Showing Compound Tyramine (FDB000433)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:34 UTC

Update date

2020-09-17 15:42:26 UTC

Primary ID

FDB000433

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Tyramine

Description

Tyramine 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.

CAS Number

51-67-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-(p-Hydroxyphenyl)ethylamine	ChEBI
4-Hydroxy-beta-phenylethylamine	ChEBI
4-Hydroxyphenethylamine	ChEBI
4-Hydroxyphenylethylamine	ChEBI
beta-(4-Hydroxyphenyl)ethylamine	ChEBI
p-(2-Aminoethyl)phenol	ChEBI
p-Hydroxyphenethylamine	ChEBI
p-Hydroxyphenylethylamine	ChEBI
p-Tyramine	ChEBI
Tyramin	ChEBI
4-Hydroxy-b-phenylethylamine	Generator
4-Hydroxy-β-phenylethylamine	Generator
b-(4-Hydroxyphenyl)ethylamine	Generator
Β-(4-hydroxyphenyl)ethylamine	Generator
2-(4'-Hydroxyphenyl)ethylamine	HMDB
2-(4-Hydroxyphenyl)ethylamine	HMDB
4-(2-Aminoethyl)-phenol	HMDB
4-(2-Aminoethyl)-phenol(thyramin)	HMDB
4-(2-Aminoethyl)phenol	HMDB
4-Hydroxy-benzeneethanamine	HMDB
a-(4-Hydroxyphenyl)-b-aminoethane	HMDB
alpha-(4-Hydroxyphenyl)-beta-aminoethane	HMDB
p-(2-Aminoethyl)-phenol	HMDB
p-beta-Aminoethylphenol	HMDB
p-Hydroxy-b-phenethylamine	HMDB
p-Hydroxy-b-phenylethylamine	HMDB
p-Hydroxy-beta-phenethylamine	HMDB
p-Hydroxy-beta-phenylethylamine	HMDB
Systogene	HMDB
Tenosin-wirkstoff	HMDB
Tocosine	HMDB
Tyramine base	HMDB
Tyrosamine	HMDB
Uteramine	HMDB
Para-tyramine	HMDB
4 Hydroxyphenethylamine	HMDB
2-(4-Hydroxyphenyl)ethanamine	HMDB
2-(4’-hydroxyphenyl)ethylamine	HMDB
p-Hydroxy-β-phenylethylamine	HMDB
p-Β-aminoethylphenol	HMDB
Α-(4-hydroxyphenyl)-β-aminoethane	HMDB
4- (2-Aminoethyl)-phenol	HMDB
4-(2-Aminoethyl)phenol, 9CI	db_source
4-hydroxy-Benzeneethanamine	biospider
AEF	biospider
Alpha.-(4-hydroxyphenyl)-beta-aminoethane	HMDB
Beta-hydroxyphenylethylamine	biospider
L-tyramine	biospider
p-(2-aminoethyl)-Phenol	biospider
P-beta-aminoethylphenol	biospider
P-hydroxy-b-phenethylamine	biospider
P-hydroxy-b-phenylethylamine	biospider
P-hydroxy-beta-phenethylamine	biospider
P-hydroxy-beta-phenylethylamine	biospider
P-hydroxyphenethylamine	biospider
P-hydroxyphenylethylamine	biospider
P-tyramine	biospider
Tyramine	db_source
β-(4-hydroxyphenyl)ethylamine	Generator

Predicted Properties

Property	Value	Source
Water Solubility	5.72 g/L	ALOGPS
logP	-0.14	ALOGPS
logP	0.68	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	10.41	ChemAxon
pKa (Strongest Basic)	9.66	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	46.25 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.27 m³·mol⁻¹	ChemAxon
Polarizability	15.33 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C8H11NO

