(2S)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol
Levodropropizine
CAS: 99291-25-5;99291-24-4
Molecular Formula: C13H20N2O2
(2S)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol - Names and Identifiers
| Name | Levodropropizine |
| Synonyms | LVDP Danka Rapitux Levotuss l-Dropropizine Levodropropizine (S)-3-(4-Phenyl-1-piperazinyl)-1,2-propanediol (2S)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol (2R)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol (2S)-3-(4-Phenyl-1-piperazinyl)-1,2-propanediol |
| CAS | 99291-25-5 99291-24-4 |
| EINECS | 640-087-8 |
| InChI | InChI=1/C13H20N2O2/c16-11-13(17)10-14-6-8-15(9-7-14)12-4-2-1-3-5-12/h1-5,13,16-17H,6-11H2/t13-/m0/s1 |
(2S)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol - Physico-chemical Properties
| Molecular Formula | C13H20N2O2 |
| Molar Mass | 236.31 |
| Density | 1.168±0.06 g/cm3(Predicted) |
| Melting Point | 98-100°C |
| Boling Point | 412.7±34.0 °C(Predicted) |
| Flash Point | 220.9°C |
| Solubility | Slightly soluble in water, freely soluble in dilute acetic acid and in methanol, slightly soluble in ethanol (96 per cent). |
| Vapor Presure | 1.5E-07mmHg at 25°C |
| Appearance | neat |
| Color | White to Almost white |
| pKa | 14.21±0.20(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Refractive Index | 1.576 |
| Physical and Chemical Properties | Appearance: white or off-white crystalline powder |
| Use | Used as an antitussive and expectorant |
| In vitro study | Levodropropizine has affinity for H1 histamine and alpha adrenergic receptors. |
| In vivo study | In rats, Levodropropizine has a weaker central sedative effect than racemic tartrate, and it does not cause physical dependence. Levodropropizine (15 mg/kg, I. V.) simultaneously reduced the duration of asphyxia and the response of C- fibers to phenylbiguanide. Inhibition of the PBG response by LVDP-induced C- fibers averaged 50% in pulmonary fibers and 25% in non-pulmonary fibers. Levodropropizine was shown to have good antitussive activity in anesthetized guinea pigs and rabbits. In guinea pigs and rabbits with mechanically and electrically induced cough, the activity of Levodropropizine (I. V.) was 1/10 to 1/20 of that of codeine and similar to that of hydropropidine. The effect of Levodropropizine (oral) in the treatment of cough induced by irritant aerosols is similar to that of hydropropazine and codeine. Levodropropizine (40 μg/50 μL, I. c.v.) had no effect on electrically induced cough, whereas codeine (5 μg/50 μL, I. c.v.) significantly prevents coughing in guinea pigs. Levodropropizine has a secondary site of action, which is associated with sensory neuropeptides. In the rat trachea, levopropizine (10 mg/kg, 50 mg/kg as well as 200 mg/kg) dose-dependently reduced capsaicin-induced extravasation of Evans blue dye. Levodropropizine (200 mg/kg) inhibited the extravasation of substance P, but it did not affect platelet-activating factor-induced extravasation. |
(2S)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol - Standard
Authoritative Data Verified Data
This product is S-( -)-3-(4-phenyl-1-piperazinyl)-l, 2-propanediol. Calculated as dried product, the content of C13H20N202 shall not be less than 98.5%.
Last Update：2024-01-02 23:10:35
(2S)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol - Trait
Authoritative Data Verified Data
- This product is white or off-white crystalline powder; Odorless.
- This product is soluble in dichloromethane, methanol or glacial acetic acid, soluble in ethanol, slightly soluble in water.
melting point
The melting point of this product (General 0612) is 102~107°C.
specific rotation
take this product, precision weighing, plus lmol/L hydrochloric acid solution dissolved and quantitatively diluted to make a solution containing about 30mg per lml, determined according to law (General 0621), the specific rotation is from one to 29.0 ° to one to 33 °. 5 degrees.
