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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:39 UTC
HMDB IDHMDB0001387
Secondary Accession Numbers
  • HMDB01387
Metabolite Identification
Common NameN-Methylphenylethanolamine
DescriptionN-Methylphenylethanolamine, also known as (+-)-halostachine or MPEOA, belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. N-Methylphenylethanolamine exists in all living organisms, ranging from bacteria to humans. N-Methylphenylethanolamine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make N-methylphenylethanolamine a potential biomarker for the consumption of these foods. N-Methylphenylethanolamine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on N-Methylphenylethanolamine.
Structure
Data?1676999739
Synonyms
ValueSource
(+-)-alpha-((Methylamino)methyl)benzenemethanolChEBI
(+-)-HalostachineChEBI
alpha-[(Methylamino)methyl]-benzyl alcoholKegg
(+-)-a-((Methylamino)methyl)benzenemethanolGenerator
(+-)-Α-((methylamino)methyl)benzenemethanolGenerator
a-[(Methylamino)methyl]-benzyl alcoholGenerator
Α-[(methylamino)methyl]-benzyl alcoholGenerator
MPEOAMeSH
N-Methylphenylethanolamine hydrochlorideMeSH
N-Methylphenylethanolamine hydrochloride, (+-)-isomerMeSH
N-Methylphenylethanolamine, (+-)-isomerMeSH
N-Methylphenylethanolamine, (R)-isomerMeSH
2-(methylamino)-1-PhenylethanolHMDB
2-methylamino-1-PhenylethanolHMDB
alpha-((methylamino)Methyl)-DL-benzyl alcoholHMDB
alpha-(Methylaminomethyl)benzyl alcoholHMDB
DL-alpha-(Methylaminomethyl)benzyl alcoholHMDB
HalostachineHMDB
Chemical FormulaC9H13NO
Average Molecular Weight151.2056
Monoisotopic Molecular Weight151.099714043
IUPAC Name2-(methylamino)-1-phenylethan-1-ol
Traditional Namehalostachine
CAS Registry Number68579-60-2
SMILES
CNCC(O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H13NO/c1-10-7-9(11)8-5-3-2-4-6-8/h2-6,9-11H,7H2,1H3
InChI KeyZCTYHONEGJTYQV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point74 - 76 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility19.1 g/LALOGPS
logP0.73ALOGPS
logP0.9ChemAxon
logS-0.9ALOGPS
pKa (Strongest Acidic)14.12ChemAxon
pKa (Strongest Basic)9.43ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area32.26 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.27 m³·mol⁻¹ChemAxon
Polarizability17.26 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.53531661259
DarkChem[M+H]+132.53531661259
DarkChem[M-H]-129.69731661259
DarkChem[M-H]-129.69731661259
AllCCS[M+H]+133.69732859911
AllCCS[M-H]-134.53332859911
DeepCCS[M+H]+131.65130932474
DeepCCS[M-H]-127.9630932474
DeepCCS[M-2H]-165.48130932474
DeepCCS[M+Na]+140.87130932474
AllCCS[M+H]+133.732859911
AllCCS[M+H-H2O]+129.232859911
AllCCS[M+NH4]+137.932859911
AllCCS[M+Na]+139.132859911
AllCCS[M-H]-134.532859911
AllCCS[M+Na-2H]-136.032859911
AllCCS[M+HCOO]-137.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-MethylphenylethanolamineCNCC(O)C1=CC=CC=C11872.4Standard polar33892256
N-MethylphenylethanolamineCNCC(O)C1=CC=CC=C11279.4Standard non polar33892256
N-MethylphenylethanolamineCNCC(O)C1=CC=CC=C11336.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Methylphenylethanolamine,1TMS,isomer #1CNCC(O[Si](C)(C)C)C1=CC=CC=C11328.9Semi standard non polar33892256
N-Methylphenylethanolamine,1TMS,isomer #2CN(CC(O)C1=CC=CC=C1)[Si](C)(C)C1470.2Semi standard non polar33892256
N-Methylphenylethanolamine,2TMS,isomer #1CN(CC(O[Si](C)(C)C)C1=CC=CC=C1)[Si](C)(C)C1483.5Semi standard non polar33892256
N-Methylphenylethanolamine,2TMS,isomer #1CN(CC(O[Si](C)(C)C)C1=CC=CC=C1)[Si](C)(C)C1532.6Standard non polar33892256
N-Methylphenylethanolamine,2TMS,isomer #1CN(CC(O[Si](C)(C)C)C1=CC=CC=C1)[Si](C)(C)C1702.4Standard polar33892256
N-Methylphenylethanolamine,1TBDMS,isomer #1CNCC(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C11551.6Semi standard non polar33892256
N-Methylphenylethanolamine,1TBDMS,isomer #2CN(CC(O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C1702.2Semi standard non polar33892256
