Metyrosine (Metirosine)

Alias: Demser; Metirosine; Racemetirosine; α-Methyltyrosine
Cat No.:V5230 Purity: ≥98%
Metirosine (α-Methyltyrosine, Metyrosine, AMPT) is an antihypertensive drug that acts by inhibiting the enzyme tyrosine hydroxylase and, therefore, catecholamine synthesis, which, as a consequence, depletes the levels of the catecholamines dopamine, adrenaline and noradrenaline in the body.
Metyrosine (Metirosine) Chemical Structure CAS No.: 672-87-7
Product category: COX
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
50mg
100mg
250mg
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Other Forms of Metyrosine (Metirosine):

  • Metyrosine-13C9,15N,d7
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Metirosine (α-Methyltyrosine, Metyrosine, AMPT) is an antihypertensive drug that acts by inhibiting the enzyme tyrosine hydroxylase and, therefore, catecholamine synthesis, which, as a consequence, depletes the levels of the catecholamines dopamine, adrenaline and noradrenaline in the body. Metirosine has been shown to suppress catecholamine synthesis and alleviate symptoms related to catecholamine excess, including hypertension, headache, tachycardia, constipation, and tremor. Metirosine is primarily used to reduce these symptoms in patients with pheochromocytoma. It is contraindicated for the treatment of essential hypertension. However it is now rarely used in medicine, its primary use being in scientific research to investigate the effects of catecholamine depletion on behavior. There is evidence that catecholamine depletion causes a increase in sleepiness that is more pronounced than sleep deprivation, and that the fatigue lingers after the drug is discontinued. Negative mood is also a reported side effect of catecholamine depletion, although this is reported less consistently than sleepiness.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
Metyrosine induces sleep by blocking tyrosine kinases, which releases stored catecholamines [2].
ln Vivo
Carrageenan modulator is lowered by metyrosine (50–200 mg/kg; ip) [1]. Male albino Wistar rats with carrageenan-induced rat paw edema are the animal model of resistance to the anti-activity of metyrosine (50–200 mg/kg; ip) at dosages of 50, 100, and 200 mg/kg [2].
Animal Protocol
Animal/Disease Models: Male albino Wistar rats (carrageenan-induced rat paw edema)[2]
Doses: 50, 100 or 200 mg/kg
Route of Administration: I.p.
Experimental Results: diminished carrageenan inflammation at 50, 100 and 200 mg/kg doses (40%, 67% and 87%, respectively, at 4 h).
References
[1]. Albayrak A, Polat B, Cadirci E, et al. Gastric anti-ulcerative and anti-inflammatory activity of metyrosine in rats. Pharmacol Rep. 2010;62(1):113‐119.
[2]. Garg MK, et al. Medical management of pheochromocytoma: Role of the endocrinologist. Indian J Endocrinol Metab. 2011;15 Suppl 4(Suppl4):S329‐S336.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H13NO3
Molecular Weight
195.2151
CAS #
672-87-7
SMILES
O=C(O)[C@@](C)(N)CC1=CC=C(O)C=C1
InChi Key
NHTGHBARYWONDQ-JTQLQIEISA-N
InChi Code
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
Chemical Name
(S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
Synonyms
Demser; Metirosine; Racemetirosine; α-Methyltyrosine
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~5 mg/mL (~25.61 mM)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.1224 mL 25.6121 mL 51.2243 mL
5 mM 1.0245 mL 5.1224 mL 10.2449 mL
10 mM 0.5122 mL 2.5612 mL 5.1224 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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