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Aminoguanidine bicarbonate showcases its prowess in cellular defense mechanisms, safeguarding cells from adenovirus-induced chromosomal damage and bolstering the immune response against viral infections.
By mitigating vascular impairments associated with diabetes, Aminoguanidine bicarbonate actively contributes to preserving cardiovascular health, potentially reducing the risk of severe complications arising from diabetic-related vascular issues.
Aminoguanidine bicarbonate's versatility as a raw material plays a pivotal role in advancing drug development and therapeutic solutions, making it an indispensable resource in the pursuit of better healthcare.
CAS Number: 2582-30-1
EC Number: 219-956-7
Chemical Formula: CH6N4·H2CO3
Molecular Weight: 136.11
Synonyms: Aminoguanidine bicarbonate, 2582-30-1, Aminoguanidine hydrogen carbonate, 2200-97-7, 2-aminoguanidine;carbonic acid, Aminoguanidinium bicarbonate, Aminoguanidine carbonate (1:1), Aminoguanidium hydrogen carbonate, N1-Aminoguanidine carbonate (1:1), Aminoguanidine carbonate, Aminoguanidine hydrogencarbonate, MFCD00012949, BA 51-090222, NSC7887, N''-aminoguanidine; carbonic acid, amino(diaminomethylidene)azanium;hydrogen carbonate, 1-Aminoguanidine bicarbonate, Hydrazinecarboximidamide carbonate, NSC 7887, EINECS 219-956-7, Amino guanidine bicarbonate, Guanidine, amino-, hydrogen carbonate, Ba 51-090222 (VAN), N(sup 1)-Aminoguanidine carbonate (1:1), AI3-52138, Guanylhydrazine hydrogencarbonate, UNII-X2151435R9, aminoguandine bicarbonate, EC 219-956-7, SCHEMBL40128, CH6N4.H2CO3, 1-aminoguanidine; carbonic acid, DTXSID2062537, Aminoguanidine bicarbonate, 97%, Amino guanidine hydrogen carbonate, OTXHZHQQWQTQMW-UHFFFAOYSA-N, 1-aminoguanidine carbonic acid salt, AMINOGUANIDINE; CARBONIC ACID, HB0111, AKOS015894487, AKOS015901290, hydrazinecarboximidamide bicarbonate salt, hydrazinecarboximidamide carbonic acid salt, LS-12944, A0307, F87308, Q27293343, [amino(hydrazinyl)methylidene]azanium hydrogen carbonate, F0001-0859, Carbonic acid compound with hydrazinecarboximidamide (1:1)
Aminoguanidine bicarbonate is a pharmaceutical drug that has been used for the treatment of chronic renal failure and congestive heart failure.
Aminoguanidine bicarbonate has also been studied for its potential use in Alzheimer's disease.
Aminoguanidine bicarbonate is the most commonly used form of aminoguanidine in clinical trials.
Aminoguanidine bicarbonate can be synthesized by reacting malonic acid with hydrochloric acid and copper metal hydroxide, which produces copper complexes and Aminoguanidine bicarbonate.
Aminoguanidine bicarbonate inhibits the production of inflammatory cytokines, such as tumor necrosis factor-α and interleukins, and activates endothelial nitric oxide synthase, leading to vasodilation and inhibition of platelet aggregation.
Aminoguanidinium bicarbonate or Aminoguanidine bicarbonate is a chemical compound used as precursor for the preparation of aminoguanidine compounds.
Aminoguanidine bicarbonate has the chemical formula C2H8N4O3.
Aminoguanidine bicarbonate, also referred to as Aminoguanidine hydrogen carbonate, is an organic compound with the molecular formula C2H8N4O3.
Aminoguanidine bicarbonate has a wide range of applications in the pharmaceutical and specialty chemical industries.
The potential of Aminoguanidine bicarbonate to shield cells from adenovirus-induced chromosomal damage showcases Aminoguanidine bicarbonate prowess in cellular defense mechanisms, promising to bolster the immune response against viral infections.
