CHEBI:15760 - tyramine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name tyramine
ChEBI ID CHEBI:15760
Definition A primary amino compound obtained by formal decarboxylation of the amino acid tyrosine.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:9799, CHEBI:15276, CHEBI:27174
Supplier Information ChemicalBook:CB7152784, eMolecules:533064, ZINC000000002233
Download Molfile XML SDF
Wikipedia License
Tyramine ( TY-rə-meen) (also spelled tyramin), also known under several other names, is a naturally occurring trace amine derived from the amino acid tyrosine. Tyramine acts as a catecholamine releasing agent. Notably, it is unable to cross the blood-brain barrier, resulting in only non-psychoactive peripheral sympathomimetic effects following ingestion. A hypertensive crisis can result, however, from ingestion of tyramine-rich foods in conjunction with the use of monoamine oxidase inhibitors (MAOIs).
Read full article at Wikipedia
Formula C8H11NO
Net Charge 0
Average Mass 137.17900
Monoisotopic Mass 137.08406
InChI InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2
InChIKey DZGWFCGJZKJUFP-UHFFFAOYSA-N
SMILES NCCc1ccc(O)cc1
Metabolite of Species Details
Solanum campaniforme (IPNI:818569-1) Found in leaf (BTO:0000713). Dried leaves were extracted with ethyl alcohol. See: PubMed
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
EC 3.1.1.8 (cholinesterase) inhibitor
An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).
neurotransmitter
An endogenous compound that is used to transmit information across the synapse between a neuron and another cell.
molecular messenger

(via monoamine molecular messenger )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing tyramine (CHEBI:15760) has role Escherichia coli metabolite (CHEBI:76971)
tyramine (CHEBI:15760) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733)
tyramine (CHEBI:15760) has role human metabolite (CHEBI:77746)
tyramine (CHEBI:15760) has role mouse metabolite (CHEBI:75771)
tyramine (CHEBI:15760) has role neurotransmitter (CHEBI:25512)
tyramine (CHEBI:15760) is a monoamine molecular messenger (CHEBI:25375)
tyramine (CHEBI:15760) is a primary amino compound (CHEBI:50994)
tyramine (CHEBI:15760) is a tyramines (CHEBI:27175)
tyramine (CHEBI:15760) is conjugate base of tyraminium (CHEBI:327995)
Incoming γ-glutamyltyramine (CHEBI:84215) has functional parent tyramine (CHEBI:15760)
3-nitrotyramine (CHEBI:71233) has functional parent tyramine (CHEBI:15760)
N,O-dimethyltyramine (CHEBI:75143) has functional parent tyramine (CHEBI:15760)
N-trans-cinnamoyltyramine (CHEBI:177872) has functional parent tyramine (CHEBI:15760)
N-acetyltyramine (CHEBI:125610) has functional parent tyramine (CHEBI:15760)
N-butanoyltyramine (CHEBI:166900) has functional parent tyramine (CHEBI:15760)
N-hexanoyltyramine (CHEBI:166901) has functional parent tyramine (CHEBI:15760)
norbelladine (CHEBI:80666) has functional parent tyramine (CHEBI:15760)
tyramine phosphate (CHEBI:142808) has functional parent tyramine (CHEBI:15760)
tyramine sulfate (CHEBI:133530) has functional parent tyramine (CHEBI:15760)
tyraminium (CHEBI:327995) is conjugate acid of tyramine (CHEBI:15760)
IUPAC Name
4-(2-aminoethyl)phenol
Synonyms Sources
2-(p-Hydroxyphenyl)ethylamine KEGG COMPOUND
4-Hydroxy-beta-phenylethylamine HMDB
4-hydroxyphenethylamine ChEBI
4-Hydroxyphenylethylamine HMDB
beta-(4-Hydroxyphenyl)ethylamine HMDB
p-(2-Aminoethyl)phenol HMDB
p-(2-aminoethyl)phenol ChEBI
p-hydroxyphenethylamine HMDB
p-hydroxyphenylethylamine HMDB
p-tyramine HMDB
Tyramin ChemIDplus
Tyramine KEGG COMPOUND
Manual Xrefs Databases
2784 DrugCentral
AEF PDBeChem
C00001435 KNApSAcK
C00483 KEGG COMPOUND
HMDB0000306 HMDB
LSM-19016 LINCS
Tyramine Wikipedia
TYRAMINE MetaCyc
View more database links
Registry Numbers Types Sources
1099914 Reaxys Registry Number Reaxys
51-67-2 CAS Registry Number KEGG COMPOUND
51-67-2 CAS Registry Number ChemIDplus
51-67-2 CAS Registry Number NIST Chemistry WebBook
82946 Gmelin Registry Number Gmelin
Citations
Park S, Lee K, Kim YS, Chi YT, Shin JS, Back K (2012)
Induced tyramine overproduction in transgenic rice plants expressing a rice tyrosine decarboxylase under the control of methanol-inducible rice tryptophan decarboxylase promoter.
Bioprocess and biosystems engineering 35, 205-210 [PubMed:21909937]
[show Abstract]
Chen JJ, Wilkinson JR (2012)
The monoamine oxidase type B inhibitor rasagiline in the treatment of Parkinson disease: is tyramine a challenge?
Journal of clinical pharmacology 52, 620-628 [PubMed:21628600]
[show Abstract]
Bordbar A, Mo ML, Nakayasu ES, Schrimpe-Rutledge AC, Kim YM, Metz TO, Jones MB, Frank BC, Smith RD, Peterson SN, Hyduke DR, Adkins JN, Palsson BO (2012)
Model-driven multi-omic data analysis elucidates metabolic immunomodulators of macrophage activation.
