Buy Tyramine Cas 51-67-2

Buy Tyramine Cas 51-67-2

Tyramine (/ˈtaɪrəmiːn/ TY-rə-meen) (also spelled tyramin), also known under several other names,^{[note 1]} is a naturally occurring trace amine derived from the amino acid tyrosine.^[4] 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).

Tyramine occurs widely in plants^[5] and animals, and is metabolized by various enzymes, including monoamine oxidases. In foods, it often is produced by the decarboxylation of tyrosine during fermentation or decay. Foods that are fermented, cured, pickled, aged, or spoiled have high amounts of tyramine. Tyramine levels go up when foods are at room temperature or go past their freshness date.

Specific foods containing considerable amounts of tyramine include:^[6][7]

• Strong or aged cheeses: cheddar, Swiss, Parmesan, Stilton, Gorgonzola or blue cheeses, Camembert, feta, Muenster
• Meats that are cured, smoked, or processed: such as salami, pepperoni, dry sausages, hot dogs, bologna, bacon, corned beef, pickled or smoked fish, caviar, aged chicken livers, soups or gravies made from meat extract
• Pickled or fermented foods: sauerkraut, kimchi, tofu (especially stinky tofu), pickles, miso soup, bean curd, tempeh, sourdough breads
• Condiments: soy, shrimp, fish, miso, teriyaki, and bouillon-based sauces
• Drinks: beer (especially tap or home-brewed), vermouth, red wine, sherry, liqueurs
• Beans, vegetables, and fruits: fermented or pickled vegetables, overripe fruits
• Chocolate^[8]

Scientists more and more consider tyramine in food as an aspect of safety.^[9] They propose projects of regulations aimed to enact control of biogenic amines in food by various strategies, including usage of proper fermentation starters, or preventing their decarboxylase activity.^[10] Some authors wrote that this has already given positive results, and tyramine content in food is now lower than it has been in the past.^[11]

Mistletoe (toxic and not used by humans as a food, but historically used as a medicine).^[12]

Tyramine also plays a role in animals including: In behavioral and motor functions in Caenorhabditis elegans;^[13] Locusta migratoria swarming behaviour;^[14] and various nervous roles in Rhipicephalus, Apis, Locusta, Periplaneta, Drosophila, Phormia, Papilio, Bombyx, Chilo, Heliothis, Mamestra, Agrotis, and Anopheles.^[15]

Tyramine is a norepinephrine and dopamine releasing agent (NDRA) and indirectly acting sympathomimetic.^[19][18] Evidence for the presence of tyramine in the human brain has been confirmed by postmortem analysis.^[25] Additionally, the possibility that tyramine acts directly as a neuromodulator was revealed by the discovery of a G protein-coupled receptor with high affinity for tyramine, called the trace amine-associated receptor (TAAR1).^[26][27] The TAAR1 receptor is found in the brain, as well as peripheral tissues, including the kidneys.^[28] Tyramine is a full agonist of the TAAR1 in rodents and humans.^[29][30]

Tyramine is physiologically metabolized by monoamine oxidases (primarily MAO-A), FMO3, PNMT, DBH, and CYP2D6.^{[31][32][33][34][35]} Human monoamine oxidase enzymes metabolize tyramine into 4-hydroxyphenylacetaldehyde.^[36] If monoamine metabolism is compromised by the use of monoamine oxidase inhibitors (MAOIs) and foods high in tyramine are ingested, a hypertensive crisis can result, as tyramine also can displace stored monoamines, such as dopamine, norepinephrine, and epinephrine, from pre-synaptic vesicles. Tyramine is considered a “false neurotransmitter“, as it enters noradrenergic nerve terminals and displaces large amounts of norepinephrine, which enters the blood stream and causes vasoconstriction.