N-Methylphenylethanolamine,2TBDMS,isomer #1CN(CC(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C1956.6Semi standard non polar33892256
N-Methylphenylethanolamine,2TBDMS,isomer #1CN(CC(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C1960.0Standard non polar33892256
N-Methylphenylethanolamine,2TBDMS,isomer #1CN(CC(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C2004.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - N-Methylphenylethanolamine GC-EI-TOF (Non-derivatized)splash10-0fbl-3900000000-3679c2e020c8e555350d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Methylphenylethanolamine GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-26f7b8d9b9810cdaec562017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Methylphenylethanolamine GC-EI-TOF (Non-derivatized)splash10-0fbl-3900000000-3679c2e020c8e555350d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Methylphenylethanolamine GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-26f7b8d9b9810cdaec562018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Methylphenylethanolamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-fa15efabc5997da6e3d22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Methylphenylethanolamine GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9310000000-f429ae967f272b5686092017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Methylphenylethanolamine 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 - N-Methylphenylethanolamine 10V, Positive-QTOFsplash10-0f89-0900000000-b348599f4b04bdf562c42015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 20V, Positive-QTOFsplash10-0f89-0900000000-f90dd7fab94626e118282015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 40V, Positive-QTOFsplash10-0zfr-7900000000-f9602e64157769f328982015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 10V, Negative-QTOFsplash10-0udi-0900000000-811f3df9a97a473ef1732015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 20V, Negative-QTOFsplash10-0f89-2900000000-dea7a6b68785d129c5562015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 40V, Negative-QTOFsplash10-056r-9500000000-1250d1db8db14b1718692015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 10V, Negative-QTOFsplash10-0ufr-3900000000-0f2b52640015d34b8f972021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 20V, Negative-QTOFsplash10-0fb9-8900000000-e361fe87072f77e77c4d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 40V, Negative-QTOFsplash10-0fbc-9600000000-cedaced89cfcbb8f52892021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 10V, Positive-QTOFsplash10-001i-3900000000-61e18a02be7d3706c2a22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 20V, Positive-QTOFsplash10-0006-9100000000-89cd36302e4945d395eb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 40V, Positive-QTOFsplash10-0006-9100000000-bf697c44241fe58f470e2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022596
KNApSAcK IDNot Available
Chemspider ID889
KEGG Compound IDC03711
BioCyc IDN-METHYLPHENYLETHANOLAMINE
BiGG IDNot Available
Wikipedia LinkHalostachine
METLIN ID6207
PubChem Compound913
PDB IDNot Available
ChEBI ID16913
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSyrneva, Yu. I. The pharmacology of the new alkaloid halostachine. Farmakologiya i Toksikologiya (Moscow) (1941), 4(No. 1), 45-51.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Suzuki O, Oya M, Katsumata Y: Characterization of N-methylphenylethylamine and N-methylphenylethanolamine as substrates for type A and type B monoamine oxidase. Biochem Pharmacol. 1980 Oct 1;29(19):2663-7. [PubMed:6775642 ]

Enzymes

General function:
Involved in methyltransferase activity
Specific function:
Converts noradrenaline to adrenaline.
Gene Name:
PNMT
Uniprot ID:
P11086
Molecular weight:
30854.745
Reactions
S-Adenosylmethionine + 2-Hydroxyphenethylamine → S-Adenosylhomocysteine + N-Methylphenylethanolaminedetails