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6-Aminocaproic acid, molecular formula C6H13NO2, white or off-white crystalline powder at room temperature, no odor, slightly soluble in water, ethanol and chloroform, almost insoluble in ether and benzene. is a medicine also known as amikapic acid. It falls under the category of hemostatic drugs and is used in the treatment of heavy bleeding. It works by preventing fibrinolysis, thereby reducing the activity of lysinogen in the plasma, helping to control bleeding. It is also used to treat hereditary and acquired fibrinolysis and other coagulation disorders and to provide hemostatic control after surgery or trauma. It is also used in dental surgery and post-obstetric surgery for haemostatic control and has been widely used.
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Chemical Formula |
C6H13NO2 |
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Exact Mass |
131 |
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Molecular Weight |
131 |
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m/z |
131 (100.0%), 132 (6.5%) |
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Elemental Analysis |
C, 54.94; H, 9.99; N, 10.68; O, 24.39 |
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6-Aminocaproic acid is a white crystalline powdery organic compound, belonging to anti fibrinolytic agents. Its unique chemical properties make it widely applicable in various fields such as medicine, organic synthesis, biomedical science, etc.
Applications in the field of medicine
1. Hemostatic drugs
The most widely used application in the field of medicine is as a hemostatic drug. It achieves hemostasis by inhibiting plasminogen activator and blocking the process of fibrinolysis. Specifically, it can inhibit the activation factor of plasminogen, preventing it from being activated into plasmin, thereby reducing the degradation of fibrin and achieving hemostasis. This mechanism makes it particularly suitable for bleeding caused by elevated fibrinolytic enzyme activity, such as gynecological bleeding, bleeding after internal organ surgeries such as prostate, liver, pancreas, and lung.
Surgical bleeding: In surgical procedures, it is commonly used to reduce intraoperative bleeding and decrease blood transfusion volume. It can be administered intravenously or orally to quickly achieve effective hemostatic concentration. For patients with surgical bleeding or massive internal bleeding, rapid hemostasis requires reaching an effective concentration in the blood quickly. The initial dose can be 4-6 grams dissolved in 100 milliliters of physiological saline or 5% -10% glucose solution, and dropped in 15-30 minutes. The continuous dose is 1 gram per hour, which can be taken orally or injected, and maintained for 12-24 hours or longer, depending on the condition.
Obstetrics and Gynecology Bleeding: It has significant therapeutic effects on bleeding related diseases in obstetrics and gynecology, such as postpartum hemorrhage and excessive menstruation. It can improve patient symptoms by inhibiting the fibrinolytic system, reducing bleeding volume.
Internal organ surgery bleeding: It can also play an important role in stopping bleeding in internal organ surgeries such as prostate, liver, pancreas, and lungs. It can reduce bleeding during surgery and improve the success rate of the operation.
2. Assist in improving symptoms of other diseases
In addition to its hemostatic effect, it has also been found to have some auxiliary effects in improving symptoms of other diseases. For example:
Improving liver function: It can assist in the metabolism of liver cells and to some extent improve abnormal liver function. This has a certain adjuvant therapeutic effect for patients with liver function impairment.
Improving sleep: It can stimulate neurotransmitters in the brain, thereby achieving the effect of improving sleep. Therefore, it can be used to assist in improving insomnia symptoms and enhancing the quality of sleep for patients.
Improving skin condition: It can promote skin metabolism, help the skin absorb nutrients, and thus assist in improving skin condition. This has a certain improvement effect on problems such as dry and rough skin.
Applications in the field of organic synthesis
1. Synthetic nylon 6
6-Aminocaproic acid is an important intermediate in the field of organic synthesis, with the most famous application being the synthesis of nylon 6. Nylon 6 is an important polyamide polymer material widely used in industries such as machinery, chemical, instrumentation, automotive manufacturing, medical, and textile. Nylon 6 monomer, caprolactam, can be synthesized through polymerization reaction to produce nylon 6. This process not only provides an important source of raw materials for the production of nylon 6, but also promotes the development of related industries.
2. Synthesize other organic compounds
In addition to synthesizing nylon 6, it can also be used to synthesize various other organic compounds with special functions. For example:
Synthetic polyurethane materials: can serve as precursors for polyurethane materials and react with other compounds to produce polyurethane products with specific properties.
Synthesis of nitrogen-containing small molecules: It can also be used to synthesize some biologically active nitrogen-containing small molecules, which have potential application value in fields such as drug development.