Additionally, cocaine has been found to block blood pressure rise that is originally attributed to tyramine, which is explained by the blocking of adrenaline by cocaine from reabsorption to the brain.^[37]

The first signs of this effect were discovered by a British pharmacist who noticed that his wife, who at the time was on MAOI medication, had severe headaches when eating cheese.^[38] For this reason, it is still called the “cheese reaction” or “cheese crisis”, although other foods can cause the same problem.^[39]

Most processed cheeses do not contain enough tyramine to cause hypertensive effects, although some aged cheeses (such as Stilton) do.^[40][41]

A large dietary intake of tyramine (or a dietary intake of tyramine while taking MAO inhibitors) can cause the tyramine pressor response, which is defined as an increase in systolic blood pressure of 30 mmHg or more. The increased release of norepinephrine (noradrenaline) from neuronal cytosol or storage vesicles is thought to cause the vasoconstriction and increased heart rate and blood pressure of the pressor response. In severe cases, adrenergic crisis can occur.^{[medical citation needed]} Although the mechanism is unclear, tyramine ingestion also triggers migraine attacks in sensitive individuals and can even lead to stroke.^[42] Vasodilation, dopamine, and circulatory factors are all implicated in the migraines. Double-blind trials suggest that the effects of tyramine on migraine may be adrenergic.^[43]

Research reveals a possible link between migraines and elevated levels of tyramine. A 2007 review published in Neurological Sciences^[44] presented data showing migraine and cluster diseases are characterized by an increase of circulating neurotransmitters and neuromodulators (including tyramine, octopamine, and synephrine) in the hypothalamus, amygdala, and dopaminergic system. People with migraine are over-represented among those with inadequate natural monoamine oxidase, resulting in similar problems to individuals taking MAO inhibitors. Many migraine attack triggers are high in tyramine.^[45]

If one has had repeated exposure to tyramine, however, there is a decreased pressor response; tyramine is degraded to octopamine, which is subsequently packaged in synaptic vesicles with norepinephrine (noradrenaline).^{[citation needed]} Therefore, after repeated tyramine exposure, these vesicles contain an increased amount of octopamine and a relatively reduced amount of norepinephrine. When these vesicles are secreted upon tyramine ingestion, there is a decreased pressor response, as less norepinephrine is secreted into the synapse, and octopamine does not activate alpha or beta adrenergic receptors.^{[medical citation needed]}

When using a MAO inhibitor (MAOI), an intake of approximately 10 to 25 mg of tyramine is required for a severe reaction, compared to 6 to 10 mg for a mild reaction.^[46]

Tyramine, like phenethylamine, is a monoaminergic activity enhancer (MAE) of serotonin, norepinephrine, and dopamine in addition to its catecholamine-releasing activity.^[47][48][49] That is, it enhances the action potential-mediated release of these monoamine neurotransmitters.^[47][48][49] The compound is active as a MAE at much lower concentrations than the concentrations at which it induces the release of catecholamines.^[47][48][49] The MAE actions of tyramine and other MAEs may be mediated by TAAR1 agonism.^[50][51]

Biochemically, tyramine is produced by the decarboxylation of tyrosine via the action of the enzyme tyrosine decarboxylase.^[52] Tyramine can, in turn, be converted to methylated alkaloid derivatives N-methyltyramine, N,N-dimethyltyramine (hordenine), and N,N,N-trimethyltyramine (candicine).

• 
  Tyramine
• 
  N-Methyltyramine
• 
  N,N-Dimethyltyramine (hordenine)
• 
  N,N,N-Trimethyltyramine (candicine)

In humans, tyramine is produced from tyrosine, as shown in the following diagram.

Biosynthetic pathways for catecholamines and trace amines in the human brain[33][34][35] L-Phenylalanine L-Tyrosine L-DOPA Epinephrine Phenethylamine p-Tyramine Dopamine Norepinephrine N-Methylphenethylamine N-Methyltyramine p-Octopamine Synephrine 3-Methoxytyramine Buy Tyramine Cas 51-67-2, Buy Tyramine Cas 51-67-2, Buy Tyramine Cas 51-67-2, Buy Tyramine Cas 51-67-2, Buy Tyramine Cas 51-67-2, Buy Tyramine Cas 51-67-2, Buy Tyramine Cas 51-67-2, Buy Tyramine Cas 51-67-2, Buy Tyramine Cas 51-67-2, Buy Tyramine Cas 51-67-2, Buy Tyramine Cas 51-67-2, Buy Tyramine Cas 51-67-2, Buy Tyramine Cas 51-67-2 In humans, catecholamines and phenethylaminergic trace amines are derived from the amino acid L-phenylalanine.

