{"Abbreviation":"","Aliases":["4-Hydroxyphenethylamine","2-(4-Hydroxyphenyl)ethylamine","Uteramine","Tyrosamine","Tocosine","Tyramin","Systogene","Phenol, 4-(2-aminoethyl)-","4-Hydroxyphenylethylamine","p-(2-Aminoethyl)phenol"],"Boiling Point":"166 °C","CAS":"51-67-2","ChEBI":"CHEBI:15760","ChEMBL":"CHEMBL11608","ChemicalClasses":["phenethylamine"],"Chirality":"achiral","Classes":["Neurotransmitter","Sympathomimetic"],"Color/Form":"CRYSTALS FROM BENZENE OR ALCOHOL","Drug Warnings":"...PREPARATIONS HAVE NOT CAUSED DEATH, BUT...THERAPEUTIC USE PRODUCES SIDE ACTIONS WHICH ARE OFTEN UNPLEASANT. /TYRAMINE HYDROCHLORIDE/","DrugClasses":[],"DurationOfAction":"","EINECS":"200-115-8","EliminationHalfLife":"","Erowid Experience Reports":[],"Esters":["acetate"],"European Community (EC) Number":"200-115-8","FullSalts":["Tyramine hydrochloride"],"HMDB ID":"HMDB0000306","HeavyAtomCount":10,"IUPACName":"4-(2-aminoethyl)phenol","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","MeSH Pharmacological Classification":"Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. (See all compounds classified as Sympathomimetics.)","Melting Point":"164-165 °C","MolecularFormula":"C\u003csub\u003e8\u003c/sub\u003eH\u003csub\u003e11\u003c/sub\u003eNO","MolecularWeight":"137.18 g/mol","Physical Description":"Solid","PrevSalts":["hydrochloride"],"PubChemId":5610,"Record Description":["Tyramine is a primary amino compound obtained by formal decarboxylation of the amino acid tyrosine. It has a role as an EC 3.1.1.8 (cholinesterase) inhibitor, a human metabolite, an Escherichia coli metabolite, a mouse metabolite and a neurotransmitter. It is a monoamine molecular messenger, a primary amino compound and a member of tyramines. It is a conjugate base of a tyraminium.","Tyramine (4-hydroxyphenethylamine; para-tyramine, mydrial or uteramin) is a naturally occurring monoamine compound and trace amine derived from the amino acid tyrosine. Tyramine acts by inducing the release of catecholamine. An important characteristic of this product is its impediment to cross the blood-brain barrier which restrains its side effects to only nonpsychoactive peripheral sympathomimetic effects. There have been reports of hypertensive crisis in patients ingesting tyramine-rich diet in conjunction with monoamine oxidase inhibitors (MAOIs).","Tyramine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).","Tyramine has been reported in Magnolia officinalis, Senegalia berlandieri, and other organisms with data available.","TYRAMINE is a small molecule drug with a maximum clinical trial phase of III (across all indications) and has 3 investigational indications.","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.","Tyramine is a metabolite found in or produced by Saccharomyces cerevisiae.","An indirect sympathomimetic that occurs naturally in cheese and other foods. Tyramine does not directly activate adrenergic receptors, but it can serve as a substrate for adrenergic uptake systems and MONOAMINE OXIDASE to prolong the actions of adrenergic transmitters. It also provokes transmitter release from adrenergic terminals and may be a neurotransmitter in some invertebrate nervous systems.","See also: Tyramine hydrochloride (is active moiety of); Cytisus scoparius flowering top (part of); Selenicereus grandiflorus stem (part of).","Tyramine is a primary amino compound obtained by formal decarboxylation of the amino acid tyrosine. It has a role as an EC 3.1.1.8 (cholinesterase) inhibitor, a human metabolite, an Escherichia coli metabolite, a mouse metabolite and a neurotransmitter. It is a monoamine molecular messenger, a primary amino compound and a member of tyramines. It is a conjugate base of a