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2-Amino-5-phenylpyridine

Alias: 2Amino5phenylpyridine; 2 Amino 5 phenylpyridine
Cat No.:V38761 Purity: ≥98%
2-Amino-5-phenylpyridine is a mutagenic heterocyclic aromatic amine formed by the pyrolysis of phenylalanine in proteins.
2-Amino-5-phenylpyridine
2-Amino-5-phenylpyridine Chemical Structure CAS No.: 33421-40-8
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
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Product Description
2-Amino-5-phenylpyridine is a mutagenic heterocyclic aromatic amine formed by the pyrolysis of phenylalanine in proteins. 2-Amino-5-phenylpyridine is found in foods like grilled sardines and is potentially carcinogenic.
2-Amino-5-phenylpyridine is a heterocyclic aromatic amine. It has a molecular formula of C11H10N2 and a molecular weight of 170.21. It is formed by the pyrolysis of phenylalanine in proteins and is found in cooked foods, such as broiled sardines. It is considered potentially carcinogenic and is used as a synthetic intermediate for the construction of various bioactive molecules.
Biological Activity I Assay Protocols (From Reference)
Targets
2-Amino-5-phenylpyridine does not have a specific therapeutic target. As a mutagenic heterocyclic amine, it is known to induce mutations at the molecular level, potentially leading to various cellular effects. Its primary relevance is in toxicology and food safety as a potential carcinogen.
ln Vitro
However, 5-phenyl-2-pyridylamine (PPA) shares a lot of structural similarities with aminobiphenyls, a different class of well-known aromatic amines that cause cancer [2].
In vitro, 2-amino-5-phenylpyridine is used as a model mutagenic compound. Its mutagenic properties can be assessed using the Ames test (Salmonella typhimurium assay). It can also be used to study the mechanisms of DNA adduct formation and mutagenesis. It serves as a key synthetic intermediate for constructing bioactive molecules.
ln Vivo
In vivo, 2-amino-5-phenylpyridine is not used as a therapeutic agent. Its presence in the diet is a concern for its potential carcinogenic effects. It is metabolically activated to form DNA adducts, which can lead to mutations and cancer.
Enzyme Assay
Non-cellular assays for 2-amino-5-phenylpyridine include the Ames test, which uses Salmonella typhimurium strains to detect its mutagenic potential. It can also be used in assays to study its metabolic activation by cytochrome P450 enzymes, where it is incubated with liver microsomes and DNA to detect adduct formation.
Cell Assay
2-Amino-5-phenylpyridine is not typically used in standard pharmacological cellular assays. Its effects on cells are studied in the context of genotoxicity. Cellular assays may measure its ability to induce DNA damage (e.g., comet assay, γ-H2AX foci) or mutations in mammalian cell lines.
Animal Protocol
In vivo animal experiments with 2-amino-5-phenylpyridine are conducted to study its carcinogenic potential. Rodents are fed the compound, and the incidence of tumors in various organs is monitored over time. These studies help assess the risk of dietary exposure to heterocyclic amines.
ADME/Pharmacokinetics
2-Amino-5-phenylpyridine is a small, lipophilic molecule with a molecular weight of 170.21. It is soluble in organic solvents. Its pharmacokinetic properties are related to its metabolism and clearance. The compound is typically stored at room temperature.
Toxicity/Toxicokinetics
2-Amino-5-phenylpyridine is considered a potential carcinogen. It is a mutagenic heterocyclic aromatic amine. It is not approved for human therapeutic use. Standard laboratory safety precautions should be followed when handling this compound.
References

[1]. Comparative carcinogenicity of the food pyrolysis product, 2-amino-5-phenylpyridine, and the known human carcinogen, 4-aminobiphenyl, in the neonatal B6C3F1 mouse. Cancer Lett. 1988 Jul;41(1):99-103.

[2]. Syntheses of 5-phenyl-2-pyridinamine, a possibly carcinogenic pyrolysis product of phenylalanine, and some of its putative metabolites. Carcinogenesis. 1985 Jan;6(1):13-9.

Additional Infomation
5-Phenylacetyl-2-pyridylamine is a phenylpyridine.
2-Amino-5-phenylpyridine is a mutagenic heterocyclic aromatic amine formed during the cooking of protein-rich foods. It is considered potentially carcinogenic and is used as a synthetic intermediate. It is also used as a model compound in genotoxicity and food safety research.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C₁₁H₁₀N₂
Molecular Weight
170.21
Exact Mass
170.084
CAS #
33421-40-8
PubChem CID
105097
Appearance
White to off-white solid powder
Density
1.133g/cm3
Boiling Point
323.6ºC at 760mmHg
Melting Point
132 °C
Flash Point
175.6ºC
Index of Refraction
1.625
LogP
2.912
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Heavy Atom Count
13
Complexity
152
Defined Atom Stereocenter Count
0
InChi Key
OAPVIBHQRYFYSE-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H10N2/c12-11-7-6-10(8-13-11)9-4-2-1-3-5-9/h1-8H,(H2,12,13)
Chemical Name
5-phenylpyridin-2-amine
Synonyms
2Amino5phenylpyridine; 2 Amino 5 phenylpyridine
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 (~587.51 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 2.5 mg/mL (14.69 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
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 (14.69 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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (14.69 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.8751 mL 29.3755 mL 58.7510 mL
5 mM 1.1750 mL 5.8751 mL 11.7502 mL
10 mM 0.5875 mL 2.9375 mL 5.8751 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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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.

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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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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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