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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-13 11:48:37 UTC
Update Date2022-03-07 02:57:14 UTC
HMDB IDHMDB0041932
Secondary Accession Numbers
  • HMDB41932
Metabolite Identification
Common NameMethylephedrine
DescriptionMethylephedrine belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Based on a literature review very few articles have been published on Methylephedrine.
Structure
Data?1563863715
Synonyms
ValueSource
(1R,2S)-(-)-N-MethylephedrineHMDB
(1Rs,2Rs)-2-Dimethylamino-1-phenylpropan-1-olHMDB
DL-Methylephedrine hydrochlorideHMDB
Erythro-alpha-[1-(dimethylamino)ethyl]benzyl alcoholHMDB
L-Methylephedrine hydrochlorideHMDB
MethylephedrinHMDB
N,N-DimethylnorephedrineHMDB
N,N-Dimethylnorephedrine2-dimethylamino-1-phenylpropanolHMDB
N-MethylephedrineHMDB
N-Methylephedrine hydrochloride, (r*,s*)-(+-)-isomerHMDB
N-Methylephedrine hydrochloride, (S-(r*,r*))-isomerHMDB
N-Methylephedrine hydrochloride, (r*,r*)-(+-)-isomerHMDB
N-Methylephedrine hydrochloride, (r*,s*)-isomerHMDB
N-Methylephedrine, (r*,s*)-(+-)-isomerHMDB
N-Methylephedrine, (r*,s*)-isomerHMDB
MethylpseudoephedrineHMDB
N-Methylephedrine, (R-(r*,s*))-isomerHMDB
N-Methylephedrine hydrochloride, (R-(r*,s*))-isomerHMDB
N-Methylephedrine, (r*,r*)-isomerHMDB
N-Methylephedrine, (S-(r*,r*))-isomerHMDB
MethylephedrineMeSH
Chemical FormulaC11H17NO
Average Molecular Weight179.2588
Monoisotopic Molecular Weight179.131014171
IUPAC Name2-(dimethylamino)-1-phenylpropan-1-ol
Traditional NameN-methylephedrine
CAS Registry Number552-79-4
SMILES
CC(C(O)C1=CC=CC=C1)N(C)C
InChI Identifier
InChI=1S/C11H17NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9,11,13H,1-3H3
InChI KeyFMCGSUUBYTWNDP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • Aralkylamine
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Organic nitrogen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point87.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility15.4 g/LALOGPS
logP1.73ALOGPS
logP1.7ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)13.88ChemAxon
pKa (Strongest Basic)8.86ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.98 m³·mol⁻¹ChemAxon
Polarizability20.74 ųChemAxon
Number of Rings1ChemAxon
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]+140.18331661259
DarkChem[M-H]-138.61231661259
DeepCCS[M+H]+142.8230932474
DeepCCS[M-H]-140.42530932474
DeepCCS[M-2H]-175.35830932474
DeepCCS[M+Na]+149.75730932474
AllCCS[M+H]+141.532859911
AllCCS[M+H-H2O]+137.332859911
AllCCS[M+NH4]+145.532859911
AllCCS[M+Na]+146.632859911
AllCCS[M-H]-143.632859911
AllCCS[M+Na-2H]-144.732859911
AllCCS[M+HCOO]-146.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MethylephedrineCC(C(O)C1=CC=CC=C1)N(C)C1979.9Standard polar33892256
MethylephedrineCC(C(O)C1=CC=CC=C1)N(C)C1405.6Standard non polar33892256
MethylephedrineCC(C(O)C1=CC=CC=C1)N(C)C1430.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methylephedrine,1TMS,isomer #1CC(C(O[Si](C)(C)C)C1=CC=CC=C1)N(C)C1411.4Semi standard non polar33892256
Methylephedrine,1TBDMS,isomer #1CC(C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N(C)C1646.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methylephedrine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9200000000-79b7f4e29a3be48106782017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylephedrine GC-MS (1 TMS) - 70eV, Positivesplash10-00b9-9610000000-cc8cbc37dfe647d1c62e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylephedrine 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 - Methylephedrine 10V, Positive-QTOFsplash10-03e9-0900000000-ee71548fbb81afb3eaef2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylephedrine 20V, Positive-QTOFsplash10-03k9-3900000000-52e91d48126d1292242c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylephedrine 40V, Positive-QTOFsplash10-05fu-9200000000-d5c2133d3865c1ce7e8e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylephedrine 10V, Negative-QTOFsplash10-004i-0900000000-e105f7644e81238b9c1e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylephedrine 20V, Negative-QTOFsplash10-01t9-1900000000-009c8f68a7f75f06cb0f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylephedrine 40V, Negative-QTOFsplash10-056r-9700000000-ab9a9815af94ed2724652017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylephedrine 10V, Positive-QTOFsplash10-03e9-0900000000-7c8dfad7057790bea0972021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylephedrine 20V, Positive-QTOFsplash10-03dl-5900000000-443c3e784905396fa14e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylephedrine 40V, Positive-QTOFsplash10-004l-9200000000-2e9f3fe06765b55738532021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylephedrine 10V, Negative-QTOFsplash10-004i-3900000000-105d6f16ea1eaadeff3d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylephedrine 20V, Negative-QTOFsplash10-016r-4900000000-b624ea1de4838ea268df2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylephedrine 40V, Negative-QTOFsplash10-004i-9100000000-763c68e4539ea362dffc2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00032016
Chemspider ID4221
KEGG Compound IDC13639
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylephedrine
METLIN IDNot Available
PubChem Compound4374
PDB IDNot Available
ChEBI ID90046
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 ReferencesNot Available