2,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}aniline hydrochloride
bromohexine hydrochloride
CAS: 611-75-6
Molecular Formula: C14H21Br2ClN2
2,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}aniline hydrochloride - Names and Identifiers
| Name | bromohexine hydrochloride |
| Synonyms | bisolvon bromessina BROMHEXINE HCL bisolvonhydrochloride BROMHEXINE HYDROCHLORIDE bromohexine hydrochloride 2-amino-n-cyclohexyl-3,5-dibromo-n-methyl-benzylaminhydrochloride 2-amino-n-cyclohexyl-3,5-dibromo-n-methylbenzylaminehydrochloride 2-Amino-3,5-dibromo-N-cyclohexyl-N-methylbenzylamine hydrochloride 2-AMINO-3,5-DIBROMO-N-CYCLOHEXYL-N-METHYLBENZY-LAMINE HYDROCHLORIDE N-(2-Amino-3,5-dibromobenzyl)-N-methylcyclohexylamine hydrochloride n-(2-amino-3,5-dibromobenzyl)-n-methylcyclohexylamine hydrochloride 2,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}aniline hydrochloride 2-amino-3,5-dibromo-n-cyclohexyl-n-methyl-benzenemethanaminmonohydrochlo |
| CAS | 611-75-6 |
| EINECS | 210-280-8 |
| InChI | InChI=1/C14H20Br2N2.ClH/c1-18(12-5-3-2-4-6-12)9-10-7-11(15)8-13(16)14(10)17;/h7-8,12H,2-6,9,17H2,1H3;1H |
| InChIKey | UCDKONUHZNTQPY-UHFFFAOYSA-N |
2,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}aniline hydrochloride - Physico-chemical Properties
| Molecular Formula | C14H21Br2ClN2 |
| Molar Mass | 412.59 |
| Melting Point | 240-244°C |
| Boling Point | 441.5°C at 760 mmHg |
| Flash Point | 220.8°C |
| Solubility | Soluble in water (<1 mg/ml at 25 °C), ethanol (5 mg/ml at 25 °C), methanol (1:50), a |
| Vapor Presure | 3.37E-08mmHg at 25°C |
| Appearance | powder |
| Color | White to Light Beige |
| Maximum wavelength(λmax) | ['307nm(Decane)(lit.)'] |
| Merck | 14,1391 |
| BRN | 4848376 |
| Storage Condition | Sealed in dry,Room Temperature |
| Sensitive | Sensitive to light |
| MDL | MFCD00056626 |
| Physical and Chemical Properties | melting point 240-244°C |
| Use | Used as an expectorant |
2,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}aniline hydrochloride - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 2 |
| RTECS | XS9950000 |
| HS Code | 29215990 |
2,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}aniline hydrochloride - Standard
Authoritative Data Verified Data
This product is N-methyl-N-cyclohexyl-2-amino -3, 5-dibromobenzylamine hydrochloride. Based on the dry product, the content of C14H20Br2N2 • HCl should be between 98.0% and 102.0%.
Last Update：2024-01-02 23:10:35
2,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}aniline hydrochloride - Trait
Authoritative Data Verified Data
- This product is white or white crystalline powder; Odorless.
- This product is slightly soluble in methanol, slightly soluble in ethanol, and slightly soluble in water.
absorption coefficient
take this product, precision weighing, plus ethanol dissolution and quantitative dilution of about 20% per lml solution, according to UV-visible spectrophotometry (General 0401 ), the absorbance was measured at a wavelength of 249nm, and the absorption coefficient was 262 to 278.
Last Update：2022-01-01 15:35:27
2,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}aniline hydrochloride - Differential diagnosis
Authoritative Data Verified Data
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 402).
- take about 10mg of this product, add 1ml of ethanol, slightly heat dissolved, the solution shows the identification reaction of aromatic first amine (General rule 0301).
- Take 10mg of this product, add 2ml of ethanol, slightly heat dissolved, the solution showed chloride identification (1) reaction (General rule 0301).