Last Update：2022-01-01 11:35:57
(2S)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 4.232 ml | 21.159 ml | 42.317 ml |
| 5 mM | 0.846 ml | 4.232 ml | 8.463 ml |
| 10 mM | 0.423 ml | 2.116 ml | 4.232 ml |
| 5 mM | 0.085 ml | 0.423 ml | 0.846 ml |
Last Update：2024-01-02 23:10:35
(2S)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol - Differential diagnosis
Authoritative Data Verified Data
- take about 30mg of this product, add 5ml of water to dissolve, and add trinitrophenol solution Dropwise to produce yellow precipitate.
- take an appropriate amount of this product, add water to dissolve and dilute to prepare a solution containing about 10ug per lml, and measure it by UV-Vis spectrophotometry (General rule 0401), there is a maximum absorption at a wavelength of 237nm and a minimum absorption at a wavelength of 217nm.
- The infrared absorption spectrum of this product should be consistent with that of the reference product (General rule 0402).
Last Update：2022-01-01 11:35:57
(2S)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol - Exam
Authoritative Data Verified Data
alkalinity
take 0.2g of this product, add 20ml of water to dissolve it, and determine it according to law (General rule 0631). The pH value should be 9.0~10.0.
Related substances
take this product, precision weighing, add mobile phase to dissolve and dilute to make a solution containing about 0.5mg per 1ml, as a test solution; Precision weighing to take an appropriate amount of phenyl piperazine reference, add methanol to dissolve and quantitatively dilute to prepare a solution containing about 50ug per 1ml, which is used as a reference stock solution. Take 1ml in a precision volume, put it in a 100ml measuring flask, dilute it to the scale with mobile phase, and shake it well, as a reference solution; 5ml of each of the test solution and the reference stock solution were taken respectively, placed in a 25ml measuring flask, diluted to the scale with mobile phase, and shaken, as a system applicable solution. According to the test of high-performance liquid chromatography (General rule 0512), silica gel bonded with eighteen alkyl silane was used as the filler; 6.81g of phosphate buffer solution (potassium dihydrogen phosphate) was added, and of water was added for dissolution, the pH was adjusted to 3.0 with phosphoric acid)-methanol (88:12) as the mobile phase; The detection wavelength was 254mn. The applicable solution 20 u1 of the system is taken and injected into the liquid chromatograph. The number of theoretical plates shall not be less than 2000 according to the peak of levodropropizine, and the separation degree between the peak of levodropropizine and the peak of phenylpiperazine shall be greater than 2.0. 20 u1 of the test solution and the reference solution were respectively injected into the human liquid chromatograph, and the chromatogram was recorded to 3 times of the retention time of the main component peak. If there is a chromatographic peak in the test solution that is consistent with the retention time of phenylpiperazine, the peak area shall not exceed 0.1% based on the external standard method; Other single impurities shall be compared with the main peak area of the reference solution, according to the external standard method, the peak area shall not exceed 0.1%, and the total amount of other impurities shall not exceed 0.2%. The chromatogram of the test solution is 0.1 times smaller than the main peak area of the control solution.
dexdropropizine
take this product, precision weighing, plus n-hexane-anhydrous ethanol (60:40) dissolved and diluted to make a solution containing about 60ug per 1ml, as a test solution; 1ml was accurately weighed, placed in a 200ml measuring flask, diluted to the scale with n-hexane-absolute ethanol (60:40), and shaken to obtain a control solution. Take the right dropropizine control and levodropropizine control each appropriate amount, plus n-hexane-absolute ethanol (60:40) dissolved and diluted to make each 1mL solution containing 0.3ug and 60ug respectively, as a system suitability solution. According to the test of high performance liquid chromatography (General 0512), amylose carbamate was used as filler, and N-hexyl-ethanol-diethylamine (80:20:0.2) was used as mobile phase; the detection wavelength was 250Nm. Take the applicable solution 20 u1 of the system and inject it into human Liquid Chromatograph. The number of theoretical plates shall not be less than 2000 based on the peak of levodropropizine. Accurately take 20 u1 of the test solution and the control solution, respectively inject human liquid chromatograph, record the chromatogram, and if there are chromatographic peaks in the chromatogram of the test solution that are consistent with the retention time of the right dropropizine, the peak area shall not be greater than the main peak area of the control solution (0.5%).
