| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| Other Sizes |
| Targets |
3-O-Methyldopa primarily targets the enzyme catechol-O-methyltransferase (COMT), as it is a product of this enzyme's activity. It also interacts with the pharmacodynamics of L-DOPA and dopamine, competitively inhibiting their effects. This interaction can impact dopamine replacement therapies by competing with L-DOPA for transport and receptor binding.
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| ln Vitro |
In cell-free systems, 3-O-Methyldopa is used to study the activity of COMT. It is a substrate for the enzyme, and its formation from L-DOPA can be measured. Additionally, it can be used in competition assays to study the binding of L-DOPA and dopamine to their targets, as it competitively inhibits their pharmacodynamics. In cellular assays, 3-O-Methyldopa is studied for its effects on dopamine metabolism and signaling. It can compete with L-DOPA for transport into cells and for binding to dopamine receptors, thereby modulating dopaminergic activity. Its accumulation is a concern in Parkinson's disease patients on L-DOPA therapy, as it may contribute to reduced efficacy and increased side effects.
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| ln Vivo |
In vivo, 3-O-Methyldopa is a significant metabolite of L-DOPA. Its levels increase in patients treated with L-DOPA, and it has a long half-life. It competes with L-DOPA for transport across the blood-brain barrier and may interfere with the therapeutic effects of L-DOPA in Parkinson's disease. Animal models are used to study its pharmacokinetics and pharmacodynamics.
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| Enzyme Assay |
Cell-free assays for 3-O-Methyldopa typically involve measuring COMT activity. The enzyme is incubated with L-DOPA and a methyl donor, and the formation of 3-O-Methyldopa is quantified, often by HPLC or LC-MS. Competition assays can also be performed to study its interaction with L-DOPA and dopamine receptors.
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| Cell Assay |
Cellular assays for 3-O-Methyldopa can be conducted using neuronal cell lines. Cells are treated with the compound, and its effects on dopamine uptake, receptor binding, and signaling are measured. These studies help to elucidate its role in modulating dopaminergic neurotransmission.
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| Animal Protocol |
The pharmacokinetics of 3-O-Methyldopa are characterized by a long half-life, as it is not readily metabolized by COMT and is poorly cleared by the kidneys. It competes with L-DOPA for transport across the blood-brain barrier, which can reduce the effectiveness of L-DOPA therapy in Parkinson's disease.
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| Toxicity/Toxicokinetics |
Toxicity Summary
Methoxytyrosine is one of the main biochemical markers of aromatic L-amino acid decarboxylase deficiency, a congenital metabolic defect that affects the biosynthesis of serotonin and dopamine. Elevated levels of 3-methoxytyrosine are found in cerebrospinal fluid, plasma, and urine. Catechol-O-methyltransferase, the enzyme responsible for the production of 3-methoxytyrosine, is derived from levodopa in many organs. However, its half-life (approximately 15 hours) is longer than that of levodopa (approximately 1 hour). This means it accumulates in the plasma and brain tissue of patients receiving long-term levodopa treatment (e.g., those with Parkinson's disease). 3-Methoxytyrosine has some influence on levodopa-related motor dysfunction, including inhibiting striatal tyrosine uptake, competing with levodopa for transport along the blood-brain barrier, and inhibiting dopamine release. 3-Methoxytyrosine also increases homocysteine levels, an amino acid that can induce cardiovascular disease and neuronal damage. Other toxic effects may include oxidative DNA damage (which can lead to cell death), decreased motility, and reduced mitochondrial membrane potential. (Wikipedia) 3-O-Methyldopa is a metabolite and is not a therapeutic agent. Its accumulation in patients on L-DOPA therapy can be associated with side effects and reduced efficacy. It is not considered toxic in the traditional sense, but its interference with dopamine replacement therapy is a significant clinical concern. |
| References | |
| Additional Infomation |
3-O-methyldopa is a derivative of L-tyrosine, specifically a 3-methoxy derivative of L-DOPA. It plays a metabolic role in the human body. It is an L-tyrosine derivative, a monomethoxybenzene, and a non-protein-derived L-α-amino acid. Functionally, it is related to L-DOPA. It is a zwitterion tautomer of 3-O-methyldopa.
3-O-Methyldopa is a research compound used to study L-DOPA metabolism, catecholamine regulation, and the impact of COMT activity on dopamine replacement therapies. It is a key metabolite in the pharmacokinetics of L-DOPA and is studied to improve the treatment of Parkinson's disease. It is not approved for clinical use. |
| Molecular Formula |
C10H13NO4
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|---|---|
| Molecular Weight |
211.21
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| Exact Mass |
211.084
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| CAS # |
300-48-1
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| Related CAS # |
3-O-Methyl-DL-DOPA;7636-26-2;3-O-Methyldopa-d3;586954-09-8;3-O-Methyldopa-d3 hydrate
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| PubChem CID |
9307
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.321g/cm3
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| Boiling Point |
407.3ºC at 760mmHg
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| Flash Point |
200.1ºC
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| Index of Refraction |
1.591
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| LogP |
1.055
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
15
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| Complexity |
222
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| Defined Atom Stereocenter Count |
1
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| SMILES |
COC1=C(C=CC(=C1)C[C@@H](C(=O)O)N)O
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| InChi Key |
PFDUUKDQEHURQC-ZETCQYMHSA-N
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| InChi Code |
InChI=1S/C10H13NO4/c1-15-9-5-6(2-3-8(9)12)4-7(11)10(13)14/h2-3,5,7,12H,4,11H2,1H3,(H,13,14)/t7-/m0/s1
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| Chemical Name |
(2S)-2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoic acid
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
H2O: 16.67 mg/mL (78.93 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 10 mg/mL (47.35 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.7346 mL | 23.6731 mL | 47.3462 mL | |
| 5 mM | 0.9469 mL | 4.7346 mL | 9.4692 mL | |
| 10 mM | 0.4735 mL | 2.3673 mL | 4.7346 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.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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