Tyramine

Log Kow = 0.72

-0.24

CRYSTALS FROM BENZENE OR ALCOHOL

PLATES OR NEEDLES FROM BENZENE, NEEDLES FROM WATER

SOL IN WATER /TYRAMINE HYDROCHLORIDE/

1 G DISSOLVES IN 10 ML BOILING ALCOHOL

SPARINGLY SOL IN BENZENE, XYLENE

Slightly soluble in water, benzene; soluble in ethanol, xylene

Water solubility = 10.4E+3 mg/L @ 15 °C

10.4 mg/mL at 15 °C

164-165 °C

MP: 269 °C /TYRAMINE HYDROCHLORIDE/

164 - 165 °C

Solid

Colourless to yellow solid; Sweet meaty aroma

123.43 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]

129.74 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

138.4 Ų [M+Na]+

This chemical does not meet GHS hazard criteria for 65.9% (91 of 138) of all reports.

Warning

H315 (32.6%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 138 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: Phenol, 4-(2-aminoethyl)-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Status: Active Update: 05-01-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/16729

Phenol, 4-(2-aminoethyl)-: Does not have an individual approval but may be used under an appropriate group standard

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

ANTIBACTERIAL ACTION OF FURAZOLIDONE IS ACCOMPANIED BY PROGRESSIVE & GENERALIZED INHIBITION OF MONOAMINE OXIDASE... TYRAMINE HAS...BEEN REPORTED TO INTERACT WITH FURAZOLIDONE...

PHENYLPROPANOLAMINE & OTHER INDIRECT-ACTING SYMPATHOMIMETIC AMINES (EG, TYRAMINE) PRODUCE HYPERTENSIVE CRISIS & RELATED SYMPTOMS IN SOME INDIVIDUALS CURRENTLY RECEIVING OR PREVIOUSLY BEING TREATED WITH TRANYLCYPROMINE OR OTHER MONOAMINE OXIDASE INHIBITORS /SUCH AS ISOCARBOXAZID, PARGYLINE & PHENELZINE/. ...MAY BE FATAL.

ALTHOUGH SELECTIVE MONOAMINE OXIDASE INHIBITOR (-)-DEPRENYL SUBSTANTIALLY INHIBITS TYRAMINE (I)-OXIDIZING ABILITY IN PIG, IV TYRAMINE CHALLENGE AFTER PRETREATMENT WITH THIS DRUG FAILED TO PRODUCE PRESSOR RESPONSE ("CHEESE EFFECT") ASSOC WITH OTHER IRREVERSIBLE MAO INHIBITORS.

PRETREATMENT OF THYROIDECTOMIZED RATS WITH T3 & RESERPINE ABOLISHED TYRAMINE INDUCED HYPOTENSIVE ACTION. PRETREATMENT WITH PHENOXYBENZAMINE INHIBITED ACTION IN INTACT RAT AS WELL, WHEREAS CYPROHEPTADINE INCR ACTION IN THYROIDECTOMIZED RAT BUT NOT IN INTACT RATS

For more Interactions (Complete) data for TYRAMINE (11 total), please visit the HSDB record page.

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Tyramine is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

Symptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.

...TYRAMINE.../ARISES/ FROM MICROBIOLOGICAL DECARBOXYLATION OF CHOLINE, TRYPTOPHAN, TYROSINE, AND OTHER AMINO ACIDS PRESENT IN FOODSTUFF RESIDUES IN INTESTINAL TRACT. ...ALSO FOUND IN PUTREFYING FOODSTUFFS, SUCH AS CHEESE, HIGH GAME & SPOILED FISH, & ETHYLAMINE...

...THE SCLEROTIA /OF ERGOT/ CONTAIN A LARGE NUMBER OF AMINES AND OTHER NITROGENOUS COMPOUNDS, SOME, SUCH AS...TYRAMINE...HAVING PHYSIOLOGICAL ACTIVITY.

...FOODS CONTAINING TYRAMINE.../INCLUDE/ PICKLED HERRING, BEER, WINE (ESP RED WINE), & CHICKEN LIVERS...

BASE FOUND IN MISTLETOE...

