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2,3-Diaminonaphthalene

Cat No.:V29364 Purity: ≥98%
2,3-Diaminonaphthalene is a selective colorimetric and fluorescent reagent that can be used for selenium detection and fluorometric determination of nitrite.
2,3-Diaminonaphthalene
2,3-Diaminonaphthalene Chemical Structure CAS No.: 771-97-1
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
2,3-Diaminonaphthalene is a selective colorimetric and fluorescent reagent that can be used for selenium detection and fluorometric determination of nitrite.
2,3-Diaminonaphthalene (CAS# 771-97-1) is an electron-rich, polycyclic aromatic diamine with a molecular weight of 158.2 and a molecular formula of C10H10N2. It is a highly selective colorimetric and fluorometric reagent, widely used in analytical chemistry for the determination of nitrite/nitrate levels in biological fluids and cellular extracts as an indicator of nitric oxide (NO) activity. It is also used for the quantitative detection of selenium at low concentrations.
Biological Activity I Assay Protocols (From Reference)
Targets
2,3-Diaminonaphthalene does not have a specific pharmacological target but serves as a chemical reagent. It reacts with nitrite under acidic conditions to form the highly fluorescent triazole derivative 2,3-naphthotriazole, which is the basis for its use in nitrite detection and NO activity assays. It also forms stable complexes with transition metals and reacts with carbonyl compounds.
ln Vitro
Poly(2,3-diaminonaphthalene) microspheres are being employed as novel quenchers for fluorescence-enhanced nucleic acid detection [1]. DAN, or 2,3-diaminonaphthalene, has the potential to cause cancer [2].
In vitro, 2,3-Diaminonaphthalene is used as a fluorometric reagent for the determination of nitrite in biological samples. It is also utilized for the detection of selenium, ketones, and alpha-keto acids. Its strong nucleophilic character allows it to form stable complexes with transition metals and react readily with carbonyl compounds, making it valuable in organic synthesis and coordination chemistry.
ln Vivo
2,3-Diaminonaphthalene is not administered as a therapeutic agent in vivo. Its utility is limited to in vitro and ex vivo applications as an analytical reagent for detecting nitrite, nitrate, and selenium in biological and environmental samples.
Enzyme Assay
In vitro assays using 2,3-Diaminonaphthalene are based on its reaction with nitrite under acidic conditions to form a highly fluorescent triazole product. The fluorescence intensity is measured at excitation/emission wavelengths of ~365/415 nm. Samples (biological fluids, cellular extracts) are treated with the reagent, and the fluorescence is quantified against a standard curve. Selenium detection involves a similar fluorometric approach.
Cell Assay
Cellular assays for 2,3-Diaminonaphthalene involve the measurement of nitrite/nitrate levels in cell culture supernatants or lysates as an indicator of nitric oxide (NO) production. Cells are treated with stimulants (e.g., LPS, cytokines) to induce NO production. The culture medium is collected, and nitrite is measured using the 2,3-diaminonaphthalene fluorometric assay.
Animal Protocol
2,3-Diaminonaphthalene is not used in in vivo animal studies as a therapeutic agent. It may be used in ex vivo applications to measure nitrite/nitrate levels in tissue homogenates or biological fluids collected from animal studies.
ADME/Pharmacokinetics
2,3-Diaminonaphthalene is a chemical reagent and does not have pharmacokinetic properties as a drug. It is not administered systemically.
Toxicity/Toxicokinetics
2,3-Diaminonaphthalene is a chemical reagent and is not intended for human consumption. Standard laboratory safety precautions should be followed. It may cause skin and eye irritation. No significant toxicity data are available for this compound as a therapeutic agent.
References

[1]. Poly(2,3-diaminonaphthalene) microspheres as a novel quencher for fluorescence-enhanced nucleic acid detection. Analyst. 2011 Jun 7;136(11):2221-4.

[2]. Immobilization and characterization of 2,3-diaminonaphthalene/cyclodextrin complexes in a sol-gel matrix: a new fluorimetric sensor for nitrite. J Fluoresc. 2009 Jan;19(1):119-25.

[3]. Effects of aminosalicylates and immunosuppressive agents on nitric oxide-dependent N-nitrosation reactions. Biochem Pharmacol. 1994 May 18;47(10):1897-902.

Additional Infomation
2,3-Diaminonaphthalene (DAN) is a highly selective colorimetric and fluorometric reagent for the determination of nitrite and selenium. It is widely used in analytical chemistry and biological research to measure nitrite/nitrate levels as an indicator of nitric oxide (NO) activity. It has a molecular weight of 158.2 and formula C10H10N2. It is not a drug and has no clinical applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H10N2
Molecular Weight
158.1998
Exact Mass
158.084
CAS #
771-97-1
PubChem CID
69872
Appearance
Light yellow to brown solid powder
Density
1.2±0.1 g/cm3
Boiling Point
370.6±15.0 °C at 760 mmHg
Melting Point
197-203 °C
Flash Point
212.3±19.9 °C
Vapour Pressure
0.0±0.8 mmHg at 25°C
Index of Refraction
1.757
LogP
1.28
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
0
Heavy Atom Count
12
Complexity
140
Defined Atom Stereocenter Count
0
InChi Key
XTBLDMQMUSHDEN-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H10N2/c11-9-5-7-3-1-2-4-8(7)6-10(9)12/h1-6H,11-12H2
Chemical Name
naphthalene-2,3-diamine
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

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
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)
DMSO : ~100 mg/mL (~632.11 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (15.80 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 25.0 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: ≥ 2.5 mg/mL (15.80 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 25.0 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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.3211 mL 31.6056 mL 63.2111 mL
5 mM 1.2642 mL 6.3211 mL 12.6422 mL
10 mM 0.6321 mL 3.1606 mL 6.3211 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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