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| Targets |
6-Aminonicotinic acid is a GABAA receptor agonist (activator) with a reported Ki value of 4.4 nM. It exhibits bioactivity related to GABAA receptors, demonstrating moderate binding affinity with Ki values around 4,000 nM for the GABAA receptor in rat brain synaptic membranes. However, it shows low potency when tested for agonist activity at the human GABAA receptor, with EC50 values greater than 300,000 nM. The compound also inhibits both human recombinant DAO (D-amino acid oxidase) and DDO (D-aspartate oxidase) enzymes. Additionally, 6-aminonicotinic acid has been reported as an inhibitor of bacterial DNA gyrase and topoisomerase IV, showing inhibitory activity against various bacteria including E. coli K-12.
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| ln Vitro |
In vitro, 6-aminonicotinic acid exhibits bioactivity related to GABAA receptors with moderate binding affinity (Ki ~4,000 nM) in rat brain synaptic membrane preparations. It shows low potency as a GABAA receptor agonist in human receptor assays with EC50 >300,000 nM. The compound inhibits human recombinant DAO and DDO enzymes expressed in E. coli BL21(DE3) using D-Asp and D-Ala as substrates, with IC50 values >2,500,000 nM for DAO and 2,364,000 nM for DDO as measured via 2-oxo acid production after 10 minutes by colorimetric assay. 6-Aminonicotinic acid has a pKa value of 6.2. It has also been shown to inhibit bacterial DNA gyrase and topoisomerase IV. The compound can be formed via electrocatalytic synthesis at silver cathodes.
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| ln Vivo |
In vivo studies have demonstrated that 6-aminonicotinic acid has profound effects on brain development when administered to immature animals. It inhibits ornithine decarboxylase activity in the cerebellum of neonatal rats, an enzyme involved in cellular replication and differentiation. The compound has been used in developmental biology research to study its teratogenic effects. Studies in rabbits have examined embryonic mitosis disturbances and developmental abnormalities following administration of 6-aminonicotinic acid and related compounds. 6-Aminonicotinic acid and its derivatives have also been investigated for their potential to target metabolic pathways in cancer cells, with 6-aminonicotinic acid esters showing ability to reverse the epigenetic state of distant metastatic pancreatic carcinoma and exhibit antiproliferative activity. The compound serves as a biochemical building block for in vivo research applications in medicinal chemistry and pharmaceutical development.
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| Enzyme Assay |
For GABAA receptor binding assays, rat brain synaptic membranes are prepared and incubated with radiolabeled ligands and varying concentrations of 6-aminonicotinic acid. Non-specific binding is determined using excess unlabeled reference compound. Following incubation at appropriate temperature (typically 0-4°C for 30-60 minutes), bound and free radioligands are separated by rapid filtration through glass fiber filters. Filters are washed, dried, and radioactivity counted by liquid scintillation. Ki values are calculated from competitive binding curves using Cheng-Prusoff equation. For DAO/DDO enzyme inhibition assays, human recombinant enzymes expressed in E. coli BL21(DE3) are incubated with substrates (D-Asp for DAO, D-Ala for DDO) and test compound at 37°C for 10 minutes. Enzyme activity is measured via colorimetric detection of 2-oxo acid production. IC50 values are determined from dose-response curves.
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| Cell Assay |
For in vitro cellular assays, cells of interest (e.g., GABA receptor-expressing cell lines or primary neuronal cultures) are cultured in appropriate media under standard conditions (37°C, 5% CO2). Cells are seeded in multi-well plates and allowed to adhere overnight. Test compound 6-aminonicotinic acid is dissolved in DMSO or appropriate solvent and diluted in culture medium to desired concentrations (typically ranging from nM to mM). Cells are treated with compound for specified durations (e.g., 24-72 hours for proliferation assays, or minutes to hours for signaling assays). Agonist activity at GABAA receptors is assessed by measuring changes in intracellular calcium, membrane potential, or chloride flux using fluorescence-based assays or electrophysiology. For antiproliferative studies, cell viability is measured using MTT, CCK-8, or ATP-luminescence assays. Each concentration is tested in replicate wells, and appropriate vehicle controls and positive controls are included.
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| Animal Protocol |
For in vivo animal studies, 6-aminonicotinic acid is typically administered via intraperitoneal (i.p.) or subcutaneous (s.c.) injection in appropriate formulation (e.g., saline or DMSO/PEG mixtures). Dosing regimens vary by study objective: for developmental studies, pregnant animals (e.g., rabbits, rats) receive compound during specific gestational periods; for neonatal studies, immature animals receive single or repeated doses. For pharmacokinetic studies, blood samples are collected at predetermined time points post-administration, and plasma drug concentrations are quantified by LC-MS/MS. For efficacy studies in disease models, animals are randomized to treatment groups and dosed daily or as scheduled. Body weight, clinical signs, and behavioral parameters are monitored throughout. At study termination, tissues/organs are collected for histopathological examination, biomarker analysis, or biochemical assays (e.g., ornithine decarboxylase activity measurement in cerebellum). All procedures follow institutional animal care and use committee guidelines.