Acting as an inhibitor of NOS, Aminoguanidine bicarbonate exerts control over the intricate nitric oxide synthesis process, paving the way for therapeutic interventions in conditions where excess nitric oxide could cause detrimental effects.
Significantly, Aminoguanidine bicarbonate's role in combating diabetic vascular dysfunction highlights Aminoguanidine bicarbonate clinical relevance in managing diabetes.
By mitigating vascular impairments associated with diabetes, Aminoguanidine bicarbonate contributes to the preservation of cardiovascular health, potentially reducing the risk of severe complications stemming from diabetic-related vascular issues.
Beyond Aminoguanidine bicarbonate's biological effects, Aminoguanidine bicarbonate emerges as an indispensable resource in the realm of chemical synthesis.
As a foundational building block for diverse pharmaceuticals, Aminoguanidine bicarbonate empowers researchers and manufacturers to create innovative drugs targeting a wide range of medical conditions.
Additionally, Aminoguanidine bicarbonate's application in pesticide production fortifies agricultural practices, ensuring enhanced crop protection and improved yields.
Furthermore, the compound's relevance in the production of dyes and foaming agents underscores Aminoguanidine bicarbonate's significance in the industrial sector.
Aminoguanidine bicarbonate's unique properties make it an ideal candidate for creating vibrant and durable dyes, catering to various industries such as textiles, cosmetics, and more.
Simultaneously, Aminoguanidine bicarbonate's capacity as a foaming agent plays a crucial role in the production of numerous consumer products, ranging from personal care items to industrial materials.
Aminoguanidine bicarbonate has chemical structure H2NC(=NH)NHNH2·H2CO3.
Aminoguanidine bicarbonate appears as white crystalline powder.
Aminoguanidine bicarbonate is hygroscopic in nature.
Aminoguanidine bicarbonate or Aminoguanidine hydrogen carbonate or Guanylhydrazine hydrogencarbonate is White crystalline powder, negligibly soluble in water, insoluble in alcohol and other acids.
Aminoguanidine bicarbonate can be used as a raw material for the synthesis of medicines, pesticides, dyes, photographic chemicals and foaming agents.
Aminoguanidine bicarbonate Amino guanidine bicarbonate is used as a drug intermediate.
Aminoguanidine bicarbonate, also known as Aminoguanidine hydrogen carbonate, is an organic compound with the molecular formula C2H8N4O3, highly valued for Aminoguanidine bicarbonate's applications in the pharmaceutical industry.
In the pharmaceutical sector, Aminoguanidine bicarbonate's remarkable capabilities shine through.
Aminoguanidine bicarbonate showcases its prowess in cellular defense mechanisms, safeguarding cells from adenovirus-induced chromosomal damage and bolstering the immune response against viral infections.
Additionally, as an effective inhibitor of NOS (nitric oxide synthase), this compound plays a crucial role in controlling the intricate nitric oxide synthesis process.
As a result, Aminoguanidine bicarbonate opens up avenues for therapeutic interventions in conditions where excessive nitric oxide levels could lead to harmful effects.
One of the most significant clinical applications of Aminoguanidine bicarbonate lies in managing diabetes.
By mitigating vascular impairments associated with diabetes, Aminoguanidine bicarbonate actively contributes to preserving cardiovascular health, potentially reducing the risk of severe complications arising from diabetic-related vascular issues.
However, Aminoguanidine bicarbonate's primary role in the pharmaceutical industry is Aminoguanidine bicarbonate's utility as a foundational building block for a diverse range of pharmaceuticals.
This unique characteristic empowers researchers and manufacturers to create innovative drugs that target a wide spectrum of medical conditions.
Aminoguanidine bicarbonate is versatility as a raw material plays a pivotal role in advancing drug development and therapeutic solutions, making Aminoguanidine bicarbonate an indispensable resource in the pursuit of better healthcare.
Applications of Aminoguanidine bicarbonate:
Aminoguanidine bicarbonate was used to study the effect of addition of polyamines to rat embryo cell cultures infected with adenovirus type 5.
