Record Information
Version2.0
Creation Date2012-05-31 10:26:14 -0600
Update Date2015-09-13 12:56:07 -0600
Secondary Accession Numbers
  • ECMDB00306
Identification
Name:Tyramine
DescriptionTyramine is a monoamine compound derived from the amino acid tyrosine. Tyramine is metabolized by the enzyme monoamine oxidase. In foods, it is often produced by the decarboxylation of tyrosine during fermentation or decay. In E.coli, tyramine is invilved in several metabolic pathways, tyrosine metabolism, isoquinolome alkaloid biosynthesis and biosynthesis of alkaloids derived from shikimate pathway.
Structure
Thumb
Synonyms:
  • 2-(4'-Hydroxyphenyl)ethylamine
  • 2-(4-Hydroxyphenyl)ethylamine
  • 2-(p-hydroxyphenyl)ethylamine
  • 2-(p-Hydroxyphenyl)ethylamine
  • 4- (2-Aminoethyl)-Phenol
  • 4-(2-Aminoethyl)-Phenol
  • 4-(2-Aminoethyl)-phenol(thyramin)
  • 4-(2-Aminoethyl)phenol
  • 4-Hydroxy-b-phenylethylamine
  • 4-Hydroxy-Benzeneethanamine
  • 4-Hydroxy-beta-phenylethylamine
  • 4-Hydroxy-β-phenylethylamine
  • 4-Hydroxyphenethylamine
  • 4-Hydroxyphenylethylamine
  • p-hydroxyphenethylamine
  • A-(4-Hydroxyphenyl)-b-aminoethane
  • Alpha-(4-Hydroxyphenyl)-beta-aminoethane
  • Alpha.-(4-hydroxyphenyl)-b-aminoethane
  • Alpha.-(4-Hydroxyphenyl)-beta-aminoethane
  • Alpha.-(4-hydroxyphenyl)-β-aminoethane
  • B-(4-Hydroxyphenyl)ethylamine
  • Beta-(4-Hydroxyphenyl)ethylamine
  • P-(2-Aminoethyl)-Phenol
  • P-(2-Aminoethyl)phenol
  • P-b-Aminoethylphenol
  • P-beta-Aminoethylphenol
  • P-Hydroxy-b-phenethylamine
  • P-Hydroxy-b-phenylethylamine
  • P-Hydroxy-beta-phenethylamine
  • P-Hydroxy-beta-phenylethylamine
  • P-Hydroxy-β-phenethylamine
  • P-Hydroxy-β-phenylethylamine
  • P-Hydroxyphenethylamine
  • P-Hydroxyphenylethylamine
  • P-Tyramine
  • P-β-Aminoethylphenol
  • Systogene
  • Tenosin-wirkstoff
  • Tocosine
  • Tyramin
  • Tyramine base
  • Tyrosamine
  • Uteramine
  • α-(4-Hydroxyphenyl)-β-aminoethane
  • β-(4-Hydroxyphenyl)ethylamine
Chemical Formula:C8H11NO
Weight:Average: 137.179
Monoisotopic: 137.084063979
InChI Key:DZGWFCGJZKJUFP-UHFFFAOYSA-N
InChI:InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2
CAS number:51-67-2
IUPAC Name:4-(2-aminoethyl)phenol
Traditional IUPAC Name:tyramine
SMILES:NCCC1=CC=C(O)C=C1
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
State:Solid
Charge:1
Melting point:164-165 °C
Experimental Properties:
PropertyValueSource
Water Solubility:10.4 mg/mL at 15 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility5.72 g/LALOGPS
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-2900000000-273503edc6a220e152b6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-2900000000-80980d19fa83d4b86f91View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9700000000-78d2ae48da1eee18358eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9200000000-50c21473a7d48011358cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-1900000000-9b1000a8978b57919c35View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-2900000000-273503edc6a220e152b6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-2900000000-80980d19fa83d4b86f91View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9700000000-78d2ae48da1eee18358eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-2900000000-69892c95ab2778a208b3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9600000000-1d5276a762318a00832dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-7900000000-8f3b164f36bc5a4df4d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-3229081a448a277191a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004l-9300000000-e2fc12d41e4c40a9a296View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-92f0b12d0a64443cede8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-001i-9200000000-50c21473a7d48011358cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-d7e9a8705227b4504c5cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-3f02b334907c40a8315cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-e98b3afc6fad78d45d38View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-54239e66d89de3096ca8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0079-0902000000-f09759fc06ef461f3aa5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-9ffe6ee0ce68182216f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-020a5decfb44fc4f97dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0930000000-32ccc375e75dbab3195cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-51c6cc08017f1672b791View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-1900000000-55c25dd64462c06c5316View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0f96-9500000000-83a70aec6da00b51a6dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-004i-9100000000-5f044e831c0d2db255faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004i-9000000000-99edae3913507430bf9fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-4900000000-8944003750ac547c2024View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-0900000000-066947a256844eb6cbdcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0900000000-8fb72547243614622ba3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-44bf2322645e5e00b029View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uml-9400000000-343b8fa44c724b1395c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-7da5f9953041f5148f8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-e62cf6efa07eeeaf1f51View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-7900000000-4f78b5370ece8150a8c4View in MoNA
