Conditions | Yield |
---|---|
With pyridoxal 5'-phosphate; aromatic L-amino acid decarboxylase In various solvent(s) at 30℃; for 48h; | 99% |
at 300 - 340℃; | |
Bestrahlen der Kristalle mit Roentgen-Strahlen; |
Conditions | Yield |
---|---|
With ammonium bromide; ethylenediamine at 80℃; for 5h; Microwave irradiation; Inert atmosphere; neat (no solvent); | 98% |
With recombinant Arabidopsis thaliana histone deacetylase 14 In aq. buffer at 30℃; pH=8; Reagent/catalyst; Enzymatic reaction; |
Conditions | Yield |
---|---|
With acetic acid In methanol for 2h; Ambient temperature; Irradiation; other N-subsituted amides of o-hydroxy-trans-cinnamic acid; | A 95% B 100 % Spectr. |
N-{2-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]ethyl}formamide
tyrosamine
Conditions | Yield |
---|---|
With ethanol; sodium hydroxide at 78℃; for 8h; Reagent/catalyst; Temperature; | 87% |
1-(benzyloxy)-4-(2-nitroethyl)benzene
tyrosamine
Conditions | Yield |
---|---|
With ethanol; hydrogen at 100℃; Flow reactor; | 85% |
Conditions | Yield |
---|---|
Stage #1: formic acid; phenol With boron trifluoride In diethyl ether at 15℃; for 2h; Stage #2: nitromethane With ammonium acetate In diethyl ether at 110℃; for 2h; Stage #3: With hydrogen In ethanol at 50℃; for 4h; Temperature; | 82.3% |
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; copper hydroxide In 1-methyl-pyrrolidin-2-one at 210℃; for 5h; Inert atmosphere; Green chemistry; | 68% |
in Gegenwart von Fleischbruehe; | |
at 270℃; |
(4-Hydroxyphenyl)acetaldehyd-dimethylhydrazon
tyrosamine
Conditions | Yield |
---|---|
With hydrogen; rhenium; nickel In methanol under 760 Torr; for 12h; Ambient temperature; | 58% |
N-(p-hydroxyphenylethyl)-N-(6-bromo-3-hydroxy-4-methoxybenzyl)amine
A
tyrosamine
B
2-bromoisovanillin
Conditions | Yield |
---|---|
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccase from Trametes versicolor In 1,4-dioxane at 25℃; for 3h; pH=4.5; | A 33% B 37% C 8% |
p-Aminophenethylamine
tyrosamine
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite | |
With hydrogenchloride; tin(IV) chloride; sodium nitrite anschliessend Erwaermen; |
Conditions | Yield |
---|---|
With palladium on activated charcoal; acetic acid Hydrogenation; |
3-(4-hydroxyphenyl)propanoic acid amide
tyrosamine
Conditions | Yield |
---|---|
With sodium hypochlorite |
(E)-1-(4-hydroxyphenyl)-2-nitroethene
tyrosamine
Conditions | Yield |
---|---|
With sulfuric acid; acetic acid; platinum Hydrogenation; |
4-(2-Nitrovinyl)benzoic acid methyl ester
tyrosamine
Conditions | Yield |
---|---|
With sulfuric acid; acetic acid; platinum Hydrogenation; |
(4-hydroxy-phenyl)-acetaldehyde-(4-nitro-phenylhydrazone)
tyrosamine
Conditions | Yield |
---|---|
With sodium amalgam; ethanol; acetic acid |
tyrosamine
Conditions | Yield |
---|---|
With palladium on activated charcoal; acetic acid Hydrogenation; | |
Multi-step reaction with 2 steps 1: palladium/charcoal; ethanol / Hydrogenation 2: palladium/charcoal; acetic acid / Hydrogenation View Scheme |
Conditions | Yield |
---|---|
at 280 - 290℃; |
Diphenylmethane
L-tyrosine
A
tyrosamine
B
methylammonium carbonate
Conditions | Yield |
---|---|
at 245℃; |
Conditions | Yield |
---|---|
at 260℃; |
Conditions | Yield |
---|---|
at 230℃; |
L-tyrosine
A
tyrosamine
B
methylammonium carbonate
Conditions | Yield |
---|---|
at 270℃; |
Conditions | Yield |
---|---|
With hydrogenchloride at 160 - 170℃; | |
With hydrogen iodide | |
With hydrogen bromide at 160℃; | |
With hydrogenchloride Heating; | |
With hydrogen bromide; acetic acid for 4h; Reflux; |
2-(4-hydroxyphenyl)-1-nitroethane
tyrosamine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol Product distribution; |
Conditions | Yield |
---|---|
With Tyrosine decarboxylase apoenzyme; pyridoxal 5'-phosphate In water at 37℃; Product distribution; Effect of pH 5-6.2, other enzyme concentration and activity and temperature on reaction rate; |
4-(β-Aminoethyl)benzene Oxide
tyrosamine
Conditions | Yield |
---|---|
In d(4)-methanol |
Conditions | Yield |
---|---|
at 240 - 280℃; beim Destillieren; |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran; methanol at 0 - 20℃; | 100% |
In tetrahydrofuran for 3.5h; | 100% |
With triethylamine In N,N-dimethyl-formamide | 99% |
tyrosamine