glycidol
take this product about l.O g, weigh precisely, put it in a 5ml measuring flask, add dichloromethane to dissolve and dilute to the scale, shake well, as a test solution; Take another glycidol reference about 0.2g, add methylene chloride to dissolve and dilute to the scale, shake well, take 0.5ml accurately, put it in the 100ml measuring flask, dilute to the scale with methane dihydrate, shake, as a reference solution; Take about l of this product. Add 0.5ml of reference solution into a 5ml measuring flask, add dichloromethane to dissolve and dilute to the scale, shake well, and serve as a control solution. According to the test of gas chromatography (General 0521), a capillary column with 6% cyanopropyl phenyl-94% dimethyl polysiloxane as stationary liquid; The inlet temperature is 170°C, the column temperature is 140°C, the detector temperature was 250°C; The carrier gas was nitrogen and the detector was a flame ionization detector (FID). The number of theoretical plates shall not be less than 5000 based on the glycidol peak. The test solution and the control solution shall be respectively injected into the human gas chromatograph to record the chromatogram. If there is a peak in the chromatogram of the test solution that is consistent with the retention time of glycidol, the peak area shall not be greater than 0.5 times (5ppm) of the main peak area of the control solution.
residual solvent
take about 0.3g of this product, weigh it accurately, place it in the top empty bottle, and add about l of sodium chloride. Og, Precision Add dimethyl sulfoxide 5ml, sealed, as a test solution; Precision weighing acetone, methylene chloride, chloroform, toluene, prepare mixed solution containing about 300ug, 36ug, 3.6ug and 53ug respectively in each lml by quantitative dilution with dimethyl sulfoxide. Take 5ml for precise measurement, place it in the top empty bottle, and add about l of vaporized sodium. O g, sealed, as a control solution. According to the test for determination of residual solvents (General Principle 0861, second method), 6% cyanopropylphenyl-94% dimethylpolysiloxane is used as the fixing solution (or similar to the polarity); The initial temperature is 50°C, and the solution is maintained for 10 minutes, the temperature was raised to 150°C at a rate of 20°C per minute for 5 minutes; The detector temperature was 250°C; And the inlet temperature was 250°C. The Headspace bottle equilibration temperature was 80°C and the equilibration time was 20 minutes. 1.0ml of the reference solution was injected into the headspace, and the separation degree between the peaks of each component should meet the requirements. Then 1.0ml of test solution and reference solution were injected by Headspace, and the chromatograms were recorded. According to the external standard method to calculate the peak area, the residual amount of acetone, dichloromethane, chloroform and toluene should be in accordance with the provisions.
loss on drying
take this product l.O g, at 80°C under reduced pressure drying to constant weight, weight loss should not exceed 0.5% (General rule 0831).
ignition residue
take this product 1.Og, check according to law (General rule 0841), residue shall not exceed 0.1%.
precious 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 11:35:59
(2S)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol - Content determination
Authoritative Data Verified Data
take this product about 0. LG, precision weighing, add 50ml anhydrous acetic acid to dissolve, according to the potential titration method (General rule 0701), with perchloric acid titration solution (0.1 mol/L) titration, with the second burst point as the titration end point, and the results of the titration were corrected with a blank test. Each 1 ml of perchloric acid titration solution (0.1 mol/ L) corresponds to 11.82mg of C13H20N2O2.
Last Update：2022-01-01 11:35:59
(2S)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol - Category
Authoritative Data Verified Data
antitussive drugs.
Last Update：2022-01-01 11:35:59
(2S)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol - Storage
Authoritative Data Verified Data
light shielding, sealed storage.
Last Update：2022-01-01 11:35:59
(2S)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol - Levohydroxypipramine tablets
Authoritative Data Verified Data
This product contains levodropropizine (C13H20N2O2) should be 90.0% to 110.0% of the label.
trait
This product is white or white-like tablets or film-coated tablets, white or white-like after removing the coating.
identification
- take an appropriate amount of fine powder of this product (about 60mg of levodropropizine), add 10ml of water, shake, filter, take the filtrate, Dropwise add trinitrophenol test solution, resulting in yellow precipitate.
