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04632

Sigma-Aldrich

N-Methyl-L-tyrosine

≥98% (HPLC)

Synonym(s):

(S)-3-(4-Hydroxyphenyl)-2-(methylamino)propionic acid, N-Me-Tyr-OH, Surinamine

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About This Item

Empirical Formula (Hill Notation):
C10H13NO3
CAS Number:
537-49-5
Molecular Weight:
195.22
Beilstein:
2646795
EC Number:
208-670-8
MDL number:
MFCD00238322
UNSPSC Code:
12352202
PubChem Substance ID:
329747962

Assay

≥98% (HPLC)

form

powder or crystals

optical activity

[α]/D +16.0±1.0°, c = 1 in 1 M HCl

composition

carbon, 60.7-62.3%
nitrogen, 6.9-7.5%

color

colorless to white

application(s)

cell analysis

SMILES string

CN[C@@H](Cc1ccc(O)cc1)C(O)=O

InChI

1S/C10H13NO3/c1-11-9(10(13)14)6-7-2-4-8(12)5-3-7/h2-5,9,11-12H,6H2,1H3,(H,13,14)/t9-/m0/s1

InChI key

AXDLCFOOGCNDST-VIFPVBQESA-N

Application

N-Methyl-L-tyrosine was used in experiments as a control group to show that methylation of the imino group in N-p-phenylpropionyl-L-tyrosine eliminates its inhibitory effect on the firing of the giant neurone of the giant African snail.

Biochem/physiol Actions

N-Methyl amino acids play an important role in investigations on prevention or therapy of Alzheimer′s disease, neurofibrillary tangles or amyloid plaque are physiological characteristics of this disease and ?-amyloid(40) fibrillogenesis and disassembly of ?-amyloid(40) fibrils is inhibited by short ?-amyloid congeners containing N-methyl amino acids at alternate residue.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Precautionary Statements

P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Y Ariyoshi et al.
British journal of pharmacology, 77(4), 631-639 (1982-12-01)
1 Inhibitory effects of N-beta-phenylpropionyl-L-tyrosine, N-beta-phenylpropionyl-L-tryptophan and their derivatives on an identifiable giant neurone, TAN (tonically autoactive neurone) of an African giant snail (Achatina fulica Férussac) were examined in an attempt to elucidate which structural features are necessary to produce
D J Gordon et al.
Biochemistry, 40(28), 8237-8245 (2001-07-11)
A potential goal in the prevention or therapy of Alzheimer's disease is to decrease or eliminate neuritic plaques composed of fibrillar beta-amyloid (Abeta). In this paper we describe N-methyl amino acid containing congeners of the hydrophobic "core domain" of Abeta

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