Aminoguanidine is used as an intermediate for the synthesis of pharmaceuticals, agrochemicals, dyestuffs and other organic derivatives (photochemicals, explosives).
Aminoguanidine bicarbonate is used in the purification of acrylic acid to remove aldehydes.
Aminoguanidine bicarbonate protects the cells infected with adenovirus from chromosomal damage.
Aminoguanidine is a specific and highly effective inhibitor of diamine oxidase present in fetal calf serum.
Uses of Aminoguanidine bicarbonate:
Aminoguanidine bicarbonate is also used as a selective inhibitor of inducible nitric oxide synthase in biochemistry.
Aminoguanidine bicarbonate (AGB) is of practical importance because of Aminoguanidine bicarbonate is use in dyes, dispersants, explosives and other commercial applications.
Aminoguanidine bicarbonate is used in the synthesis of antitumor agents and antileukemic activity.
Aminoguanidine bicarbonate is also used in the synthesis of neuraminidase inhibitors in the inhibition of influenze.
Industry Uses:
Intermediate
Other
Biochem/physiol Actions of Aminoguanidine bicarbonate:
Aminoguanidine bicarbonate protects the cells infected with adenovirus from chromosomal damage.
Aminoguanidine is a specific and highly effective inhibitor of diamine oxidase present in fetal calf serum.
General Manufacturing Information of Aminoguanidine bicarbonate:
Industry Processing Sectors:
All Other Chemical Product and Preparation Manufacturing
Preparation of Aminoguanidine bicarbonate:
Aminoguanidinium bicarbonate can be prepared by reacting calcium cyanamide with hydrazine sulfate.
Aminoguanidine bicarbonate can also be easily prepared by reducing nitroguanidine with zinc powder.
Diachrynic used this route obtaining a great yield:
41.14 g zinc powder (629 mmol, 3.3 molar eq.) are weighed and put to the side.
Into a reaction flask of at least 500 mL are put 20.00 g nitroguanidine (192 mmol, 1 molar eq.) and 47.62 g of ammonium sulfate (360 mmol, 1.88 molar eq.) in 285 mL of water.
The suspension is stirred and not everything dissolves, this is expected.
The reaction flask is immersed in an ice bath and equipped with magnetic stirring and a thermometer.
Stirring is started.
Once the solution reaches 10 °C the addition of small spatulas of zinc powder at a time is started.
Monitor the exotherm and don't add too much at once, however the reaction is fairly easy to control.
3-4 spatulas of zinc can be added at a time, making the temperature jump up by 5-8 °C.
The reaction was kept between 5-15 °C, leaning to the latter temperature.
The complete addition of zinc took about 1 hour, during which the ice bath was refilled just once.
Afterwards the reaction was left stirring at about 15 °C for a further 30 minutes.
The pH rose to about 8-9.
Using a fritted vacuum filter the zinc oxide sludge was removed, Aminoguanidine bicarbonate filtered fairly easily.
The yellow colored filtrate is put into a flask with magnetic stirring, and 8.57 g of 25% ammonia solution (126 mmol, 0.66 molar eq.) are added as well as 28.57 g of sodium bicarbonate (340 mmol, 0.94 molar eq.) with stirring, Aminoguanidine bicarbonate dissolves after a short while.
The solution is left standing for 12 h during which the Aminoguanidine bicarbonate slowly precipitates.
Afterwards Aminoguanidine bicarbonate is vacuum filtered off and air dried.
Yield of Aminoguanidine bicarbonate: 15.700 g (115 mmol, 60% based on nitroguanidine)
Production of Aminoguanidine bicarbonate:
1-) Two hundred and sixteen grams (2.07 moles) of nitroguanidine1 and 740 g. (11.3 moles) of purified zinc dust are thoroughly ground together in a mortar, and then enough water (about 400 ml.) is added with stirring with the pestle to form a thick paste.
