What Is 3-Amino-5-nitrosalicylic acid

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Last updated: April 15, 2026

Quick Answer: 3-Amino-5-nitrosalicylic acid is a derivative of salicylic acid with both amino and nitro functional groups, used primarily in research for its potential anti-inflammatory and antimicrobial properties. It has the molecular formula C7H6N2O5 and is structurally related to other aminosalicylates like mesalazine.

Key Facts

3-Amino-5-nitrosalicylic acid has the molecular formula C7H6N2O5 and a molecular weight of 198.13 g/mol
It is a derivative of salicylic acid, modified with an amino group at position 3 and a nitro group at position 5
The compound is primarily used in laboratory research, not approved for clinical use as of 2023
It shows potential antimicrobial activity against certain Gram-positive bacteria in vitro
Its structural similarity to mesalazine suggests possible anti-inflammatory applications under investigation

Overview

3-Amino-5-nitrosalicylic acid is an organic compound derived from salicylic acid, modified with an amino group at the third carbon and a nitro group at the fifth carbon of the aromatic ring. This modification alters its chemical reactivity and biological activity, making it a subject of interest in medicinal chemistry research.

Unlike widely used aminosalicylates such as mesalazine (5-aminosalicylic acid), this compound is not currently approved for therapeutic use. It remains primarily a research chemical, studied for its physicochemical properties and potential pharmacological effects.

Molecular formula: The compound has the chemical formula C7H6N2O5, indicating seven carbon, six hydrogen, two nitrogen, and five oxygen atoms.
Structure: It features a salicylic acid backbone with an amino group (-NH2) at position 3 and a nitro group (-NO2) at position 5 on the benzene ring.
Molecular weight: Its molar mass is precisely 198.13 grams per mole, which influences solubility and pharmacokinetic behavior.
Solubility: It exhibits limited solubility in water but dissolves better in polar organic solvents like dimethyl sulfoxide (DMSO) and ethanol.
Stability: The compound is stable under dry, cool conditions but may degrade when exposed to light or moisture over time.

How It Works

The biological activity of 3-amino-5-nitrosalicylic acid stems from its dual functional groups, which may interact with cellular enzymes and redox systems. Its mechanism is not fully understood but is under investigation in biochemical and microbiological studies.

Redox activity: The nitro group can undergo reduction in bacterial cells, potentially generating reactive species that disrupt microbial metabolism.
Enzyme inhibition: It may inhibit key bacterial enzymes such as dihydropteroate synthase, similar to other sulfonamide-like compounds.
Antimicrobial action: Studies show in vitro activity against Staphylococcus aureus, with MIC values ranging from 25–50 µg/mL in some assays.
Anti-inflammatory potential: Due to structural similarity to mesalazine, it may interfere with pro-inflammatory cytokine production in gut epithelial cells.
Chelation properties: The ortho-hydroxy carboxylic acid group enables metal ion binding, which could influence oxidative stress pathways.
Cell permeability: Its moderate lipophilicity allows partial membrane penetration, though less than fully nonpolar drugs.

Comparison at a Glance

Below is a comparison of 3-amino-5-nitrosalicylic acid with related salicylate derivatives commonly used in medicine and research.

Compound	Molecular Weight (g/mol)	Functional Groups	Primary Use	Clinical Status
3-Amino-5-nitrosalicylic acid	198.13	3-NH2, 5-NO2, COOH	Research	Not approved
Mesalazine (5-ASA)	153.14	3-OH, 4-NH2, COOH	Ulcerative colitis treatment	Approved
Salicylic acid	138.12	2-OH, COOH	Topical acne treatment	Approved
Sulfasalazine	398.42	SO2, 5-N=N-benzene, NH2	IBD, rheumatoid arthritis	Approved
5-Nitrosalicylic acid	184.11	5-NO2, COOH	Research intermediate	Not approved

This table highlights how structural differences affect molecular weight and application. While mesalazine and sulfasalazine are clinically established, 3-amino-5-nitrosalicylic acid remains experimental. Its unique substitution pattern may offer novel mechanisms, but further toxicological and pharmacokinetic studies are required before clinical development.

Why It Matters

Though not a marketed drug, 3-amino-5-nitrosalicylic acid contributes to the development of new anti-inflammatory and antimicrobial agents. Its structure provides insights into how chemical modifications influence biological activity in salicylate derivatives.

Drug design: It serves as a scaffold for designing new aminonitrosalicylates with improved potency or reduced toxicity.
Antibiotic resistance research: Its activity against Gram-positive bacteria supports exploration in the context of rising antibiotic resistance.
Inflammatory bowel disease: Structural similarity to 5-ASA suggests potential for targeted colonic delivery systems.
Prodrug development: It may be modified into ester or azo-linked prodrugs for site-specific release in the gut.
Chemical probe: Used in labs to study nitroreductase enzyme activity in microbial metabolism.
Safety profiling: Early studies help identify toxicophores associated with nitroaromatic compounds.

As research continues, this compound may inform the next generation of targeted therapies, particularly in gastrointestinal and infectious diseases. Its role in medicinal chemistry underscores the importance of exploring diverse chemical space in drug discovery.