- 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.
- take an appropriate amount of fine powder of this product (about 12mg of levodropropizine), add water to dissolve and dilute to prepare a solution containing about 12ug of levodropropizine per 1 ml, filter and take the filtrate, as determined by UV-Vis spectrophotometry (General rule 0401), there is a maximum absorption at a wavelength of 237mn and a minimum absorption at a wavelength of 217mn.
- take an appropriate amount of fine powder of this product (about 120mg equivalent to levodropropizine), add 50ml of water, shake, and add 20ml of methane gas, shake extraction, take dichloromethane layer at 60°C water bath to dry, the residue was dried under reduced pressure for 12 hours, and the infrared light absorption spectrum thereof should be consistent with that of the reference substance (General rule 0402).
examination
- the relevant substances should be collected in an appropriate amount of fine powder of wood products, accurately weighed, dissolved and quantitatively diluted with mobile phase ultrasound to make a solution containing 0.5mg of levodropropizine per 1ml, filtered, take the continued filtrate as the test solution; Accurately weigh the appropriate amount of phenylpiperazine reference, add methanol to dissolve and quantitatively dilute to make a solution containing about 50ug per 1ml, and accurately take 1ml, place in a 50ml measuring flask, dilute to the scale with the mobile phase, shake well, and use as a control solution. If there are chromatographic peaks in the chromatogram of the test solution consistent with the retention time of phenylpiperazine, the peak area shall be calculated according to the external standard method, and 0.2% of the labeled amount shall not be exceeded; for other single impurities, the main peak area of the reference solution is taken as the control, and the peak area is calculated by the external standard method, and 0.2% of the total amount of impurities shall not be overlabeled, and 0.5% of the total amount of impurities shall not be overlabeled. The chromatogram of the test solution is 0.1 times smaller than the main peak area of the control solution.
- the dissolution of this product, according to the dissolution and release determination method (General rule 0931 The first method), with water 1000ml as the dissolution medium, the speed is 50 rpm, according to the law, after 20 minutes, take the appropriate amount of solution, filter, take the appropriate amount of filtrate, dilute with water to make a solution containing about 12UG of levodropropizine per 1 ml, measure absorbance at the wavelength of 237nm according to UV-Vis spectrophotometry (General rule 0401); Take appropriate amount of levodropropizine reference by precise weighing, water was added to dissolve and quantitatively diluted to prepare a solution containing about 12ug per 1 ml, which was determined by the same method, and the dissolution amount of each tablet was calculated. The limit is 80% 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 (weigh 6.81g potassium dihydrogen phosphate, add water to dissolve 1000ml, adjust pH to 3.0 with phosphoric acid)-Methanol (88:12) as mobile phase; Detection wavelength of 254mn. Take appropriate amount of phenylpiperazine and levodropropizine, add appropriate amount of methanol to dissolve, and then dilute with mobile phase to prepare solution containing about 10ug and 100ug respectively in each lml, which is used as system applicable solution, take the applicable solution 20 u1 of the system and inject it into human Liquid Chromatograph. The number of theoretical plates shall not be less than 2000 according to the peak of levodropropizine, and the separation degree of levodropropizine peak and phenylpiperazine peak shall be greater than 2.0.
- determination of 20 tablets of this product, precision weighing, fine grinding, precision weighing an appropriate amount (about 10mg equivalent to levodropropizine), put in a 100ml measuring flask, add mobile phase to dissolve and dilute to the scale, after shaking, filtering, the filtrate was taken as the test solution, and 20ul was accurately measured and injected into the liquid chromatograph. The chromatogram was recorded, the mobile phase was added for dissolution and quantitative dilution to make about 0.lmg solution, the same method for determination. According to the external standard method to calculate the peak area, that is.
category
Same as levodropropizine.
specification
(l)30mg (2)60mg
storage
light shielding, sealed storage.
Last Update：2022-01-01 11:36:00
(2S)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol - Levodropropizine capsules
Authoritative Data Verified Data
This product contains levodropropizine (C13H20N2O2) should be 90.0% to 110.0% of the label.
trait
The content of this product is white or white particles or powder.
identification
- take an appropriate amount of the content of this product (about 60mg of levodropropizine), add 10ml of water, shake to dissolve levodropropizine, filter, take the filtrate, Dropwise add trinitrophenol test solution, resulting in yellow precipitate.
