6-Aminonicotinic acid
[CAS# 3167-49-5]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Other amino acid derivatives
• Name: 6-Aminonicotinic acid
• Synonyms: 6-Aminopyridine-3-carboxylic acid
• Molecular Formula: C₆H₆N₂O₂
• Molecular Weight: 138.12
• CAS Registry Number: 3167-49-5
• EC Number: 221-630-4
• SMILES: C1=CC(=NC=C1C(=O)O)N

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 320 °C (Expl.)
• Index of Refraction: 1.649, Calc.^*
• Boiling Point: 373.6±27.0 °C (760 mmHg), Calc.^*
• Flash Point: 179.8±23.7 °C, Calc.^*
• Water solubility: ~1.0 g/L (20 °C)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

6-Aminonicotinic acid is a derivative of nicotinic acid, a compound that is widely recognized for its role as a precursor to important biomolecules such as NAD+ (nicotinamide adenine dinucleotide) and NADP+ (nicotinamide adenine dinucleotide phosphate). 6-Aminonicotinic acid contains an amino group at the 6-position of the pyridine ring, which distinguishes it from other nicotinic acid derivatives. Its molecular formula is C₆H₆N₂O₂, and it is synthesized by introducing an amino group at the 6-position of the nicotinic acid structure.

The discovery of 6-aminonicotinic acid is attributed to the ongoing research into the modification of nicotinic acid to create various derivatives with distinct biological properties. Nicotinic acid, as a naturally occurring compound, has been studied for its involvement in metabolic processes, particularly in relation to its role in the production of NAD+ and NADP+. 6-Aminonicotinic acid was identified as a derivative with potentially altered properties, especially in terms of its interaction with enzymes and its effects on cellular processes.

One of the primary applications of 6-aminonicotinic acid is in biochemical and pharmaceutical research. Due to its structure, it has been studied for its potential role in the biosynthesis of NAD+ and its possible influence on enzymes involved in this pathway. NAD+ is a crucial coenzyme in a variety of metabolic reactions, including redox reactions, DNA repair, and cellular energy production. As such, 6-aminonicotinic acid has been investigated for its potential effects on these processes, though its specific biological activities are still being explored.

6-Aminonicotinic acid has also been studied for its potential to serve as an intermediate in the synthesis of other biologically active compounds. For example, it may be used in the creation of more complex nicotinic acid derivatives that could have applications in treating diseases related to metabolism, inflammation, and oxidative stress. The amino group at the 6-position of the pyridine ring may alter the chemical reactivity of the compound, making it a useful building block in organic synthesis.

In addition to its role in biochemical research, 6-aminonicotinic acid has been explored for its potential as a ligand in metal coordination chemistry. The pyridine ring and amino group can coordinate with metal ions, which could lead to the development of metal-based catalysts or complexes with specific reactivity. This application is still under investigation, but it could be of interest for various industrial processes, such as catalysis or the development of materials with unique properties.

While 6-aminonicotinic acid is of interest in the fields of biochemistry and organic chemistry, its use is primarily in research contexts, where it serves as a reagent or intermediate in the synthesis of more complex compounds. It is commercially available for laboratory use, where it is typically employed in studies related to enzyme activity, metabolism, and the design of new bioactive molecules.

Overall, 6-aminonicotinic acid plays a role in the study of nicotinic acid derivatives and their effects on cellular processes. It has potential applications in drug discovery, where it could be used to create compounds that modify NAD+ biosynthesis or interact with other biological pathways. While more research is needed to fully understand its biological and chemical properties, it remains a valuable compound in both synthetic and medicinal chemistry.

References

2022. Effects of 6-Aminonicotinic Acid Esters on the Reprogrammed Epigenetic State of Distant Metastatic Pancreatic Carcinoma. ACS Medicinal Chemistry Letters, 13(12).
DOI: 10.1021/acsmedchemlett.2c00404

2016. Investigating the binding mechanism of novel 6-aminonicotinate-based antagonists with P2Y12 by 3D-QSAR, docking and molecular dynamics simulations. Journal of Biomolecular Structure and Dynamics, 35(10).
DOI: 10.1080/07391102.2016.1237381

2015. Microwave-Assisted Synthesis of 2,2'-Azopyridine-Labeled Amines, Amino Acids, and Peptides. Synthesis, 47(24).
DOI: 10.1055/s-0035-1560523