In the laboratory, tyramine can be synthesized in various ways, in particular by the decarboxylation of tyrosine.^[53][54][55]

51-67-2

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• Basic information

  1. Product Name: Tyramine
  2. Synonyms: 4-(2-aminoethyl)-pheno;4-(2-Aminoethyl)-phenol (thyramin);4-hydroxy-benzeneethanamin;4-Hydroxy-beta-phenylethylamine;alpha-(4-Hydroxyphenyl)-beta-aminoethane;Benzeneethanamine, 4-hydroxy-;beta-(4-Hydroxyphenyl)ethylamine;beta-Hydroxyphenylethylamine
  3. CAS NO:51-67-2
  4. Molecular Formula: C₈H₁₁NO
  5. Molecular Weight: 137.17904
  6. EINECS: 200-115-8
  7. Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
  8. Mol File: 51-67-2.mol

• Chemical Properties

  1. Melting Point: 160-162 °C(lit.)
  2. Boiling Point: 175-181 °C8 mm Hg(lit.)
  3. Flash Point: 165°C
  4. Appearance: Clear yellow to orange to slightly brown, may darken on storage/Liquid
  5. Density: 1.0630 (rough estimate)
  6. Vapor Pressure: 0.000123mmHg at 25°C
  7. Refractive Index: 1.5849 (estimate)
  8. Storage Temp.: Refrigerator, Under Inert Atmosphere
  9. Solubility: DMSO (Slightly), Methanol (Slightly)
  10. PKA: 9.74(at 25℃)
  11. Water Solubility: 1g/95mL (15 ºC)
  12. Stability: Stable. Incompatible with strong acids, strong oxidizing agents.
  13. Merck: 14,9835
  14. BRN: 1099914
  15. CAS DataBase Reference: Tyramine(CAS DataBase Reference)
  16. NIST Chemistry Reference: Tyramine(51-67-2)
  17. EPA Substance Registry System: Tyramine(51-67-2)
• Product Description:Product Name: tyramine CAS NO: 51-67-2 

  Synonyms:

  4-(2-aminoethyl)-pheno;

  2-(4-Hydroxyphenyl)ethylamine;

  4-hydroxy-phenethylamine;

   

  Chemical & Physical Properties:

  Appearance: Yellow to brown crystals

  Assay :≥98.0%

  Density: 1.103g/cm3

  Boiling Point: 175-181℃ (8 mmHg)

  Melting Point: 155-163℃

  Flash Point: 165℃

  Water Solubility: 1g/95mL (15℃)

  Stability: Stable. Incompatible with strong acids, strong oxidizing agents.

  Storage Condition: Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

   

  Safety Information:

  RTECS: SJ5950000

  Safety Statements: S26-S37/39

  HS Code: 2922299090

  WGK Germany: 3

  Risk Statements: R36/37/38

  Hazard Code: Xi

  Symbol: GHS07

  Signal Word: Warning

  Hazard Statements: H315-H319-H335

  Precautionary Statements: P261-P305 + P351 + P338

   

  Tyramine, also known by several other names, is a naturally occurring monoamine and 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. A hypertensive crisis can result, however, from ingestion of tyramine-rich foods in conjunction with monoamine oxidase inhibitors (MAOIs).

   

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Properties

IUPAC Name	4-(2-aminoethyl)phenol	Source
InChI	InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2	Source
InChI Key	DZGWFCGJZKJUFP-UHFFFAOYSA-N	Source
Canonical SMILES	C1=CC(=CC=C1CCN)O	Source
Molecular Formula	C8H11NO	Source
Related CAS	71495-67-5	Source
DSSTOX Substance ID	DTXSID2043874	Source
Molecular Weight	137.18 g/mol	Source
Physical Description	Solid, Colourless to yellow solid; Sweet meaty aroma	Source
Boiling Point	166 °C @ 2 MM HG	Source
Solubility	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, Soluble in water, Soluble (in ethanol)	Source
Color/Form	CRYSTALS FROM BENZENE OR ALCOHOL, PLATES OR NEEDLES FROM BENZENE, NEEDLES FROM WATER
CAS No.	51-67-2	Source
Melting Point	164-165 °C, MP: 269 °C /TYRAMINE HYDROCHLORIDE/, 164 – 165 °C	Source