(4aS,6S,7R,7aS)-6-Acetoxy-7-methyl-1-oxo-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester
Conditions | Yield |
---|---|
In methanol | 100% |
Conditions | Yield |
---|---|
Stage #1: tyrosamine; benzaldehyde In DMF (N,N-dimethyl-formamide); toluene Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol at 0 - 20℃; for 1h; | 100% |
Stage #1: tyrosamine; benzaldehyde In methanol for 2h; Heating / reflux; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; Product distribution / selectivity; | 91% |
Stage #1: tyrosamine; benzaldehyde In methanol for 1h; Heating / reflux; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h; Product distribution / selectivity; | 61% |
tyrosamine
4-Nitrophenyl isocyanate
4-hydroxyphenethylamino-4-nitroanilinomethanone
Conditions | Yield |
---|---|
With pyridine at 0 - 20℃; | 100% |
tyrosamine
1-azido-2-(4-hydroxyphenyl)ethane
Conditions | Yield |
---|---|
With methanol; copper(ll) sulfate pentahydrate; triflic azide; sodium hydrogencarbonate In water at 20℃; | 100% |
With fluorosulfonyl azide; potassium hydrogencarbonate In tert-butyl methyl ether; water; N,N-dimethyl-formamide at 20℃; for 0.0833333h; | 86% |
With imidazole-1-sulfonyl azide hydrochloride; potassium carbonate; copper(II) sulfate In methanol at 20℃; for 4h; | 84% |
tyrosamine
phenyl chloroformate
phenyl N-[2-(4-hydroxyphenyl)ethyl]carbamate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 4h; Inert atmosphere; | 100% |
tyrosamine
methyl 3-(2-chlorophenyl)-1-(2-chloropyrimidin-4-yl)-1H-pyrazole-4-carboxylate
methyl 3-(2-chlorophenyl)-1-(2-{[2-(4-hydroxyphenyl)ethyl]amino}pyrimidin-4-yl)-1H-pyrazole-4-carboxylate
Conditions | Yield |
---|---|
In acetonitrile at 80℃; | 100% |
Conditions | Yield |
---|---|
Stage #1: tyrosamine With potassium carbonate In tetrahydrofuran; water at 20℃; for 1h; Inert atmosphere; Stage #2: propionyl chloride In tetrahydrofuran; water for 2h; Inert atmosphere; | 100% |
tyrosamine
methyl chloroformate
4-hydroxyphenyl-2-ethylcarbamic acid methyl ester
Conditions | Yield |
---|---|
With water; sodium hydrogencarbonate In tetrahydrofuran at 0℃; for 3h; | 100% |
With N-ethyl-N,N-diisopropylamine In dichloromethane Inert atmosphere; Cooling with ice; | 52% |
tyrosamine
Thioctic acid
Conditions | Yield |
---|---|
Stage #1: Thioctic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at -20 - 20℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: tyrosamine In dichloromethane; N,N-dimethyl-formamide at 20℃; Schlenk technique; Inert atmosphere; | 100% |
Stage #1: Thioctic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran for 0.5h; Stage #2: tyrosamine In tetrahydrofuran at 20℃; for 12h; | 75% |
Conditions | Yield |
---|---|
In methanol at 20℃; | 100% |
Conditions | Yield |
---|---|
In methanol at 20℃; | 100% |
tyrosamine
1,4,5,8-naphthalenetetracarboxylic dianhydride
N,N'-bis[2-(4-hydroxyphenyl)ethyl]-1,4,5,8-naphthalenetetracarboxylic acid diimide
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane; N,N-dimethyl-formamide Inert atmosphere; Reflux; | 99% |
tyrosamine
Conditions | Yield |
---|---|
With dihydrogen peroxide; iodine In water at 55℃; for 3h; | 99% |
tyrosamine
dithio-bis(ethyl 1H-imidazole-1-carboxylate)
tyramine-DIC
Conditions | Yield |
---|---|
In isopropyl alcohol at 40℃; for 24h; | 99% |
In isopropyl alcohol at 40℃; for 24h; | 59% |
Conditions | Yield |
---|---|
With Trimethylacetic acid at 90℃; for 24h; Inert atmosphere; chemoselective reaction; | 99% |
tyrosamine
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 23℃; for 16h; Inert atmosphere; | 99% |
tyrosamine
9-benzoyl-9H-carbazole
N-<2-(4-hydroxyphenyl)ethyl>benzamide
Conditions | Yield |
---|---|
In tetrahydrofuran at 30℃; for 24h; chemoselective reaction; | 99% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; for 10h; Inert atmosphere; | 98.62% |
tyrosamine
3,5-dibromo-4-hydroxy-β-phenethylamine
Conditions | Yield |
---|---|
With pyridine; pyridinium hydrobromide perbromide In chloroform for 24h; | 98% |
With bromine In acetic acid | 98% |
With bromine; acetic acid | 93% |
With tetrabuthylammonium tribromide In methanol; dichloromethane at 20℃; for 0.5h; | 63% |
With bromine; acetic acid |
tyrosamine
(tert-butoxycarbonyl)-L-phenylalanine N-hydroxysuccinimide ester
N-(tert-Butoxycarbonyl)-L-phenyl-alanyltyramide
