Human Metabolome Database Version 3.5

Showing metabocard for Tyramine (HMDB00306)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:17 -0700
HMDB ID HMDB00306
Secondary Accession Numbers None
Metabolite Identification
Common Name Tyramine
Description Tyramine 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. Foods containing considerable amounts of tyramine include fish, chocolate, alcoholic beverages, cheese, soy sauce, sauerkraut, and processed meat. A large dietary intake of tyramine can cause an increase in systolic blood pressure of 30 mmHg or more. Tyramine acts as a neurotransmitter via a G protein-coupled receptor with high affinity for tyramine called TA1. The TA1 receptor is found in the brain as well as peripheral tissues including the kidney. An indirect sympathomimetic, Tyramine can also serve as a substrate for adrenergic uptake systems and monoamine oxidase so it prolongs the actions of adrenergic transmitters. It also provokes transmitter release from adrenergic terminals.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-(4'-Hydroxyphenyl)ethylamine
  2. 2-(4-Hydroxyphenyl)ethylamine
  3. 2-(p-Hydroxyphenyl)ethylamine
  4. 4- (2-Aminoethyl)-Phenol
  5. 4-(2-Aminoethyl)-Phenol
  6. 4-(2-Aminoethyl)-phenol(thyramin)
  7. 4-(2-Aminoethyl)phenol
  8. 4-Hydroxy-b-phenylethylamine
  9. 4-Hydroxy-Benzeneethanamine
  10. 4-Hydroxy-beta-phenylethylamine
  11. 4-Hydroxyphenethylamine
  12. 4-Hydroxyphenylethylamine
  13. a-(4-Hydroxyphenyl)-b-aminoethane
  14. alpha-(4-Hydroxyphenyl)-beta-aminoethane
  15. alpha.-(4-Hydroxyphenyl)-beta-aminoethane
  16. b-(4-Hydroxyphenyl)ethylamine
  17. beta-(4-Hydroxyphenyl)ethylamine
  18. p-(2-Aminoethyl)-Phenol
  19. p-(2-Aminoethyl)phenol
  20. P-beta-Aminoethylphenol
  21. P-Hydroxy-b-phenethylamine
  22. P-Hydroxy-b-phenylethylamine
  23. P-Hydroxy-beta-phenethylamine
  24. P-Hydroxy-beta-phenylethylamine
  25. P-Hydroxyphenethylamine
  26. P-Hydroxyphenylethylamine
  27. P-Tyramine
  28. Systogene
  29. Tenosin-wirkstoff
  30. Tocosine
  31. Tyramin
  32. Tyramine base
  33. Tyrosamine
  34. Uteramine
Chemical Formula C8H11NO
Average Molecular Weight 137.179
Monoisotopic Molecular Weight 137.084063979
IUPAC Name 4-(2-aminoethyl)phenol
Traditional IUPAC Name tyramine
CAS Registry Number 51-67-2
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 Key DZGWFCGJZKJUFP-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenethylamines
Sub Class N/A
Other Descriptors
  • Biogenic amines(KEGG)
  • Organic Compounds
  • Tyramine derivatives(KEGG)
  • primary amine(ChEBI)
  • tyramines(ChEBI)
Substituents
  • Phenol
  • Phenol Derivative
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Phenethylamines
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 164 - 165 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 10.4 mg/mL at 15 °C Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 5.72 g/L ALOGPS
LogP -0.14 ALOGPS
LogP 0.68 ChemAxon
LogS -1.38 ALOGPS
pKa (strongest acidic) 10.41 ChemAxon
pKa (strongest basic) 9.66 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 46.25 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 41.27 ChemAxon
Polarizability 15.33 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (Unknown)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Fibroblasts
  • Intestine
  • Placenta
  • Liver
  • Brain
  • Adipose Tissue
  • Adrenal Medulla
  • Nerve Cells
  • Platelet
  • Spleen
Pathways
Name SMPDB Link KEGG Link
Tyrosine Metabolism SMP00006 map00350 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.0095 +/- 0.0021 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
0.00049 +/- 0.00037 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.33 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.237 (0.2-0.275) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.38 (0.23-0.78) umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.0017 +/- 0.00088 uM Adult (>18 years old) Both Comment Cirrhosis
Associated Disorders and Diseases
Disease References
Cirrhosis
  • Yonekura T, Kamata S, Wasa M, Okada A, Yamatodani A, Watanabe T, Wada H: Simultaneous determination of plasma phenethylamine, phenylethanolamine, tyramine and octopamine by high-performance liquid chromatography using derivatization with fluorescamine. J Chromatogr. 1988 Jun 3;427(2):320-5. Pubmed: 3137238 Link_out
