N-(2,6-DIOXO-3-PIPERIDINYL)PHTHALIMIDE
thalidomide
CAS: 50-35-1;731-40-8
Molecular Formula: C13H10N2O4
N-(2,6-DIOXO-3-PIPERIDINYL)PHTHALIMIDE - Names and Identifiers
| Name | thalidomide |
| Synonyms | thalidomide THALIDOMIDE N-PHTHALOLYLGLUTAMIMIDE α-Phthalimidoglutarimide 3-PHTHALIMIDOGLUTARIMIDE 2-phthalimidoglutarimide N-(2,6-DIOXO-3-PIPERIDINYL)PHTHALIMIDE 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione 2-(2,6-dioxo-3-piperidinyl)-1h-isoindole-1,3(2h)-dione |
| CAS | 50-35-1 731-40-8 |
| EINECS | 200-031-1 |
| InChI | InChI=1/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17) |
| InChIKey | UEJJHQNACJXSKW-UHFFFAOYSA-N |
N-(2,6-DIOXO-3-PIPERIDINYL)PHTHALIMIDE - Physico-chemical Properties
| Molecular Formula | C13H10N2O4 |
| Molar Mass | 258.23 |
| Density | 1.2944 (rough estimate) |
| Melting Point | 269-271°C |
| Boling Point | 401.48°C (rough estimate) |
| Flash Point | 262.1°C |
| Water Solubility | <0.1 g/100 mL at 22 ºC |
| Solubility | 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.6mg/mL |
| Vapor Presure | 1.65E-10mmHg at 25°C |
| Appearance | White solid |
| Color | white |
| Maximum wavelength(λmax) | ['300nm(lit.)'] |
| Merck | 14,9255 |
| pKa | 10.70±0.40(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| Refractive Index | 1.5300 (estimate) |
| Physical and Chemical Properties | Melting point 269-271°C water-soluble <0.1g/100 mL at 22°C |
| Use | Sedatives, for various types of leprosy reactions such as Fever, erythema nodosum, neuralgia, Arthralgia, Lymph Node Tumefaction, etc. have a certain effect, no therapeutic effect on leprosy |
| In vitro study | Thalidomide must be metabolized by the liver to form epoxides, which may be the active teratogenic metabolite. Thalidomide selectively inhibits the production of tumor necrosis factor alpha (TNF-α) by human monocytes stimulated by lipopolysaccharide and other agonists. Thalidomide exerts its inhibitory effect on tumor necrosis factor alpha by enhancing mRNA degradation. Thalidomide acts directly on MM cell lines and MM cells of patients resistant to melphalan, doxorubicin and dexamethasone by inducing apoptosis and G1 phase growth arrest. Thalidomide enhances the anti-MM activity of Semetasone, whereas interleukin-6 inhibits its activity. Thalidomide is a potent co-stimulatory molecule for primary human T cells in vitro to synergistically increase interleukin-2 mediated T cell proliferation and interferon gamma production via the T cell receptor complex. Thalidomide also increases primary CD8 cytotoxic T cell responses induced by allogeneic dendritic cells in the absence of CD4 T cells. |
| In vivo study | Thalidomide(200 mg/kg) caused inhibition of vascularized corneal regions in rabbits, with inhibition rates ranging from 30% to 51% in three experiments, with a median inhibition rate of 36%. |
N-(2,6-DIOXO-3-PIPERIDINYL)PHTHALIMIDE - Risk and Safety
| Hazard Symbols | T - Toxic |
| Risk Codes | R46 - May cause heritable genetic damage R61 - May cause harm to the unborn child R21 - Harmful in contact with skin R25 - Toxic if swallowed R62 - Possible risk of impaired fertility R22 - Harmful if swallowed |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. S22 - Do not breathe dust. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| UN IDs | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | TI4375000 |
| HS Code | 29337900 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 oral in mouse: 2gm/kg |
N-(2,6-DIOXO-3-PIPERIDINYL)PHTHALIMIDE - Standard
Authoritative Data Verified Data
This product is (±)-N-(2, 6-dioxo-3-piperidinyl)-phthalimide. The content of C13H10N204 shall be 98.0% ~ 102.0% calculated as dry product.