tyraminium."],"RefCount":3,"References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Tyramine","Name":"Tyramine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q165930","Name":"Tyramine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB08841","Name":"Tyramine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/5610","Name":"Tyramine","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL11608","Name":"Tyramine","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15760","Name":"Tyramine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=51-67-2","Name":"Tyramine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0000306","Name":"Tyramine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C00483","Name":"Tyramine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/X8ZC7V0OX3","Name":"Tyramine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID2043874","Name":"Tyramine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 5610, Tyramine. Accessed June 28, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/5610\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/5610\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Tyramine. UNII: X8ZC7V0OX3. Global Substance Registration System. Accessed June 28, 2025. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/X8ZC7V0OX3\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/X8ZC7V0OX3\u003c/a\u003e"],"SMILES":"C1=CC(=CC=C1CCN)O","Salts":["hydrochloride"],"SaltsAcidCount":[1],"SaltsAmineCount":[1],"SaltsUNII":["Z5KDH3H147"],"Scheduling":[],"Solubility":"SOL IN WATER /TYRAMINE HYDROCHLORIDE/","StoreUNII":["X8ZC7V0OX3"],"StructureBase64":"PHN2ZyB4bWxucz0iaHR0cDovL3d3dy53My5vcmcvMjAwMC9zdmciIHhtbG5zOnhsaW5rPSJodHRwOi8vd3d3LnczLm9yZy8xOTk5L3hsaW5rIiBoZWlnaHQ9IjM2LjU3MW1tIiB2ZXJzaW9uPSIxLjIiIHZpZXdCb3g9IjAgMCA5NS42MjYgMzYuNTcxIiB3aWR0aD0iOTUuNjI2bW0iPgogICAgICAKICAgIDxkZXNjPkdlbmVyYXRlZCBieSB0aGUgQ2hlbWlzdHJ5IERldmVsb3BtZW50IEtpdCAoaHR0cDovL2dpdGh1Yi5jb20vY2RrKTwvZGVzYz4KICAgICAgCiAgICA8ZyBmaWxsPSIjMzA1MEY4IiBzdHJva2U9IiMwMDAwMDAiIHN0cm9rZS1saW5lY2FwPSJyb3VuZCIgc3Ryb2tlLWxpbmVqb2luPSJyb3VuZCIgc3Ryb2tlLXdpZHRoPSIuNyI+CiAgICAgICAgICAgIAogICAgICAgIDxyZWN0IGZpbGw9IiNGRkZGRkYiIGhlaWdodD0iMzcuMCIgc3Ryb2tlPSJub25lIiB3aWR0aD0iOTYuMCIgeD0iLjAiIHk9Ii4wIi8+CiAgICAgICAgICAgIAogICAgICAgIDxnIGNsYXNzPSJtb2wiIGlkPSJtb2wxIj4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxnIGNsYXNzPSJib25kIiBpZD0ibW9sMWJuZDEiPgogICAgICAgICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgICAgIDxsaW5lIHgxPSIzMy41MTciIHgyPSIyMC4zMTkiIHkxPSIzLjAwMSIgeTI9IjEwLjYyMSIvPgogICAgICAgICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgICAgIDxsaW5lIHgxPSIzMy41MTciIHgyPSIyMi43NTgiIHkxPSI1LjgxNyIgeTI9IjEyLjAyOSIvPgogICAgICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDwvZz4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxsaW5lIGNsYXNzPSJib25kIiBpZD0ibW9sMWJuZDIiIHgxPSIyMC4zMTkiIHgyPSIyMC4zMjQiIHkxPSIxMC42MjEiIHkyPSIyNS44NyIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGcgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kMyI+CiAgICAgICAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICAgICAgPGxpbmUgeDE9IjIwLjMyNCIgeDI9IjMzLjUyNyIgeTE9IjI1Ljg3IiB5Mj0iMzMuNDk4Ii8+CiAgICAgICAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICAgICAgPGxpbmUgeDE9IjIyLjc2MiIgeDI9IjMzLjUyNyIgeTE9IjI0LjQ2MiIgeTI9IjMwLjY4MiIvPgogICAgICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDwvZz4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxsaW5lIGNsYXNzPSJib25kIiBpZD0ibW9sMWJuZDQiIHgxPSIzMy41MjciIHgyPSI0Ni43MjUiIHkxPSIzMy40OTgiIHkyPSIyNS44NzgiLz4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxnIGNsYXNzPSJib25kIiBpZD0ibW9sMWJuZDUiPgogICAgICAgICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgICAgIDxsaW5lIHgxPSI0Ni43MjUiIHgyPSI0Ni43MiIgeTE9IjI1Ljg3OCIgeTI9IjEwLjYzIi8+CiAgICAgICAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICAgICAgPGxpbmUgeDE9IjQ0LjI4NiIgeDI9IjQ0LjI4MiIgeTE9IjI0LjQ3MSIgeTI9IjEyLjAzNyIvPgogICAgICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDwvZz4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxsaW5lIGNsYXNzPSJib25kIiBpZD0ibW9sMWJuZDYiIHgxPSIzMy41MTciIHgyPSI0Ni43MiIgeTE9IjMuMDAxIiB5Mj0iMTAuNjMiLz4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxsaW5lIGNsYXNzPSJib25kIiBpZD0ibW9sMWJuZDciIHgxPSI0Ni43MiIgeDI9IjU5LjkxOCIgeTE9IjEwLjYzIiB5Mj0iMy4wMSIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGxpbmUgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kOCIgeDE9IjU5LjkxOCIgeDI9IjczLjExNyIgeTE9IjMuMDEiIHkyPSIxMC42MyIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGxpbmUgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kOSIgeDE9IjczLjExNyIgeDI9IjgzLjE2MSIgeTE9IjEwLjYzIiB5Mj0iNC44MyIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGxpbmUgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kMTAiIHgxPSIyMC4zMjQiIHgyPSIxMC40MDQiIHkxPSIyNS44NyIgeTI9IjMxLjU5NyIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGcgY2xhc3M9ImF0b20iIGlkPSJtb2wxYXRtOSI+CiAgICAgICAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICAgICAgPHBhdGggZD0iTTg4LjI1NSA1LjQ1OWgtLjcybC0yLjYxOSAtNC4wNjZoLS4wM3EuMDEyIC4yMzkgLjAzIC41OTZxLjAyNCAuMzU3IC4wMjQgLjczMnYyLjczOGgtLjU2NnYtNC44OTloLjcxNGwyLjYwOCA0LjA1NGguMDNxLS4wMDYgLS4xMDcgLS4wMTggLS4zMjdxLS4wMTIgLS4yMjEgLS4wMjQgLS40NzdxLS4wMDYgLS4yNjIgLS4wMDYgLS40ODJ2LTIuNzY4aC41Nzd2NC44OTl6IiBzdHJva2U9Im5vbmUiLz4KICAgICAgICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgICAgICA8cGF0aCBkPSJNOTIuNTYyIDUuNDU5aC0uNjE5di0yLjI4NmgtMi41MTN2Mi4yODZoLS42MTN2LTQuODk5aC42MTN2Mi4wNzJoMi41MTN2LTIuMDcyaC42MTl2NC44OTl6IiBzdHJva2U9Im5vbmUiLz4KICAgICAgICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgICAgICA8cGF0aCBkPSJNOTUuMDY2IDYuOTQ5aC0xLjk0M3YtLjNsLjc3MiAtLjc3OXEuMjIxIC0uMjIxIC4zNzEgLS4zOTNxLjE1NCAtLjE3NSAuMjMzIC0uMzM5cS4wNzggLS4xNjggLjA3OCAtLjM2NHEuMCAtLjI0MyAtLjE0NiAtLjM2OHEtLjE0MyAtLjEyOSAtLjM3MiAtLjEyOXEtLjIxNCAuMCAtLjM3OCAuMDc1cS0uMTYxIC4wNzUgLS4zMjkgLjIwN2wtLjE5MyAtLjI0M3EuMTcyIC0uMTQ2IC4zOTMgLS4yNDZxLjIyNSAtLjEgLjUwNyAtLjFxLjQxMSAtLjAgLjY1IC4yMDdxLjI0IC4yMDcgLjI0IC41NzVxLS4wIC4yMjkgLS4wOTcgLjQzMnEtLjA5MyAuMiAtLjI2NCAuMzk3cS0uMTY4IC4xOTYgLS4zOTMgLjQxOGwtLjYxNCAuNjAzdi4wMThoMS40ODV2LjMyOXoiIHN0cm9rZT0ibm9uZSIvPgogICAgICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDwvZz4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxnIGNsYXNzPSJhdG9tIiBpZD0ibW9sMWF0bTEwIj4KICAgICAgICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgICAgICA8cGF0aCBkPSJNOS4zODUgMzMuNDg3cS0uMCAuNzU2IC0uMjU2IDEuMzI3cS0uMjU2IC41NjYgLS43NTYgLjg4MXEtLjUgLjMxNiAtMS4yNDUgLjMxNnEtLjc1NiAtLjAgLTEuMjYyIC0uMzE2cS0uNTA2IC0uMzE1IC0uNzU2IC0uODg3cS0uMjQ0IC0uNTcxIC0uMjQ0IC0xLjMzM3EuMCAtLjc1IC4yNDQgLTEuMzFxLjI1IC0uNTY1IC43NTYgLS44ODFxLjUwNiAtLjMxNSAxLjI3NCAtLjMxNXEuNzMzIC0uMCAxLjIzMyAuMzE1cS41IC4zMSAuNzU2IC44NzVxLjI1NiAuNTY2IC4yNTYgMS4zMjh6TTUuNTIxIDMzLjQ4N3EuMCAuOTIyIC4zODcgMS40NThxLjM5MyAuNTMgMS4yMiAuNTNxLjg0IC4wIDEuMjIxIC0uNTNxLjM4NyAtLjUzNiAuMzg3IC0xLjQ1OHEtLjAgLS45MjkgLS4zODcgLTEuNDUzcS0uMzgxIC0uNTI0IC0xLjIwOSAtLjUyNHEtLjgzMyAuMCAtMS4yMjYgLjUyNHEtLjM5MyAuNTI0IC0uMz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Effects":{"Cognitive Effects":["Thought acceleration","Wakefulness"],"Physical Effects":["Stamina enhancement","Dehydration","Dry mouth","Restless legs","Shakiness","Abnormal heartbeat","Increased blood pressure","Increased heart rate","Vasoconstriction"],"Visual Effects":[]},"Therapeutic Uses":"Adrenergic alpha-Agonists; Adrenergic Agents; Adrenergic Uptake Inhibitors; Sympathomimetics","Title":"Tyramine","UNII":"X8ZC7V0OX3","Wikidata":"Q165930","Wikipedia":"Tyramine","XLogP":1.1}