Last Update：2022-01-01 15:35:28
2,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}aniline hydrochloride - Exam
Authoritative Data Verified Data
Related substances
take this product, precision weighing, add methanol to dissolve and dilute to make a solution containing about 2.5mg per 1 ml, as a test solution; Take the appropriate amount of precision, A solution containing 5ug per 1 ml was prepared as a control solution by quantitative dilution with methanol. According to the chromatographic conditions under the content determination item, respectively inject l0ul of the test solution and the control solution into the liquid chromatograph to record the chromatogram to twice the retention time of the main component peak. If there is a chromatographic peak consistent with retention time of impurity I in the chromatogram of the test solution, the peak area shall not be greater than 0.75 times (0.15%) of the main peak area of the control solution, other single impurity peak area shall not be greater than 0.5 times (0.1%) of the main peak area of the control solution, and the sum of each impurity peak area shall not be greater than 1.5 times (0.3%) of the main peak area of the control solution.
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
take l.Og of this product and check it according to law (General rule 0841). The residue left 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).
Last Update：2022-01-01 15:35:29
2,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}aniline hydrochloride - Content determination
Authoritative Data Verified Data
measured by high performance liquid chromatography (General 0512).
chromatographic conditions and system suitability test
silica gel bonded with eighteen alkyl silane as filler; Phosphate buffer (potassium dihydrogen phosphate l. Add 900ml water to dissolve, adjust the pH value to 7.0 with 0.5mol /L sodium hydroxide solution, dilute to 1000ml with water, and shake to obtain)-acetonitrile (20:80) as mobile phase; the column temperature was 40°C and the detection wavelength was 245Nm. Appropriate amounts of the reference substance for impurity I and the reference substance for Bromhexine hydrochloride were dissolved in methanol and diluted to prepare a mixed reference substance solution containing about 5ug and 2.5mg per 1 mL respectively. Lol was injected into the liquid chromatograph and the chromatogram was recorded, the degree of separation between the impurity I peak and the Bromhexine peak should be greater than 2.0.
assay
take an appropriate amount of this product, weigh it accurately, add methanol to dissolve and dilute it quantitatively to make a solution containing about 0.5mg per lml, and use it as a test solution, and take 10 u1 accurately, injection into the liquid chromatograph, record the chromatogram; Take the appropriate amount of Bromhexine hydrochloride reference, accurately weigh, add methanol to dissolve and quantitatively dilute to make a solution containing about 0.5mg per 1 ml, and determine with the same method. According to the external standard method to calculate the peak area, that is.
Last Update：2022-01-01 15:35:30
2,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}aniline hydrochloride - Category
Authoritative Data Verified Data
expectorant.
Last Update：2022-01-01 15:35:30
2,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}aniline hydrochloride - Storage
Authoritative Data Verified Data
sealed storage.
Last Update：2022-01-01 15:35:30
2,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}aniline hydrochloride - Bromhexine hydrochloride tablets
Authoritative Data Verified Data
This product contains Bromhexine hydrochloride (C14H20Br2N2 • HCl) should be 93.0% ~ 107.0% of the label amount.
trait
This product is white tablet.
identification
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
- the solution under the content uniformity was taken and measured by ultraviolet-visible spectrophotometry (General 0401), and there was a maximum absorption at a wavelength of Nm.
examination
- Related substances take an appropriate amount of the fine powder of this product (about 50mg of Bromhexine hydrochloride), put it in a 20ml measuring flask, add appropriate amount of methanol to ultrasonically dissolve Bromhexine hydrochloride, dilute it to the scale with methanol, shake well, filter, the filtrate was taken as a test solution; An appropriate amount was taken in a precise amount and quantitatively diluted with methanol to prepare a solution containing about 5ug Bromhexine hydrochloride per 1 ml as a control solution. According to the chromatographic conditions under the content determination item, 10 u1 of the test solution and 10 u1 of the control solution are respectively injected into the liquid chromatograph, and the chromatogram is recorded to 2 times of the retention time of the main component peak. If there is a chromatographic peak consistent with retention time of impurity I in the chromatogram of the test solution, the peak area shall not be greater than the main peak area of the control solution (0.2%), other single impurity peak area shall not be greater than 0.5 times (0.1%) of the main peak area of the control solution, and the sum of each impurity peak area shall not be greater than 1.5 times (0.3%) of the main peak area of the control solution.
