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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 09:39:07 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 exists as a solid, slightly soluble (in water), and a very weakly acidic compound (based on its pKa). m-Tyramine has been detected in multiple biofluids, such as urine and blood. Within the cell, m-tyramine is primarily located in the cytoplasm.
Structure
Thumb
Synonyms
ValueSource
2-(3-Hydroxyphenyl)ethylamineChEMBL
3-(2-Aminoethyl)phenolHMDB
3-HydroxyphenethylamineHMDB
3-HydroxyphenylethylamineHMDB
3-TyramineHMDB
m-HydroxyphenethylamineHMDB
Meta-tyramineHMDB
MetatyramineHMDB
3-Tyramine hydrobromideMeSH
3-Tyramine hydrochlorideMeSH
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
DescriptionThis compound belongs to the class of organic compounds known as phenethylamines. These 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9700000000-2524df02b3faf73efd51View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0089-9800000000-6cabd95c9a4e0db447d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0900000000-c3561d44b3cf39001019View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-bb8118ca8a5fb8d17068View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0umi-9300000000-9e5708dd981cd7611372View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-b71daf1700720243b917View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-bcc3c69fabeaccd757c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-8900000000-bfeab516e28533c7ad32View in MoNA
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
FoodDB IDFDB023573
KNApSAcK IDNot Available
Chemspider ID11008
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7240
PubChem Compound11492
PDB IDNot Available
ChEBI ID341165
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 ]