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Merck
CN

04632

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
EC Number:
208-670-8
UNSPSC Code:
12352202
PubChem Substance ID:
329747962
Beilstein/REAXYS Number:
2646795
MDL number:
MFCD00238322

Key Documents

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InChI key

AXDLCFOOGCNDST-VIFPVBQESA-N

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

SMILES string

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

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

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.

signalword

Warning

pictograms

Exclamation mark
GHS07

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBG2178V
BCBT1436
BCBK3102V
BCBC2779

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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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