Tyramine is a sympathomimetic amine that is without effect when ingested in food because of its rapid biotransformation by monoamine oxidase in the gut and liver. This ... does not occur when monoxidase oxidase is inhibited.

... The role of food additives, tyramine and acetylsalicylic acid, was investigated by double blind placebo controlled challenges in 25 children with severe atopic dermatitis. All children challenged with foods (n = 24), except 1, showed one or more positive reactions to the double blind placebo controlled challenges with foods. Positive reactions presented different combinations of flares of skin symptoms, intestinal symptoms and respiratory systems. Seventeen children (78%) showed a positive challenge to egg, 12% to wheat (50%), eight to milk (33.3%) and eight to soya. Six children underwent double blind placebo controlled challenges with food additives, tyramine and acetylsalicylic acid. All were found to demonstrate positive skin and/or intestinal reactions to at least one of the food additives. Two children reacted to tartrazine, three to sodium benzoate, two to sodium glutamate, two to sodium metabisulfite, four to acetylsalicylic acid and one to tyramine. ... Foods, food additives, tyramine and acetylsalicylic acid can cause positive double blind placebo controlled challenges in children with severe atopic dermatitis.

Drug Induced Liver Injury Rank (DILIrank 2.0)

Tyramine

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

THERE HAVE BEEN SEVERAL...METABOLIC STUDIES OF TYRAMINE IN MAMMALS, & TRACERS HAVE BEEN USED. ...SMALL AMT OF P-HYDROXYMANDELIC ACID, VANILMANDELIC ACID, & HOMOVANILLIC ACID /HAVE BEEN INDENTIFIED/.

WHEN TYRAMINE...WAS INJECTED INTO RATS, MAJOR URINARY METABOLITE WAS FREE P-HYDROXYPHENYLACETIC ACID...

...TYRAMINE...PRESENT IN CHEESE AND IN YEAST EXTRACT...IS NORMALLY DETOXICATED BY MONOAMINE OXIDASE, PRESENT IN INTESTINE AND LIVER, TO YIELD PARA-HYDROXYPHENYLETHANOL, PARA-HYDROXYPHENYLACETIC ACID AND ITS GLYCINE CONJUGATE, PARA-HYDROXYPHENACETURIC ACID, AND...N-ACETYLTYRAMINE.

WHEN HUMAN/S/...TREATED WITH (14)C-TYRAMINE.../URINARY METABOLITE/ P-HYDROXYPHENYLACETALDEHYDE...CONTRIBUTED LESS THAN 0.5%.

For more Metabolism/Metabolites (Complete) data for TYRAMINE (6 total), please visit the HSDB record page.

Tyramine has known human metabolites that include Dopamine and Tyramine glucuronide.

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.

Drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants (ANTIDEPRESSIVE AGENTS, TRICYCLIC) and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin.

96% OF (14)C WAS EXCRETED IN 24-HR URINE OF RATS GIVEN IP DOSE OF...(14)C TYRAMINE. 67% WAS EXCRETED IN 3 HR, BUT THIS AMT WAS MARKEDLY REDUCED IF RATS WERE PRETREATED WITH MONOAMINE OXIDASE INHIBITOR. /HUMANS/...EXCRETED 58% OF (14)C IN 24-HR URINE FOLLOWING IV DOSE...

WHEN TYRAMINE...WAS INJECTED INTO RATS, MAJOR URINARY METABOLITE WAS FREE P-HYDROXYPHENYLACETIC ACID...(77% OF THAT PROPORTION OF DOSE EXCRETED IN URINE)...

.../TYRAMINE IS/ POORLY ABSORBED FROM BOWEL, BUT.../IS/ READILY ABSORBED FROM SC INJECTION. .../IT/ MAY BE ABSORBED TO A GREATER OR LESS EXTENT FROM NASAL MUCOSA.

(14)C-LABELED TYRAMINE BOUND TO PLASMA PROTEINS OF RABBITS IN DOSE- & TIME OF INCUBATION-RELATED MANNER. MAX BINDING CAPACITY EST AS 70.2 UG/G. AFFINITY FOR PLASMA PROTEINS MUCH LOWER THAN THAT OF NORADRENALINE.

MEDICATION

Phenethylamines are important precursors of isoquinoline alkaloids and important neuroamines /dopamine and tyramine/.

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index