6-AMINOHEXANOIC ACID
6-Aminocaproic acid
CAS: 60-32-2
Molecular Formula: C6H13NO2
6-AMINOHEXANOIC ACID - Names and Identifiers
| Name | 6-Aminocaproic acid |
| Synonyms | ACS EACA 177jd 177j.d. 177 J.D 177 J.D. H-EAhx-OH Acepramin Acepramine H-6-Aca-OH H-6-Ahx-OH 6-aminohexanoate Aminocaproic acid 6-Aminocaproic acid 6-amino-hexanoicaci E-AMINOCAPROIC ACID 6-Aminohexanoic acid epsilon-Aminocaproic acid |
| CAS | 60-32-2 |
| EINECS | 200-469-3 |
| InChI | InChI=1/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)/p-1 |
| InChIKey | SLXKOJJOQWFEFD-UHFFFAOYSA-N |
6-AMINOHEXANOIC ACID - Physico-chemical Properties
| Molecular Formula | C6H13NO2 |
| Molar Mass | 131.17 |
| Density | 1.042 g/cm3 |
| Melting Point | 207-209 °C (dec.) (lit.) |
| Boling Point | 242.49°C (rough estimate) |
| Flash Point | 207-209°C |
| Water Solubility | SOLUBLE |
| Solubility | Soluble in water (50 mg/ml), ethanol (≥1 mg/ml), methanol (sparingly soluble), ether, |
| Vapor Presure | <0.1 hPa (20 °C) |
| Appearance | Odor-free white solid |
| Color | white |
| Odor | Odorless |
| Merck | 14,432 |
| BRN | 906872 |
| pKa | 4.373(at 25℃) |
| PH | 7.0-7.5 (50g/l, H2O, 20℃) |
| Storage Condition | Store below +30°C. |
| Refractive Index | 1.4870 (estimate) |
| MDL | MFCD00008238 |
| Physical and Chemical Properties | White or yellowish crystalline powder. Soluble in water, its 3.52% aqueous solution is isotonic solution. Melting Point 204-207 ℃, can hinder the formation of fibrinolytic enzyme, thus inhibiting the dissolution of fibrin to achieve the purpose of hemostasis. |
| Use | For surgical bleeding, obstetrics and gynecology bleeding, pulmonary hemorrhage, upper gastrointestinal bleeding. |
6-AMINOHEXANOIC ACID - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 2 |
| RTECS | MO6300000 |
| TSCA | Yes |
| HS Code | 29224995 |
| Toxicity | LD50 in rats (g/kg): 7.0 i.p.; ~3.3 i.v. (Hallesy) |
6-AMINOHEXANOIC ACID - Upstream Downstream Industry
| Raw Materials | epsilon-Caprolactam |
6-AMINOHEXANOIC ACID - Reference
| Reference Show more | 1. Li, Wei, et al. "Measurement and Correlation of the Solubility of Aminocaproic Acid in Some Pure and Binary Solvents." Journal of Chemical & Engineering Data 64.12 (2019): 5312-5323.https://doi.org/10.1021/acs.jced.9b00543 2. [IF=9.229] Guanying Xie et al."Low-Dimensional Hybrid Lead Iodide Perovskites Single Crystals via Bifunctional Amino Acid Cross-Linkage: Structural Diversity and Properties Controllability."Acs Appl Mater Inter. 2021;13(2):3325–3335 |
6-AMINOHEXANOIC ACID - Standard
Authoritative Data Verified Data
This product is 6-aminocaproic acid. Calculated as dried product, the content of C6H13N02 shall not be less than 98.5%.
Last Update：2024-01-02 23:10:35
6-AMINOHEXANOIC ACID - Trait
Authoritative Data Verified Data
- This product is white crystalline powder; Odorless.
- This product is soluble in water, slightly soluble in ethanol, and almost insoluble in chloroform or ether.
Last Update：2022-01-01 15:37:25
6-AMINOHEXANOIC ACID - Differential diagnosis
Authoritative Data Verified Data
- appropriate amounts of this product and the amino-hexanoic acid reference product were added with water, dissolved and diluted to prepare a solution containing about 2.5mg per 1 ml as the test solution and the reference solution. Draw 2ul of each of the above two solutions, and test according to the chromatographic conditions under the item of related substances. The position and color of the main spot of the test solution should be the same as that of the reference solution.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 415).
