Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

enzymes (5) Show 5 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-08-13 02:17:17 UTC

Update Date

2023-02-21 17:16:45 UTC

HMDB ID

HMDB0003633

Secondary Accession Numbers

HMDB0060283
HMDB0060284
HMDB03633
HMDB60283
HMDB60284

Metabolite Identification

Common Name

N-Methyltyramine

Description

N-methyltyramine (NMT) is a phenolic amine. NMT is a potent stimulant of gastrin release present in alcoholic beverages produced by alcoholic fermentation, but not by distillation (i.e.: beer.). NMT is well absorbed in the small intestine, especially in the duodenum and jejunum. NMT is metabolized in the liver (the site of first-pass metabolism), but not in the small-intestinal mucosa. NMT is occasionally present in the stools of children and infants. Satisfactory results have been obtained in treating infective shock with injection of natural Fructus Aurantii immaturus (nat-FAI); the anti-shock effective compositions in FAI have been proved to be synephrine and NMT. (PMID: 10772638 , 2570680 ).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Hydroxy-N-methylphenethylamine	ChEBI
Methyl-4-tyramine	ChEBI
p-(2-Methylaminoethyl)phenol	ChEBI
4-(2-(Methylamino)ethyl)-phenol	HMDB
4-(2-Methylaminoethyl)phenol	HMDB
4-[2-(Methylamino)ethyl]-phenol	HMDB
4-[2-(Methylamino)ethyl]phenol	HMDB
Methyl tyramine	HMDB
N-Methyl-p-tyramine	HMDB
N-Methyltyraminium	HMDB
NMT	HMDB
p-(2-(Methylamino)ethyl)phenol	HMDB
p-[2-(Methylamino)ethyl]-phenol	HMDB
{p-[2-(methylamino)ethyl]phenol}	HMDB
N-Methyltyrosamine	HMDB
Methyl-4-tyramine hydrochloride	HMDB
Methyl-4-tyramine hydrobromide	HMDB

Chemical Formula

C₉H₁₃NO

Average Molecular Weight

151.2056

Monoisotopic Molecular Weight

151.099714043

IUPAC Name

4-[2-(methylamino)ethyl]phenol

Traditional Name

N-methyltyramine

CAS Registry Number

370-98-9

SMILES

CNCCC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C9H13NO/c1-10-7-6-8-2-4-9(11)5-3-8/h2-5,10-11H,6-7H2,1H3

InChI Key

AXVZFRBSCNEKPQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Phenethylamines

Alternative Parents

Substituents

Phenethylamine
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tyramines (CHEBI:17458 )
Tyramine derivatives (C02442 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003633)

Source

Endogenous

Endogenous (HMDB: HMDB0003633)

Plant

Plant (HMDB: HMDB0003633)
Poaceae (HMDB: HMDB0003633)

Exogenous

Food

Food (HMDB: HMDB0003633)

Animal origin

Poultry

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)

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Fruit

Citrus

Lemon (FooDB: FOOD00054)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antineoplastic agent

Cancer preventive (HMDB: HMDB0003633)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	1.455	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.4 g/L	ALOGPS
logP	0.48	ALOGPS
logP	0.96	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	10.54	ChemAxon
pKa (Strongest Basic)	9.82	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	46.04 m³·mol⁻¹	ChemAxon
Polarizability	17.42 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]+	133.203	31661259
DarkChem	[M-H]-	131.04	31661259
DeepCCS	[M+H]+	133.03	30932474
DeepCCS	[M-H]-	129.199	30932474
DeepCCS	[M-2H]-	166.753	30932474
DeepCCS	[M+Na]+	142.269	30932474
AllCCS	[M+H]+	132.9	32859911
AllCCS	[M+H-H2O]+	128.4	32859911
AllCCS	[M+NH4]+	137.1	32859911
AllCCS	[M+Na]+	138.3	32859911
AllCCS	[M-H]-	135.2	32859911
AllCCS	[M+Na-2H]-	136.7	32859911
AllCCS	[M+HCOO]-	138.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Methyltyramine	CNCCC1=CC=C(O)C=C1	2323.2	Standard polar	33892256
N-Methyltyramine	CNCCC1=CC=C(O)C=C1	1447.4	Standard non polar	33892256
N-Methyltyramine	CNCCC1=CC=C(O)C=C1	1474.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Methyltyramine,1TMS,isomer #1	CNCCC1=CC=C(O[Si](C)(C)C)C=C1	1473.5	Semi standard non polar	33892256
N-Methyltyramine,1TMS,isomer #2	CN(CCC1=CC=C(O)C=C1)[Si](C)(C)C	1666.6	Semi standard non polar	33892256
N-Methyltyramine,2TMS,isomer #1	CN(CCC1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	1702.1	Semi standard non polar	33892256
N-Methyltyramine,2TMS,isomer #1	CN(CCC1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	1693.0	Standard non polar	33892256
N-Methyltyramine,2TMS,isomer #1	CN(CCC1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	1749.5	Standard polar	33892256
N-Methyltyramine,1TBDMS,isomer #1	CNCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	1714.0	Semi standard non polar	33892256
N-Methyltyramine,1TBDMS,isomer #2	CN(CCC1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	1881.3	Semi standard non polar	33892256
N-Methyltyramine,2TBDMS,isomer #1	CN(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2183.1	Semi standard non polar	33892256
N-Methyltyramine,2TBDMS,isomer #1	CN(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2172.1	Standard non polar	33892256
N-Methyltyramine,2TBDMS,isomer #1	CN(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2040.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methyltyramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-14293e75666be4e27019	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methyltyramine GC-MS (1 TMS) - 70eV, Positive	splash10-00xr-7920000000-4709651ba3c22c23b463	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methyltyramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-89ff5a43bc3e7737bcb6	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methyltyramine 10V, Positive-QTOF	splash10-0uk9-0900000000-0f335d13104342fdeed5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methyltyramine 20V, Positive-QTOF	splash10-0fk9-2900000000-037595c7cc0c504058c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methyltyramine 40V, Positive-QTOF	splash10-0kk9-9500000000-376efc98f806aac30929	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methyltyramine 10V, Negative-QTOF	splash10-0udi-0900000000-27ea78b166d8b3172ce1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methyltyramine 20V, Negative-QTOF	splash10-0udi-1900000000-fb693eca1267a0ba9685	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methyltyramine 40V, Negative-QTOF	splash10-05al-6900000000-6d964137e90c9e3293d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methyltyramine 10V, Positive-QTOF	splash10-00di-1900000000-6ac9e0419aa31060260b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methyltyramine 20V, Positive-QTOF	splash10-00dl-7900000000-7fd4cbc25b6ff2a2bf1e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methyltyramine 40V, Positive-QTOF	splash10-004l-9100000000-7021336d37b527e2e5fd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methyltyramine 10V, Negative-QTOF	splash10-0udi-0900000000-1c71ef4ed8c1b09fb863	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methyltyramine 20V, Negative-QTOF	splash10-0udi-0900000000-4f21e6ca90b01b880bf4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methyltyramine 40V, Negative-QTOF	splash10-00kf-9600000000-4a0119f5c8223bec2ae4	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, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+H]+)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)	2022-02-11	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+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