      Associated OMIM IDs None
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB000433
      KNApSAcK ID C00001435 Link_out
      Chemspider ID 5408 Link_out
      KEGG Compound ID C00483 Link_out
      BioCyc ID CPD-7650 Link_out
      BiGG ID 35110 Link_out
      Wikipedia Link Tyramine Link_out
      NuGOwiki Link HMDB00306 Link_out
      Metagene Link HMDB00306 Link_out
      METLIN ID 60 Link_out
      PubChem Compound 5610 Link_out
      PDB ID AEF Link_out
      ChEBI ID 15760 Link_out
      References
      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)
      General References
      1. 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 Link_out
      2. 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 Link_out
      3. 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 Link_out
      4. 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 Link_out
      5. 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 Link_out
      6. 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 Link_out
      7. Yin SJ, Lee SC: Tyramine interference in assay of serum dopamine-beta-hydroxylase. Clin Chem. 1977 Mar;23(3):617-8. Pubmed: 319927 Link_out
      8. 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 Link_out
      9. 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 Link_out
      10. 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 Link_out
      11. 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 Link_out
      12. 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 Link_out
      13. 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 Link_out
      14. 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 Link_out
      15. 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 Link_out
      16. 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 Link_out
      17. 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 Link_out
      18. 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 Link_out

      Enzymes
      Name: Tyrosinase
      Reactions:
      Tyramine + Oxygen + NADH + Hydrogen Ion unknown Dopamine + NAD + Water details
      Gene Name: TYR
      Uniprot ID: P14679 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Amine oxidase [flavin-containing] B
      Reactions:
      Tyramine + Water + Oxygen unknown 4-Hydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxide details
      Gene Name: MAOB
      Uniprot ID: P27338 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Amine oxidase [flavin-containing] A
      Reactions:
      Tyramine + Water + Oxygen unknown 4-Hydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxide details
      Gene Name: MAOA
      Uniprot ID: P21397 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Aromatic-L-amino-acid decarboxylase
      Reactions:
      L-Tyrosine unknown Tyramine + Carbon dioxide details
      Gene Name: DDC
      Uniprot ID: P20711 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Amiloride-sensitive amine oxidase [copper-containing]
      Reactions: Not Available
      Gene Name: ABP1
      Uniprot ID: P19801 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Membrane primary amine oxidase
      Reactions:
      Tyramine + Water + Oxygen unknown 4-Hydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxide details
      Gene Name: AOC3
      Uniprot ID: Q16853 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Retina-specific copper amine oxidase
      Reactions:
      Tyramine + Water + Oxygen unknown 4-Hydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxide details
      Gene Name: AOC2
      Uniprot ID: O75106 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Alpha-2A adrenergic receptor
      Reactions: Not Available
      Gene Name: ADRA2A
      Uniprot ID: P08913 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Alpha-2B adrenergic receptor
      Reactions: Not Available
      Gene Name: ADRA2B
      Uniprot ID: P18089 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Trace amine-associated receptor 1
      Reactions: Not Available
      Gene Name: TAAR1
      Uniprot ID: Q96RJ0 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA