
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19091890
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19372478
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20212014
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=20237038
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20346873
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=20645912
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21262843
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21958857
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=7109845