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97240-79-4

Basic Information
CAS No.: 97240-79-4
Name: Topiramate
Molecular Structure:
Molecular Structure of 97240-79-4 (Topiramate)
Formula: C12H21NO8S
Molecular Weight: 339.36
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
Transport Information:
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;
627538-01-6

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

97240-79-4

topiramate

Conditions
ConditionsYield
With sodium hydroxide In DMF (N,N-dimethyl-formamide) at 20 - 80℃; for 12h; Product distribution / selectivity;

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

97240-79-4

topiramate

Conditions
ConditionsYield
With hydrogen; palladium on activated carbon In ethanol at 20℃; under 2585.81 Torr; for 5h; Product distribution / selectivity;
topiramate base

topiramate base

97240-79-4

topiramate

Conditions
ConditionsYield
In water; acetone at 0 - 35℃; Purification / work up;
57-48-7

D-Fructose

97240-79-4

topiramate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid
2: SULFAMIDE; pyridine / 5,5-dimethyl-1,3-cyclohexadiene / 130 - 140 °C
View Scheme
7660-25-5

D-fructose

97240-79-4

topiramate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: zinc(II) chloride / 2 h / 58 °C
2: sulfuryl dichloride; 1H-imidazole / dichloromethane / 2.5 h / 0 °C / Molecular sieve
3: ammonia / ethanol / 6 h / 20 °C / Green chemistry; Industrial scale
View Scheme
6347-01-9

fructopyranose

97240-79-4

topiramate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid / acetone / 0 - 15 °C / Inert atmosphere; Large scale
2: sulfuryl dichloride; pyridine / dichloromethane; toluene / 3 h / -10 - 20 °C
3: ammonia / tetrahydrofuran; hexane / 3 h / 20 °C
View Scheme
97240-79-4

topiramate

106881-35-0

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

Conditions
ConditionsYield
With fluorosulfonyl azide; potassium hydrogencarbonate In tert-butyl methyl ether; water; N,N-dimethyl-formamide at 20℃; for 0.0833333h;99%
4641-57-0

1-phenylpyrrolidin-2-one

97240-79-4

topiramate

((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-3a-yl)methyl ((E)-1-phenylpyrrolidin-2-ylidene)sulfamate

Conditions
ConditionsYield
With diazoacetic acid ethyl ester; zinc trifluoromethanesulfonate In cyclohexane for 12h; Reflux; stereoselective reaction;98%
67-56-1

methanol

97240-79-4

topiramate

106881-46-3, 106881-47-4

methyl D-fructopyranoside sulfamate

Conditions
ConditionsYield
With hydrogenchloride at 23℃; for 24h;94%
75-03-6

ethyl iodide

97240-79-4

topiramate

N-ethyl topiramate

Conditions
ConditionsYield
With potassium fluoride on basic alumina In acetonitrile at 80℃; for 48h;88%
3130-75-4

4-phthalimidobutyric acid

97240-79-4

topiramate

C24H30N2O11S

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;88%
97240-79-4

topiramate

74-88-4

methyl iodide

97240-80-7

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

Conditions
ConditionsYield
With potassium fluoride on basic alumina In acetonitrile at 80℃; for 48h;86%
97240-79-4

topiramate

68-12-2, 33513-42-7

N,N-dimethyl-formamide

C15H26N2O8S

Conditions
ConditionsYield
With thionyl chloride In chloroform at 60℃; for 3h;80%
2466-76-4

N-Acetylimidazole

97240-79-4

topiramate

Acetyl-sulfamic acid (3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-ylmethyl ester; compound with 1H-imidazole

Conditions
ConditionsYield
In toluene for 7h; Heating;78%
107-08-4

1-iodo-propane

97240-79-4

topiramate

N-propyl topiramate

Conditions
ConditionsYield
With potassium fluoride on basic alumina In acetonitrile at 80℃; for 48h;77%
100-39-0

benzyl bromide

97240-79-4

topiramate

A

N,N'-dibenzyl topiramate

B

N-benzyl topiramate

Conditions
ConditionsYield
With potassium fluoride on basic alumina In acetonitrile at 80℃; for 36h;A 7%
B 77%
108-86-1

bromobenzene

97240-79-4

topiramate

106881-36-1

((3aR,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-3a-yl)methyl phenylsulfamate

Conditions
ConditionsYield
With (1,2-dimethoxyethane)dichloronickel(II); (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 30℃; for 24h; Inert atmosphere; Irradiation; Sealed tube;73%
97240-79-4

topiramate

589-15-1

1-bromomethyl-4-bromobenzene

A

N-(4-bromobenzyl)topiramate

B

N,N-di(4-bromobenzyl)topiramate

Conditions
ConditionsYield
With potassium fluoride on basic alumina In acetonitrile at 80℃; for 36h;A 68%
B 11%
97240-79-4

topiramate

1765-40-8

(bromomethyl)pentafluorobenzene

A

C19H22F5NO8S

B

N,N-di(pentaflourobenzyl)topiramate

Conditions
ConditionsYield
With potassium fluoride on basic alumina In acetonitrile at 80℃; for 36h;A 64%
B 28%
128-13-2

ursodeoxycholic acid

97240-79-4

topiramate

C36H59NO11S

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 6h;60%
623-73-4

diazoacetic acid ethyl ester

97240-79-4

topiramate

103-84-4

Acetanilid

ethyl N-phenyl-N-((E)-1-(((((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-3a-yl)methoxy)sulfonyl)imino)ethyl)glycinate

Conditions
ConditionsYield
With zinc trifluoromethanesulfonate In cyclohexane at 90℃; for 12h;57%
97240-79-4

topiramate

70-11-1

α-bromoacetophenone

A

C20H27NO9S

B

C28H33NO10S

Conditions
ConditionsYield
With potassium fluoride on basic aluminaA 54%
B 33%
3618-96-0

(S)-N-acetylphenylalanine

97240-79-4

topiramate

methyl (1-(((((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-3a-yl)methoxy)sulfonyl)imino)ethyl)-L-phenylalaninate

Conditions
ConditionsYield
With diazoacetic acid ethyl ester; manganese(II) perchlorate hexahydrate In cyclohexane at 90℃; for 12h; chemoselective reaction;48%
6651-36-1

1-(Trimethylsilyloxy)cyclohexene

97240-79-4

topiramate

106881-40-7

4,5-O-cyclohexylidene-2,3-O-(1-methyl-ethylidene)-β-D-fructopyranose sulfamate

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran for 0.0833333h;43%
97240-79-4

topiramate

3,6-dioxa-2-thia-1-azaspiro<4.5>decane-8α,9α,10β-triol 2,2-dioxide

Conditions
ConditionsYield
With Amberlite IR-45 (anion-exchange resin, hydroxide form); trifluoroacetic acid for 18h; Ambient temperature;43%
97240-79-4

topiramate

106881-41-8

2,3-O-(1-Methylethylidene)-β-D-fructopyranose 1-sulfamate

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran at 45℃; for 3.5h;31%
633-65-8

berberine chloride

97240-79-4

topiramate

C31H35N2O11S(1+)*Cl(1-)

Conditions
ConditionsYield
In ethanol for 16h; Reflux;20%
Downstream Products
106881-41-8
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    97240-79-4

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    Description 1)Product Name: Topiramate 2)CAS:97240-79-4 3)Molecular Formula:C12H21NO8S 4)Molecular Weight:339.36 5

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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

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    Topiramate Basic information Broad-spectrum anti-epileptic drugs Pharmacological effects Pharmacokinetics Dosage Clinical evaluationAdverse reactions and precautions Chemical Properties Product Name:

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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