- 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.
- take an appropriate amount of the content of this product (about 12mg of levodropropizine), add water to dissolve and dilute to prepare a solution containing about 12ug of levodropropizine per 1 ml, filter and take the filtrate, as determined by UV-Vis spectrophotometry (General 0401), there is a maximum absorption at a wavelength of 237nm and a minimum absorption at a wavelength of 217mn.
- take an appropriate amount of the content of this product (about 120mg equivalent to levodropropizine), add 50ml of water, shake to dissolve levodropropizine, add 20ml of dichloromethane, shake to extract, the dimethane layer was evaporated to dryness in a water bath at 60 ° C., and the residue was dried under reduced pressure at 60 ° C. For 12 hours. The infrared absorption spectrum thereof should be consistent with that of the reference substance (General rule 0402).
examination
- relevant substances the content of this product is appropriately weighed, and then dissolved and quantitatively diluted with mobile phase ultrasound to make a solution containing 0.5mg of levodropropizine per 1ml, and filtered, take the continued filtrate as the test solution; Accurately weigh the appropriate amount of phenylpiperazine reference, add methanol to dissolve and quantitatively dilute to make a solution containing about 50ug per 1ml, and accurately take 1ml, place in a 50ml measuring flask, dilute to the scale with the mobile phase, shake well, and use as a control solution. If there are chromatographic peaks in the chromatogram of the test solution consistent with the retention time of phenylpiperazine, the peak area shall be calculated according to the external standard method, and 0.2% of the labeled amount shall not be exceeded; for other single impurities, the main peak area of the reference solution is taken as the control, and the peak area is calculated by the external standard method, and 0.2% of the total amount of impurities shall not be overlabeled, and 0.5% of the total amount of impurities shall not be overlabeled. The chromatogram of the test solution is 0.1 times smaller than the main peak area of the control solution.
- the dissolution of this product, according to the dissolution and release determination method (General rule 0931 The first method), with water 1000ml as the dissolution medium, the speed is 75 rpm, according to the law, after 20 minutes, take the appropriate amount of solution, filter, take the appropriate amount of filtrate, dilute with water to make a solution containing about 12mg of levodropropizine per 1 ml, measure absorbance at the wavelength of 237nm according to UV-Vis spectrophotometry (General rule 0401); Take appropriate amount of levodropropizine reference by precise weighing, water was added to dissolve and quantitatively diluted to prepare a solution containing about 12ug per 1 ml, which was determined by the same method, and the dissolution amount of each particle was calculated. The limit is 80% of the labeled amount and shall be in accordance with the provisions.
- others should comply with the relevant provisions under the capsule (General 0103).
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 (weigh 6.81g potassium dihydrogen phosphate, add water to dissolve 1000ml, adjust pH to 3.0 with phosphoric acid)-Methanol (88:12) as mobile phase; Detection wavelength of 254mn. Take appropriate amount of phenylpiperazine and levodropropizine, add appropriate amount of methanol to dissolve, and dilute with mobile phase to prepare solution containing about 10ug and 100ug respectively in each lm, as system applicable solution, take 204 injection human liquid chromatograph, and the number of theoretical plates shall not be less than 2000 calculated by levodropropizine peak, and the separation degree between levodropropizine peak and phenylpiperazine peak shall be greater than 2.0.
- the content under the item of difference in loading amount was measured, and the content was finely divided. The appropriate amount was accurately weighed and placed in a 100ml measuring flask, and the mixture was dissolved with mobile phase and diluted to the standard, after shaking, filtering, the filtrate was taken as the test solution, and 20ul was accurately measured and injected into the human liquid chromatograph, and the chromatogram was recorded, the mobile phase was added for dissolution and quantitative dilution to make about 0.lmg solution, the same method for determination. The peak area is calculated according to the external standard method, I .e.
category
Same as levodropropizine.
specification
60mg
storage
light shielding, sealed storage.
Last Update：2022-01-01 11:36:02
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