Last Update：2022-01-01 15:37:25
6-AMINOHEXANOIC ACID - Exam
Authoritative Data Verified Data
alkalinity
take this product 5. G, add new boiling cold water 25ml to dissolve, according to the law (General 0631),pH value should be 7.5~8.0.
clarity and color of solution
take the solution under the alkalinity, the solution should be clear and colorless. If it is turbid, it should not be more concentrated than No. 1 turbidity standard solution (General 0902 first method), and after 24 hours, the clarity should not be more concentrated than No. 1 turbidity standard solution.
sulfate
take l.Og of this product and check it according to law (General rule 0802). Compared with the control solution made of 1.0ml of standard potassium sulfate solution, it should not be more concentrated (0.01%).
Related substances
take an appropriate amount of this product, add water to dissolve and dilute to make a solution containing about 10mg per lml as a test solution; Take 1ml for precision measurement and put it in a 200ml measuring flask, as a control solution, it was diluted to the scale with water and shaken. In addition, 10mg of aminocaproic acid and 10mg of leucine were added into the same 25ml measuring flask, dissolved with water and diluted to the scale, and then shaken, as a system applicable solution. According to the thin layer chromatography (General 0502) test, absorb the above three solutions each 5 u1, respectively, on the same silica gel G thin layer plate, with n-butanol-water-glacial acetic acid (60:20:20) for the purpose of development, after spreading for 15cm, air-drying, spray with 1, 3 ninhydrin solution [0.2% g of ninhydrin, add n-butanol -2mol/L acetic acid solution (95:5) 0.2 to dissolve], heating at 100~105°C for 15 minutes, check, system applicable solution should show two completely separated spots; Test solution such as impurity spots, compared with the main spot of the control solution, not deeper (0.5%).
loss on drying
take this product, dry to constant weight at 105°C, weight loss shall not exceed 0.5% (General rule 0831).
ignition residue
This product l.O g, inspection according to law (General 0841), residue shall not exceed 0.1%.
Heavy metals
The residue left under the item of taking the ignition residue shall not contain more than 10 parts per million of heavy metal when examined by law (General Principles 0821, Law II).
calcium salt
take 1.0g of this product, add 20ml of water to dissolve, add 2 ml of ammonia test solution, shake well, and divide into two equal parts; Add 1ml of ammonium oxalate test solution and 1ml of water in one part, shake well and leave for 5 minutes, and both solutions should be equally clear.
arsenic salt
take this product l.O g, add water 23ml after dissolution, according to the law inspection (General Principles 0822 The first law), should comply with the provisions (0.0002%).
Last Update：2022-01-01 15:37:26
6-AMINOHEXANOIC ACID - Content determination
Authoritative Data Verified Data
take this product about 0.2g, precision weighing, add formaldehyde solution 5ml dissolved, add ethanol 20ml and phenolphthalein indicator solution 2 drops, with sodium hydroxide titration solution (0.lmol/L) titration to the solution of microscopic red; Another 15ml of fresh boiling cold water, add 5ml of formaldehyde solution and 20ml of ethanol for blank test correction. Each 1 ml of sodium hydroxide titration solution (0.1 mol/L) corresponds to 13.12mg of C6H13N02.
Last Update：2022-01-01 15:37:27
6-AMINOHEXANOIC ACID - Category
Authoritative Data Verified Data
hemostatic drugs.
Last Update：2022-01-01 15:37:27
6-AMINOHEXANOIC ACID - Storage
Authoritative Data Verified Data
sealed and stored in a dry place.
Last Update：2022-01-01 15:37:27
6-AMINOHEXANOIC ACID - Aminocaproic Acid Injection
Authoritative Data Verified Data
This product is a sterile aqueous solution of aminocaproic acid. The amino-containing hexanoic acid (C6H13N02) shall be between 95.0% and 105.0% of the labeled amount.
trait
This product is colorless or almost colorless clear liquid.
identification
- take 0.2ml of this product, add 5ml of water, add about 5mg of Trione, heat, the solution should be blue purple.
- take an appropriate amount of this product and dilute it with water to make a solution containing about 2.5mg per 1 ml as a test solution, water was added to dissolve and diluted to prepare a solution containing about 2.5mg per 1 ml as a control solution. According to the chromatographic condition test under the item of related substances, the position and color of the main spot of the test solution should be the same as that of the reference solution.
examination
- the pH value should be 7.0 to 8.0 (General 0631).
- appropriate amount of related substances should be taken and diluted with water to prepare a solution containing about 10mg per 1 ml as a sample solution; Appropriate amount should be taken for precision measurement, A solution containing about 0.05mg per 1 ml was prepared as a control solution by quantitative dilution with water. In addition, 10mg of aminocaproic acid and 10mg of leucine were added into the same 25ml measuring flask, dissolved with water and diluted to the scale, and then shaken, as a system applicable solution. According to the thin layer chromatography (General 0502) test, absorb the above three solutions each 5 u1, respectively, on the same silica gel G thin layer plate, with n-butanol-water-glacial acetic acid (60:20:20) for the purpose of development, after spreading, air-drying, spray with 0.2% indantrone, solution [0.2g ninhydrin, add n-butanol -2mol/L acetic acid solution (95:5) to dissolve,], heated at 100~105°C for 15 minutes, check, the control solution should show a clear spot, the system applicable solution should show two obvious spots, test solution such as impurity spots, compared with the control solution main spot, not deeper (0.5%).
- caprolactam precise amount of this product, quantitative dilution with water to make a solution containing about 10 mg per 1 ml, shake, as a test solution; Take an appropriate amount of caprolactam reference, precision weighing, adding water to dissolve and quantitatively dilute the solution contained in about 1 ml, shake well and use it as a reference solution; Take an appropriate amount of this product and heat it at 105°C for 24 hours, A solution containing about 10 mg of aminocaproic acid per 1 ml was prepared by dilution with water, and was shaken well as a system-suitable solution. According to the high performance liquid chromatography (General 0512) determination, with the eighteen alkyl silane bonded silica gel as filler 9 take potassium dihydrogen phosphate 10G, add solvent (take sodium hexanesulfonate 0. 55g, add water to dissolve and dilute to 1000ml, then obtain) 600ml to dissolve, add methanol 250ml to mix, adjust pH to 2.2 with phosphoric acid, dilute to 1000ml with the above solvent as mobile phase, the detection wavelength was 210nm. 20ul of the applicable solution of the system shall be injected into the liquid chromatograph, and the separation degree between caprolactam peak and adjacent chromatographic peak shall meet the requirements; Then 20ul of the sample solution and the reference solution shall be accurately measured and injected into the liquid chromatograph respectively, the chromatogram was recorded. If there is a chromatographic peak in the chromatogram of the test solution that is consistent with the retention time of the caprolactam peak, the peak area shall be calculated according to the external standard method, and 0.15% of the labeled amount of the amino acid shall not be allowed.
- bacterial endotoxin take this product, check according to law (General rule 1143), the amount of endotoxin per 1 mg of aminocaproic acid should be less than 0.016EU.
- others should comply with the relevant provisions under injection (General 0102).
Content determination
take an appropriate amount of this product (about equivalent to 0.2g of aminocaproic acid), add 5ml of formaldehyde solution, shake well, add 20ml of ethanol and 2 drops of phenolphthalein indicator solution, and use sodium hydroxide titration solution (0.lmol/L) titration; Another 15ml of fresh boiling cold water was taken, and 5ml of formaldehyde solution and 20ml of ethanol were added for blank test correction. Each 1 ml of sodium hydroxide titration solution (0.1 mol/L) corresponds to 13.12mg of C6H13N02.
category
aminocaproic acid.
specification
(l)10ml:2g (2)20ml:4g
storage
sealed storage.
Last Update：2022-01-01 15:37:28
6-AMINOHEXANOIC ACID - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| hemostatics | 6-aminocaproic acid also known as aminocaproic acid, aminocaproic acid, ε-aminocaproic acid, antifibrinolytic acid, it is a commonly used anti-fibrinolytic hemostatic agent for SAH, which has anti-fibrinolytic effect, can produce competitive inhibition with plasminogen activator, and inhibit the process of converting plasminogen to plasmin, there is also a weak direct inhibition of plasmin, slowing the cleavage of fibrin into polypeptides and amino acids. This product in the blood concentration of 130mg/L or more to inhibit the plasminogen into plasmin, direct inhibition of plasmin must reach 1300mg/L, so as to inhibit the dissolution of fibrin, to achieve hemostatic effect. Its function is weak, the excretion is fast, and the maintenance time is short. The drug in the gastrointestinal absorption is rapid, complete, bioavailability of 80%. 