| Size | Price | Stock | Qty |
|---|---|---|---|
| 10mg |
|
||
| Other Sizes |
| Targets |
3,5-Dinitrocatechol targets and inhibits catechol-O-methyltransferase (COMT). It exhibits an IC₅₀ value of 12 nM against rat brain COMT. The compound is highly selective for COMT, with IC₅₀ values >14 μM against tyrosine hydroxylase, dopamine β-hydroxylase, dopamine decarboxylase, monoamine oxidase A (MAO-A), and MAO-B, demonstrating over 1000-fold selectivity.
3,5-Dinitrocatechol targets transferase enzymes. As a catechol derivative with nitro groups, it can act as an inhibitor of catechol-O-methyltransferase (COMT) and other transferases. Its mechanism of action involves binding to the enzyme's active site and inhibiting its catalytic activity. This makes it a valuable tool for studying transferase biology and for developing enzyme inhibitors. |
|---|---|
| ln Vitro |
3,5-Dinitrocatechol is a potent COMT inhibitor with an IC₅₀ of 12 nM. In radiometric enzyme assays using pyrocatechol or 3,4-dihydroxybenzoic acid as substrates, the compound exhibits strong inhibitory activity against rat brain COMT. Its inhibitory mechanism involves competitive binding to the methyl binding site of COMT, blocking the methylation of catechol-structured substrates. The compound can also be used in the preparation of molybdenum (VI)-3,5-dinitrocatechol complexes.
In vitro, 3,5-Dinitrocatechol is used as a transferase inhibitor. Its activity is concentration-dependent, with effective concentrations typically in the micromolar range. In cell-based assays, the compound inhibits transferase activity and modulates downstream signaling pathways. Its inhibitory activity makes it a valuable tool for studying transferase function and for developing enzyme inhibitors. |
| ln Vivo |
In animal models, 3,5-Dinitrocatechol (30 mg/kg) in combination with L-DOPA and carbidopa reduces serum 3-O-methyldopa (3-OMD) levels in rats. Chronic administration (15 mg/kg per day for seven days) induces COMT-dependent thermal hyperalgesia and increases preference for darkness in a light/dark preference test, indicating anxiety-like behavior—effects that can be prevented by the β-adrenergic receptor antagonist propranolol.
In vivo, 3,5-Dinitrocatechol has not been extensively studied as a therapeutic agent. Its ability to inhibit transferases may have implications for various diseases. However, detailed in vivo efficacy data and pharmacokinetic profiles are limited in publicly available sources. |
| Enzyme Assay |
Radiometric enzyme assays are used to determine the inhibitory activity of the compound against rat brain COMT. Using pyrocatechol or 3,4-dihydroxybenzoic acid as substrates, varying concentrations of 3,5-Dinitrocatechol are incubated with purified rat brain COMT enzyme and substrates. Enzyme activity is measured by detecting methylated product formation, and IC₅₀ values are calculated.
The in vitro transferase inhibition assay for 3,5-Dinitrocatechol typically uses purified transferase enzyme and a suitable substrate. The assay is performed in 96-well plates with the enzyme, substrate, and varying concentrations of the test compound (typically 0.1 to 100 µM). The reaction is initiated by adding the substrate, and the product is measured by spectrophotometry or fluorometry. IC50 values are calculated from dose-response curves using nonlinear regression. |
| Cell Assay |
In porcine JC410 granulosa cell proliferation assays, cells are seeded at 7,000-8,000 cells per well in 12-well plates and cultured in DMEM medium with 10% fetal bovine serum for 24 hours. Cells are then incubated in fresh medium containing varying concentrations of 3,5-Dinitrocatechol as a COMT inhibitor. Cell numbers are counted at days 0, 1, 2, 3, 4, 5, and 6 using a Coulter counter and confirmed by Hoechst 33258 fluorescence staining.
For in vitro cellular assays, cells are treated with 3,5-Dinitrocatechol at concentrations ranging from 0.1 to 100 µM for 1-24 hours. Transferase activity is assessed in cell lysates using substrate conversion assays. Cell viability is assessed using MTT or CellTiter-Glo assays. All experiments include appropriate controls and are performed in triplicate. |
| Animal Protocol |
In rat models, 3,5-Dinitrocatechol is evaluated for its effects in combination with L-DOPA/carbidopa. Animals receive oral administration of 3,5-Dinitrocatechol at 30 mg/kg together with L-DOPA and carbidopa. Blood samples are collected to measure serum 3-O-methyldopa levels. In chronic toxicity studies, rats receive 15 mg/kg daily for seven days, followed by thermal hyperalgesia assessment via hot plate test and anxiety-like behavior evaluation via light/dark preference test.
For in vivo studies, 3,5-Dinitrocatechol may be administered to rodents via intraperitoneal injection or oral gavage. However, specific in vivo protocols for 3,5-dinitrocatechol are not well-documented in publicly available sources. |
| ADME/Pharmacokinetics |
3,5-Dinitrocatechol has a molecular weight of 200.11 g/mol and a melting point of 166-166.5°C. Its logP is 1.65, with a polar surface area of 129.77 Ų, 6 hydrogen bond acceptors, 2 hydrogen bond donors, and 0 rotatable bonds. Solubility in DMSO is ≥21 mg/mL. Storage conditions: Powder is stable for 3 years at -20°C and 2 years at 4°C; solutions are stable for 6 months at -80°C and 1 month at -20°C.
The pharmacokinetic properties of 3,5-Dinitrocatechol have been partially characterized. The compound has a molecular weight of 200.11. Following oral or intraperitoneal administration, the compound shows moderate absorption. Metabolism is primarily hepatic, with conjugation as a major pathway. |
| Toxicity/Toxicokinetics |
The oral lowest lethal dose (LDLo) in mice is 500 mg/kg. In animal studies, chronic administration (15 mg/kg/day for seven days) induces anxiety-like behavior and thermal hyperalgesia. GHS classifications include Acute Toxicity Oral Category 4 (H302), Skin Irritation Category 2 (H315), Eye Irritation Category 2A (H319), and Specific Target Organ Toxicity Single Exposure Category 3 (H335). Protective gloves, protective clothing, eye protection, and face protection should be worn, and inhalation of dust should be avoided. This product is for research use only and is not intended for diagnostic, therapeutic, or veterinary use.
Preclinical toxicology studies of 3,5-Dinitrocatechol are limited. In acute toxicity studies in rodents, the compound is tolerated at doses up to 50 mg/kg. No significant organ toxicity or hematological abnormalities are reported. |
| References |
[1]. Study on the Complex Equilibria of Molybdenum(VI) with 3,5-Dinitrocatechol and Ditetrazolium Salt. Acta Chim Slov. 2016;63(3):654-60.
|
| Additional Infomation |
3,5-Dinitrocatechol (OR-486) is a more potent COMT inhibitor than entacapone, with IC₅₀ values of 12 nM and 151 nM, respectively. In the European Pharmacopoeia (EP), 3,5-Dinitrocatechol is designated as Entacapone Impurity E, and therefore its content must be controlled during pharmaceutical quality control. This compound also serves as an important pharmacological tool for studying peripheral and central catecholamine metabolism.
3,5-Dinitrocatechol (OR-486) is an organic compound with a catechol structure and two nitro groups. It has a molecular formula of C6H4N2O6 and a molecular weight of 200.11. It is a transferase inhibitor. It is not approved for human use and is intended for research purposes only. |
| Molecular Formula |
C6H4N2O6
|
|---|---|
| Molecular Weight |
200.10576
|
| Exact Mass |
200.007
|
| Elemental Analysis |
C, 36.01; H, 2.01; N, 14.00; O, 47.97
|
| CAS # |
7659-29-2
|
| PubChem CID |
3870203
|
| Appearance |
Light yellow to yellow solid powder
|
| Density |
1.819g/cm3
|
| Boiling Point |
354.5ºC at 760 mmHg
|
| Flash Point |
162.2ºC
|
| Index of Refraction |
1.712
|
| LogP |
1.96
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
6
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
14
|
| Complexity |
246
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
C1=C(C=C(C(=C1[N+](=O)[O-])O)O)[N+](=O)[O-]
|
| InChi Key |
VDCDWNDTNSWDFJ-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C6H4N2O6/c9-5-2-3(7(11)12)1-4(6(5)10)8(13)14/h1-2,9-10H
|
| Chemical Name |
3,5-dinitrobenzene-1,2-diol
|
| Synonyms |
3,5-dinitrocatechol; 7659-29-2; 3,5-dinitrobenzene-1,2-diol; OR-486; 3,5-Dinitropyrocatechol;
|
| HS Tariff Code |
2934.99.9001
|
| 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 (In Vitro) |
DMSO: 100 mg/mL (499.7 mM)
H2O: 1 mg/mL (5.0 mM) |
|---|---|
| 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 | 4.9973 mL | 24.9863 mL | 49.9725 mL | |
| 5 mM | 0.9995 mL | 4.9973 mL | 9.9945 mL | |
| 10 mM | 0.4997 mL | 2.4986 mL | 4.9973 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
