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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 02:17:17 UTC
Update Date2019-07-23 05:45:50 UTC
HMDB IDHMDB0003633
Secondary Accession Numbers
  • HMDB0060283
  • HMDB0060284
  • HMDB03633
  • HMDB60283
  • HMDB60284
Metabolite Identification
Common NameN-Methyltyramine
DescriptionN-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
Data?1563860750
Synonyms
ValueSource
4-Hydroxy-N-methylphenethylamineChEBI
Methyl-4-tyramineChEBI
p-(2-Methylaminoethyl)phenolChEBI
4-(2-(Methylamino)ethyl)-phenolHMDB
4-(2-Methylaminoethyl)phenolHMDB
4-[2-(Methylamino)ethyl]-phenolHMDB
4-[2-(Methylamino)ethyl]phenolHMDB
Methyl tyramineHMDB
N-Methyl-p-tyramineHMDB
N-MethyltyraminiumHMDB
NMTHMDB
p-(2-(Methylamino)ethyl)phenolHMDB
p-[2-(Methylamino)ethyl]-phenolHMDB
{p-[2-(methylamino)ethyl]phenol}HMDB
N-MethyltyrosamineHMDB
Methyl-4-tyramine hydrochlorideHMDB
Methyl-4-tyramine hydrobromideHMDB
Chemical FormulaC9H13NO
Average Molecular Weight151.2056
Monoisotopic Molecular Weight151.099714043
IUPAC Name4-[2-(methylamino)ethyl]phenol
Traditional NameN-methyltyramine
CAS Registry Number370-98-9
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 KeyAXVZFRBSCNEKPQ-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentPhenethylamines
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.455Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.4 g/LALOGPS
logP0.48ALOGPS
logP0.96ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)10.54ChemAxon
pKa (Strongest Basic)9.82ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area32.26 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.04 m³·mol⁻¹ChemAxon
Polarizability17.42 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-14293e75666be4e27019JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00xr-7920000000-4709651ba3c22c23b463JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0900000000-0f335d13104342fdeed5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-2900000000-037595c7cc0c504058c6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kk9-9500000000-376efc98f806aac30929JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-27ea78b166d8b3172ce1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-fb693eca1267a0ba9685JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05al-6900000000-6d964137e90c9e3293d1JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-89ff5a43bc3e7737bcb6JSpectraViewer | MoNA
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
FoodDB IDFDB000435
KNApSAcK IDC00027432
Chemspider ID9345
KEGG Compound IDC02442
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Methyltyramine
METLIN IDNot Available
PubChem Compound9727
PDB IDNot Available
ChEBI ID17458
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]

Enzymes

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
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-Adenosylhomocysteinedetails
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-Adenosylhomocysteinedetails
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-Adenosylhomocysteinedetails
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-Adenosylhomocysteinedetails