Methyl 5-aminonicotinate
[CAS# 36052-25-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Aminopyridine
• Name: Methyl 5-aminonicotinate
• Synonyms: 5-Aminonicotinic acid methyl ester; Methyl 5-amino-3-pyridinecarboxylate
• Molecular Formula: C₇H₈N₂O₂
• Molecular Weight: 152.15
• CAS Registry Number: 36052-25-2
• EC Number: 625-834-8
• SMILES: COC(=O)C1=CC(=CN=C1)N

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 135-137 °C
• Index of Refraction: 1.571, Calc.^*
• Boiling Point: 319.4±22.0 °C (760 mmHg), Calc.^*
• Flash Point: 147.0±22.3 °C, Calc.^*

^* 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
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332

Discovery and Applications

Methyl 5-aminonicotinate is an organic compound with the molecular formula C7H8N2O2. It is derived from nicotinic acid (vitamin B3) by introducing a methyl ester at the carboxyl group and an amino group at the 5-position of the pyridine ring. This compound is a valuable derivative used primarily in chemical and pharmaceutical applications.

The synthesis of methyl 5-aminonicotinate is based on the well-established methods for modifying nicotinic acid derivatives. The functionalization of the pyridine ring with an amino group at the 5-position allows for the creation of new compounds that can be used as intermediates in further chemical reactions. The esterification of the carboxyl group to form the methyl ester enhances the compound's solubility, making it more suitable for various applications.

In the pharmaceutical industry, methyl 5-aminonicotinate has been investigated for its potential bioactivity. Its structure, with both an amino and ester group, makes it a promising precursor for the synthesis of biologically active molecules. Nicotinic acid derivatives, including methyl 5-aminonicotinate, have been studied for their ability to influence lipid metabolism and improve cardiovascular health. These compounds are often researched for their potential to treat conditions like hyperlipidemia and atherosclerosis, where managing cholesterol levels and lipid profiles is critical.

Beyond medicinal applications, methyl 5-aminonicotinate is also used in organic synthesis. As a functionalized pyridine derivative, it serves as a valuable building block for creating more complex molecules. The amino and ester groups enable various chemical reactions, such as nucleophilic substitution or condensation reactions, which are crucial in the development of new chemical entities.

In addition to its roles in pharmaceutical and chemical synthesis, methyl 5-aminonicotinate has been explored for its potential applications in materials science. Pyridine derivatives, including this compound, have been shown to form stable complexes with metal ions, which may be useful in catalytic processes or as part of new materials with specialized properties.

In summary, methyl 5-aminonicotinate is an important chemical compound with established uses in pharmaceutical research, organic synthesis, and materials science. Its versatility as a building block for drug development and its potential for creating novel chemical entities make it a valuable substance in chemical research and industrial applications.

References

2021. 5-[(3-Carboxy-4-hydroxyphenyl)diazenyl] nicotinic acid, an azo-linked mesalazine-nicotinic acid conjugate, is a colon-targeted mutual prodrug against dextran sulfate sodium-induced colitis in mice. Journal of Pharmaceutical Investigation, 51(3).
DOI: 10.1007/s40005-021-00517-z

2020. Structural elucidation, molecular docking, α-amylase and α-glucosidase inhibition studies of 5-amino-nicotinic acid derivatives. BMC Chemistry, 14(1).
DOI: 10.1186/s13065-020-00695-1

2021. Preparation and Evaluation of Colon-Targeted Prodrugs of the Microbial Metabolite 3-Indolepropionic Acid as an Anticolitic Agent. Molecular Pharmaceutics, 18(3).
DOI: 10.1021/acs.molpharmaceut.0c01228