Record Information
Version1.0
Creation Date2016-09-30 22:28:09 UTC
Update Date2020-05-21 16:28:47 UTC
MCDB ID BMDB0000306
Secondary Accession Numbers
  • BMDB00306
Metabolite Identification
Common NameTyramine
DescriptionTyramine, also known as para-tyramine or systogene, 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. Tyramine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Tyramine exists in all living species, ranging from bacteria to humans. Tyramine participates in a number of enzymatic reactions, within cattle. In particular, Tyramine can be biosynthesized from L-tyrosine; which is catalyzed by the enzyme aromatic-L-amino-acid decarboxylase. In addition, Tyramine can be converted into dopamine; which is mediated by the enzyme tyrosinase. In cattle, tyramine is involved in the metabolic pathway called the tyrosine metabolism pathway. Tyramine is a potentially toxic compound. Tyramine has been found to be associated with several diseases known as brunner syndrome, ulcerative colitis, crohn's disease, and eosinophilic esophagitis; also tyramine has been linked to the inborn metabolic disorders including celiac disease.
Structure
Thumb
Synonyms
ValueSource
2-(p-Hydroxyphenyl)ethylamineChEBI
4-Hydroxy-beta-phenylethylamineChEBI
4-HydroxyphenethylamineChEBI
4-HydroxyphenylethylamineChEBI
beta-(4-Hydroxyphenyl)ethylamineChEBI
p-(2-Aminoethyl)phenolChEBI
p-HydroxyphenethylamineChEBI
p-HydroxyphenylethylamineChEBI
p-TyramineChEBI
TyraminChEBI
4-Hydroxy-b-phenylethylamineGenerator
4-Hydroxy-β-phenylethylamineGenerator
b-(4-Hydroxyphenyl)ethylamineGenerator
Β-(4-hydroxyphenyl)ethylamineGenerator
2-(4'-Hydroxyphenyl)ethylamineHMDB
2-(4-Hydroxyphenyl)ethylamineHMDB
4-(2-Aminoethyl)-phenolHMDB
4-(2-Aminoethyl)-phenol(thyramin)HMDB
4-(2-Aminoethyl)phenolHMDB
4-Hydroxy-benzeneethanamineHMDB
a-(4-Hydroxyphenyl)-b-aminoethaneHMDB
alpha-(4-Hydroxyphenyl)-beta-aminoethaneHMDB
p-(2-Aminoethyl)-phenolHMDB
p-beta-AminoethylphenolHMDB
p-Hydroxy-b-phenethylamineHMDB
p-Hydroxy-b-phenylethylamineHMDB
p-Hydroxy-beta-phenethylamineHMDB
p-Hydroxy-beta-phenylethylamineHMDB
SystogeneHMDB
Tenosin-wirkstoffHMDB
TocosineHMDB
Tyramine baseHMDB
TyrosamineHMDB
UteramineHMDB
Para-tyramineHMDB
4 HydroxyphenethylamineHMDB
2-(4-Hydroxyphenyl)ethanamineHMDB
2-(4’-hydroxyphenyl)ethylamineHMDB
p-Hydroxy-β-phenylethylamineHMDB
p-Β-aminoethylphenolHMDB
Α-(4-hydroxyphenyl)-β-aminoethaneHMDB
Chemical FormulaC8H11NO
Average Molecular Weight137.179
Monoisotopic Molecular Weight137.084063979
IUPAC Name4-(2-aminoethyl)phenol
Traditional Nametyramine
CAS Registry Number51-67-2
SMILES
NCCC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2
InChI KeyDZGWFCGJZKJUFP-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-2-unsubstituted benzenoid
  • Aralkylamine
  • Phenol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
logP-0.14ALOGPS
logP0.68ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)10.41ChemAxon
pKa (Strongest Basic)9.66ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.27 m³·mol⁻¹ChemAxon
Polarizability15.33 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-2900000000-273503edc6a220e152b62014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-2900000000-80980d19fa83d4b86f912014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9700000000-78d2ae48da1eee18358e2014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9200000000-50c21473a7d48011358c2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-1900000000-9b1000a8978b57919c352017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-2900000000-273503edc6a220e152b62017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-2900000000-80980d19fa83d4b86f912017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9700000000-78d2ae48da1eee18358e2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-2900000000-69892c95ab2778a208b32017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9600000000-1d5276a762318a00832d2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-7900000000-8f3b164f36bc5a4df4d72017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-0900000000-066947a256844eb6cbdc2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-0900000000-4b0f190d7304f2cec82d2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-2feedb2abf4fe54134522021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-052r-0900000000-e67940e0a4f0f1b565c42021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00lr-9400000000-47a2e802a22167ed8a632021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-3229081a448a277191a22012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004l-9300000000-e2fc12d41e4c40a9a2962012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-92f0b12d0a64443cede82012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-001i-9200000000-50c21473a7d48011358c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-d7e9a8705227b4504c5c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-3f02b334907c40a8315c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-e98b3afc6fad78d45d382012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-54239e66d89de3096ca82012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0079-0902000000-f09759fc06ef461f3aa52012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-9ffe6ee0ce68182216f72012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-020a5decfb44fc4f97df2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0930000000-32ccc375e75dbab3195c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-51c6cc08017f1672b7912012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-1900000000-55c25dd64462c06c53162012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0f96-9500000000-83a70aec6da00b51a6df2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-004i-9100000000-5f044e831c0d2db255fa2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004i-9000000000-99edae3913507430bf9f2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-4900000000-8944003750ac547c20242012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-00e85becc8cfc59bdb102017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-58e8539844dcdbc977cc2017-09-14View Spectrum
MSMass Spectrum (Electron Ionization)splash10-053r-9500000000-6deb2b5d214f768ca4482014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2021-10-10View Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0000306
DrugBank IDDB08841
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000433
KNApSAcK IDC00001435
Chemspider ID5408
KEGG Compound IDC00483
BioCyc IDTYRAMINE
BiGG ID35110
Wikipedia LinkTyramine
METLIN ID60
PubChem Compound5610
PDB IDNot Available
ChEBI ID15760
References
Synthesis ReferenceWang, Yalou; Xie, Dongmei. Improved synthesis method of tyramine. Zhongguo Yaowu Huaxue Zazhi (1994), 4(2), 128-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]