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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:05 UTC
NP-MRD IDNP0000398
Secondary Accession NumbersNone
Natural Product Identification
Common NameTyramine
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. 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. Tyramine is a biomarker for the consumption of cheese
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 Mass137.1790 Da
Monoisotopic Mass137.08406 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 1H] 2D NMR Spectrum (experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)V.dorna832021-08-09View Spectrum
Species
Species of Origin
Species NameSourceReference
Acacia angustissimaKNApSAcK Database
Acacia greggiiKNApSAcK Database
Acacia rigidula Benth.KNApSAcK Database
Acacia roemerianaKNApSAcK Database
Actaea racemosaKNApSAcK Database
Adenocarpus hispanicusKNApSAcK Database
Allium victorialisKNApSAcK Database
Antirrhinum majusKNApSAcK Database
Arabidopsis thalianaKNApSAcK Database
Argemone mexicanaKNApSAcK Database
Aristolochia giganteaKNApSAcK Database
Berberis amurensisKNApSAcK Database
Berberis aquifoliumKNApSAcK Database
Berberis aristataKNApSAcK Database
Berberis thunbergiiKNApSAcK Database
Berberis vulgarisKNApSAcK Database
Berberis wilsoniaeKNApSAcK Database
Brassica olereaceaKNApSAcK Database
Capsella bursa-pastorisKNApSAcK Database
Caulophyllum thalicroidesKNApSAcK Database
Chelidonium majusKNApSAcK Database
Cissampelos pareiraKNApSAcK Database
Citrus aurantium L. var. amaraKNApSAcK Database
Citrus bergamiaKNApSAcK Database
Citrus limonKNApSAcK Database
Citrus medicaKNApSAcK Database
Citrus reticulataKNApSAcK Database
Citrus sinensisKNApSAcK Database
Clematis parvilobaKNApSAcK Database
Cocculus diversifoliusKNApSAcK Database
Cocculus japonicusKNApSAcK Database
Coptis japonicaKNApSAcK Database
Corydalis cavaKNApSAcK Database
Cyclea barbataKNApSAcK Database
Cyclea peltataKNApSAcK Database
Cytisus scopariusKNApSAcK Database
Datura innoxiaKNApSAcK Database
Delphinium pentagynumKNApSAcK Database
Dendrolobium triangulareKNApSAcK Database
Desmodium elegansKNApSAcK Database
Desmodium triflorumKNApSAcK Database
Dicentra spectabilisKNApSAcK Database
Erythrina crista-galliKNApSAcK Database
Eschscholzia californicaKNApSAcK Database
Espostoa huanucensisKNApSAcK Database
Fumaria officinalisKNApSAcK Database
Glaucium flavumKNApSAcK Database
Gleditsia triacanthosKNApSAcK Database
Glycine maxKNApSAcK Database
Gnetum montanumKNApSAcK Database
Hordeum vulgareKNApSAcK Database
Hydrastis canadensisKNApSAcK Database
Hypecoum lactiflorumKNApSAcK Database
Lamium barbatumKNApSAcK Database
Lindera angustifoliaKNApSAcK Database
Liparia parvaKNApSAcK Database
Liparia splendensKNApSAcK Database
Lolium multiflorumKNApSAcK Database
Lophophora williamsiiKNApSAcK Database
Lyallia kerguelensisKNApSAcK Database
Macleaya cordataKNApSAcK Database
Magnolia obovataKNApSAcK Database
Magnolia officinalisKNApSAcK Database
Mahonia aquifoliumKNApSAcK Database
Meconopsis cambricaKNApSAcK Database
Monodora junodiiKNApSAcK Database
Musa acuminataKNApSAcK Database
Musa sapientumKNApSAcK Database
Panicum miliaceumKNApSAcK Database
Papaver bracteatumKNApSAcK Database
Papaver rhoeasKNApSAcK Database
Papaver somniferumKNApSAcK Database
Pereskia aculeataKNApSAcK Database
Persea americanaKNApSAcK Database
Phaseolus vulgarisKNApSAcK Database
Phellodendron chinensisKNApSAcK Database
Piper nigrumKNApSAcK Database
Pisum sativumKNApSAcK Database
Plantago majorKNApSAcK Database
Portulaca grandifloraKNApSAcK Database
Prosopis albaKNApSAcK Database
Prosopis glandulosaKNApSAcK Database
Prosopis nigraKNApSAcK Database
Rhodiola roseaKNApSAcK Database
Rhodiola sachalinensisKNApSAcK Database
Romneya coulteriKNApSAcK Database
Senna alataKNApSAcK Database
Silybum marianumKNApSAcK Database
Solanum esculentumKNApSAcK Database
Solanum lycopersicum L.KNApSAcK Database
Solanum melanogenaKNApSAcK Database
Solanum tuberosumKNApSAcK Database
Spinacia oleraceaKNApSAcK Database
Stapelia hirsutaKNApSAcK Database
Stephania hernandifoliaKNApSAcK Database
Stephania tetrandraKNApSAcK Database
Tephrosia noctifloraKNApSAcK Database
Thalictrum flavumKNApSAcK Database
Theobroma cacaoKNApSAcK Database
Tinospora cordifoliaKNApSAcK Database
Trichocereus candicansKNApSAcK Database
Trichocereus pachanoiKNApSAcK Database
Trichocereus spachianusKNApSAcK Database
Viscum albumKNApSAcK Database
Xylopia parvifloraKNApSAcK Database
Zizyphus jujuba var. spinosaKNApSAcK Database
Species Where Detected
Species NameSourceReference
Claviceps purpureaKNApSAcK Database
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 Point277.00 to 278.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility10.4 mg/mL at 15 °CNot Available
LogP3.894 (est)The Good Scents Company Information System
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External Links
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
Good Scents IDrw1565911
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  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 ]
  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 ]
  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 ]
  7. Yin SJ, Lee SC: Tyramine interference in assay of serum dopamine-beta-hydroxylase. Clin Chem. 1977 Mar;23(3):617-8. [PubMed:319927 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]