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| CAS No.: | 97240-79-4 |
|---|---|
| Name: | Topiramate |
| Article Data: | 24 |
| Molecular Structure: | |
|
|
|
| Formula: | C12H21NO8S |
| Molecular Weight: | 339.367 |
| Synonyms: | McN-4853;Epitomax;2,3:4,5-bis-o-(1-methylethylidene)-beta-d-fructopyranos sulfamate;a-D-Fructopyranose,2,3:4,5-bis-O-(1-methylethylidene)-,sulfamate;Tipiramato [Spanish];Topamax;Topiramate [USAN:BAN:INN];2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate;beta-D-Fructopyranose, 2,3:4,5-bis-O-(1-methylethylidene)-, sulfamate;Topiramate;Topamax;RWJ-17021-000;2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamate;Topiramate (JAN/USAN);Tipiramate [French];Topamax (TN); |
| EINECS: | 200-659-6 |
| Density: | 1.336 g/cm3 |
| Melting Point: | 125 °C |
| Boiling Point: | 438.7 °C at 760 mmHg |
| Flash Point: | 219.1 °C |
| Solubility: | DMSO Solubility : ~44 mg/mL |
| Appearance: | white to off-white crystalline powder |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 26-36 |
| PSA: | 123.92000 |
| LogP: | 1.38570 |
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- 98025-62-8(5-METHYL-[1,3,4]THIADIAZOL-2-YL)-HYDRAZINE
- 99724-17-1Dimethyl-pyrrolidin-3-ylmethyl-amine
- 97484-82-71-allyl-7-methyl-1H-pyrido[2,3-d][1,3]oxazine-2,4-dione
- 98084-25-4CESIUM TITANATE 99.9+%
- 150609-95-3
2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester
- 97240-79-4
topiramate
| Conditions | Yield |
|---|---|
| With ammonia In tetrahydrofuran; hexane at 20℃; for 3h; Solvent; Temperature; | 96.7% |
| With ammonia In tetrahydrofuran; Petroleum ether at 20℃; for 3h; Solvent; | 95.2% |
| With pyridine; SULFAMIDE In 5,5-dimethyl-1,3-cyclohexadiene at 128 - 133℃; for 3h; | 91.1% |
- 97240-79-4
topiramate
| Conditions | Yield |
|---|---|
| With hydrazine hydrate In ethanol at 20℃; for 1h; | 90% |
- 20880-92-6
2,3;4,5-di-O-isopropylidene-β-D-fructopyranose
- 97240-79-4
topiramate
| Conditions | Yield |
|---|---|
| With pyridine; 2,2,2-trifluoro-1-(trifluoromethyl)ethyl sulfamate In dichloromethane at 30℃; for 8h; | 88% |
| With 4-methyl-morpholine; sulphamoyl chloride In di-isopropyl ether; N,N-dimethyl-formamide at 5℃; for 1h; Product distribution / selectivity; Crude product recrystalization; | 76% |
| With sulphamoyl chloride; triethylamine In di-isopropyl ether; N,N-dimethyl acetamide at 5℃; for 1h; Product distribution / selectivity; Crude product recrystalization; | 75% |
- 97240-79-4
topiramate
| Conditions | Yield |
|---|---|
| With palladium on activated charcoal In methanol at 20℃; under 9000.9 Torr; for 3h; | 83% |
- 97240-79-4
topiramate
| Conditions | Yield |
|---|---|
| With water; sodium acetate; acetic acid In acetone at 68 - 70℃; for 1 - 1.5h; pH=3.5; Product distribution / selectivity; Heating / reflux; | 67% |
| With sodium acetate; acetic acid In water; acetone at 68 - 70℃; for 1 - 1.5h; pH=3.5; Product distribution / selectivity; Heating / reflux; | 67% |
| With water In acetone at 70℃; for 2h; pH=3.5; aq. acetate buffer; |
- 97240-79-4
topiramate
| Conditions | Yield |
|---|---|
| With water; sodium acetate; acetic acid In acetone at 70℃; for 2 - 2.5h; pH=3.5; Product distribution / selectivity; Heating / reflux; | 63% |
| With sodium acetate; acetic acid In water; acetone at 70℃; for 2 - 2.5h; pH=3.5; Product distribution / selectivity; Heating / reflux; | 63% |
- 876403-98-4
N-[(diethylamino)carbonyl]-2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate
- 97240-79-4
topiramate
| Conditions | Yield |
|---|---|
| Stage #1: N-[(diethylamino)carbonyl]-2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate With sodium hydroxide; water; acetic acid In acetone at 78 - 79℃; for 1 - 8.5h; pH=2.5 - 5; Heating / reflux; Stage #2: With sodium hydroxide In water; acetone Product distribution / selectivity; | 61% |
| With sodium hydroxide; acetic acid In water; acetone at 78 - 79℃; for 1 - 8.5h; pH=2.5 - 5.0; Product distribution / selectivity; Heating / reflux; | 61% |
| With water; sodium acetate; acetic acid In acetonitrile at 80℃; for 1.5 - 2h; pH=3.5; Product distribution / selectivity; |
- 106881-41-8
2,3-O-(1-Methylethylidene)-β-D-fructopyranose 1-sulfamate
- 122-51-0
orthoformic acid triethyl ester
- 433-27-2
Trifluoroacetaldehyde ethyl hemiacetal
- 97240-79-4
topiramate
| Conditions | Yield |
|---|---|
| With sulfuric acid | 30% |
- 106881-35-0
2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose azidosulfate
- 97240-79-4
topiramate
| Conditions | Yield |
|---|---|
| With hydrogen; 5%-palladium/activated carbon In ethyl acetate under 2844.39 - 3102.97 Torr; for 8h; |
- 97240-79-4
topiramate
| Conditions | Yield |
|---|---|
| With hydrogenchloride; water In acetone at 20℃; for 1.5h; Product distribution / selectivity; |
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Specification
1. Introduction of Topiramate
Topiramate, with the systematic name of beta-D-Fructopyranose, 2,3:4,5-bis-O-(1-methylethylidene)-, sulfamate, is one kind of white powder. This chemical belongs to the Product Categories which include Active Pharmaceutical Ingredients; APIs; Health & Beauty; Carbohydrates & Derivatives; Pharmaceuticals; Glutamate receptor. It is used as an anticonvulsant and an antidepressant. It is also used to treat Post Traumatic Stress Disorder.
2. Properties of Topiramate
Topiramate has the properties: (1)Molecular Formula: C12H21NO8S; (2)Molecular Weight: 339.362040 g/mol; (3)Index of Refraction: 1.497; (4)Molar Refractivity: 74.32 cm3; (5)Molar Volume: 253.8 cm3; (6)Surface Tension: 53.3 dyne/cm; (7)Density: 1.336 g/cm3; (8)Flash Point: 219.1 °C; (9)Enthalpy of Vaporization: 69.55 kJ/mol; (10)Boiling Point: 438.7 °C at 760 mmHg; (11)Vapour Pressure: 6.76E-08 mmHg at 25 °C; (12)Melting Point: 125°C ; (13)DMSO Solubility : ~44 mg/mL; (14)Storage Temp.: 2-8°C.
3. Toxicity of Topiramate
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| rat | LD50 | intraperitoneal | > 1500mg/kg (1500mg/kg) | Drugs of the Future. Vol. 14, Pg. 342, 1989. |
4. Safety Information of Topiramate
Safety Information of Topiramate (CAS NO. 97240-79-4):
Hazard Codes: Xi 
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36:Wear suitable protective clothing
WGK Germany: 3
RTECS: LS7083000