- Content uniformity: Take 1 tablet of this product, put it in a mortar, grind it finely, add an appropriate amount of ethanol, grind it, and transfer it to a 50ml measuring flask in fractions with ethanol, and warm it to dissolve Bromhexine hydrochloride, dilute to the scale with ethanol, shake well, filter, Take 5ml of filtrate accurately, put it in 50ml measuring flask, dilute to the scale with ethanol, shake well, the absorbance was measured at a wavelength of 249mn according to UV-Vis spectrophotometry (General rule 0401), and the content of each tablet was calculated as having an absorption coefficient of C14H20Br2N2. HCl of 270. The provisions shall be met (General rule 0941).
- the dissolution of this product, according to the dissolution and release determination method (General rule 0931 second method), water 900ml as the dissolution medium, the speed of 75 rpm, according to the law, after 45 minutes, 10ml of the solution was taken and filtered with an organic membrane, at least 5ml of the initial filtrate was discarded, and the continued filtrate was taken as the test solution. In addition, about 16mg of the Bromhexine hydrochloride reference substance was taken, and the sample was accurately weighed, put it in a 100ml measuring flask, add 4ml of ethanol to shake to dissolve, dilute it to scale with water, shake well, take 1ml with precision, put it in a 20ml measuring flask, dilute it to scale with water, shake well, as a control solution. The sample solution and the reference solution are respectively 50 u1, and the dissolution amount of each tablet is calculated by the peak area according to the external standard method. The limit is 70% of the labeled amount and shall be in accordance with the provisions.
- others shall be in accordance with the relevant provisions under the item of tablets (General rule 0101).
Content determination
- measured by high performance liquid chromatography (General 0512).
- chromatographic conditions and system suitability test using eighteen alkyl silane bonded silica gel as filler; Phosphate buffer (take potassium dihydrogen phosphate 1.0g, add water 900ml to dissolve, adjust pH value to 0.5 with 7.0 mol/ L sodium hydroxide solution, dilute to ML with water, shake well, then get)-acetonitrile (20:80) as mobile phase; Column temperature is 40°C; the detection wavelength was 245Nm. Take appropriate amount of impurity I reference substance and Bromhexine hydrochloride reference substance, add methanol to dissolve and dilute to prepare mixed reference substance solution containing about 5ug and 2.5mg respectively per 1 ml, inject 10ul into liquid chromatograph, record chromatogram, the degree of separation between the impurity I peak and the Bromhexine peak should be greater than 2.0.
- determination of 20 tablets of this product, precision weighing, fine grinding, precision weighing an appropriate amount (equivalent to 12.5 mg Bromhexine hydrochloride), put in a 25ml measuring flask, add an appropriate amount of methanol, the Bromhexine hydrochloride was dissolved by ultrasound and diluted to scale with methanol, then shaken well, filtered, and the filtrate was taken as the test solution. The lOul was accurately measured and injected into the liquid chromatograph, and the chromatogram was recorded; in addition, the appropriate amount of Bromhexine hydrochloride reference substance was accurately weighed, dissolved in methanol and quantitatively diluted to make a solution containing about 0.5mg per 1 ml, which was determined by the same method. According to the external standard method to calculate the peak area, that is.
category
with Bromhexine hydrochloride.
specification
8mg
storage
sealed storage.
