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Aminoguanidine Bicarbonate is an organic compound primarily used as an intermediate in pharmaceuticals, dyes, and agricultural chemicals.
It is known for its role as a hydrazine derivative and has applications in the synthesis of biologically active compounds.
CAS Number:
2582-30-1
Synonyms:
Aminoguanidine hydrogen carbonate,Aminoguanidinium bicarbonate
Guanidinohydrazine bicarbonate,AG bicarbonate,3-Azanyl-1H-1,2,4-triazol-5-amine bicarbonate
Introduction
Aminoguanidine bicarbonate is a chemical compound known for its biological activity and potential applications in the pharmaceutical, medical, and industrial fields.
Aminoguanidine itself is a well-documented compound with significant pharmacological potential, particularly in the inhibition of advanced glycation end-products (AGEs).
The bicarbonate form of aminoguanidine serves as a stable salt that can be utilized in various experimental and practical settings.
The interest in aminoguanidine bicarbonate stems from its promising roles in anti-aging research, diabetic complications, and potential protective effects against oxidative stress.
This document aims to deliver an in-depth exploration of the chemical, physical, biological, and industrial characteristics of aminoguanidine bicarbonate.
Chemical Identity and Properties
IUPAC Name: Aminoguanidine hydrogen carbonate
Synonyms: Aminoguanidine bicarbonate, Guanidine, aminomethyl-, hydrogen carbonate
Chemical Formula: CH6N4.H2CO3
Molecular Weight: 136.1 g/mol
Structure: The compound consists of an aminoguanidine cation (CH6N4+) and a bicarbonate anion (HCO3-).
Physical Properties
Appearance: White crystalline powder
Solubility: Soluble in water, slightly soluble in ethanol
Melting Point: Decomposes before melting
Density: ~1.6 g/cm3
pH (aqueous solution): Slightly basic
Chemical Properties
Aminoguanidine bicarbonate is relatively stable under normal conditions.
It decomposes upon strong heating, releasing gases like carbon dioxide and ammonia.
It reacts with strong acids to release carbon dioxide and aminoguanidine salts.
Synthesis and Manufacturing
Laboratory Synthesis
Aminoguanidine bicarbonate can be synthesized by reacting aminoguanidine with carbonic acid or more commonly by bubbling carbon dioxide into an aqueous solution of aminoguanidine base.
Reaction:
CH6N4 + H2CO3 → CH6N4.H2CO3
Industrial Production
The industrial production of aminoguanidine bicarbonate typically involves large-scale bubbling of CO2 into aminoguanidine-containing solutions under controlled pH and temperature to precipitate the bicarbonate salt.
Raw Materials
Aminoguanidine base (produced from hydrazine and cyanamide)
Carbon dioxide (CO2)
Water
Analytical Methods
Spectroscopy
Infrared (IR): Shows characteristic peaks for N-H stretching, C-N stretching, and bicarbonate functionalities
NMR: Proton and carbon spectra confirm the structure
UV-Vis: Limited direct activity unless conjugated with chromophores
Chromatography
HPLC and GC: Utilized for purity and quantification with derivatization
TLC: Preliminary identification using suitable stains
Titrimetric and Gravimetric Analysis
Acid-base titration: To determine bicarbonate concentration
Gravimetric method: For estimation of CO2 release upon decomposition
Mechanism of Action
Aminoguanidine bicarbonate acts by trapping reactive carbonyl compounds, especially dicarbonyl intermediates such as methylglyoxal and glyoxal.
This prevents the formation of AGEs, which are implicated in many pathological conditions.
Mechanistically, the nucleophilic nitrogen atoms in aminoguanidine attack electrophilic carbon atoms in carbonyl compounds, forming stable adducts.
This action mitigates glycation-related oxidative stress and tissue damage.
Applications
Pharmaceutical and Biomedical Applications
Inhibitor of AGE formation
Treatment of diabetic complications (neuropathy, nephropathy)
Potential for anti-aging interventions
Neuroprotection
Intermediate in Chemical Synthesis
Used in synthesis of heterocycles, hydrazones
Reagent for derivatization in analytical chemistry
Industrial Applications
Corrosion inhibitors
Catalysis and polymer stabilization
Potential in Anti-aging and Diabetic Research
AGE inhibition is a key strategy in preventing tissue damage due to hyperglycemia
Under investigation in preclinical and clinical studies
Biological Activity
Antioxidant Properties
Aminoguanidine exhibits indirect antioxidant activity by reducing oxidative damage from AGEs and dicarbonyl stress.
Anti-inflammatory and Antiglycation Effects
Downregulates NF-κB pathway
Reduces inflammatory cytokines (TNF-α, IL-1β)
Inhibits formation of protein carbonyls
Cellular and Enzymatic Interactions
Inhibits inducible nitric oxide synthase (iNOS)
Modulates activity of enzymes like aldose reductase
SAFETY INFORMATION ABOUT DE AMINGUANIDINE BICARBONATE
First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.
Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.
If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product
