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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:39 UTC

HMDB ID

HMDB0001387

Secondary Accession Numbers

HMDB01387

Metabolite Identification

Common Name

N-Methylphenylethanolamine

Description

N-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-alpha-((Methylamino)methyl)benzenemethanol	ChEBI
(+-)-Halostachine	ChEBI
alpha-[(Methylamino)methyl]-benzyl alcohol	Kegg
(+-)-a-((Methylamino)methyl)benzenemethanol	Generator
(+-)-Α-((methylamino)methyl)benzenemethanol	Generator
a-[(Methylamino)methyl]-benzyl alcohol	Generator
Α-[(methylamino)methyl]-benzyl alcohol	Generator
MPEOA	MeSH
N-Methylphenylethanolamine hydrochloride	MeSH
N-Methylphenylethanolamine hydrochloride, (+-)-isomer	MeSH
N-Methylphenylethanolamine, (+-)-isomer	MeSH
N-Methylphenylethanolamine, (R)-isomer	MeSH
2-(methylamino)-1-Phenylethanol	HMDB
2-methylamino-1-Phenylethanol	HMDB
alpha-((methylamino)Methyl)-DL-benzyl alcohol	HMDB
alpha-(Methylaminomethyl)benzyl alcohol	HMDB
DL-alpha-(Methylaminomethyl)benzyl alcohol	HMDB
Halostachine	HMDB

Chemical Formula

C₉H₁₃NO

Average Molecular Weight

151.2056

Monoisotopic Molecular Weight

151.099714043

IUPAC Name

2-(methylamino)-1-phenylethan-1-ol

Traditional Name

halostachine

CAS Registry Number

68579-60-2

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 Key

ZCTYHONEGJTYQV-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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Aralkylamines

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

phenylethanolamines (CHEBI:16913 )
alkaloid (CHEBI:16913 )

