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Bupivacaine

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Identification
Molecular formula
C18H28N2O
CAS number
38396-39-3
IUPAC name
N-[3-(dimethylamino)propyl]-N-(2,6-dimethylphenyl)-3-phenyl-propanamide
State
State

At room temperature, bupivacaine is found as a solid.

Melting point (Celsius)
107.00
Melting point (Kelvin)
380.00
Boiling point (Celsius)
543.80
Boiling point (Kelvin)
816.80
General information
Molecular weight
288.44g/mol
Molar mass
288.4380g/mol
Density
1.0230g/cm3
Appearence

Bupivacaine is typically a white or off-white crystalline powder. It is odorless and has a bitter taste.

Comment on solubility

Solubility of N-[3-(dimethylamino)propyl]-N-(2,6-dimethylphenyl)-3-phenyl-propanamide

N-[3-(dimethylamino)propyl]-N-(2,6-dimethylphenyl)-3-phenyl-propanamide, a compound with both polar and non-polar characteristics, exhibits interesting solubility behaviors. The solubility of this compound can be influenced by several factors:

  • Polarity: The presence of the dimethylamino group introduces a polar functional group, which can enhance solubility in polar solvents such as water, albeit to a limited extent.
  • Hydrophobic Interaction: The bulky 2,6-dimethylphenyl and phenyl groups increase the hydrophobic character, making the compound more soluble in non-polar solvents, like hexane or benzene.
  • Temperature: Increased temperature often enhances solubility; therefore, the solubility in both polar and non-polar solvents may improve when the temperature is raised.
  • pH Levels: The solubility may be affected by the pH of the solution due to potential protonation of the amino group, altering its charge and interaction with solvents.

In summary, while N-[3-(dimethylamino)propyl]-N-(2,6-dimethylphenyl)-3-phenyl-propanamide is expected to have limited solubility in water due to its hydrophobic segments, it should show considerable solubility in organic solvents. As one expert noted, "The diversity in substituents and functional groups can lead to unpredictable solubility patterns based on the molecular interactions at play."

Interesting facts

Interesting Facts about N-[3-(dimethylamino)propyl]-N-(2,6-dimethylphenyl)-3-phenyl-propanamide

N-[3-(dimethylamino)propyl]-N-(2,6-dimethylphenyl)-3-phenyl-propanamide, often referred to in research contexts, exhibits some fascinating characteristics and potential applications:

  • Pharmaceutical Potential: This compound is being studied for its ability to modulate biological processes and has attracted interest in pharmacology due to its potential efficacy as a drug molecule.
  • Dual Functionality: The presence of both amide and dimethylamino functionalities suggests its capability in acting as a versatile building block for diverse chemical syntheses or as an active pharmaceutical ingredient.
  • Chemical Interactions: The structure allows for various stereochemical arrangements, potentially enhancing its interaction with biological targets such as receptors and enzymes.
  • Research Applications: Being an amide compound, it may serve as a model for studying amide bond reactivity, stability, and hydrolysis in chemical education and advanced research.

Moreover, the compound's complex structure highlights the importance of substituent groups in altering the compound's reactivity and biological activity. As chemists explore its properties, they may uncover important insights into the mechanism of action in biological systems, leading to novel therapeutic approaches.

In conclusion, N-[3-(dimethylamino)propyl]-N-(2,6-dimethylphenyl)-3-phenyl-propanamide is not just a chemical entity; it represents a promising frontier in medicinal chemistry that combines the art of synthesis with the science of biological function. As research progresses, the implications of this compound could extend far beyond what we currently understand.

Synonyms
SA 149
17307-24-3
HYDROCINNAMANILIDE, N-(3-(DIMETHYLAMINO)PROPYL)-2',6'-DIMETHYL-
N-(3-(Dimethylamino)propyl)-2',6'-dimethylhydrocinnamanilide
DTXSID50169510
DTXCID8092001
N-[3-(dimethylamino)propyl]-N-(2,6-dimethylphenyl)-3-phenylpropanamide
N-(3-Dimethylaminopropyl)-N-(2,6-dimethylphenyl)benzenepropanamide
SCHEMBL30395170