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Bupivacaine

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Identification
Molecular formula
C18H28ClN2O
CAS number
2180-92-9
IUPAC name
2-[6-chlorohexyl(methyl)amino]-N-(2,6-dimethylphenyl)acetamide
State
State

At room temperature, Bupivacaine is typically in the form of a crystalline solid. For pharmaceutical applications, it is used in injectable solutions as a hydrochloride salt.

Melting point (Celsius)
107.00
Melting point (Kelvin)
380.15
Boiling point (Celsius)
489.30
Boiling point (Kelvin)
762.45
General information
Molecular weight
324.89g/mol
Molar mass
324.8930g/mol
Density
0.9706g/cm3
Appearence

Bupivacaine appears as a white crystalline powder and is odorless. It is soluble in water, and its solubility increases with the presence of hydrochloride, where it is often provided as bupivacaine hydrochloride for medical applications.

Comment on solubility

Solubility of 2-[6-chlorohexyl(methyl)amino]-N-(2,6-dimethylphenyl)acetamide

The solubility of 2-[6-chlorohexyl(methyl)amino]-N-(2,6-dimethylphenyl)acetamide can be quite complex due to its structural characteristics.

Key factors influencing the solubility of this compound include:

  • Polarity: The presence of polar functional groups can enhance solubility in polar solvents, while non-polar regions may facilitate solubility in non-polar solvents.
  • Hydrogen Bonding: The ability to form hydrogen bonds can significantly improve solubility in water and other polar solvents.
  • Molecular Size: Larger molecular structures may exhibit decreased solubility due to steric hindrance.

In a solvent system, such as water, compounds similar to this structure might have limited solubility due to the bulky hydrophobic portions that can restrict interaction with water molecules. However, they may be more soluble in organic solvents such as ethanol or acetone, which can interact more favorably with both the polar and non-polar sections of the molecule.

Understanding the degree of solubility in various solvents is crucial for practical applications, as it affects formulation development and bioavailability. As noted, solubility is a key factor in determining the efficacy of pharmaceutical compounds and their delivery systems. It's essential to conduct empirical tests to gauge the solubility comprehensively.

Interesting facts

Exploring 2-[6-chlorohexyl(methyl)amino]-N-(2,6-dimethylphenyl)acetamide

This fascinating compound is a member of the acetamide family, which plays an essential role in various biological and chemical processes. Let's delve into some intriguing aspects of this compound:

  • Pharmacological Potential: Due to its unique structure, this compound may exhibit interesting pharmacological activities, making it a candidate for drug development.
  • Structural Features: The presence of a chloro group and a dimethylphenyl moiety suggests potential interactions with biological targets, which could be pivotal in medicinal chemistry.
  • Functional Groups: The compound contains amine and acetamide functional groups, which are known for their reactivity and versatility in organic synthesis.
  • Research Applications: Compounds like this one are often utilized in research studies to explore their effects on various biological systems or to develop new therapeutic agents.
  • Importance of Substituents: The specific substituents on the hexyl and phenyl groups influence the compound's properties, potentially altering its behavior in complex biological environments.

As noted by chemists, "the relationship between molecular structure and biological activity is a pivotal focus in drug design." This compound provides a rich canvas for investigating such relationships, offering insights into how slight modifications in structure can lead to significant changes in the compound's activity.

Moreover, its synthetic pathway can contribute to understanding organic reaction mechanisms, making it a valuable substance not just for pharmacology but also for advancing chemistry itself.