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| ADME/Pharmacokinetics |
Detailed pharmacokinetic data for 6-aminonicotinic acid in mammalian systems are limited in publicly available literature. The compound has a LogP of -0.74, suggesting moderate hydrophilicity and potentially limited passive membrane permeability. It is a metabolite that can be converted by enzymes of the pyridine nucleotide cycle to 6-aminonicotinamide adenine dinucleotide (6-amino-NAD) and 6-aminonicotinamide adenine dinucleotide phosphate (6-amino-NADP). The compound exhibits high affinity for the enzymatic system that converts it to 6-aminonicotinic acid mononucleotide. 6-Aminonicotinic acid can be formed via electrocatalytic synthesis at silver cathodes. Solubility: DMSO 1.39 mg/mL (10.06 mM), with sonication recommended. Storage: powder at -20°C for 3 years or 4°C for 2 years; in solvent at -80°C for 6 months or -20°C for 1 month.
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| Toxicity/Toxicokinetics |
According to safety data sheets, 6-aminonicotinic acid is classified as an irritant. GHS Hazard Statements include: H315 (Causes skin irritation), H319 (Causes serious eye irritation), and H335 (May cause respiratory irritation). Precautionary statements include P261 (Avoid breathing dust/fume/gas/mist/vapours/spray), P264 (Wash skin thoroughly after handling), P271 (Use only outdoors or in a well-ventilated area), P280 (Wear protective gloves/eye protection/face protection), P302+P352 (IF ON SKIN: Wash with plenty of soap and water), and P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes). The compound is incompatible with strong acids/alkalis and strong oxidizing/reducing agents. Under fire conditions, it may decompose and emit toxic fumes. Risk phrases include R36/37/38 (Irritating to eyes, respiratory system and skin). Safety phrases include S26 (In case of contact with eyes, rinse immediately with plenty of water and seek medical advice) and S37 (Wear suitable gloves). WGK Germany classification: 3.
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| References |
[1]. Petersen JG, et al. Synthesis and pharmacological evaluation of 6-aminonicotinic acid analogues as novel GABA(A) receptor agonists. Eur J Med Chem. 2014 Sep 12;84:404-16.
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| Additional Infomation |
6-Aminonicotinic acid is an aminonicotinic acid with its amino group located at the 6-position of the pyridine ring. It is a metabolite. It is an aromatic amine, an aminopyridine, and an aminonicotinic acid. It is functionally related to nicotinic acid.
See also: 3-hydroxybenzoic acid (note moved to). 6-Aminonicotinic acid is a naturally occurring pyridine derivative and a metabolite. It is an aromatic amine, an aminopyridine, and an aminonicotinic acid functionally related to nicotinic acid. The compound has been investigated as a protein synthesis inhibitor, vitamin B3 agonist, and modulating agent in chemotherapy. A series of 6-aminonicotinic acid analogues have been synthesized and pharmacologically characterized at native and recombinant GABAA receptors, with Ki values ranging from 1.1-24 μM. In cancer research, 6-aminonicotinic acid esters have shown potential to reverse epigenetic states of metastatic pancreatic carcinoma and exhibit antiproliferative activity. The compound has also been used as a crosslinking agent in perovskite solar cell research. No clinical development has been reported for this compound. The compound is for research use only, not for human therapeutic use. |
| Molecular Formula |
C6H6N2O2
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| Molecular Weight |
138.12
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| Exact Mass |
138.042
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| CAS # |
3167-49-5
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| PubChem CID |
18496
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| Appearance |
White to light yellow solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
222.6±50.0 °C at 760 mmHg
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| Melting Point |
>300 °C(lit.)
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| Flash Point |
88.4±30.1 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.630
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| LogP |
-0.74
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
10
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| Complexity |
138
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O([H])C(C1=C([H])N=C(C([H])=C1[H])N([H])[H])=O
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| InChi Key |
ZCIFWRHIEBXBOY-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H6N2O2/c7-5-2-1-4(3-8-5)6(9)10/h1-3H,(H2,7,8)(H,9,10)
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| Chemical Name |
6-aminopyridine-3-carboxylic acid
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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 |
| 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 | 7.2401 mL | 36.2004 mL | 72.4008 mL | |
| 5 mM | 1.4480 mL | 7.2401 mL | 14.4802 mL | |
| 10 mM | 0.7240 mL | 3.6200 mL | 7.2401 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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