Molecular systems biology 8, 558 [PubMed:22735334]
[show Abstract]
Niwa T, Murayama N, Umeyama H, Shimizu M, Yamazaki H (2011)
Human liver enzymes responsible for metabolic elimination of tyramine; a vasopressor agent from daily food.
Drug metabolism letters 5, 216-219 [PubMed:21679153]
[show Abstract]
Choi IS, Cho JH, Lee MG, Jang IS (2011)
Tyramine reduces glycinergic transmission by inhibiting presynaptic Ca(2+) channels in the rat trigeminal subnucleus caudalis.
European journal of pharmacology 664, 29-35 [PubMed:21570963]
[show Abstract]
Bromek E, Haduch A, Gołembiowska K, Daniel WA (2011)
Cytochrome P450 mediates dopamine formation in the brain in vivo.
Journal of neurochemistry 118, 806-815 [PubMed:21651557]
[show Abstract]
Di Stefano AF, Rusca A (2011)
Pressor response to oral tyramine during co-administration with safinamide in healthy volunteers.
Naunyn-Schmiedeberg's archives of pharmacology 384, 505-515 [PubMed:21850574]
[show Abstract]
Cooper SE, Venton BJ (2009)
Fast-scan cyclic voltammetry for the detection of tyramine and octopamine.
Analytical and bioanalytical chemistry 394, 329-336 [PubMed:19189084]
[show Abstract]
Vierk R, Pflueger HJ, Duch C (2009)
Differential effects of octopamine and tyramine on the central pattern generator for Manduca flight.
Journal of comparative physiology. A, Neuroethology, sensory, neural, and behavioral physiology 195, 265-277 [PubMed:19137318]
[show Abstract]
Masson P, Froment MT, Gillon E, Nachon F, Lockridge O, Schopfer LM (2008)
Kinetic analysis of effector modulation of butyrylcholinesterase-catalysed hydrolysis of acetanilides and homologous esters.
The FEBS journal 275, 2617-2631 [PubMed:18422653]
[show Abstract]
Punakivi K, Smolander M, Niku-Paavola ML, Mattinen J, Buchert J (2006)
Enzymatic determination of biogenic amines with transglutaminase.
Talanta 68, 1040-1045 [PubMed:18970430]
[show Abstract]
Balbi T, Fusco M, Vasapollo D, Boschetto R, Cocco P, Leon A, Farruggio A (2005)
The presence of trace amines in postmortem cerebrospinal fluid in humans.
Journal of forensic sciences 50, 630-632 [PubMed:15932098]
[show Abstract]
Alkema MJ, Hunter-Ensor M, Ringstad N, Horvitz HR (2005)
Tyramine Functions independently of octopamine in the Caenorhabditis elegans nervous system.
Neuron 46, 247-260 [PubMed:15848803]
[show Abstract]
Jacob G, Costa F, Vincent S, Robertson D, Biaggioni I (2003)
Neurovascular dissociation with paradoxical forearm vasodilation during systemic tyramine administration.
Circulation 107, 2475-2479 [PubMed:12707242]
[show Abstract]
Bairras C, Ferrand C, Atgié C (2003)
Effect of tyramine, a dietary amine, on glycerol and lactate release by isolated adipocytes from old rats.
Journal of physiology and biochemistry 59, 161-167 [PubMed:15000446]
[show Abstract]
D'Andrea G, Terrazzino S, Fortin D, Cocco P, Balbi T, Leon A (2003)
Elusive amines and primary headaches: historical background and prospectives.
Neurological sciences : official journal of the Italian Neurological Society and of the Italian Society of Clinical Neurophysiology 24 Suppl 2, S65-7 [PubMed:12811595]
[show Abstract]
Li LB, Cui XN, Reith MA (2002)
Is Na(+) required for the binding of dopamine, amphetamine, tyramine, and octopamine to the human dopamine transporter?
Naunyn-Schmiedeberg's archives of pharmacology 365, 303-311 [PubMed:11919655]
[show Abstract]
Nagaya Y, Kutsukake M, Chigusa SI, Komatsu A (2002)
A trace amine, tyramine, functions as a neuromodulator in Drosophila melanogaster.
Neuroscience letters 329, 324-328 [PubMed:12183041]
[show Abstract]
Antal EJ, Hendershot PE, Batts DH, Sheu WP, Hopkins NK, Donaldson KM (2001)
Linezolid, a novel oxazolidinone antibiotic: assessment of monoamine oxidase inhibition using pressor response to oral tyramine.
Journal of clinical pharmacology 41, 552-562 [PubMed:11361052]
[show Abstract]
Hiroi T, Imaoka S, Funae Y (1998)
Dopamine formation from tyramine by CYP2D6.
Biochemical and biophysical research communications 249, 838-843 [PubMed:9731223]
[show Abstract]
Lin J, Cashman JR (1997)
Detoxication of tyramine by the flavin-containing monooxygenase: stereoselective formation of the trans oxime.
Chemical research in toxicology 10, 842-852 [PubMed:9282832]
[show Abstract]
Yonekura T, Kamata S, Wasa M, Okada A, Yamatodani A, Watanabe T, Wada H (1988)
Simultaneous determination of plasma phenethylamine, phenylethanolamine, tyramine and octopamine by high-performance liquid chromatography using derivatization with fluorescamine.
Journal of chromatography 427, 320-325 [PubMed:3137238]
Causon RC, Brown MJ (1984)
Measurement of tyramine in human plasma, utilising ion-pair extraction and high-performance liquid chromatography with amperometric detection.
Journal of chromatography 310, 11-17 [PubMed:6501508]
[show Abstract]
Yin SJ, Lee SC (1977)
Tyramine interference in assay of serum dopamine-beta-hydroxylase.
Clinical chemistry 23, 617-618 [PubMed:319927]
Last Modified
30 May 2022