2 hours after taking the peak blood concentration. Most of them are excreted by urine in the prototype, t1/2 is about 103 minutes. Applicable to the primary or secondary fibrinolysis caused by hemorrhage, such as serious infections, gynecological accidents, leukemia, malignant tumors and severe liver disease caused by bleeding; Other such as surgical bleeding, obstetrics and gynecology bleeding, lung, upper digestive tract, prostate, liver, pancreas and other bleeding. Intraoperative or preoperative medication can reduce intraoperative bleeding and reduce the amount of blood transfusion. 6-aminocaproic acid, haemostatic cyclic acid (AMCA) and p-hydroxybenzylamine (PAMBA) are commonly used antifibrinolytic agents in clinical practice. All of them can inhibit the activation factor of fibrinolytic enzyme, so that the former can not be activated to become fibrinolytic enzyme, thereby prolonging the dissolution period of the blood clot blocking the rupture and reducing the chance of rebleeding during the waiting period. Antifibrinolytic therapy is necessary because of the increased activity of fibrinases in the cerebrospinal fluid after subarachnoid hemorrhage. Most researchers believe that 6-aminocaproic acid and haemostatic cyclic acid to prevent the recent rebleeding effect is better, and the earlier the application, the better the effect. |
| indication, usage and dosage | antifibrinolytic drugs, clinical mainly for the prevention and treatment of hyperfibrinolysis caused by a variety of bleeding. Oral: 2g each time, 3~4 times a day, according to the disease with 7~10 days or more; Children each 0.1g/kg, 3~4 times a day. The absorption of this product is rapid and complete, and the effective concentration in blood can be reached 1~2 hours after taking it. Intravenous drip: the initial dose of 4.0~6.0g,30 minutes to finish, maintain the dose of 1.0g/h, the daily dose of not more than 20g. for the prevention and treatment of primary hyperfibrinolysis and disseminated intravascular coagulation secondary hyperfibrinolysis caused by various bleeding. It can also be used for brain, lung, prostate, thyroid, adrenal, uterine and other surgical bleeding, as well as traumatic bleeding, upper gastrointestinal bleeding, hemoptysis, cirrhosis bleeding, thrombocytopenic purpura and leukemia and other bleeding symptomatic treatment. Adults: oral, 2G, tid or qid; Intravenous drip, the first dose of 4~6G dissolved in GS or NS 100 ~ 250ml, drip within 15~30 minutes, maintain the amount of 1.00~1.25g per hour. Daily dosage of not more than 20g, can be used for several days, until bleeding control. Children: oral, 0.1g/kg,tid or qid, 7~10 days or more as appropriate; Intravenous drip, the first dose of 0.08~0.12g/kg, after 0.033g/kg per hour, 24 hours of the total amount of not more than 18g/m2, the use of the same as adults. Also applied topically: 0.5% solution to flush the bladder for postoperative bladder bleeding. After tooth extraction, the wound was filled with a 10% solution and a cotton ball soaked in the liquid medicine. |
| medication instructions | 1. Those with thrombophilia or history of embolic vascular disease should be used with caution or contraindicated, newborns are contraindicated. 2, heart, liver, kidney damage should be reduced, with caution. 3, urinary surgery patients with hematuria with caution, this product is excreted from the kidney, and can inhibit urokinase, can form blood clots and cause urinary tract obstruction. 4, this product can not prevent small artery bleeding, if there is active arterial bleeding, still need ligation to stop bleeding. 5, for non-fibrinolytic hemorrhage, no hemostatic effect, should not be abused. The excretion rate of 6, 6-aminocaproic acid is fast, and the administration should be maintained to ensure the effective plasma concentration (0.13 μg/ml). 7, urinary surgery in patients with hematuria with caution, so as not to form blood clots, blocking the urinary tract. 8, this product can resist the pharmacological effects of urokinase and streptokinase, so it can be used to fight them when they are excessive. Women with oral contraceptives have a greater risk of thrombosis after using this product. |
| adverse reactions and precautions | There are many adverse reactions, the most common are gastrointestinal reactions, such as heartburn, Nausea, vomit, Diarrhea, followed by vertigo, tinnitus, Nasal Congestion, rash, general malaise and so on. The general reaction was mild and could disappear after drug withdrawal. When intravenous administration is too fast, there may be hypotension, bradycardia, arrhythmia, and a few people may have convulsions, heart or liver damage, etc. Large doses or more than 4 weeks of treatment can cause myalgia, weakness, myoglobinuria, and even renal failure; The most serious adverse reactions for systemic thrombosis. 6-aminocaproic acid is excreted from the kidney, with high concentration in urine, and can inhibit urokinase, which can form a blood clot to block the urinary tract. Therefore, it should be used with caution in patients with hematuria after urinary tract surgery. Pregnant women, have a tendency to thrombosis or thromboembolic disease history with caution. |
