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W421501

Sigma-Aldrich

Tyramine

98%, FG

Synonym(s):

2-(4-Hydroxyphenyl)ethylamine, 4-(2-Aminoethyl)phenol, 4-Hydroxyphenethylamine

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About This Item

Linear Formula:
HOC6H4CH2CH2NH2
CAS Number:
51-67-2
Molecular Weight:
137.18
FEMA Number:
4215
Beilstein/REAXYS Number:
1099914
EC Number:
200-115-8
MDL number:
MFCD00008193
UNSPSC Code:
12164502
PubChem Substance ID:
329830683
Flavis number:
11.007
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

FG

reg. compliance

EU Regulation 1334/2008 & 872/2012
FDA 21 CFR 110

assay

98%

bp

175-181 °C/8 mmHg (lit.)

mp

160-162 °C (lit.)

application(s)

flavors and fragrances

documentation

see Safety & Documentation for available documents

food allergen

no known allergens

organoleptic

meaty; phenolic

SMILES string

NCCc1ccc(O)cc1

InChI

1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2

InChI key

DZGWFCGJZKJUFP-UHFFFAOYSA-N

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Biochem/physiol Actions

Can enter catecholaminergic terminals and be released as a false transmitter.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Stephan A Chalon et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 28(9), 1685-1693 (2003-06-05)
Evidence suggests that compounds that increase the synaptic availability of more than one neurotransmitter have greater efficacy in the treatment of depression than single-acting drugs. Preclinical studies indicate that duloxetine acts to inhibit serotonin (5-HT) and norepinephrine (NE) transporters. The
Giris Jacob et al.
Circulation, 107(19), 2475-2479 (2003-04-23)
Despite the widespread use of tyramine as a pharmacological tool to assess the effects of norepinephrine release from sympathetic nerve terminals, its vascular effects are not adequately characterized. In particular, previous results indicate that intravenous tyramine produces little if any
Thomas Roeder
Annual review of entomology, 50, 447-477 (2004-09-10)
Octopamine (OA) and tyramine (TA) are the invertebrate counterparts of the vertebrate adrenergic transmitters. They are decarboxylation products of the amino acid tyrosine, with TA as the biological precursor of OA. Nevertheless, both compounds are independent neurotransmitters that act through
D R Varma et al.
The Journal of pharmacology and experimental therapeutics, 265(3), 1096-1104 (1993-06-01)
At concentrations higher than that required to produce maximal vasoconstriction, tyramine caused concentration-dependent relaxation of rat aortic strips contracted maximally by tyramine, norepinephrine, phenylephrine, 5-hydroxytryptamine, prostaglandin F2 alpha, endothelin, angiotensin II and potassium; isoproterenol did not relax potassium-contracted strips. The
Moussa B H Youdim et al.
Neurotoxicology, 25(1-2), 243-250 (2003-12-31)
The major side effect with the use of first generation of non selective monoamine oxidase (MAO) inhibitors as neuropsychiatric drugs was what became known as the "cheese reaction". Namely, potentiation of sympathomimetic activity of ingested tyramine present in cheese and
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