Aminoguanidine bicarbonate
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Product Description
Aminoguanidine bicarbonate is primarily used as a pharmaceutical intermediate, particularly in the synthesis of sartan-class drugs like Valsartan, which are crucial for treating high blood pressure and heart failure. Additionally, it serves as a building block for synthesizing tetrazole rings in various active pharmaceutical ingredients. Aminoguanidine bicarbonate also has significant applications in biomedical research as an inhibitor of advanced glycation end-products (AGEs), which are linked to diabetes complications, aging, and chronic diseases. It can inhibit the inducible form of nitric oxide synthase (iNOS), making it useful in studying inflammatory processes.
Synthesis Methods
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Hydrazine Hydrate and Lime Nitrogen Method:
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Aminoguanidine bicarbonate was synthesized using hydrazine hydrate, lime nitrogen, sulfuric acid, and ammonium bicarbonate as raw materials.
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Optimum reaction conditions:
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Water dosage: 100 mL
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Reaction temperature: 45°C
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Mole ratio of hydrazine hydrate to lime nitrogen: 1:2
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pH value: 7.2-7.5
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Heating time: 3 hours at 70°C
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Optimum crystallization conditions:
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Crystallization temperature: 10°C
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Crystallization time: 4 hours
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Yield: 96.07%
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Purity: 98%
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Carboxylic Acids Reaction:
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Aminoguanidine bicarbonate reacts with various carboxylic acids (e.g., oxamic, oxalic, malonic, and sulfoacetic acids) to form different salts.
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These salts have been studied for their structural and thermal properties.
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Some of these salts have shown potential to inhibit human butyrylcholinesterase (human BChE) receptors.
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Uses and Applications
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Pharmaceuticals:
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Used in the treatment of diabetes-related complications due to its antioxidant and anti-inflammatory properties.
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Acts as a specific inhibitor of advanced glycation end-products (AGEs).
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May protect cells from chromosomal damage in adenovirus infections.
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Chemical Synthesis:
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Acts as a precursor for guanidine derivatives.
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Employed in producing medicines, pesticides, dyes, photographic agents, foaming agents, explosives, and corrosion inhibitors.
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Other Industries:
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Involved in analytical chemistry, research, and as a reagent for synthesis.
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Molecular Formula and Weight
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Molecular Formula: C₂H₈N₄O₃
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Molecular Weight: 136.11 g/mol
IUPAC Name
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2-aminoguanidine; carbonic acid
Synonyms
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Aminoguanidine hydrogen carbonate
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N''-aminoguanidine carbonic acid
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1-aminoguanidine carbonate
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Guanylhydrazine bicarbonate salt
Chemical Structure
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Cation: Aminoguanidinium ion (H₂N-C(=NH)-NH-NH₂⁺)
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Anion: Bicarbonate ion (HCO₃⁻)
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Structural Formula: H₂NNHC(=NH)NH₂ · H₂CO₃
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SMILES Notation: C(=N)(NN)N.OC(=O)O
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InChI Key: OTXHZHQQWQTQMW-UHFFFAOYSA-N
Physical and Chemical Properties
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Appearance: White crystalline powder; hygroscopic
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Melting Point: 170–172 °C (with decomposition)
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Boiling Point: Approximately 422.4 °C
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Density: 1.6 g/cm³
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Bulk Density: 700 kg/m³
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Solubility: Soluble in water at 2.7 g/L (at 20 °C); generally low solubility in most solvents
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Storage: Recommended to store below +30 °C in a cool, dry place
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Purity: Commercially available at 97–99% purity levels
Safety and Hazards
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Handling Precautions:
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Hygroscopic, so avoid exposure to moisture.
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Store in tightly sealed containers.
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Toxicity and Risks:
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Limited detailed toxicity data is available, but standard lab safety protocols apply (e.g., use gloves, eye protection, and adequate ventilation).
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May decompose upon heating, releasing gases like carbon dioxide or nitrogen oxides.
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