Last Update：2022-01-01 15:35:31
2,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}aniline hydrochloride - Reference Information
| Introduction | Bromhexine hydrochloride is a mucolytic agent, which can directly act on the bronchial glands and promote the release of lysosomes of mucus secreting cells, the differentiation and lysis of mucopolysaccharide fibers in sputum, sputum dilution, easy to cough. Clinically, it is mainly used for acute and chronic bronchitis, asthma, bronchiectasis, emphysema, especially for white sputum expectoration difficulties and critical emergencies caused by sputum extensive obstruction of small bronchi. Bromhexine hydrochloride tablets, solutions, aerosols, injection, freeze-dried powder injection, infusion and other dosage forms. |
| preparation | 2.0g of 2-amino -3, 5-dibromobenzaldehyde, 1.2g of N-methyl cyclohexylamine is dissolved in 20ml of methanol, and 4g of tetraisopropyl titanate is slowly dropped into the reaction solution under stirring at room temperature, and after adding, the reaction is continued at room temperature for 5 hours; 0.3g of sodium borohydride was added to the reaction solution in portions, and the reaction was stirred at room temperature for 2H. The reaction was complete by TLC. After the reaction, add 20ml of water to the reaction solution to quench the reaction, precipitate a large number of solids, filter, filter cake washed with ethyl acetate for 3 times, combine filtrate and wash, extract with ethyl acetate to obtain organic phase, the organic phase was washed sequentially with sodium carbonate solution and saturated brine. 5ml of 6N hydrochloric acid was added dropwise to the organic phase at room temperature under stirring, and the mixture was stirred for 3H for crystallization. A white solid was obtained by filtration, recrystallized from ethanol and dried to obtain 2.3g of Bromhexine hydrochloride. Yield: 78%. |
| biological activity | Bromhexine HCl is a drug that treats Cough of hard sputum by dissolving it. |
| Use | this strain is based on the active ingredient proposed in the medicinal plant duckbill flower (hyonidine) the structure of the synthesis of a new type of mucus soluble expectorant, has a strong role in dissolving phlegm. Can make sputum mucopolysaccharide fiber differentiation and lysis, can also inhibit the synthesis of mucopolysaccharides, so that sputum sialic acid (one of the acidic mucopolysaccharides) content reduced, thereby reducing the viscosity of sputum, there are Nausea of the expectorant effect after oral administration, so that sputum is easy to cough, so that the respiratory tract is smooth. It is clinically used for the treatment of acute and chronic bronchitis, asthma, bronchiectasis and emphysema, especially for the difficulty of expectoration of white phlegm, and the shortness of breath caused by extensive obstruction of small bronchi by sputum. Adverse Reactions: taking this product occasionally Nausea, stomach discomfort, reduction or discontinuation can disappear. A small number of patients with temporary elevated serum transaminase. Patients with gastric ulcer should be used with caution. The toxicity of this product is very small. used as expectorant This product is a new type of mucolytic expectorant, which can differentiate and split the mucopolysaccharide fibers in sputum, reduce the viscosity of sputum and increase the secretion, thus thinning the sputum, easy to cough, make respiratory tract unobstructed, relieve symptoms |
| production method | There are a variety of process routes. One of them is o-toluidine as raw material, first bromination to produce 2, 4-dibromo-6-toluidine, and acetic anhydride reaction to acetylated amino to produce N,N-diacetyl-2, 4-dibromo-6-methylaniline; The amino group is protected and then brominated again to form N, n-diacetyl-2, 4-dibromo-6-bromomethylaniline; condensation with N-methylcyclohexylamine to N, n-diacetyl-2, 4-dibromo-6-(N-methyl) cyclohexylamine methylaniline. Finally, hydrochloric acid is used to hydrolyze the acetyl group and salt to obtain the finished product. |
| category | toxic substances |
| toxicity grade | poisoning |
| Acute toxicity | oral-rat LD50: 6000 mg/kg; Oral-mouse LD50: 4800 mg/kg |
| flammability hazard characteristics | toxic nitrogen oxides, bromide and hydrochloric acid fumes emitted by thermal decomposition |
| storage and transportation characteristics | warehouse ventilation and low temperature drying |
| fire extinguishing agent | water, foam, sand, carbon dioxide, dry powder |
Last Update：2024-04-10 22:29:15
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