The paste is transferred to a 3-l (enameled can or beaker surrounded by an ice bath)
A solution of 128 g. (2.14 moles) of glacial acetic acid in 130 ml of water is cooled to 5° in another 3-l (Beaker, which is fitted with a strong mechanical stirrer and surrounded by an ice bath)
The paste of nitroguanidine and zinc dust, cooled to 5°, is added slowly with mechanical stirring, the temperature of the reaction mixture being kept between 5° and 15°.
A total of about 1 kg of cracked ice is added to the mixture from time to time as the mixture becomes too warm or too thick to stir.
The addition of the paste takes about 8 hours, and the final volume of the mixture is about 1.5 l.
The mixture is then slowly warmed to 40° on a water bath with continued stirring, and this temperature is maintained for 1–5 minutes, until reduction is complete.
The solution is immediately separated from the insoluble material by filtration on a 20-cm.
Büchner funnel, and the cake is sucked as dry as possible.
The residue is transferred to the 3-l (beaker, triturated well with 1 l) of water, and then separated from the liquid by filtration.
In the same manner, the residue is washed twice more with two 600-ml. portions of water.
The filtrates are combined and placed in a 5-l (round-bottomed flask)
Two hundred grams of ammonium chloride is added, and the solution is mechanically stirred until solution is complete.
The stirring is continued, and 220 g. (2.62 moles) of sodium bicarbonate is added during a period of about 10 minutes.
The Aminoguanidine bicarbonate begins to precipitate after a few minutes, and the solution is then placed in a refrigerator overnight.
The precipitate is collected by filtration on a Büchner funnel.
The cake is removed to a 1-l (beaker and mixed with a 400-ml) portion of a 5% solution of ammonium chloride and filtered.
Aminoguanidine bicarbonate is again washed with two 400-ml portions of distilled water, the wash solution being removed each time by filtration.
Finally the solid is pressed down on the Büchner funnel; the mat is broken up with a spatula and washed while on the funnel with two 400-ml (portions of 95% ethanol and then with one 400-ml) (portion of ether)
After air drying, the Aminoguanidine bicarbonate amounts to 180–182 g.
2-) 1. The zinc is purified by stirring 1.2 kg of commercial zinc dust with 3 l of 2% hydrochloric acid for 1 minute.
The acid is removed by filtration, and the zinc is washed in a 4-l beaker with one 3-l portion of 2% hydrochloric acid, three 3-l portions of distilled water, two 2-l portions of 95% ethanol, and finally with one 2-l portion of absolute ether, the wash solutions being removed each time by filtration.
Then the material is thoroughly dried and any lumps are broken up in a mortar.
2. The solution becomes basic to litmus after one-half to three-fourths of the paste has been added.
Lower yields are obtained if a larger excess of acetic acid is employed.
3. The state of reduction can be determined by placing 3 drops of the reaction mixture in a test tube containing 5 ml of a 10% solution of sodium hydroxide and then adding 5 ml of a freshly prepared saturated solution of ferrous ammonium sulfate.
A red coloration indicates incomplete reduction; when the reduction is complete, only a greenish precipitate is observed.
The mixture should not be heated after this test shows that reduction is complete.
4. The presence of the ammonium chloride prevents the coprecipitation of zinc salts when sodium bicarbonate is added to the solution to precipitate the aminoguanidine as the bicarbonate.
If the solution is not clear at this step, Aminoguanidine bicarbonate should be filtered.
5. The Aminoguanidine bicarbonate is pure enough for most purposes.
Aminoguanidine bicarbonate should not be recrystallized from hot water, since decomposition will occur.
6. W. W. Hartman and Ross Philips have submitted a procedure suitable for the preparation of Aminoguanidine bicarbonate on a larger scale.
The sulfates of methylisothiourea and of hydrazine are allowed to react with the evolution of methyl mercaptan.
In a 30-gal crock are placed 10 l of water and 5760 g (20 moles) of methylisothiourea sulfate In a 22-l flask, 5.2 kg (40 moles) of hydrazine sulfate is stirred with 12 l of water, and 40% sodium hydroxide is added until all the hydrazine sulfate has dissolved and the solution is just neutral to Congo paper.
The exact amount of alkali is noted and a duplicate amount added.
