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M8131

Sigma-Aldrich

α-Methyl-L-tyrosine

≥98% (TLC)

Synonym(s):

L-2-Methyl-3-(4-hydroxy­phenyl)alanine, L-AMPT

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About This Item

Empirical Formula (Hill Notation):
C10H13NO3
CAS Number:
672-87-7
Molecular Weight:
195.22
Beilstein:
2368400
EC Number:
211-599-5
MDL number:
MFCD00064201
UNSPSC Code:
12352200
PubChem Substance ID:
24278155
NACRES:
NA.32

Assay

≥98% (TLC)

form

powder

storage temp.

−20°C

SMILES string

C[C@](N)(Cc1ccc(O)cc1)C(O)=O

InChI

1S/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)/t10-/m0/s1

InChI key

NHTGHBARYWONDQ-JTQLQIEISA-N

Gene Information

human ... TH(7054)

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Application

α-Methyl-L-tyrosine has been used as an inhibitor tyrosine hydroxylase:
  • to test its effect during acute stress in zebrafish
  • in cannabinoid receptor type-1 (CB1) knockout and wild type mice, to test its effect on norepinephrine turnover
  • to test catecholamines depletion on stress in rat spleen samples
  • to block dopamine synthesis in dopaminergic neurons

α-Methyl-L-tyrosine is used to determine whether Fe2/ methamphetamine (METH) -induced cell death is dependent on cytosolic dopamine and iron mediated oxidative stress.

Biochem/physiol Actions

α-Methyl-L-tyrosine (L-AMPT) acts as a competitive inhibitor of tyrosine hydroxylase and inhibits the conversion of tyrosine to L-DOPA and eventually lowers dopamine synthesis in cytosol. AMPT at low concentrations can be used as a potent therapeutic for refractory dystonia or dyskinesia. It also helps in decreasing catecholamine concentration in pheochromocytoma patients.
Tyrosine hydroxylase inhibitor.

Other Notes

Active isomer

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000074420
0000069401
0000066986
0000066830
0000065551

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