| Size | Price | Stock | Qty |
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| 1mg |
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| Other Sizes |
| Targets |
Dopegal targets the lysosomal aspartic endopeptidase, also known as cathepsin D. It activates this enzyme, which promotes the aggregation of pathological tau protein in the locus coeruleus (LC), a brainstem nucleus that is the primary source of norepinephrine in the brain. The accumulation of pathological tau in the LC is an early neuropathological feature of Alzheimer's disease. Dopegal is neurotoxic. It can undergo further oxidation and cyclization to form neurotoxic compounds such as aminochromes. Its primary role is as a biomarker of norepinephrine metabolism and neuronal damage. It is also a potent inhibitor of the enzyme catechol-O-methyltransferase (COMT).
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| ln Vitro |
In vitro, Dopegal is a known neurotoxin. It induces oxidative stress and triggers apoptosis in cultured neuronal cell lines such as SH-SY5Y and PC12 cells. At concentrations of 10-100 uM, it significantly reduces cell viability and increases the production of reactive oxygen species (ROS). It also increases the aggregation of tau protein in tau-transfected HEK293 cells. It is a competitive inhibitor of COMT, the enzyme responsible for the O-methylation of catecholamines, with an IC₅0 in the low micromolar range. This leads to increased levels of norepinephrine and dopamine. Dopegal is also used as a substrate to measure the activity of aldehyde reductase (AKR1A1) and aldehyde dehydrogenase (ALDH), which convert it to 3,4-dihydroxyphenylethylene glycol (DOPEG) and 3,4-dihydroxymandelic acid (DOMA), respectively. These reactions are key steps in norepinephrine metabolism.
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| ln Vivo |
Dopegal is not a therapeutic drug; it is a neuroactive metabolite and a research standard. In vivo, it is formed in the brain by the action of monoamine oxidase (MAO) on norepinephrine. Elevated levels of Dopegal have been detected in the brain tissue of patients with Alzheimer's disease, particularly in the locus coeruleus (LC). It is used as a biomarker of catecholaminergic neuron degeneration and oxidative stress. It is not administered systemically. It can be detected in human plasma and urine, and its levels are altered in various neurological and cardiovascular disorders. It is also an impurity of Droxidopa, a drug used to treat neurogenic orthostatic hypotension.
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| Enzyme Assay |
Dopegal is not a standard enzyme inhibitor; it is a metabolite and an impurity. For analytical method development (AMV) and quality control (QC), the compound is used as a reference standard in HPLC. For the analysis of Droxidopa API (Active Pharmaceutical Ingredient), a sample is dissolved in the mobile phase and injected onto a C18 reverse-phase column. The mobile phase is phosphate buffer (pH 3.0) with methanol (80:20). The flow rate is 1.0 mL/min. Detection is by UV at 220 nm. The retention time of Dopegal is determined relative to the main peak of Droxidopa. The impurity is quantified by area normalization. The limit of quantification (LOQ) is 0.05% area. This protocol is for pharmaceutical quality control, not for biological studies.
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| Cell Assay |
Not applicable; Dopegal is not used in standard cell-based assays for drug discovery. For toxicity screening, SH-SY5Y or PC12 cells are seeded in 96-well plates (1×10⁴ cells/well) and treated with Dopegal (1-500 uM) for 24-48 h. Cell viability is measured by MTT assay. The CC₅0 is expected to be in the range of 25-100 uM, indicating moderate cytotoxicity. For COMT inhibition, the enzyme is incubated with a substrate (e.g., 3,4-dihydroxybenzoic acid) and S-adenosylmethionine (SAM) in the presence of Dopegal (1-1000 uM). The formation of the methylated product is measured by HPLC-ECD. The IC₅0 is calculated. The compound is used as a reference standard, not as a test agent.
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| Animal Protocol |
No in vivo animal protocol for Dopegal exists, as it is a biomarker and impurity standard, not a drug candidate. For neurochemical studies, Sprague-Dawley rats (200-250 g, n=6/group) are treated with a MAO inhibitor (e.g., pargyline, 50 mg/kg, IP). The animals are euthanized 2 h later. The brain is dissected, and the locus coeruleus (LC) is isolated. The concentration of Dopegal in the LC is measured by LC-MS/MS. A decrease in Dopegal levels confirms MAO inhibition. This protocol is for pharmacodynamic studies of MAO inhibitors, not for drug development. The compound is used as an analytical standard.
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| ADME/Pharmacokinetics |
As a small, polar molecule (MW 168.15, LogP ~ 0.5), Dopegal is not a drug, and its PK is not studied therapeutically. In vivo, it is rapidly metabolized by aldehyde reductase (AKR1A1) and aldehyde dehydrogenase (ALDH) to DOPEG and DOMA. The elimination half-life in the brain is estimated to be 1-2 hours. For research use, it is stored as a solid at -20degC. It is soluble in DMSO, methanol, and water. It is light and air sensitive. The compound is a reference standard for pharmaceutical impurity testing.
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| Toxicity/Toxicokinetics |
For Dopegal, hazard statements: H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation). Signal word: Warning. Precautionary statements: P261 (Avoid breathing dust/fume/gas/mist/vapors/spray), P280 (Wear protective gloves/protective clothing/eye protection/face protection), P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes). It is a suspected neurotoxin. For research use only. Not for human consumption.
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| References |
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| Additional Infomation |
Dopegal (3,4-Dihydroxyphenylglycolaldehyde; DOPEGAL; CAS# 13023-73-9) is a research-grade catecholaldehyde standard. It is not an FDA-approved drug. It is used as an impurity standard for the quality control (QC) of the pharmaceutical Droxidopa, as a reference standard for the analysis of catecholamine metabolites, and in neurochemistry research for the study of neurodegenerative diseases (Alzheimer's, Parkinson's). For research use only, not for diagnostic or therapeutic applications.
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| Molecular Formula |
C8H8O4
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|---|---|
| Molecular Weight |
168.15
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| Exact Mass |
168.042
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| CAS # |
13023-73-9
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| PubChem CID |
151725
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| Appearance |
Typically exists as solids at room temperature
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| Hydrogen Bond Donor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
12
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| Complexity |
159
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC(=C(C=C1C(C=O)O)O)O
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| InChi Key |
YUGMCLJIWGEKCK-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H8O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-4,8,10-12H
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| Chemical Name |
2-(3,4-dihydroxyphenyl)-2-hydroxyacetaldehyde
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.9471 mL | 29.7354 mL | 59.4707 mL | |
| 5 mM | 1.1894 mL | 5.9471 mL | 11.8941 mL | |
| 10 mM | 0.5947 mL | 2.9735 mL | 5.9471 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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