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NADPH tetracyclohexanamine

Alias: Dihydronicotinamide-adenine dinucleotide phosphate; cyclohexyl ammonium salt; NADPH cyclohexyl ammonium salt; NADPH Cy4N
Cat No.:V34159 Purity: ≥98%
NADPH tetracyclohexanamine (NADPH;β-NADPH; TPNH), thetetracyclohexanamine salt form of NADPH (β-Nicotinamide adenine dinucleotide phosphate),is a potent cofactor and biological reducing agent, alsoan electron donor and a cofactor for nitric oxide synthetase.
NADPH tetracyclohexanamine
NADPH tetracyclohexanamine Chemical Structure CAS No.: 100929-71-3
Product category: Ferroptosis
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
25mg
50mg
100mg
250mg
Other Sizes

Other Forms of NADPH tetracyclohexanamine:

  • NADPH tetrasodium salt
Official Supplier of:
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Product Description
NADPH tetracyclohexanamine (NADPH;β-NADPH; TPNH), thetetracyclohexanamine salt form of NADPH (β-Nicotinamide adenine dinucleotide phosphate),is a potent cofactor and biological reducing agent, as well as an electron donor and a cofactor for nitric oxide synthase.
NADPH tetracyclohexanamine (CAS# 100929-71-3), also known as β-NADPH or TPNH, is the tetracyclohexanamine salt form of NADPH (β-nicotinamide adenine dinucleotide phosphate). It is a ubiquitous cofactor and biological reducing agent, an electron donor, and a cofactor for nitric oxide synthetase. The compound plays a vital role in the biosynthesis of fatty acids, chiral alcohols, and biopolymers.
Biological Activity I Assay Protocols (From Reference)
Targets
Human Endogenous Metabolite
NADPH tetracyclohexanamine targets numerous enzymes that require NADPH as a cofactor. It is an essential electron donor for reductive biosynthesis (fatty acids, cholesterol, nucleotides) and antioxidant defense (glutathione reductase, thioredoxin reductase). It also serves as a cofactor for cytochrome P450 enzymes and nitric oxide synthase. The tetracyclohexanamine salt form enhances the compound's stability and solubility.
ln Vitro
In vitro, NADPH tetracyclohexanamine is used as a cofactor in enzymatic assays and cell-free systems. It is an endogenous inhibitor of ferroptosis and plays a vital role in the biosynthesis of fatty acids and biopolymers. The compound is also required for lipid biosynthesis, biomass formation, and cell replication. Its activity as a reducing agent has been characterized in various biochemical assays.
ln Vivo
In vivo, NADPH is essential for numerous metabolic processes, including fatty acid biosynthesis, cholesterol synthesis, and antioxidant defense. The NADP⁺/NADPH redox pair facilitates electron transfer in anabolic reactions and protects against reactive oxygen species accumulation. The tetracyclohexanamine salt is used in research to study NADPH-dependent processes in animal models.
Enzyme Assay
For in vitro enzyme assays, NADPH tetracyclohexanamine is used as a cofactor for NADPH-dependent enzymes. The enzyme is incubated with the substrate and varying concentrations of NADPH tetracyclohexanamine in a suitable buffer. Enzyme activity is measured by monitoring the consumption of NADPH (absorbance at 340 nm) or the production of the reaction product using spectrophotometric or fluorometric methods.
Cell Assay
For in vitro cell-based assays, NADPH tetracyclohexanamine is typically used to supplement cell culture media for NADPH-dependent studies. Cells are treated with the compound at various concentrations (typically 0.1-10 mM) for 1-24 hours. Cellular NADPH levels are measured using enzymatic cycling assays or LC-MS. Oxidative stress markers are assessed using fluorescent probes. Lipid biosynthesis can be measured by incorporating radiolabeled acetate.
Animal Protocol
For in vivo animal experiments, NADPH tetracyclohexanamine is typically administered intraperitoneally or intravenously to rodents. The compound is given at doses ranging from 10-100 mg/kg. Blood and tissue samples are collected to measure NADPH levels and redox status. The compound's effects on lipid biosynthesis, antioxidant defense, and other NADPH-dependent processes can be evaluated.
ADME/Pharmacokinetics
NADPH tetracyclohexanamine has a molecular weight of 1142.12 g/mol and formula C₄₅H₈₂N₁₁O₁₇P₃. The tetracyclohexanamine salt form is stable and soluble in aqueous solutions. The compound is typically stored at 4°C in a sealed container away from moisture. Its pharmacokinetics are determined by the stability and distribution of the NADPH molecule itself.
Toxicity/Toxicokinetics
Toxicological data for NADPH tetracyclohexanamine are limited. As an endogenous cofactor, NADPH is non-toxic at physiological concentrations. The tetracyclohexanamine salt may have different toxicity profiles, but comprehensive studies have not been reported. The compound is classified as a research-grade reagent and is not for human therapeutic use. Standard laboratory safety practices should be followed when handling.
Additional Infomation
NADPH tetracyclohexanamine is a research-use only compound and has not been approved for clinical applications. It is also known as β-NADPH and TPNH. Its molecular weight is 1142.12, and its formula is C₄₅H₈₂N₁₁O₁₇P₃. The compound is used as a cofactor in biochemical assays and as a research tool to study NADPH-dependent metabolic processes. It is available from various research chemical suppliers.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H30N7O17P3.4[C6H13N]
Molecular Weight
1142.11748
Exact Mass
1141.51
Elemental Analysis
C, 47.32; H, 7.24; N, 13.49; O, 23.81; P, 8.14
CAS #
100929-71-3
Related CAS #
NADPH tetrasodium salt;2646-71-1
PubChem CID
71312102
Appearance
White to light yellow solid powder
LogP
6.562
Hydrogen Bond Donor Count
13
Hydrogen Bond Acceptor Count
26
Rotatable Bond Count
13
Heavy Atom Count
76
Complexity
1450
Defined Atom Stereocenter Count
8
SMILES
NC1=C2C(N([C@H]3[C@H](OP(O)(O)=O)[C@H](O)[C@@H](COP(OP(O)(OC[C@@H]4[C@@H](O)[C@@H](O)[C@H](N5C=C(C(N)=O)CC=C5)O4)=O)(O)=O)O3)C=N2)=NC=N1.NC6CCCCC6.NC7CCCCC7.NC8CCCCC8.NC9CCCCC9
InChi Key
PTKRUDMLGIIORX-ITGWJZMWSA-N
InChi Code
InChI=1S/C21H30N7O17P3.4C6H13N/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32;4*7-6-4-2-1-3-5-6/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35);4*6H,1-5,7H2/t10-,11-,13-,14-,15-,16-,20-,21-;;;;/m1..../s1
Chemical Name
[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate;cyclohexanamine
Synonyms
Dihydronicotinamide-adenine dinucleotide phosphate; cyclohexyl ammonium salt; NADPH cyclohexyl ammonium salt; NADPH Cy4N
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: Please store this product in a sealed and protected environment, 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)
Solubility Data
Solubility (In Vitro)
H2O: ≥100 mg/mL (~87.6 mM)
DMSO: ≥84 mg/mL (`73.6 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
(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 0.8756 mL 4.3778 mL 8.7556 mL
5 mM 0.1751 mL 0.8756 mL 1.7511 mL
10 mM 0.0876 mL 0.4378 mL 0.8756 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

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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?
  • 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)
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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:
  • 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:
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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.

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  • 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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