Ontology

Not Available

Endogenous (HMDB: HMDB0001387)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	74 - 76 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	19.1 g/L	ALOGPS
logP	0.73	ALOGPS
logP	0.9	ChemAxon
logS	-0.9	ALOGPS
pKa (Strongest Acidic)	14.12	ChemAxon
pKa (Strongest Basic)	9.43	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	32.26 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	45.27 m³·mol⁻¹	ChemAxon
Polarizability	17.26 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	132.535	31661259
DarkChem	[M+H]+	132.535	31661259
DarkChem	[M-H]-	129.697	31661259
DarkChem	[M-H]-	129.697	31661259
AllCCS	[M+H]+	133.697	32859911
AllCCS	[M-H]-	134.533	32859911
DeepCCS	[M+H]+	131.651	30932474
DeepCCS	[M-H]-	127.96	30932474
DeepCCS	[M-2H]-	165.481	30932474
DeepCCS	[M+Na]+	140.871	30932474
AllCCS	[M+H]+	133.7	32859911
AllCCS	[M+H-H2O]+	129.2	32859911
AllCCS	[M+NH4]+	137.9	32859911
AllCCS	[M+Na]+	139.1	32859911
AllCCS	[M-H]-	134.5	32859911
AllCCS	[M+Na-2H]-	136.0	32859911
AllCCS	[M+HCOO]-	137.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Methylphenylethanolamine	CNCC(O)C1=CC=CC=C1	1872.4	Standard polar	33892256
N-Methylphenylethanolamine	CNCC(O)C1=CC=CC=C1	1279.4	Standard non polar	33892256
N-Methylphenylethanolamine	CNCC(O)C1=CC=CC=C1	1336.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Methylphenylethanolamine,1TMS,isomer #1	CNCC(O[Si](C)(C)C)C1=CC=CC=C1	1328.9	Semi standard non polar	33892256
N-Methylphenylethanolamine,1TMS,isomer #2	CN(CC(O)C1=CC=CC=C1)[Si](C)(C)C	1470.2	Semi standard non polar	33892256
N-Methylphenylethanolamine,2TMS,isomer #1	CN(CC(O[Si](C)(C)C)C1=CC=CC=C1)[Si](C)(C)C	1483.5	Semi standard non polar	33892256
N-Methylphenylethanolamine,2TMS,isomer #1	CN(CC(O[Si](C)(C)C)C1=CC=CC=C1)[Si](C)(C)C	1532.6	Standard non polar	33892256
N-Methylphenylethanolamine,2TMS,isomer #1	CN(CC(O[Si](C)(C)C)C1=CC=CC=C1)[Si](C)(C)C	1702.4	Standard polar	33892256
N-Methylphenylethanolamine,1TBDMS,isomer #1	CNCC(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	1551.6	Semi standard non polar	33892256
N-Methylphenylethanolamine,1TBDMS,isomer #2	CN(CC(O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	1702.2	Semi standard non polar	33892256
N-Methylphenylethanolamine,2TBDMS,isomer #1	CN(CC(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	1956.6	Semi standard non polar	33892256
N-Methylphenylethanolamine,2TBDMS,isomer #1	CN(CC(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	1960.0	Standard non polar	33892256
N-Methylphenylethanolamine,2TBDMS,isomer #1	CN(CC(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2004.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - N-Methylphenylethanolamine GC-EI-TOF (Non-derivatized)	splash10-0fbl-3900000000-3679c2e020c8e555350d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Methylphenylethanolamine GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-26f7b8d9b9810cdaec56	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Methylphenylethanolamine GC-EI-TOF (Non-derivatized)	splash10-0fbl-3900000000-3679c2e020c8e555350d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Methylphenylethanolamine GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-26f7b8d9b9810cdaec56	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methylphenylethanolamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-fa15efabc5997da6e3d2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methylphenylethanolamine GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9310000000-f429ae967f272b568609	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methylphenylethanolamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 10V, Positive-QTOF	splash10-0f89-0900000000-b348599f4b04bdf562c4	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 20V, Positive-QTOF	splash10-0f89-0900000000-f90dd7fab94626e11828	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 40V, Positive-QTOF	splash10-0zfr-7900000000-f9602e64157769f32898	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 10V, Negative-QTOF	splash10-0udi-0900000000-811f3df9a97a473ef173	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 20V, Negative-QTOF	splash10-0f89-2900000000-dea7a6b68785d129c556	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 40V, Negative-QTOF	splash10-056r-9500000000-1250d1db8db14b171869	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 10V, Negative-QTOF	splash10-0ufr-3900000000-0f2b52640015d34b8f97	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 20V, Negative-QTOF	splash10-0fb9-8900000000-e361fe87072f77e77c4d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 40V, Negative-QTOF	splash10-0fbc-9600000000-cedaced89cfcbb8f5289	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 10V, Positive-QTOF	splash10-001i-3900000000-61e18a02be7d3706c2a2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 20V, Positive-QTOF	splash10-0006-9100000000-89cd36302e4945d395eb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylphenylethanolamine 40V, Positive-QTOF	splash10-0006-9100000000-bf697c44241fe58f470e	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022596

KNApSAcK ID

Not Available

Chemspider ID

889

KEGG Compound ID

C03711

BioCyc ID

N-METHYLPHENYLETHANOLAMINE

BiGG ID

Not Available

Wikipedia Link

Halostachine

METLIN ID

6207

PubChem Compound

913

PDB ID

Not Available

ChEBI ID

16913

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Syrneva, 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

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

Enzyme Details

1. Phenylethanolamine N-methyltransferase

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-Methylphenylethanolamine	details

Showing metabocard for N-Methylphenylethanolamine (HMDB0001387)

MOL for HMDB0001387 (N-Methylphenylethanolamine)

3D MOL for HMDB0001387 (N-Methylphenylethanolamine)

3D SDF for HMDB0001387 (N-Methylphenylethanolamine)

3D-SDF for HMDB0001387 (N-Methylphenylethanolamine)

PDB for HMDB0001387 (N-Methylphenylethanolamine)

3D PDB for HMDB0001387 (N-Methylphenylethanolamine)

SMILES for HMDB0001387 (N-Methylphenylethanolamine)

INCHI for HMDB0001387 (N-Methylphenylethanolamine)

Structure for HMDB0001387 (N-Methylphenylethanolamine)

3D Structure for HMDB0001387 (N-Methylphenylethanolamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions