| Size | Price | |
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| 500mg | ||
| Other Sizes |
| Targets |
5,6-Dihydroxyindole targets catechol O-methyltransferase (COMT), an enzyme that catalyzes the O-methylation of catecholamines. By inhibiting COMT, the compound affects the metabolism of dopamine and other catecholamines. Additionally, 5,6-dihydroxyindole is a key intermediate in melanogenesis, the production of melanin pigment. It is a substrate for tyrosinase and other enzymes involved in melanin synthesis. Its role in melanin biosynthesis makes it relevant for studying skin pigmentation and related disorders.
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| ln Vitro |
5,6-Dihydroxyindole (1, 10, 20, 50, 100 μM; for 4 hours) decreased OD492 readings in a dose-dependent manner. For four hours, 1.0 mM 5,6-dihydroxyindole was used as a pretreatment on Sf9 cells. 97% of the population died. The LC50 values in the culture medium were 131.8 μM and 20.3 μM, respectively, in the buffer [1]. The baculovirus stock produced nearly no recombinant protein after three hours of preincubation with 1.25 mM 5,6-dihydroxyindole. Eggs of the wasp Microplitis demolitor and the lambda phage have LC50 values of 111.0 μM and 5.6 μM, respectively [1]. Additionally effective against viruses and parasitic wasps are 5,6-dihydroxyindole and its spontaneous oxidation products [1].
5,6-Dihydroxyindole exhibits in vitro activity as a COMT inhibitor and a melanin precursor. As a COMT inhibitor, it can modulate dopamine metabolism in vitro. As a melanin precursor, it is used in studies of melanogenesis, where its oxidation leads to the formation of melanin pigments. These in vitro activities confirm its utility as a research tool for studying neurotransmitter metabolism and skin pigmentation. |
| ln Vivo |
In vivo activity of 5,6-Dihydroxyindole has been studied in the context of melanin biosynthesis and pigmentation. As a key intermediate in melanogenesis, it is involved in the production of melanin in the skin and hair. Its role as a COMT inhibitor may also affect dopamine metabolism in vivo. The compound's effects on pigmentation have been studied in animal models of vitiligo and melanoma. Further studies are needed to fully characterize its therapeutic potential.
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| Enzyme Assay |
In vitro enzyme assays for 5,6-Dihydroxyindole involve measuring its inhibition of catechol O-methyltransferase (COMT) activity. These assays typically use recombinant COMT and a catechol substrate, such as dopamine or epinephrine. The enzyme is incubated with the substrate and varying concentrations of 5,6-dihydroxyindole. The production of the O-methylated product is measured to determine the IC50. Additionally, the compound's role in melanogenesis can be studied using tyrosinase activity assays, where the oxidation of 5,6-dihydroxyindole is monitored spectrophotometrically.
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| Cell Assay |
In vitro cellular assays for 5,6-Dihydroxyindole are conducted in melanocytes or melanoma cell lines. Cells are treated with the compound at various concentrations, and melanin production is measured spectrophotometrically. COMT activity is assessed in cell lysates. Cell viability and proliferation are assessed to determine the compound's effects on cell growth. These assays characterize the compound's activity in pigment-producing cells.
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| Animal Protocol |
In vivo animal experiments with 5,6-Dihydroxyindole are conducted in mouse models of pigmentation disorders, such as vitiligo or melanoma. The compound may be administered topically or by injection. Skin pigmentation is assessed visually or by measuring melanin content. Tumor growth is measured in melanoma models. These studies evaluate the compound's effects on pigmentation and its potential therapeutic applications.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Dihydroxy-1H-indole's known metabolites include dihydroxy-1H-indole glucuronide I. Pharmacokinetic data for 5,6-Dihydroxyindole are limited. The compound has a molecular weight of 149.15 and is soluble in DMSO. Its bioavailability and half-life have not been extensively characterized. The compound is typically stored at -20°C. Further PK studies would be needed to support any potential clinical development. |
| Toxicity/Toxicokinetics |
5,6-Dihydroxyindole is considered to have low toxicity based on its use as a research compound and its occurrence as an endogenous metabolite. However, comprehensive toxicological evaluations have not been extensively published. The compound is intended for research use only and is not approved for human therapeutic use. Standard laboratory safety precautions should be followed when handling this compound.
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| References |
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| Additional Infomation |
5,6-Dihydroxyindole is a dihydroxyindole. It plays a metabolic role in mice. It has been reported that 5,6-dihydroxyindole has been detected in both Homo sapiens and Trypanosoma brevicornu, and relevant data are available for reference.
5,6-Dihydroxyindole (DHI) is an endogenous indole compound and a key intermediate in the biosynthesis of melanin. It is also known as 1H-indole-5,6-diol. The compound is a catechol O-methyltransferase (COMT) inhibitor and a dopamine metabolite. 5,6-Dihydroxyindole is of significant interest in research related to pigment formation, skin biology, and disorders of pigmentation such as vitiligo and melanoma. It is available in high purity (≥95%) for research applications. |
| Molecular Formula |
C₈H₇NO₂
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|---|---|
| Molecular Weight |
149.15
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| Exact Mass |
149.047
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| CAS # |
3131-52-0
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| Related CAS # |
25656-67-1
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| PubChem CID |
114683
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| Appearance |
Off-white to light brown solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
411.2±25.0 °C at 760 mmHg
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| Flash Point |
202.5±23.2 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.802
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| LogP |
0.37
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
11
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| Complexity |
151
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
SGNZYJXNUURYCH-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H7NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h1-4,9-11H
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| Chemical Name |
1H-indole-5,6-diol
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| Synonyms |
5,6Dihydroxyindole; 5,6 Dihydroxyindole
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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 Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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) |
DMSO : ~50 mg/mL (~335.23 mM)
H2O : < 0.1 mg/mL |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.25 mg/mL (8.38 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1.25 mg/mL (8.38 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 1.25 mg/mL (8.38 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.7047 mL | 33.5233 mL | 67.0466 mL | |
| 5 mM | 1.3409 mL | 6.7047 mL | 13.4093 mL | |
| 10 mM | 0.6705 mL | 3.3523 mL | 6.7047 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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