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Name	Topiramate	EINECS	200-659-6
CAS No.	97240-79-4	Density	1.336 g/cm³
PSA	123.92000	LogP	1.38570
Solubility	DMSO Solubility : ~44 mg/mL	Melting Point	125 °C
Formula	C₁₂H₂₁NO₈S	Boiling Point	438.7 °C at 760 mmHg
Molecular Weight	339.367	Flash Point	219.1 °C
Transport Information	N/A	Appearance	white to off-white crystalline powder
Safety	26-36	Risk Codes	36/37/38
Molecular Structure		Hazard Symbols	Xi
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);	Article Data	24

Topiramate Synthetic route

: 150609-95-3
2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester

: 97240-79-4
topiramate

Conditions

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%

: C15H26N2O8S

: 97240-79-4
topiramate

Conditions

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

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%

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

: 97240-79-4
topiramate

Conditions

Conditions	Yield
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

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;

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

: 97240-79-4
topiramate

Conditions

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

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

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

Conditions	Yield
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

Conditions	Yield
With hydrogenchloride; water In acetone at 20℃; for 1.5h; Product distribution / selectivity;

Topiramate 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

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