IUPAC name

4-(2-aminoethyl)phenol

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

Isomeric SMILES

NCCC1=CC=C(O)C=C1

Average Molecular Weight

137.179

Monoisotopic Molecular Weight

137.084063979

Classification

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Phenethylamines

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

monoamine molecular messenger (CHEBI:15760 )
primary amino compound (CHEBI:15760 )
tyramines (CHEBI:15760 )
Biogenic amines (C00483 )
Tyramine derivatives (C00483 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 70.04%; H 8.08%; N 10.21%; O 11.66%	DFC
Melting Point	Mp 164-164.5° (161°)	DFC
Boiling Point	Not Available
Experimental Water Solubility	10.4 mg/mL at 15 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	Not Available
Experimental pKa	pKa2 10.9 (25°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-053r-9500000000-6deb2b5d214f768ca448	2014-09-20	View Spectrum
GC-MS	Tyramine, 3 TMS, GC-MS Spectrum	splash10-00di-2900000000-273503edc6a220e152b6	Spectrum
GC-MS	Tyramine, non-derivatized, GC-MS Spectrum	splash10-00di-2900000000-80980d19fa83d4b86f91	Spectrum
GC-MS	Tyramine, 3 TMS, GC-MS Spectrum	splash10-00di-9700000000-78d2ae48da1eee18358e	Spectrum
GC-MS	Tyramine, non-derivatized, GC-MS Spectrum	splash10-001i-9200000000-50c21473a7d48011358c	Spectrum
GC-MS	Tyramine, non-derivatized, GC-MS Spectrum	splash10-00di-1900000000-9b1000a8978b57919c35	Spectrum
GC-MS	Tyramine, non-derivatized, GC-MS Spectrum	splash10-00di-2900000000-273503edc6a220e152b6	Spectrum
GC-MS	Tyramine, non-derivatized, GC-MS Spectrum	splash10-00di-2900000000-80980d19fa83d4b86f91	Spectrum
GC-MS	Tyramine, non-derivatized, GC-MS Spectrum	splash10-00di-9700000000-78d2ae48da1eee18358e	Spectrum
GC-MS	Tyramine, non-derivatized, GC-MS Spectrum	splash10-00di-2900000000-69892c95ab2778a208b3	Spectrum
Predicted GC-MS	Tyramine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-9600000000-1d5276a762318a00832d	Spectrum
Predicted GC-MS	Tyramine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fk9-7900000000-8f3b164f36bc5a4df4d7	Spectrum
Predicted GC-MS	Tyramine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tyramine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tyramine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tyramine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0900000000-3229081a448a277191a2	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004l-9300000000-e2fc12d41e4c40a9a296	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9000000000-92f0b12d0a64443cede8	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-001i-9200000000-50c21473a7d48011358c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-d7e9a8705227b4504c5c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-9000000000-3f02b334907c40a8315c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-e98b3afc6fad78d45d38	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-54239e66d89de3096ca8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0079-0902000000-f09759fc06ef461f3aa5	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-9000000000-9ffe6ee0ce68182216f7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-020a5decfb44fc4f97df	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-0930000000-32ccc375e75dbab3195c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-0900000000-51c6cc08017f1672b791	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-1900000000-55c25dd64462c06c5316	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0f96-9500000000-83a70aec6da00b51a6df	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-004i-9100000000-5f044e831c0d2db255fa	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-004i-9000000000-99edae3913507430bf9f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-4900000000-8944003750ac547c2024	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-0900000000-066947a256844eb6cbdc	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-0900000000-8fb72547243614622ba3	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-44bf2322645e5e00b029	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uml-9400000000-343b8fa44c724b1395c6	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-7da5f9953041f5148f8e	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-e62cf6efa07eeeaf1f51	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066r-7900000000-4f78b5370ece8150a8c4	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H 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

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15760

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00306

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1051461

SuperScent ID

Not Available

Wikipedia ID

Tyramine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Adrenergic	37962	An agent that stimulates the adrenergic nervous system, mimicking the effects of adrenaline. It plays a biological role in regulating heart rate, blood pressure, and energy. Therapeutically, adrenergic agents are used to treat conditions such as asthma, hypertension, and cardiac arrest, with key medical uses including bronchodilation, vasoconstriction, and increased cardiac output.	DUKE
Anti-aggregant		An agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots.	DUKE
Cardiovascular	38070	A system that transports blood, oxygen, and nutrients throughout the body, playing a crucial role in overall health. Therapeutically, cardiovascular agents manage conditions like hypertension, heart failure, and atherosclerosis, with key medical uses including regulating blood pressure, preventing blood clots, and improving cardiac function.	DUKE
Hypertensive		An agent that increases blood pressure, used therapeutically to treat hypotension (low blood pressure) and shock, and medically to manage conditions such as orthostatic hypotension and postural hypotension.	DUKE
Insectifuge	24852	A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission.	DUKE
Neurotoxic	50910	A substance that damages or destroys nerve cells, disrupting normal brain function. It has no therapeutic applications, but is used in research to study neurodegenerative diseases. Key medical uses include understanding and developing treatments for conditions like Alzheimer's and Parkinson's diseases, where neurotoxicity plays a role.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Sympathomimetic	35524	An agent that mimics the effects of the sympathetic nervous system, increasing heart rate, blood pressure, and energy. Therapeutically, it's used to treat conditions like asthma, hypotension, and shock, as well as nasal decongestion and eye dilation.	DUKE
Vasoconstrictor	50514	An agent that narrows blood vessels, reducing blood flow. It plays a biological role in regulating blood pressure and is therapeutically used to treat conditions like hypotension, nasal congestion, and bleeding. Key medical uses include managing shock, reducing bleeding during surgery, and relieving migraine headaches.	DUKE
Vasopressor		An agent that causes constriction of blood vessels, increasing blood pressure. It plays a biological role in regulating blood pressure and fluid balance. Therapeutically, vasopressors are used to treat hypotension, shock, and bleeding, and have key medical applications in surgery, trauma, and critical care.	DUKE
Anti cholinesterase	37733	An agent that inhibits acetylcholinesterase, increasing acetylcholine levels, and enhancing cholinergic transmission. Therapeutically, it's used to treat myasthenia gravis, glaucoma, and Alzheimer's disease, improving muscle strength, reducing eye pressure, and enhancing cognitive function.	CHEBI
Neurotransmitter	25512	A chemical messenger that transmits signals between neurons, regulating various physiological and psychological processes. Therapeutically, neurotransmitter modulators are used to treat conditions such as depression, anxiety, and Parkinson's disease, by altering neurotransmitter levels or activity to restore balance and alleviate symptoms.	CHEBI

Enzymes

Name	Gene Name	UniProt ID
Aromatic-L-amino-acid decarboxylase	DDC	P20711
Alpha-2A adrenergic receptor	ADRA2A	P08913
Alpha-2B adrenergic receptor	ADRA2B	P18089

Pathways

Name	SMPDB Link	KEGG Link
Tyrosine Metabolism	SMP00006	map00350

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
mild	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
meaty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
dirty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cooked	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
phenolic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
rubbery	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.