Showing Compound Card for Tyramine (CDB006168)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:22:21 UTC
Updated at2022-12-13 23:36:26 UTC
CannabisDB IDCDB006168
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameTyramine
DescriptionTyramine is a monoamine compound derived from the amino acid tyrosine. It is a very strong basic compound (based on its pKa). 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 (herring), chocolate, alcoholic beverages, cheese, yogurt, soy sauce, sauerkraut, and processed meat. Tyramine in the blood or urine is often considered as a biomarker for the consumption of cheese. A large dietary intake of tyramine can cause an increase in systolic blood pressure of 30 mmHg or more and induce migraine headaches (PMID: 27424325 ). The tyramine connection to hypertensive episodes was discovered by a British pharmacist whose wife was taking an monoamine oxidase inhibitors (MAOI). He noticed that every time they had a meal with cheese, she would get a severe headache (PMID: 19742203 ). Tyramine acts as a neurotransmitter via a G protein-coupled receptor called TA1, which has a high affinity for tyramine. The TA1 receptor is found in the brain as well as peripheral tissues including the kidney. As an indirect sympathomimetic compound, tyramine can also serve as a substrate for adrenergic uptake systems and monoamine oxidase, so it prolongs the actions of adrenergic transmitters. Tyramine also provokes transmitter release from adrenergic terminals.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight137.18
Monoisotopic Molecular Weight137.0841
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point164 - 165 °CNot Available
Boiling Point206 °C at 25 mmHgWikipedia
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-053r-9500000000-6deb2b5d214f768ca4482014-09-20View Spectrum
GC-MSTyramine, 3 TMS, GC-MS Spectrumsplash10-00di-2900000000-273503edc6a220e152b6Spectrum
GC-MSTyramine, non-derivatized, GC-MS Spectrumsplash10-00di-2900000000-80980d19fa83d4b86f91Spectrum
GC-MSTyramine, 3 TMS, GC-MS Spectrumsplash10-00di-9700000000-78d2ae48da1eee18358eSpectrum
GC-MSTyramine, non-derivatized, GC-MS Spectrumsplash10-001i-9200000000-50c21473a7d48011358cSpectrum
GC-MSTyramine, non-derivatized, GC-MS Spectrumsplash10-00di-1900000000-9b1000a8978b57919c35Spectrum
GC-MSTyramine, non-derivatized, GC-MS Spectrumsplash10-00di-2900000000-273503edc6a220e152b6Spectrum
GC-MSTyramine, non-derivatized, GC-MS Spectrumsplash10-00di-2900000000-80980d19fa83d4b86f91Spectrum
GC-MSTyramine, non-derivatized, GC-MS Spectrumsplash10-00di-9700000000-78d2ae48da1eee18358eSpectrum
GC-MSTyramine, non-derivatized, GC-MS Spectrumsplash10-00di-2900000000-69892c95ab2778a208b3Spectrum
Predicted GC-MSTyramine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9600000000-1d5276a762318a00832dSpectrum
Predicted GC-MSTyramine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fk9-7900000000-8f3b164f36bc5a4df4d7Spectrum
Predicted GC-MSTyramine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTyramine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTyramine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTyramine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-0900000000-066947a256844eb6cbdc2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-0900000000-4b0f190d7304f2cec82d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-2feedb2abf4fe54134522021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-052r-0900000000-e67940e0a4f0f1b565c42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00lr-9400000000-47a2e802a22167ed8a632021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-3229081a448a277191a22012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004l-9300000000-e2fc12d41e4c40a9a2962012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-92f0b12d0a64443cede82012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-001i-9200000000-50c21473a7d48011358c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-d7e9a8705227b4504c5c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-3f02b334907c40a8315c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-e98b3afc6fad78d45d382012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-54239e66d89de3096ca82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0079-0902000000-f09759fc06ef461f3aa52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-9ffe6ee0ce68182216f72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-020a5decfb44fc4f97df2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0930000000-32ccc375e75dbab3195c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-51c6cc08017f1672b7912012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-1900000000-55c25dd64462c06c53162012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0f96-9500000000-83a70aec6da00b51a6df2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-004i-9100000000-5f044e831c0d2db255fa2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004i-9000000000-99edae3913507430bf9f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-4900000000-8944003750ac547c20242012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-00e85becc8cfc59bdb102017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-58e8539844dcdbc977cc2017-09-14View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)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)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Amine oxidase [flavin-containing] BMAOBXp11.23P27338 details
Amine oxidase [flavin-containing] AMAOAXp11.3P21397 details
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Trace amine-associated receptor 1TAAR16q23.2Q96RJ0 details
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.0124 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.00362 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.00728 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.00881 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.00786 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.0407 mg/g dry wt
    • David S. Wishart,...
 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
General References
  1. Khan MZ, Nawaz W: The emerging roles of human trace amines and human trace amine-associated receptors (hTAARs) in central nervous system. Biomed Pharmacother. 2016 Oct;83:439-449. doi: 10.1016/j.biopha.2016.07.002. Epub 2016 Jul 15. [PubMed:27424325 ]
  2. Sathyanarayana Rao TS, Yeragani VK: Hypertensive crisis and cheese. Indian J Psychiatry. 2009 Jan;51(1):65-6. doi: 10.4103/0019-5545.44910. [PubMed:19742203 ]

Enzymes

Enzyme Details
1. Amine oxidase [flavin-containing] B
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Enzyme Details
2. Amine oxidase [flavin-containing] A
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27