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Scopolamine hydrobromide

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Identification
Molecular formula
C17H21NO4 · HBr
CAS number
114-49-8
IUPAC name
[(2R,3R,5R,8R,10R,17S)-8-acetoxy-11-ethyl-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azoniahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate;bromide
State
State

At room temperature, scopolamine hydrobromide is usually in a solid state.

Melting point (Celsius)
188.00
Melting point (Kelvin)
461.15
Boiling point (Celsius)
380.00
Boiling point (Kelvin)
653.15
General information
Molecular weight
438.30g/mol
Molar mass
418.3240g/mol
Density
1.2700g/cm3
Appearence

Scopolamine hydrobromide typically appears as a white or slightly creamy, crystalline powder. It is hygroscopic, meaning it can absorb moisture from the air.

Comment on solubility

Solubility of the Compound

The solubility of the compound [(2R,3R,5R,8R,10R,17S)-8-acetoxy-11-ethyl-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azoniahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate; bromide is a complex topic due to its intricate structure and numerous functional groups.

When analyzing the solubility, several factors must be considered:

  • Polarity: The presence of multiple hydroxy (-OH) groups indicates potential for hydrogen bonding, which typically enhances water solubility.
  • Hydrophobic Regions: The hexacyclic structure and alkyl chains contribute to hydrophobic character, which may lead to lower solubility in polar solvents.
  • Ionization: The quaternary ammonium group could influence solubility in aqueous environments, often promoting increased solubility in ionic form.

Given these characteristics, it can be deduced that:

  • The compound is likely more soluble in polar solvents, especially those capable of hydrogen bonding.
  • Its solubility may decrease in nonpolar solvents due to the significant hydrophobic portions.
  • pH levels can play a critical role, as solubility may be enhanced or diminished based on ionization.

In summary, the solubility of this compound is expected to be:

  • Moderate to high in polar solvents like water or methanol.
  • Lower in organic solvents lacking polarity.
  • Dependent on environmental conditions, including temperature and solvent composition.

This nuanced understanding of solubility expands the potential applications and formulations of the compound in various fields.

Interesting facts

Interesting Facts About the Compound

This complex compound, often recognized by its long and intricate name, possesses several intriguing characteristics that make it a subject of interest for both chemists and biochemists alike.

Chemical Structure and Composition

  • The structure of this compound features a unique arrangement, with multiple chiral centers indicated by the (2R,3R,5R,8R,10R,17S) designation. This stereochemical configuration plays a critical role in the compound's biological activity.
  • It contains several functional groups, including acetoxy, hydroxy, and methoxy groups, which contribute to its chemical reactivity and interaction with biological systems.
  • With a total of six fused ring systems, the compound falls into a class of polycyclic compounds that exhibit complex three-dimensional architectures.

Biological Significance

This compound is often studied for its potential applications in medicinal chemistry. Noteworthy points include:

  • Antimicrobial Properties: Some derivatives of similar structures have demonstrated promising antibacterial and antifungal activities.
  • Pharmacological Potential: The presence of multiple hydroxyl groups suggests that this compound could interact with various biological receptors, potentially being explored for therapeutic uses.
  • Natural Product Analogues: Given its intricate structure, it may serve as a synthetic mimic of naturally occurring compounds, contributing to drug design and synthesis.

Synthesis Challenges

Due to the complexity of its structure, synthesizing this compound can present several challenges:

  • Multi-step Synthesis: The creation of such a compound often requires several reaction steps, each needing careful optimization to ensure yield and purity.
  • Stereochemistry Management: Maintaining the correct stereochemistry throughout the synthesis is essential, as incorrect configurations can lead to inactive or toxic products.

In summary, this compound embodies the intricate beauty of organic chemistry, featuring complex structures and significant biological implications that make it an exciting topic for study. As stated in the field, "The complexity in molecular architecture often leads to a richness in biological function."