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| Targets |
2-Aminonicotinaldehyde is a synthetic precursor for compounds that target specific biological receptors and enzymes. It is primarily utilized in the synthesis of 5-HT3 receptor antagonists, which target serotonin 5-HT3 receptors in the central and peripheral nervous systems for the treatment of depression, anxiety, and chemotherapy-induced nausea. The compound is also used in the synthesis of AKT inhibitors, which target the protein kinase B (AKT) signaling pathway involved in cell survival, proliferation, and metabolism, making them relevant for cancer research, including hepatocellular carcinoma. The compound's role as a synthetic intermediate means that its biological activity is mediated through its derivatives rather than the parent compound itself. In the synthesis of 5-HT3 receptor antagonists, the compound's aldehyde and amino groups enable the formation of the heterocyclic core structures required for receptor binding and antagonism.
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| ln Vitro |
In vitro, 2-aminonicotinaldehyde is used as a key intermediate in the synthesis of various bioactive compounds. It can be used to synthesize 5-HT3 receptor antagonists and AKT inhibitors. The compound enables direct synthesis of 3-iodo-1,8-naphthyridines, which have demonstrated antimicrobial activity. In medicinal chemistry, it serves as a versatile building block for constructing fused heterocyclic systems that are important for drug discovery. The compound's reactivity allows for the formation of various derivatives through condensation, cyclization, and functional group transformations. It is particularly valuable for the synthesis of compounds targeting depression and cancer. In organic synthesis, it is used to create complex molecular scaffolds through reactions such as the formation of imines, Schiff bases, and other nitrogen-containing heterocycles.
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| ln Vivo |
In vivo activity is not directly associated with the parent compound 2-aminonicotinaldehyde, but rather with its derivatives. The 5-HT3 receptor antagonists synthesized from this compound are evaluated in animal models of depression, anxiety, and nausea. These studies typically involve behavioral assays in rodents to assess antidepressant and anxiolytic effects. The AKT inhibitors synthesized from the compound are evaluated in animal models of cancer, including hepatocellular carcinoma, to assess antitumor efficacy. In these studies, tumor growth inhibition, survival rates, and biomarkers of AKT pathway activity are measured. The parent compound itself is not administered in vivo, as it is a synthetic intermediate rather than a pharmacological agent.
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| Enzyme Assay |
Cell-free assays involving 2-aminonicotinaldehyde are focused on its use as a chemical reagent in organic synthesis. Standard protocols involve condensation and cyclization reactions to form 1,8-naphthyridines or other heterocyclic systems. For example, the compound can be reacted with appropriate reagents under inert atmosphere to form 3-iodo-1,8-naphthyridines. The reaction progress is monitored by TLC or HPLC, and the products are purified by column chromatography. For the synthesis of 5-HT3 receptor antagonists or AKT inhibitors, the compound is used as a starting material in multi-step synthetic routes. The compound's aldehyde group allows for reductive amination, condensation, and other transformations, while the amino group enables acylation, alkylation, and heterocycle formation.
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| Cell Assay |
Cellular assays are not performed with the parent compound 2-aminonicotinaldehyde. Instead, its synthetic derivatives, such as 5-HT3 receptor antagonists and AKT inhibitors, are evaluated in cell-based systems. For 5-HT3 receptor antagonists, assays may involve measuring receptor binding affinity in cell lines expressing the 5-HT3 receptor, or functional assays measuring serotonin-induced calcium flux or ion channel activity. For AKT inhibitors, cancer cell lines are treated with the derivatives, and cell viability, proliferation, apoptosis, and AKT pathway phosphorylation are measured. The parent compound itself is not used as a test article in cell-based experiments due to its role as a synthetic building block.
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| Animal Protocol |
Animal studies are not conducted with the parent compound 2-aminonicotinaldehyde. Its derivatives, including 5-HT3 receptor antagonists and AKT inhibitors, are evaluated in animal models. For depression research, 5-HT3 receptor antagonists are tested in rodent models such as the forced swim test, tail suspension test, and chronic mild stress models. For cancer research, AKT inhibitors are evaluated in xenograft or orthotopic mouse models of hepatocellular carcinoma and other cancers. In these studies, parameters such as tumor growth, survival, body weight, and biomarkers are assessed. The parent compound itself is not administered to animals, as it is a synthetic intermediate.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for the parent compound 2-aminonicotinaldehyde are not available, as it is primarily a synthetic intermediate rather than a drug candidate. As a small polar molecule with a molecular weight of 122.13 g/mol, it is expected to have moderate bioavailability if administered, but it is not intended for therapeutic use. The compound's amino and aldehyde groups may influence its absorption, distribution, metabolism, and excretion. However, comprehensive pharmacokinetic studies have not been performed, as the compound is not intended for systemic administration. For research purposes, the compound is typically handled as a neat chemical and not administered to living organisms for pharmacokinetic profiling.
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| Toxicity/Toxicokinetics |
Toxicological data for 2-aminonicotinaldehyde are limited. The compound is air- and heat-sensitive, requiring storage under inert gas at 0-10°C to maintain stability. Standard safety precautions for handling aromatic amines and aldehydes apply, including the use of personal protective equipment such as gloves and safety goggles. The compound should be handled in a well-ventilated area, and contact with skin and eyes should be avoided. In case of exposure, affected areas should be rinsed thoroughly with water. The compound is not classified as a carcinogen or mutagen based on available data, but comprehensive toxicological evaluation has not been performed. As with all research chemicals, it should be handled with care and used only in accordance with safety guidelines.
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| Additional Infomation |
2-Aminonicotinaldehyde is a research chemical, not an approved drug. It has no clinical trial or marketing approval status for therapeutic use. The compound is a key intermediate in organic synthesis and is used to synthesize 5-HT3 receptor antagonists and AKT inhibitors. It can be used in the research of depression and cancer, including hepatocellular carcinoma. The compound enables direct synthesis of 3-iodo-1,8-naphthyridines with antimicrobial activity. Its exact ortho-disposition is essential for 1,8-naphthyridine formation. The compound is supplied with a purity of ≥99.85% and is typically stored under inert gas at 0-10°C. Its dual functional groups (amino and aldehyde) make it a versatile building block for constructing complex heterocyclic scaffolds in medicinal chemistry and drug discovery.
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| Molecular Formula |
C6H6N2O
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| Molecular Weight |
122.12
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| Exact Mass |
122.048
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| CAS # |
7521-41-7
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| PubChem CID |
737633
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
290.7±25.0 °C at 760 mmHg
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| Melting Point |
98-102 °C(lit.)
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| Flash Point |
129.6±23.2 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.652
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| LogP |
1.41
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
9
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| Complexity |
105
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C([H])C1C([H])=C([H])C([H])=NC=1N([H])[H]
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| InChi Key |
NXMFJCRMSDRXLD-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H6N2O/c7-6-5(4-9)2-1-3-8-6/h1-4H,(H2,7,8)
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| Chemical Name |
2-aminopyridine-3-carbaldehyde
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), 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)
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| 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
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| 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 | 8.1887 mL | 40.9433 mL | 81.8867 mL | |
| 5 mM | 1.6377 mL | 8.1887 mL | 16.3773 mL | |
| 10 mM | 0.8189 mL | 4.0943 mL | 8.1887 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.
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