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6-Aminocaproic acid (Acepramin), 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-acepramin complex
Biotin-acepramin 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.
The dominant industrial and laboratory preparation route is the hydrolysis of ε-caprolactam, which includes two mature technologies: acid hydrolysis and pressurized alkaline hydrolysis. A greener biocatalytic route serves as an emerging alternative.
(I) Acid Hydrolysis Process (Primary Route for Pharmaceutical-Grade Material)
Industrial-grade ε-caprolactam is used as the starting material, mixed with concentrated hydrochloric acid and deionized water, then refluxed at 103–106 °C for 1.5–5 hours to open the lactam ring and form 6-Aminocaproic acid hydrochloride. Thin-layer chromatography (TLC) is used to monitor the reaction until the conversion rate reaches ≥95%.
After cooling and dilution, the solution is loaded onto a strongly acidic cation exchange resin for adsorption. Washing removes chloride ions, and gradient elution with dilute aqueous ammonia yields an aqueous solution of free acepramin. Activated carbon is added for decolorization at 60 °C over 0.5 hours to eliminate colored impurities.
The filtrate is concentrated under reduced pressure at 47–70 °C until nearly dry, followed by addition of anhydrous ethanol and cooling to induce crystallization. Filtration affords crude crystals.
The crude product undergoes secondary recrystallization with a water-ethanol mixed solvent, ethanol washing, and low-temperature vacuum drying.
The final product achieves a purity above 99.2%, complying with pharmacopoeial standards for active pharmaceutical ingredients (APIs). This process features mild reaction conditions and easy impurity control, yet it generates saline wastewater and incurs high costs for regenerating ion exchange resins during post-treatment.
(II) Pressurized Alkaline Hydrolysis Process (Large-Scale Bulk Production Route)
ε-Caprolactam and dilute sodium hydroxide solution are charged into an autoclave for pressurized hydrolysis within 1.5 hours at 0.15–0.3 MPa and 115–125 °C. The strong base rapidly cleaves the amide ring, producing far fewer byproducts than atmospheric-pressure reactions.
The hydrolysate is neutralized to its isoelectric point with dilute phosphoric acid, filtered to remove inorganic salt precipitates, concentrated, and precipitated with alcohol to obtain crude solids.
Its advantages include a short reaction cycle and no severe equipment corrosion from strong acids, making it suitable for large-scale chemical manufacturing. The main drawback is difficult deep removal of neutralization salt impurities; an additional precise desalting step is required if the product is intended for pharmaceutical use.
(III) Biocatalytic Synthesis (Novel Green Process)
6-oxocaproic acid acts as the substrate, with gamma-aminobutyrate transaminase (GABA-T) as the biocatalyst, glutamic acid as the amino donor, and pyridoxal phosphate as the coenzyme. The transamination reaction proceeds at ambient temperature and atmospheric pressure with nearly 100% selectivity, producing no acidic or alkaline waste effluents.
This route is limited by high costs of enzyme preparations and lengthy fermentation cycles. It currently remains at the laboratory bench scale and has not been industrialized.
Overall Comparison
Pharmaceutical manufacturers prefer the acid hydrolysis-recrystallization route for balanced high purity and consistent process performance. The nylon chemical recycling industry predominantly adopts pressurized alkaline hydrolysis to degrade waste nylon 6 and regenerate recyclable acepramin monomers.
Research on acepramin (EACA) has evolved along two distinct lines: polymeric raw material development and hemostatic pharmaceutical development. The compound was first synthesized in caprolactam ring-opening experiments in the late 19th century. In the early days, organic chemists only studied it as an intermediate for nylon 6 monomers, with no investigations into its medical applications.
The industrialization of nylon in the 1940s matured the caprolactam hydrolysis process, enabling mass production of this compound, yet its applications remained confined to synthetic materials.
In 1962, Japanese researchers Shusuke Okamoto and Utako Okamoto launched medical research on EACA. At that time, the mortality rate from postpartum hemorrhage remained extremely high. The couple targeted fibrinolysis inhibition sites, compared the enzyme-inhibitory activities of lysine derivatives, and modified carbon chain structures to obtain acepramin.
They verified that the compound competitively binds to lysine binding sites on plasminogen and blocks fibrinolysis. Their findings, published in the Keio Journal of Medicine, pioneered the class of antifibrinolytic hemostatic agents.
Subsequent animal studies and clinical trials further validated its hemostatic efficacy, and EACA entered formal clinical use in the mid-to-late 1960s. During the same period, tranexamic acid with stronger hemostatic activity was developed by optimizing the molecular scaffold of EACA. As the first-generation antifibrinolytic drug, acepramin is still widely used for symptomatic management of intraoperative oozing.
FAQ
What is another name for aminocaproic acid?
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Aminocaproic acid (a medication used to treat and prevent excessive bleeding by stabilizing blood clots) is most commonly known by its brand name, Amicar.
What class of drug is aminocaproic acid?
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Aminocaproic acid belongs to the antifibrinolytic drug class. Also classified as a hemostatic agent or miscellaneous coagulation modifier, it works by competitively inhibiting the activation of plasminogen to plasmin, effectively slowing the breakdown of blood clots and controlling excessive bleeding.
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