The hydrazine solution is then added to the 30-gal crock with stirring, as fast as possible, without allowing the foam to overflow the crock.
The mixing is done out-of-doors, or in an efficient hood, since large volumes of methyl mercaptan are evolved.
If the reaction is carried out on a smaller scale in 12- or 22-l flasks, using appropriate amounts of material, the methyl mercaptan evolved may be absorbed in cold sodium hydroxide solution and isolated if desired.
The solution is stirred until evolution of mercaptan stops, and then a few liters of water are distilled off under reduced pressure to free the solution entirely from mercaptan.
The residual liquor is chilled in a crock, and a crop of hydrated sodium sulfate is filtered off, washed with ice water, and discarded.
The filtrate is warmed to 20–25°, 25 ml of glacial acetic acid is added, then 4 kg of sodium bicarbonate, and the solution is stirred vigorously for 5 minutes and thereafter occasionally during an hour, or until the precipitate no longer increases.
The precipitate is filtered with suction and washed with ice water and then with methanol, and is dried at a temperature not above 60–70°.
The yield is 3760 g (69% of the theoretical amount).
Hydrazine sulfate may be recovered from the final filtrate, if the filtrate is strongly acidified with sulfuric acid and allowed to cool.
3. Discussion
Numerous references for the preparation of Aminoguanidine bicarbonate and other salts can be found in an excellent review article by Lieber and Smith.
Aminoguanidine bicarbonate has also been prepared by treating a cyanamide solution at 20–50° with hydrazine and carbon dioxide, and by the electrolytic reduction of nitroguanidine.
Typical Properties of Aminoguanidine bicarbonate:
Chemical:
Addition of an equimolar amount of freebase aminoguanidine to Aminoguanidine bicarbonate will yield aminoguanidinium carbonate.
Aminoguanidinium bicarbonate will react with acids to yield their respective salts.
X-ray analysis has shown that solid Aminoguanidine bicarbonate is actually a zwitterionic molecule, 2-guanidinium-1-aminocarboxylate monohydrate.
Physical:
Aminoguanidinium bicarbonate is a white solid, slightly soluble in water.
Recrystallization from hot water is possible, but some decomposition always occurs and reprecipitation tends to be slow and incomplete.
Handling and storage of Aminoguanidine bicarbonate:
Precautions for safe handling:
Avoid breathing dust/fume/gas/mist/vapor/spray.
Hygiene criteria:
Do not take contaminated clothing out of the workplace.
Wash contaminated clothing before reuse.
Conditions for safe storage, including any incompatibilities:
Storage conditions:
Store in original container.
Store in a well-ventilated place.
Stability and reactivity of Aminoguanidine bicarbonate:
Reaction:
No additional information
Chemical stability:
Aminoguanidine bicarbonate is stable under normal conditions.
Possibility of hazardous reactions:
No additional information
Conditions to avoid:
Avoid dust formation.
Do not allow contact with water.
Incompatible materials:
No additional information
Harmful decomposition products:
No additional information
First Aid Measures of Aminoguanidine bicarbonate:
First aid measures in case of inhalation:
Remove the person to fresh air and allow them to breathe comfortably.
Give oxygen or artificial respiration if necessary.
If you feel unwell, seek medical help.
First aid measures in case of skin contact:
Wash thoroughly with plenty of soap and water.
If skin irritation occurs:
Get medical help/intervention.
First aid measures in case of eye contact:
Remove contact lenses, if present and easy to remove.
Rinse constantly.
Rinse carefully with water for a few minutes.
If eye irritation is persistent:
Get medical advice/care.
First aid measures in case of swallowing:
Rinse mouth out with water.
If you feel unwell, seek medical help.
Most important symptoms and effects, both acute and delayed:
Symptoms/effects following inhalation:
Aminoguanidine bicarbonate causes allergic skin reactions.
Initial signs that require medical attention and special treatment:
Treat symptomatically.
Fir Fighting Measures of Aminoguanidine bicarbonate:
Fire extinguishers:
Suitable extinguishing media:
Dry chemical powder, alcohol-resistant foam, carbon dioxide (CO2).