MSMass Spectrum (Electron Ionization)splash10-053r-9500000000-6deb2b5d214f768ca448View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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
  • Antal EJ, Hendershot PE, Batts DH, Sheu WP, Hopkins NK, Donaldson KM: Linezolid, a novel oxazolidinone antibiotic: assessment of monoamine oxidase inhibition using pressor response to oral tyramine. J Clin Pharmacol. 2001 May;41(5):552-62. Pubmed: 11361052
  • Balbi T, Fusco M, Vasapollo D, Boschetto R, Cocco P, Leon A, Farruggio A: The presence of trace amines in postmortem cerebrospinal fluid in humans. J Forensic Sci. 2005 May;50(3):630-2. Pubmed: 15932098
  • Causon RC, Brown MJ: Measurement of tyramine in human plasma, utilising ion-pair extraction and high-performance liquid chromatography with amperometric detection. J Chromatogr. 1984 Sep 14;310(1):11-7. Pubmed: 6501508
  • Chalon SA, Granier LA, Vandenhende FR, Bieck PR, Bymaster FP, Joliat MJ, Hirth C, Potter WZ: Duloxetine increases serotonin and norepinephrine availability in healthy subjects: a double-blind, controlled study. Neuropsychopharmacology. 2003 Sep;28(9):1685-93. Epub 2003 May 28. Pubmed: 12784100
  • Gabastou JM, Nugon-Baudon L, Robert Y, Manuel C, Vaissade P, Bourgeon E, Sibeud M, Szylit O, Bourlioux P: [Digestive amines of bacterial origin and behavior disorders. Apropos of a case] Pathol Biol (Paris). 1996 Apr;44(4):275-81. Pubmed: 8763591
  • Hiroi T, Imaoka S, Funae Y: Dopamine formation from tyramine by CYP2D6. Biochem Biophys Res Commun. 1998 Aug 28;249(3):838-43. Pubmed: 9731223
  • Jacob G, Costa F, Vincent S, Robertson D, Biaggioni I: Neurovascular dissociation with paradoxical forearm vasodilation during systemic tyramine administration. Circulation. 2003 May 20;107(19):2475-9. Epub 2003 Apr 21. Pubmed: 12707242
  • Jayanthi LD, Balasubramanian N, Balasubramanian AS: Cholinesterases exhibiting aryl acylamidase activity in human amniotic fluid. Clin Chim Acta. 1992 Feb 14;205(3):157-66. Pubmed: 1349516
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Lin J, Cashman JR: Detoxication of tyramine by the flavin-containing monooxygenase: stereoselective formation of the trans oxime. Chem Res Toxicol. 1997 Aug;10(8):842-52. Pubmed: 9282832
  • Markianos E, Backman H: Diurnal changes in dopamine-beta-hydroxylase, homovanillic acid and 3-methoxy-4-hydroxyphenylglycol in serum of man. J Neural Transm. 1976;39(1-2):79-93. Pubmed: 988114
  • Nakai T, Yamada R: Basic and clinical reevaluation of tyramine and histamine tests for the investigation of adrenomedullary sympathetic functions. J Clin Endocrinol Metab. 1983 Jul;57(1):19-23. Pubmed: 6853676
  • Tyce GM, Stockard J, Sharpless NS, Muenter MD: Excretion of amines and their metabolites by two patients in hepatic coma treated with L-dopa. Clin Pharmacol Ther. 1983 Sep;34(3):390-8. Pubmed: 6883916
  • Varma DR, Chemtob S: Endothelium- and beta-2 adrenoceptor-independent relaxation of rat aorta by tyramine and certain other phenylethylamines. J Pharmacol Exp Ther. 1993 Jun;265(3):1096-104. Pubmed: 8389852
  • Watson DG, McGhee CN, Midgley JM, Zhou P, Doig WM: Determination of acidic metabolites of biogenic amines in human aqueous humour by gas chromatography--negative ion chemical ionisation mass spectrometry. J Neurochem. 1992 Jan;58(1):116-20. Pubmed: 1727423
  • Watson DG, Midgley JM, Chen RN, Huang W, Bain GM, McDonald NM, Reid JL, McGhee CN: Analysis of biogenic amines and their metabolites in biological tissues and fluids by gas chromatography-negative ion chemical ionization mass spectrometry (GC-NICIMS). J Pharm Biomed Anal. 1990;8(8-12):899-904. Pubmed: 2100639
  • Wolrath H, Forsum U, Larsson PG, Boren H: Analysis of bacterial vaginosis-related amines in vaginal fluid by gas chromatography and mass spectrometry. J Clin Microbiol. 2001 Nov;39(11):4026-31. Pubmed: 11682525
  • Yin SJ, Lee SC: Tyramine interference in assay of serum dopamine-beta-hydroxylase. Clin Chem. 1977 Mar;23(3):617-8. Pubmed: 319927
Synthesis Reference:Wang, Yalou; Xie, Dongmei. Improved synthesis method of tyramine. Zhongguo Yaowu Huaxue Zazhi (1994), 4(2), 128-9.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID15760
HMDB IDHMDB00306
Pubchem Compound ID5610
Kegg IDC00483
ChemSpider ID5408
WikipediaTyramine
BioCyc IDTYRAMINE
EcoCyc IDTYRAMINE
Ligand ExpoAEF

Enzymes

General function:
Involved in copper ion binding
Specific function:
The enzyme prefers aromatic over aliphatic amines
Gene Name:
tynA
Uniprot ID:
P46883
Molecular weight:
84378
Reactions
RCH(2)NH(2) + H(2)O + O(2) = RCHO + NH(3) + H(2)O(2).
2-phenylethylamine + H(2)O + O(2) = phenylacetaldehyde + NH(3) + H(2)O(2).

Transporters

General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368