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Topiramate

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Identification
Molecular formula
C12H21NO8S
CAS number
97240-79-4
IUPAC name
(4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl)methyl sulfamate
State
State

At room temperature, topiramate is in a solid state. This makes it suitable for tablet and capsule formulations in pharmaceutical applications.

Melting point (Celsius)
125.50
Melting point (Kelvin)
398.70
Boiling point (Celsius)
301.00
Boiling point (Kelvin)
574.00
General information
Molecular weight
339.36g/mol
Molar mass
339.3630g/mol
Density
1.3320g/cm3
Appearence

Topiramate typically appears as a white crystalline powder. This form is odorless and has a bitter taste. It's a pharmaceutical compound commonly used as an antiepileptic drug and sometimes for migraine prevention.

Comment on solubility

Solubility of (4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl)methyl sulfamate

The compound (4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl)methyl sulfamate (C12H21NO8S) presents an intriguing solubility profile. Here are several key points regarding its solubility characteristics:

  • Polarity: The presence of multiple polar groups, such as -NO, -O, and -S, suggests that this compound is likely to exhibit good solubility in polar solvents, including water.
  • Hydrogen Bonding: The ability to form hydrogen bonds due to hydroxyl or ether like oxygens enhances its solubility in aqueous solutions.
  • Non-polar Characteristics: The tetramethyl groups may impart some non-polar characteristics, potentially reducing solubility in highly polar solvents.
  • Overall Solubility Profile: The balance between polar and non-polar elements in the compound suggests that it may be more soluble in mixed solvent systems, particularly those that incorporate both polar and non-polar characteristics.

In summary, the solubility of this compound is influenced by its unique structural features, primarily its polar functional groups alongside hydrophobic elements. As a result, it is expected to dissolve well in polar solvents, while its solubility in non-polar solvents may be limited.

Interesting facts

Interesting Facts about (4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl)methyl sulfamate

This intriguing compound is a member of the sulfamate family, known for its unique structural characteristics. Here are several fascinating insights into this complex molecule:

  • Complex Structure: The compound features a tricyclic structure that includes five oxygen atoms, contributing to its potential reactivity and interactions in chemical processes.
  • Uses in Research: Sulfamates like this one are often explored for their potential applications in medicinal chemistry, where they may serve as intermediates in the synthesis of pharmaceuticals.
  • Biological Activity: Compounds containing sulfamate groups have been under investigation for various biological activities, including antimicrobial properties, which may lead to novel therapeutic agents.
  • Environmental Impact: Investigating the behavior and degradation of this compound can also provide insights into its environmental fate and effects, which is important for sustainable chemistry.
  • Simultaneous Modifications: The multiple methyl groups attached to the structure suggest that the compound could exhibit unique steric and electronic properties, possibly influencing its reactivity compared to simpler analogs.

Researchers emphasize the importance of such compounds, often stating, "Understanding the nuances of complex molecules enriches our knowledge of chemical reactivity and potential applications." This makes (4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl)methyl sulfamate an exciting subject of study in the wide world of organic chemistry.

Synonyms
Topiramate-13C6
1217455-55-4
(4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl)methyl sulfamate
SCHEMBL4980190
DTXSID90861147
KJADKKWYZYXHBB-UHFFFAOYSA-N
STL386604
AKOS025250533
SY028640
T2755
EN300-1695301
2,3:4,5-Bis-O-isopropylidene-.beta.-d-fructopyranose sulfamate
2,3:4,5-Di-O-isopropylidene-1-O-sulfamoyl-beta-D-fructopyranose
(2,2,7,7-Tetramethyltetrahydro-2H,3aH,7H-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl)methyl sulfamate
(2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl)methyl sulfamate (non-preferred name)
{4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.0,2,6]dodecan-6-yl}methyl sulfamate
1192352-58-1