Unsuitable extinguishing media:
Do not use fire extinguishing materials containing water.
Special hazards arising from the substance or mixture:
No additional information
Advice for firefighting crews:
Protection in case of fire:
Do not attempt to take action without suitable protective equipment.
Accidental Release Measures of Aminoguanidine bicarbonate:
Emergency plans:
Avoid contact with skin, eyes and clothing.
For emergency responders:
Protective equipment:
Use personal protective equipment.
Emergency plans:
Stop exposure.
Environmental precautions:
Long-lasting, toxic effect in the aquatic environment.
Methods and materials for containment and cleaning:
Cleaning operations:
Clean up immediately by sweeping or vacuuming.
Identifiers of Aminoguanidine bicarbonate:
CAS No: [2582-30-1]
Product Code: FA33808
MDL No: MFCD00012949
Chemical Formula: CH6N4·H2CO3
Molecular Weight: 136.11 g/mol
Smiles: C(=NN)(N)N.C(=O)(O)O
Melting Point: 171.50 °C
Quality Level: 100
Assay: 97%
mp: 170-172 °C (dec.) (lit.)
solubility:
H2O: soluble 2.7 g/L at 20 °C
H2O: soluble 3.3 g/L at 30 °C
SMILES string: OC(O)=O.NNC(N)=N
InChI: 1S/CH6N4.CH2O3/c2-1(3)5-4;2-1(3)4/h4H2,(H4,2,3,5);(H2,2,3,4)
InChI key: OTXHZHQQWQTQMW-UHFFFAOYSA-N
Product Number: A0307
Purity / Analysis Method: >98.0%(T)
Molecular Formula / Molecular Weight: CH6N4·H2CO3 = 136.11
Physical State (20 deg.C): Solid
CAS RN: 2582-30-1
Reaxys Registry Number: 3569869
PubChem Substance ID: 87561960
SDBS (AIST Spectral DB): 1667
MDL Number: MFCD00012949
Synonym(s): Aminoguanidine hydrogencarbonate, Guanylhydrazine hydrogencarbonate
Linear Formula: NH2NHC(=NH)NH2 · H2CO3
CAS Number: 2582-30-1
Molecular Weight: 136.11
Beilstein: 3569869
EC Number: 219-956-7
MDL number: MFCD00012949
PubChem Substance ID: 24846902
NACRES: NA.22
Properties of Aminoguanidine bicarbonate:
Molecular Weight: 136.11 g/mol
Hydrogen Bond Donor Count: 5
Hydrogen Bond Acceptor Count: 5
Rotatable Bond Count: 0
Exact Mass: 136.05964013 g/mol
Monoisotopic Mass: 136.05964013 g/mol
Topological Polar Surface Area: 148Ų
Heavy Atom Count: 9
Complexity: 67.9
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 2
Compound Is Canonicalized: Yes
Physical State: Solid
Solubility: Soluble in water (3.3 mg/ml at 30° C), and water (2.7 mg/ml at 20° C).
Storage: Store at 4° C
Melting Point: 170-172° C (lit.)(dec.)
Boiling Point: 422.4° C at 760 mmHg
Density: 1.60 g/cm3
Refractive Index: n20D ~1.67 (Predicted)
Specifications of Aminoguanidine bicarbonate:
Appearance: White to Light yellow powder to crystal
Purity(Nonaqueous Titration): min. 98.0 %
Purity( Potassium iodate Method): min. 98.0 %
Melting Point: 125°C
Color: White
Ignition Residue: 0.3% max.
Infrared Spectrum: Authentic
Assay Percent Range: 98.5%
Packaging: Plastic Bottle
Linear Formula: H2NNHC(=NH)NH2·H2CO3
Quantity: 250 g
Beilstein: 03,117
Solubility Information: Solubility in water: <5g/L (20°C)
Formula Weight: 136.11
Percent Purity: 98.50%
Physical Form: Crystalline Powder
Chemical Name or Material: Aminoguanidine bicarbonate
