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97240-79-4

Basic Information
CAS No.: 97240-79-4
Name: Topiramate
Article Data: 24
Molecular Structure:
Molecular Structure of 97240-79-4 (Topiramate)
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: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
PSA: 123.92000
LogP: 1.38570
Synthetic route
150609-95-3

2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester

97240-79-4

topiramate

Conditions
ConditionsYield
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%

C15H26N2O8S

97240-79-4

topiramate

Conditions
ConditionsYield
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
ConditionsYield
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%

N-benzyloxycarbonyl-2,3: 4,5-di-O-(1-methylethylidene)-β-D-fructopyranosaminosulfonates potassium salt

97240-79-4

topiramate

Conditions
ConditionsYield
With palladium on activated charcoal In methanol at 20℃; under 9000.9 Torr; for 3h;83%

N-[(diphenylamino)carbonyl]-2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate

97240-79-4

topiramate

Conditions
ConditionsYield
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;

N-{[methyl(phenyl)amino]carbonyl}-2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate

97240-79-4

topiramate

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sulfuric acid30%
106881-35-0

2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose azidosulfate

97240-79-4

topiramate

Conditions
ConditionsYield
With hydrogen; 5%-palladium/activated carbon In ethyl acetate under 2844.39 - 3102.97 Torr; for 8h;

2,2,7,7,-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b,4',5'-d]pyran-3a-ylmethyl (E)-benzylidenesulfamate

97240-79-4

topiramate

Conditions
ConditionsYield
With hydrogenchloride; water In acetone at 20℃; for 1.5h; Product distribution / selectivity;
Downstream Products
106881-41-8
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    Name Topiramate Synonyms McN-4853; RWJ-17021; 2,3:4,5-bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate Molecular Formula C12H21NO8S Molecular Weight 339.36 CAS Reg

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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 Irritant
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