Last Update：2024-01-02 23:10:35
N-(2,6-DIOXO-3-PIPERIDINYL)PHTHALIMIDE - Trait
Authoritative Data Verified Data
- This product is white to off-white powder; Odorless.
- This product is dissolved in N,N-dimethylformamide or pyridine, very slightly dissolved in water, methyl spirit or ethanol, insoluble in ether and chloroform.
Last Update：2022-01-01 11:59:11
N-(2,6-DIOXO-3-PIPERIDINYL)PHTHALIMIDE - Differential diagnosis
Authoritative Data Verified Data
- take about 0.1g of this product, put it in a test tube, add 10ml of sodium hydroxide solution, heat to boiling, that is, produce ammonia odor, let it cool, add ninhydrin lOmg, and the surrounding area of indene is blue.
- The infrared absorption spectrum of this product should be consistent with that of the reference product (General rule 0402).
Last Update：2022-01-01 11:59:12
N-(2,6-DIOXO-3-PIPERIDINYL)PHTHALIMIDE - Exam
Authoritative Data Verified Data
Related substances
take about 0.lg of this product, weigh it accurately, put it in a 50ml measuring flask, add an appropriate amount of acetonitrile-water-phosphoric acid (50:50:0.1), ultrasonic to dissolve and dilute to the scale, shake well, take 10ml accurately, put it in a 100ml measuring flask, add 10ml of phosphoric acid solution (1-100), dilute it to scale with water, shake well, and use it as a test solution, add acetonitrile to dissolve and dilute to prepare a solution containing 1 mg per 1 ml as solution (1); Take an appropriate amount of phthalic acid reference substance, weigh it accurately, and use acetonitrile-water (80:5). Dissolve and quantitatively dilute to make a solution containing 1 mg per 1 ml, take an appropriate amount with precision, and quantitatively dilute with acetonitrile to make a solution containing 0 mg per 1 ml. 1 mg of the solution, as solution (2); Precision measure the solution (1), (2) each 2ml, put the same 100ml measuring flask, with acetonitrile-water-phosphoric acid (50:50:0.1) dilute to the scale, shake well, take 10ml accurately, put it in a 100ml measuring flask, add 10ml of phosphoric acid solution (1-100), dilute to the scale with water, shake well, as a control 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 (×, 4um or equivalent column); Acetonitrile-water-phosphoric acid (5:95:0.1) as mobile phase A, acetonitrile-water-phosphoric acid (15:85:0.1) as mobile phase B; Flow rate was 2ml per minute; Gradient elution was carried out according to the following table; Detection wavelength was 218nm. Take the reference solution 200 u1, inject human liquid chromatograph, adjust the flow rate, so that the retention time of thalidomide peak is about 14 minutes; The relative retention time of phthalic acid peak and thalidomide peak is about 0.3. Take 200 u1 of the test solution and the reference solution respectively, inject the human liquid chromatograph and record the chromatogram. In the chromatogram of the test solution, if there are impurity peaks, the area of the phthalic acid peak shall be calculated according to the external standard method, and the single impurity shall not exceed 0.1%, and the total amount of the impurity shall not exceed 0.3%.
residual solvent
take 0.lg of this product, precision weighing, put it in 10ml measuring flask, add dimethyl sulfoxide to dissolve and dilute to the scale, shake, as a test solution; Take an appropriate amount of N,N-dimethylformamide, precision weighing, quantitative dilution with dimethyl sulfoxide to make a solution containing 8.8ug per 1 ml, shake, as a reference solution. According to the test of residual solvent determination (General 0861 third method), polyethylene glycol (PEG-20M) is used as stationary liquid; The initial temperature is 50°C, the temperature is maintained for 3 minutes, and the temperature is raised to 200°C at a rate of 20°C per minute, it was maintained for 7 minutes; The inlet temperature was 250°C; The detector temperature was 280°C. The sample solution and the reference solution were respectively 1 u1 and injected into the gas chromatograph. According to the external standard method to calculate the peak area, N,N-dimethylformamide residues should comply with the provisions.
loss on drying
take this product and dry it at 105°C for 4 hours, and the 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 0.3%.
Heavy metals
The residue left under the item of ignition residue shall not contain more than 20 parts per million of heavy metal when examined by law (General rule 0821).