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

N-Methyltyramine

METLIN ID

Not Available

PubChem Compound

9727

PDB ID

Not Available

ChEBI ID

17458

Food Biomarker Ontology

Not Available

VMH ID

C02442

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
Kimura T, Iwasaki N, Yokoe JI, Haruta S, Yokoo Y, Ogawara KI, Higaki K: Analysis and prediction of absorption profile including hepatic first-pass metabolism of N-methyltyramine, a potent stimulant of gastrin release present in beer, after oral ingestion in rats by gastrointestinal-transit-absorption model. Drug Metab Dispos. 2000 May;28(5):577-81. [PubMed:10772638 ]
Zhao XW, Li JX, Zhu ZR, Sun DQ, Liu SC: Anti-shock effects of synthetic effective compositions of fructus aurantii immaturus. Experimental study and clinical observation. Chin Med J (Engl). 1989 Feb;102(2):91-3. [PubMed:2570680 ]

Enzymes

Enzyme Details

1. Protein arginine N-methyltransferase 3

General function:: Involved in protein methyltransferase activity
Specific function:: Methylates (mono and asymmetric dimethylation) the guanidino nitrogens of arginyl residues in some proteins
Gene Name:: PRMT3
Uniprot ID:: O60678
Molecular weight:: 59902.7

Enzyme Details

2. HemK methyltransferase family member 1

General function:: Not Available
Specific function:: N5-glutamine methyltransferase responsible for the methylation of the GGQ triplet of the mitochondrial translation release factor MTRF1L.
Gene Name:: HEMK1
Uniprot ID:: Q9Y5R4
Molecular weight:: Not Available

Reactions

N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteine	details

Enzyme Details

3. Methyltransferase-like protein 2B

General function:: Not Available
Specific function:: Probable methyltransferase (By similarity).
Gene Name:: METTL2B
Uniprot ID:: Q6P1Q9
Molecular weight:: Not Available

Reactions

N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteine	details

Enzyme Details

4. Methyltransferase-like protein 6

General function:: Not Available
Specific function:: Probable methyltransferase (By similarity).
Gene Name:: METTL6
Uniprot ID:: Q8TCB7
Molecular weight:: Not Available

Reactions

N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteine	details

Enzyme Details

5. Uncharacterized methyltransferase WBSCR22

General function:: Not Available
Specific function:: Methyltransferase that may act on DNA.
Gene Name:: WBSCR22
Uniprot ID:: O43709
Molecular weight:: Not Available

Reactions

N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteine	details

Showing metabocard for N-Methyltyramine (HMDB0003633)

MOL for HMDB0003633 (N-Methyltyramine)

3D MOL for HMDB0003633 (N-Methyltyramine)

3D SDF for HMDB0003633 (N-Methyltyramine)

3D-SDF for HMDB0003633 (N-Methyltyramine)

PDB for HMDB0003633 (N-Methyltyramine)

3D PDB for HMDB0003633 (N-Methyltyramine)

SMILES for HMDB0003633 (N-Methyltyramine)

INCHI for HMDB0003633 (N-Methyltyramine)

Structure for HMDB0003633 (N-Methyltyramine)

3D Structure for HMDB0003633 (N-Methyltyramine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions