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N-Nitrosodicyclohexylamine (NDCHA)

Cat No.:V67640 Purity: ≥98%
N-Nitrosodicyclohexylamine (NDCHA) is an N-nitroso compound with anti-androgenic activity.
N-Nitrosodicyclohexylamine (NDCHA)
N-Nitrosodicyclohexylamine (NDCHA) Chemical Structure CAS No.: 947-92-2
Product category: Androgen Receptor
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
50mg
Other Sizes
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Product Description
N-Nitrosodicyclohexylamine (NDCHA) is an N-nitroso compound with anti-androgenic activity. N-Nitrosodicyclohexylamine (NDCHA) competitively binds to the androgen receptor (AR) to inhibit 5α-dihydrotestosterone and reduce AR protein levels.
N-Nitrosodicyclohexylamine (NDCHA) is an N-nitroso compound with anti-androgenic activity. It has a molecular formula of C₁₂H₂₂N₂O and a molecular weight of 210.32 g/mol. NDCHA is a carcinogenic agent and a novel anti-androgenic compound. It functions by competitively binding to the androgen receptor (AR) to inhibit the action of 5α-dihydrotestosterone and can reduce AR protein levels. It is primarily used in chemical research, toxicology studies, and as a reference standard in nitrosamine contamination analysis. It is intended for research and analytical use only.
Biological Activity I Assay Protocols (From Reference)
Targets
N-Nitrosodicyclohexylamine targets the androgen receptor (AR), functioning as a competitive antagonist. It competitively binds to the androgen receptor to inhibit the action of 5α-dihydrotestosterone (DHT), the active metabolite of testosterone. NDCHA can also reduce AR protein levels. As an N-nitroso compound, it is recognized for its potential carcinogenicity and is used as a reference standard in nitrosamine contamination analysis. Its anti-androgenic activity makes it a tool for studying androgen signaling and endocrine disruption.
ln Vitro
In vitro, N-Nitrosodicyclohexylamine has anti-androgenic activity, competitively binding to the androgen receptor to inhibit 5α-dihydrotestosterone action and reducing AR protein levels. Its activity is assessed in cell-based assays measuring AR-mediated transcriptional activity using AR-responsive reporter gene constructs. The compound's effects on cell proliferation and AR target gene expression are evaluated in AR-positive prostate cancer cell lines. Its anti-androgenic activity makes it a tool for studying androgen signaling and endocrine disruption.
ln Vivo
Specific in vivo activity data for N-Nitrosodicyclohexylamine are not extensively documented in the publicly available literature. As a carcinogenic agent with anti-androgenic activity, the compound has been studied in toxicology and carcinogenicity studies. It is recognized for its potential carcinogenicity and requires careful handling under controlled laboratory conditions. Its anti-androgenic effects may also be evaluated in vivo in models of endocrine disruption. Further studies are needed to fully characterize its in vivo effects.
Enzyme Assay
In vitro enzyme/receptor binding assays for N-Nitrosodicyclohexylamine typically involve competitive binding experiments using androgen receptor and radiolabeled or fluorescently labeled androgen as tracer. The compound's binding affinity to AR is assessed, with IC₅₀ values determined through dose-response binding experiments. Assays are conducted in buffered solutions at physiological pH with appropriate receptor preparations. Its antagonist activity is confirmed through functional assays measuring AR-mediated transcriptional inhibition using AR-responsive reporter gene constructs.
Cell Assay
In vitro cell-based assays for N-Nitrosodicyclohexylamine utilize AR-positive cell lines to assess its anti-androgenic activity. Cells are treated with varying concentrations of the compound for 24-72 hours. AR-mediated transcriptional activity is evaluated using reporter gene assays with androgen response element (ARE)-luciferase constructs. Cell proliferation is assessed using MTT or CCK-8 assays. AR protein levels are measured by Western blot. Standard cell culture conditions (37°C, 5% CO₂) with charcoal-stripped serum are employed.
Animal Protocol
In vivo animal studies with N-Nitrosodicyclohexylamine are typically conducted in toxicology and carcinogenicity studies. The compound is administered to rodents via oral or other routes to evaluate its carcinogenic potential and anti-androgenic effects. Endpoints include assessment of tumor incidence, measurement of androgen-sensitive parameters, evaluation of reproductive toxicity, and histopathological analysis. All procedures must comply with institutional animal care and use guidelines.
ADME/Pharmacokinetics
N-Nitrosodicyclohexylamine has a molecular weight of 210.32 g/mol and a molecular formula of C₁₂H₂₂N₂O. It appears as a pale yellow to orange oily liquid. The compound is used as a reference standard in nitrosamine contamination analysis. It is recognized for its potential carcinogenicity and requires careful handling under controlled laboratory conditions. The compound is typically stored under conditions recommended for analytical reference standards.
Toxicity/Toxicokinetics
N-Nitrosodicyclohexylamine is a known carcinogenic agent and requires careful handling under controlled laboratory conditions. As an analytical reference standard, it is used in trace quantities in quality control testing and does not present significant toxicological concerns at these levels when proper safety precautions are followed. Standard laboratory safety precautions should be observed when handling this compound, including the use of appropriate personal protective equipment and proper waste disposal procedures. The compound should be handled in well-ventilated areas.
References

[1]. (2006). Anti-Androgenic Activity of N-Nitrosodibenzylamine, N-Nitrosodiphenylamine and N-Nitrosodicyclohexylamine. JOURNAL OF HEALTH SCIENCE, 52(5), 522-531.

Additional Infomation
N-Nitrosodicyclohexylamine (NDCHA) (CAS#: 947-92-2) has a molecular formula of C₁₂H₂₂N₂O and a molecular weight of 210.32 g/mol. It is an N-nitroso compound with anti-androgenic activity, competitively binding to AR to inhibit 5α-dihydrotestosterone action and reducing AR protein levels. NDCHA is a carcinogenic agent and a novel anti-androgenic compound. It is used as a reference standard in nitrosamine contamination analysis. This compound is not a drug and is strictly a research and analytical reagent.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H22N2O
Molecular Weight
210.32
Exact Mass
210.173
CAS #
947-92-2
PubChem CID
13697
Appearance
White to light yellow solid powder
Density
1.15g/cm3
Boiling Point
352.9ºC at 760mmHg
Melting Point
95-97ºC
Flash Point
167.3ºC
Index of Refraction
1.582
LogP
3.635
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
2
Heavy Atom Count
15
Complexity
178
Defined Atom Stereocenter Count
0
SMILES
C1CCC(CC1)N(C2CCCCC2)N=O
InChi Key
CYMNKXLBEMEABS-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H22N2O/c15-13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h11-12H,1-10H2
Chemical Name
N,N-dicyclohexylnitrous amide
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 Data
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
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.7547 mL 23.7733 mL 47.5466 mL
5 mM 0.9509 mL 4.7547 mL 9.5093 mL
10 mM 0.4755 mL 2.3773 mL 4.7547 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:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • 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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • 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)
  • Click the “Calculate” button
  • 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
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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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