Last Update：2022-01-01 11:59:13
N-(2,6-DIOXO-3-PIPERIDINYL)PHTHALIMIDE - 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 was used as the filler; Acetonitrile-water-phosphoric acid (15:85:0.1) was used as the mobile phase; The detection wavelength was 237nm. The number of theoretical plates shall not be less than 7000 based on the thalidomide peak.
assay
take about 0.1kg of this product, weigh it accurately, put it in a 100ml measuring flask, add 80ml of acetonitrile, dissolve it by ultrasound, let it cool, dilute it to the scale with acetonitrile, shake it well, take 10ml accurately, put it in a 100ml measuring flask, add 10ml of phosphoric acid solution (1-100), dilute with water to the scale, and shake well. 20 u1 was accurately measured, and human liquid chromatography was injected, and the chromatogram was recorded. Another thalidomide reference substance was taken, and the same method was used for determination. According to the external standard method to calculate the peak area, that is.
Last Update：2022-01-01 11:59:13
N-(2,6-DIOXO-3-PIPERIDINYL)PHTHALIMIDE - Category
Authoritative Data Verified Data
immunomodulatory drugs.
Last Update：2022-01-01 11:59:14
N-(2,6-DIOXO-3-PIPERIDINYL)PHTHALIMIDE - Storage
Authoritative Data Verified Data
sealed storage.
Last Update：2022-01-01 11:59:14
N-(2,6-DIOXO-3-PIPERIDINYL)PHTHALIMIDE - Thalidomide tablets
Authoritative Data Verified Data
This product contains thalidomide (C13H10N204) should be 93.0% to 107.0% of the label.
trait
This product is white or off-white.
identification
- take an appropriate amount of the fine powder of this product (about 0.lg of thalidomide), and show the same reaction according to the identification (1) Test under thalidomide.
- 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.
examination
- Related substances take an appropriate amount of this product's fine powder (about 0.lg equivalent to thalidomide), weigh it accurately, put it in a 50ml measuring flask, and add an appropriate amount of acetonitrile-water-phosphoric acid (50:50: 0.1), ultrasonic dissolution and dilution of thalidomide to the scale, shake well, filter, precise amount of filtrate 10ml, put 100ml flask, add 10ml phosphoric acid solution (1-100), dilute to the scale with water, as a test solution. The determination was carried out according to the method for related substances of thalidomide. In the chromatogram of the test solution, if there are impurity peaks, the phthalic acid peak area shall be calculated according to the external standard method, and the single impurity shall not exceed 0.1% of the label amount and the total impurity shall not exceed 0.3% of the label amount.
- the dissolution of this product, according to the dissolution and release determination method (General 0931 second method), with polyoxyethylene lauryl ether solution [take 5% polyoxyethylene lauryl ether solution 2.5ml, add hydrochloric acid solution (2-100) diluted to 1000ml] as the dissolution medium, the rotation speed is 75 rpm, operate according to law, after 60 minutes, take the solution filtration, continue filtrate as test solution. Take an appropriate amount of thalidomide reference substance, weigh it precisely, dissolve it with acetonitrile and dilute it quantitatively to make a solution containing 0.25mg(25mg specification) or 0.5mg(50mg specification) per 1 ml, take 10ml accurately, put in a 100ml measuring flask, Add 10ml of phosphoric acid solution (1-100), dilute with water to the scale, shake well, and use as a reference solution. According to the method under the content determination item, the dissolution amount of each tablet was 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
Take 20 tablets of this product, precision weighing, fine grinding, precision weighing appropriate amount (about equivalent to thalidomide O.lg ), put it in a 100ml measuring flask, add 80ml of acetonitrile, sonicate thalidomide to dissolve, let it cool, dilute with acetonitrile to the scale, shake well, filter, take 10ml of continued filtrate with precision, put it in a 100ml measuring flask, Add 10ml of phosphoric acid solution (1-100), dilute it to the scale with water, shake it well, and use it as a test solution, and measure it according to the method under the thalidomide content determination item.
category
Same as thalidomide.
specification
(l)25mg (2)50mg
storage
light shielding, sealed storage.
Last Update：2022-01-01 11:59:15
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View History
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PROFLAVINE(RG)
Einecs 271-233-5
1,3 - 二苯基四甲基二硅氧烷
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