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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

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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Progressive degeneration of human mesencephalic neuron-derived cells triggered by dopamine-dependent oxidative stress is dependent on the mixed-lineage kinase pathway.
Lotharius J
The Journal of Neuroscience, 25(27), 6329-6342 (2005)
Sergio Ortiz-Padilla et al.
Neuropharmacology, 166, 107920-107920 (2019-12-25)
Dopaminergic neurons have the ability to release Dopamine from their axons as well as from their soma and dendrites. This somatodendritically-released Dopamine induces an autoinhibition of Dopaminergic neurons mediated by D2 autoreceptors, and the stimulation of neighbor GABAergic neurons mediated
Low dose alpha-methyl-para-tyrosine (AMPT) in the treatment of dystonia and dyskinesia.
Ankenman R and Salvatore MF
The Journal of Neuropsychiatry and Clinical Neurosciences, 19(1), 65-69 (2007)
Renan Idalencio et al.
General and comparative endocrinology, 252, 236-238 (2017-07-19)
In this article, we show that the tyrosine hydroxylase inhibitor α-Methyl-l-tyrosine (AMPT) decreased the responsiveness of the zebrafish stress axis to an acute stressful challenge. These effects were specific for responses to stimulation, since unstimulated (basal) cortisol levels were not
Endocrine function of dopaminergic neurons of the whole rat brain in ontogeny: control of prolactin secretion.
Yu Yu Saifetyarova et al.
Doklady biological sciences : proceedings of the Academy of Sciences of the USSR, Biological sciences sections, 443, 81-83 (2012-05-09)
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