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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:25:38 UTC
HMDB IDHMDB0004989
Secondary Accession Numbers
  • HMDB04989
Metabolite Identification
Common Namem-Tyramine
Descriptionm-Tyramine 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. m-Tyramine is an amine derived from Tyrosine, Phenylethylamine and other catecholamines. m-Tyramine is a very strong basic compound (based on its pKa).
Structure
Data?1582752338
Synonyms
ValueSource
2-(3-Hydroxyphenyl)ethylamineChEBI
3-(2-Aminoethyl)phenolChEBI
3-HydroxyphenethylamineChEBI
3-HydroxyphenylethylamineChEBI
3-TyramineChEBI
m-HydroxyphenethylamineChEBI
Meta-tyramineChEBI
MetatyramineHMDB
3-Tyramine hydrobromideHMDB
3-Tyramine hydrochlorideHMDB
m-TyramineMeSH
Chemical FormulaC8H11NO
Average Molecular Weight137.179
Monoisotopic Molecular Weight137.084063979
IUPAC Name3-(2-aminoethyl)phenol
Traditional Namem-tyramine
CAS Registry Number588-05-6
SMILES
NCCC1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C8H11NO/c9-5-4-7-2-1-3-8(10)6-7/h1-3,6,10H,4-5,9H2
InChI KeyGHFGJTVYMNRGBY-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
  • 2-arylethylamine
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Primary amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point164 - 165 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10.4 mg/mL at 15 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.82 g/LALOGPS
logP-0.17ALOGPS
logP0.64ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)10.27ChemAxon
pKa (Strongest Basic)9.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.27 m³·mol⁻¹ChemAxon
Polarizability15.28 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9700000000-2524df02b3faf73efd51Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0089-9800000000-6cabd95c9a4e0db447d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0900000000-c3561d44b3cf39001019Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-bb8118ca8a5fb8d17068Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0umi-9300000000-9e5708dd981cd7611372Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-b71daf1700720243b917Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-bcc3c69fabeaccd757c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-8900000000-bfeab516e28533c7ad32Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000038 +/- 0.000011 uMAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.280 (0.152-0.408) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00034 +/- 0.0000875 uMAdult (>18 years old)BothHypertension details
FecesDetected but not Quantified Adult (>18 years old)Both
Metastatic melanoma
details
Associated Disorders and Diseases
Disease References
Hypertension
  1. Andrew R, Best SA, Watson DG, Midgley JM, Reid JL, Squire IB: Analysis of biogenic amines in plasma of hypertensive patients and a control group. Neurochem Res. 1993 Nov;18(11):1179-82. [PubMed:8255371 ]
Metastatic melanoma
  1. Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023573
KNApSAcK IDNot Available
Chemspider ID11008
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMeta-Tyramine
METLIN ID7240
PubChem Compound11492
PDB IDNot Available
ChEBI ID89626
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceFalck, B.; Hillarp, N. A.; Thieme, G.; Torp, A. Fluorescence of catecholamines and related compounds condensed with formaldehyde. Brain Research Bulletin (1982), 9(1-6), xi-xv.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Andrew R, Watson DG, Best SA, Midgley JM, Wenlong H, Petty RK: The determination of hydroxydopamines and other trace amines in the urine of parkinsonian patients and normal controls. Neurochem Res. 1993 Nov;18(11):1175-7. [PubMed:8255370 ]
  2. Durden DA, Davis BA: Determination of regional distributions of phenylethylamine and meta- and para-tyramine in rat brain regions and presence in human and dog plasma by an ultra-sensitive negative chemical ion gas chromatography-mass spectrometric (NCI-GC-MS) method. Neurochem Res. 1993 Sep;18(9):995-1002. [PubMed:8232728 ]
  3. Boulton AA, Huebert ND: Biosynthesis of some urinary trace amines in the rat and the human. Res Commun Chem Pathol Pharmacol. 1981 Nov;34(2):295-310. [PubMed:7335956 ]