| latest research results | in recent years, it has been reported that aminocaproic acid is used to treat chronic bronchitis. The mechanism may be: inhibit the secretion of bronchial mucosal cells, this product has a strong inhibitory effect on Beta hemolytic Streptococcus, has an inhibitory effect on Staphylococcus aureus, its inhibitory effect can reduce bronchial inflammation. Clinical observation of 32 cases, the control group (30 cases with ammonium chloride). Results: The total effective rate was 84.37% in the treatment group and 36.6% in the control group. However, the number of reported cases is small and needs further observation. |
| Use | hemostatic. It has obvious curative effect on some severe bleeding caused by increased fibrinolytic activity. Applicable to a variety of surgical bleeding or local bleeding. Also used for hemoptysis, gastrointestinal bleeding and obstetrics and gynecology hemorrhagic disease. hemostatic, used for surgical bleeding, obstetrics and gynecology bleeding, pulmonary hemorrhage, upper gastrointestinal bleeding, etc. used as Biochemical reagent is a hemostatic drug, which can inhibit the activated enzyme of plasminogen, so that fibrinogen can not be activated to plasmin, thereby inhibiting the dissolution of fibrin, to achieve the effect of hemostasis. At high concentrations, there is also a direct effect on plasmin. It is used for postpartum hemorrhage caused by hyperfibrinolysis and postoperative hemorrhage of prostate, liver, pancreas and lung. Intravenous injection or intravenous drip: 4-8g each time, 8-12g per day, usually the first dose of 4-6G, dissolved in sterile saline, 5% glucose injection or compound sodium chloride injection 100ml, in 15-30 minutes after injection, the maintenance dose was 1g per hour, depending on the patient's condition. |
| production method | caprolactam is obtained by hydrolysis. Caprolactam, concentrated hydrochloric acid and 3 times the amount of distilled water were added into the reaction tank, stirred, heated and refluxed for 1.5h, and the temperature was controlled at 103-106 ℃. At the end of the reaction, it was determined that the conversion should be more than 95%. Diluted with distilled water to a concentration of 10% to obtain 10% 6-aminocaproic acid hydrolysate. The hydrolyzed liquid was uniformly flowed into an ion exchange column [Charged With 001 × 7(732#) strongly acidic styrene-based cation exchange resin] at a flow rate of 5-10L per hour, and subjected to adsorption. After completion of flow, the outlet was closed and soaked overnight. The ion exchange column was washed with distilled water and the hydrochloric acid was washed away (the effluent was checked to no chloride ions). Then, 3.5% ammonium hydroxide was uniformly flowed in at a flow rate of 5-10L per hour. After completion of flow, the flow outlet was closed and soaked overnight. After completion of ammonium hydroxide on the next day, elution was performed by flowing into distilled water, and an eluate containing 6-aminocaproic acid was collected. Activated carbon was added to decolorize and filter, and the filtrate was concentrated under reduced pressure at 47-70 ° C. To near dryness. Ethanol was added while hot, and crystals were precipitated by stirring. After cooling, the crude product was obtained by filtration. The crude product was dissolved in distilled water and decolorized with activated carbon at 60 °c for 1H. Filter while hot. The filtrate was concentrated to near dryness under reduced pressure. Ethanol was added to precipitate crystals, which were cooled, filtered, washed with ethanol and dried to obtain 6-aminocaproic acid. The overall yield of p-caprolactam was 75-80%. |
| category | toxic substances |
| toxicity grade | low toxicity |
| Acute toxicity | intraperitoneal-rat LD50: 7000 mg/kg; Oral-mouse LD50:14300 mg/kg |
| stimulation data | eyes-rabbits 500 mg/24 h mild |
| flammability hazard characteristics | flammability; Toxic NOx smoke from combustion |
| storage and transportation characteristics | warehouse ventilation and low temperature drying |
| fire extinguishing agent | dry powder, foam, sand, carbon dioxide, water mist |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:01:54
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View History
6-AMINOHEXANOIC ACID
N-((二异丙基氨基)亚甲基)-N-二异丙基四氟硼酸铵
2-Oxabicyclo[2.1.1]hexane-4-carboxylic acid, 1-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-3,3-dimethyl-
2-苯胺基烟酸
3-INDAZOLECARBOXYLIC ACID
polydichloroethyl ether tetramethyl ethylene diamine
氨基-三乙二醇-羧酸
AKOS B033621
硫杂环丁-3-胺盐酸盐
5-羧基苯并三氮唑
N-((二异丙基氨基)亚甲基)-N-二异丙基四氟硼酸铵
2-Oxabicyclo[2.1.1]hexane-4-carboxylic acid, 1-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-3,3-dimethyl-
2-苯胺基烟酸
3-INDAZOLECARBOXYLIC ACID
polydichloroethyl ether tetramethyl ethylene diamine
氨基-三乙二醇-羧酸
AKOS B033621
硫杂环丁-3-胺盐酸盐
5-羧基苯并三氮唑
Raw Materials for 6-AMINOHEXANOIC ACID