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51-67-2

Basic Information
CAS No.: 51-67-2
Name: Tyramine
Article Data: 83
Molecular Structure:
Molecular Structure of 51-67-2 (Tyramine)
Formula: C8H11NO
Molecular Weight: 137.181
Synonyms: p-Hydroxyphenylethylamine;p-beta-Aminoethylphenol;Uteramine;Tyrophagus lintneriMushroom mite is also indexed at this headingTyrosamine;4-Hydroxyphenyl ethylamine;4-Hydroxy-.beta.-phenylethylamine;beta-Hydroxyphenylethylamine;Phenol, 4- (2-aminoethyl)-;4-Hydroxyphenethylamine;p-.beta.-Aminoethylphenol;Phenol, 4-(2-aminoethyl)-;2-(4-hydroxyphenyl)ethylazanium;Tocosine;Benzeneethanamine, 4-hydroxy-;alpha-(4-Hydroxyphenyl)-beta-aminoethane;p-Hydroxy-Beta-Phenethylamine;Tyramine, 4-Hydroxyphenylethylamine;
EINECS: 200-115-8
Density: 1.103 g/cm3
Melting Point: 155-163 °C
Boiling Point: 325.2 °C at 760 mmHg
Flash Point: 119.2 °C
Solubility: 1g / 95mL (15 °C) in water
Appearance: white to light beige solid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-37/39
PSA: 46.25000
LogP: 1.59370
Synthetic route
60-18-4

L-tyrosine

51-67-2

tyrosamine

Conditions
ConditionsYield
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;
1202-66-0

N-acetyltyramine

51-67-2

tyrosamine

Conditions
ConditionsYield
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;

(E)-3-(2-Hydroxy-phenyl)-N-[2-(4-hydroxy-phenyl)-ethyl]-acrylamide

A

51-67-2

tyrosamine

B

91-64-5

coumarin

Conditions
ConditionsYield
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.
1521270-08-5

N-{2-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]ethyl}formamide

51-67-2

tyrosamine

Conditions
ConditionsYield
With ethanol; sodium hydroxide at 78℃; for 8h; Reagent/catalyst; Temperature;87%
99696-06-7

1-(benzyloxy)-4-(2-nitroethyl)benzene

51-67-2

tyrosamine

Conditions
ConditionsYield
With ethanol; hydrogen at 100℃; Flow reactor;85%
64-18-6

formic acid

75-52-5

nitromethane

108-95-2

phenol

51-67-2

tyrosamine

Conditions
ConditionsYield
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
ConditionsYield
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℃;
74321-28-1

(4-Hydroxyphenyl)acetaldehyd-dimethylhydrazon

51-67-2

tyrosamine

Conditions
ConditionsYield
With hydrogen; rhenium; nickel In methanol under 760 Torr; for 12h; Ambient temperature;58%
179107-93-8

N-(p-hydroxyphenylethyl)-N-(6-bromo-3-hydroxy-4-methoxybenzyl)amine

A

51-67-2

tyrosamine

B

2973-59-3

2-bromoisovanillin

C

C16H16BrNO3

Conditions
ConditionsYield
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%
13472-00-9

p-Aminophenethylamine

51-67-2

tyrosamine

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite
With hydrogenchloride; tin(IV) chloride; sodium nitrite anschliessend Erwaermen;
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Specification

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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