Applications in the field of biomedical sciences
1. Biotin-6-aminocaproic acid complex
Biotin-6-Aminocaproic acid is a complex formed by connecting biotin and the substance through a chemical bond. Biotin is a water-soluble vitamin (vitamin B7) that has the ability to specifically bind to streptavidin or avidin. Therefore, the biotin-6-aminohexanoic acid complex has shown significant application value in biomedical, biological detection, and functional materials fields.
Biological detection: The biotin-6-aminohexanoic acid complex can serve as a biological probe for detecting specific biomolecules or cells. By utilizing the high affinity binding ability of biotin with streptavidin or avidin, efficient capture and detection of target molecules can be achieved.
Drug development: The biotin-6-aminohexanoic acid complex can also be used in the field of drug development. By linking it with drug molecules, the targeting and stability of drugs can be improved, thereby enhancing their therapeutic efficacy.
2. Synthesis of novel fluorescent probes
It can also be used to synthesize novel fluorescent probes. For example, tert butoxycarbonyl-6-aminohexanoic acid can be used to synthesize a novel fluorescent probe for the production of oxybutyron type saponins. This fluorescent probe has high sensitivity and selectivity, and can be used to detect specific biomolecules or cellular activities, providing a powerful tool for biomedical research.
Preparation method and process optimization
The preparation methods of product mainly include direct chemical synthesis, hydrolysis and refining of caprolactam or caprolactam polymer.
Chemical synthesis method:
It has the advantages of mild reaction conditions, high catalytic efficiency, and strong specificity, and is currently one of the main production methods.
Biological synthesis method:
In recent years, with the continuous development of biotechnology, it has gradually become a new approach for the preparation of this substance.
By constructing multi enzyme molecular machines or utilizing microbial fermentation methods, efficient synthesis of this substance can be achieved, providing new ideas for its industrial production.
history:
In the 1930s, scientists were in a flourishing stage of research on amino acids and proteins.
In 1932, German chemists Fischer and L. O. Weinberg first synthesized the substance in the laboratory, but at that time, their potential biological significance was not yet realized. During this period, research mainly focused on the synthesis methods of compounds and the description of their basic physical and chemical properties, with almost no understanding of their pharmacological activities.
During World War II, medical research developed vigorously, especially with a sharp increase in demand for trauma treatment and hemostatic methods.
After the war, with the rapid development of biochemistry and molecular biology, scientists began to study the mechanisms of blood coagulation and fibrinolysis more systematically.
In 1948, Swedish scientists Astrup and Pelmin discovered the phenomenon of fibrinolysis, laying the foundation for subsequent research on anti fibrinolytic drugs.
In the early 1950s, researchers accidentally discovered that 6-Aminopropionic acid had the property of prolonging clotting time when screening various amino acid derivatives. This discovery has attracted the attention of multiple research teams, including Japanese scientist Isamu Suda and American scientist Okamoto. They began systematic research on the effects on the blood system, marking the transition of the compound from simple chemotherapy to a potential therapeutic drug.
In 1957, a key breakthrough in research was made when Japanese scientist Isamu Suda and his team reported in detail for the first time the appearance of anti fibrinolytic activity. They found that the compound can significantly inhibit the process of fibrinolysis when studying the blood coagulation system.
Almost simultaneously, American scientist Okamoto independently discovered a similar effect and began exploring its molecular mechanism.
In 1959, the Okamoto team proposed a preliminary theory of the mechanism of action of this substance, suggesting that it works by competitively inhibiting the activation of plasmin. Fibrinogen is a key enzyme in the fibrinolytic system, which is activated by tissue type plasminogen activator (t-PA) or urokinase type plasminogen activator (u-PA) and converted into plasmin to degrade fibrin. Its structure is similar to lysine, and it can bind to the lysine binding site of plasmin, preventing its binding to fibrin and subsequent activation process.
During this period, the study also determined the optimal therapeutic dose and administration method. Clinical trials have shown that after intravenous injection, it rapidly distributes throughout the body and is excreted in its original form through the kidneys within 4-6 hours. These pharmacokinetic properties make it an ideal short acting anti fibrinolytic drug.
In 1962, the US Food and Drug Administration (FDA) approved 6-Aminopropionic acid for clinical use under the trade name Amicar ®, Used to treat bleeding caused by fibrinolysis, such as hemostasis in scenarios such as heart surgery, liver transplantation, and prostatectomy. This approval marks the official transition of 6-aminocaproic acid from laboratory to clinical practice, opening a new chapter in its widespread application in the medical field.
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