Tyramine

Names

[ CAS No. ]:
51-67-2

[ Name ]:
Tyramine

[Synonym ]:
Phenol, 4-(ethylamino)-
Uteramine
Tyramin
MFCD00008193
4-Ethylaminophenol
Tocosine
4-(2-aminoethyl)phenol
4-(2-aminoethyl)-pheno
p-Hydroxyphenylethylamine
Tyrosamine
Systogene
4-Hydroxyphenethylamine
p-Tyramine
4-(Ethylamino)phenol
4-(Ethylamino)benzolol
2-(4-Hydroxyphenyl)ethylamine
EINECS 200-115-8
4-hydroxy-phenethylamine

Biological Activity

[Description]:

Tyramine is an indirectly acting sympathomimetic amine that releases norepinephrine from presynaptic nerve terminals.

[Related Catalog]:

Research Areas >> Neurological Disease

Natural Products >> Others

[Target]

Human Endogenous Metabolite

[In Vitro]

Tyramine is an indirectly acting sympathomimetic amine that releases norepinephrine from presynaptic nerve terminals[1]. Tyramine potentiates the postsynaptic inhibitory effects of norepinephrine on the firing of cortical neurones in the rat[2]. Although tyramine exists in three isomerie forms, the orthoisomer and metaisomers are present in very low concentrations and it is the paraisomer that is implied when reference is made to tyramine. The tyramines are generally present in nanogram/gram concentrations in brain tissue, but they have a very rapid turnover. The CNS role of tyramine is unclear, it has been suggested that it is involved in the modulation of dopamine synthesis and may also regulate norepinephrine turnover[3].

[References]

[1]. Harrison WM, et al. The tyramine challenge test as a marker for melancholia. Arch Gen Psychiatry. 1984 Jul;41(7):681-5.

[2]. BURN JH, et al. The action of sympathomimetic amines in animals treated with reserpine. J Physiol. 1958 Dec 4;144(2):314-36.

[3]. Juorio AV, et al. A possible role for tyramines in brain function and some mental disorders. Gen Pharmacol. 1982;13(3):181-3.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
275.1±23.0 °C at 760 mmHg

[ Melting Point ]:
160-162 °C(lit.)

[ Molecular Formula ]:
C₈H₁₁NO

[ Molecular Weight ]:
137.179

[ Flash Point ]:
141.3±13.3 °C

[ Exact Mass ]:
137.084061

[ PSA ]:
46.25000

[ LogP ]:
1.38

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.600

[ Storage condition ]:
Refrigerator, Under Inert Atmosphere

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

[ Water Solubility ]:
1g/95mL (15 ºC)

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: SJ5950000

CHEMICAL NAME :: Phenol, p-(2-aminoethyl)-

CAS REGISTRY NUMBER :: 51-67-2

BEILSTEIN REFERENCE NO. :: 1099914

LAST UPDATED :: 199612

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C8-H11-N-O

MOLECULAR WEIGHT :: 137.20

WISWESSER LINE NOTATION :: Z2R DQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 225 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 229 mg/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay)

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2200 mg/kg

TOXIC EFFECTS :: Autonomic Nervous System - sympathomimetic

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intracervical

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 30 mg/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Behavioral - muscle contraction or spasticity

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 30 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: Cytogenetic analysis

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 137 mg/kg

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 240,19,1990

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
SJ5950000

[ HS Code ]:
2922299090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2922299090

[ Summary ]:
2922299090. other amino-naphthols and other amino-phenols, other than those containing more than one kind of oxygen function, their ethers and esters; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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Related Compounds

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