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In ethyl acetate at 25℃; for 20h; | 98% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 1h; Ambient temperature; | 98% |
In tetrahydrofuran for 0.5h; Ambient temperature; | 98% |
tyrosamine
tert-butylisonitrile
2-(2-formyl-phenyl)-benzoic acid
N-tert-butyl-6-(4-hydroxyphenethyl)-7-oxo-6,7-dihydro-5H-dibenzo[c,e]azepine-5-carboxamide
Conditions | Yield |
---|---|
With sodium sulfate In 2,2,2-trifluoroethanol at 110℃; for 0.833333h; Ugi 4CR reaction; Sealed; Inert atmosphere; Irradiation; | 98% |
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 20℃; | 98% |
In dimethyl sulfoxide at 20℃; for 10h; | 92% |
Conditions | Yield |
---|---|
for 24h; Reflux; | 98% |
In ethanol for 24h; Reflux; | 60% |
In ethanol for 24h; Reflux; |
Conditions | Yield |
---|---|
at 140℃; for 4h; Reagent/catalyst; Temperature; | 98% |
Conditions | Yield |
---|---|
at 140℃; for 4h; Reagent/catalyst; Temperature; | 98% |
The IUPAC name of Tyramine is 4-(2-aminoethyl)phenol. With the CAS registry number 51-67-2, it is also named as Benzeneethanamine, 4-hydroxy-. The product's categories are Anilines, Aromatic Amines and Nitro Compounds. Besides, it is white to light beige solid, which should be stored in sealed, dark place. It is stable and incompatible with strong acids, strong oxidizing agents. In addition, its molecular formula is C8H11NO and molecular weight is 137.18.
The other characteristics of this product can be summarized as: (1)EINECS: 200-115-8; (2)ACD/LogP: 0.72; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): -2.36; (5)ACD/LogD (pH 7.4): -1.82; (6)ACD/BCF (pH 5.5): 1; (7)ACD/BCF (pH 7.4): 1; (8)ACD/KOC (pH 5.5): 1; (9)ACD/KOC (pH 7.4): 1; (10)#H bond acceptors: 2; (11)#H bond donors: 3; (12)#Freely Rotating Bonds: 4; (13)Index of Refraction: 1.577; (14)Molar Refractivity: 41.21 cm3; (15)Molar Volume: 124.3 cm3; (16)Surface Tension: 48.3 dyne/cm; (17)Density: 1.103 g/cm3; (18)Flash Point: 119.2 °C; (19)Melting point: 155-163 °C; (20)Water Solubility: 1g / 95mL (15 °C); (21)Enthalpy of Vaporization: 58.99 kJ/mol; (22)Boiling Point: 325.2 °C at 760 mmHg; (23)Vapour Pressure: 0.000123 mmHg at 25 °C.
Preparation of Tyramine: this chemical occurs widely in plants and animals and is metabolized by the enzyme monoamine oxidase. Moreover, it is often produced by the decarboxylation of tyrosine during fermentation or decay. It also can be produced by the deoxidization of P-Hydroxybenzyl cyanide.
Uses of Tyramine: this chemical is used as intermediate of Bezafibrate. It is also used in organic synthesis. It can be used for the contraction of uterus, peripheral nerves, and for elevation of blood pressure in medical treatment. Additionally, it can react with Formaldehyde to get 4-(2-Dimethylamino-ethyl)-phenol.
This reaction needs H2, 10 percent Pd/C and Methanol at temperature of 20 °C. The yield is 93 %.
When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
(1)SMILES: Oc1ccc(cc1)CCN
(2)InChI: InChI=1/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2
(3)InChIKey: DZGWFCGJZKJUFP-UHFFFAOYAB
(4)Std. InChI: InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2
(5)Std. InChIKey: DZGWFCGJZKJUFP-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LDLo | subcutaneous | 30mg/kg (30mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1412, 1935. | |
mouse | LD50 | intracervical | 30mg/kg (30mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | Tohoku Yakka Daigaku Kenkyu Nempo. Annual Report of the Tohoku College of Pharmacy. Vol. 27, Pg. 131, 1980. |
mouse | LD50 | intravenous | 229mg/kg (229mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Acta Pharmacologica et Toxicologica. Vol. 38, Pg. 474, 1976. |
mouse | LDLo | intraperitoneal | 800mg/kg (800mg/kg) | Journal of Physiology. Vol. 76, Pg. 224, 1932. | |
mouse | LDLo | subcutaneous | 225mg/kg (225mg/kg) | "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. -, 1965. | |
mouse | LDLo | unreported | 2200mg/kg (2200mg/kg) | AUTONOMIC NERVOUS SYSTEM: SYMPATHOMIMETIC | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 153, Pg. 161, 1930. |
rabbit | LD50 | intravenous | 300mg/kg (300mg/kg) | "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 691, 1986. |
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