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Lofepramine

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Identification
Molecular formula
C15H20ClNO2
CAS number
23047-25-8
IUPAC name
2-amino-3-[4-[2-chloroethyl(2-fluoroethyl)amino]phenyl]propanoic acid
State
State

At room temperature, lofepramine is a solid. It is usually handled in a powdered form for pharmaceutical use. Its state of matter makes it easy to measure and mix with other compounds during drug formulation.

Melting point (Celsius)
142.00
Melting point (Kelvin)
415.00
Boiling point (Celsius)
280.00
Boiling point (Kelvin)
553.00
General information
Molecular weight
356.82g/mol
Molar mass
356.8220g/mol
Density
1.3000g/cm3
Appearence

Lofepramine is typically a white to pale yellow crystalline powder. It is often synthesized for pharmaceutical formulations. The compound may appear as a solid with a slightly glossy finish and is usually odorless or has a faint odor.

Comment on solubility

Solubility of 2-amino-3-[4-[2-chloroethyl(2-fluoroethyl)amino]phenyl]propanoic acid

The solubility of 2-amino-3-[4-[2-chloroethyl(2-fluoroethyl)amino]phenyl]propanoic acid can be influenced by various factors, including its chemical structure and the presence of functional groups. In general, the following aspects are noteworthy:

  • Polarity: The presence of amino groups and a propanoic acid moiety typically increases polarity, enhancing solubility in polar solvents such as water.
  • Hydrogen bonding: The ability to form hydrogen bonds due to the carboxylic acid and amino groups can promote solubility in aqueous environments.
  • Alkyl substitutions: The chlorinated and fluorinated ethyl groups may impact the overall solubility, as halogenated compounds can exhibit varying solubility characteristics depending on their interactions with solvents.
  • pH sensitivity: Changes in pH can significantly affect the ionization state of the carboxylic acid group, potentially increasing solubility in alkaline conditions as it becomes a negatively charged ion.

Given these statements, the solubility of this compound can be anticipated to be relatively higher in polar environments, particularly in water or aqueous solutions, although specific experimental data would be necessary for precise quantification.

Interesting facts

Exploring 2-amino-3-[4-[2-chloroethyl(2-fluoroethyl)amino]phenyl]propanoic acid

This intriguing compound possesses a unique structure that blends amino acid characteristics with functionalized groups, making it a subject of interest in pharmacology and medicinal chemistry. Here are some captivating insights:

  • Dual Functionality: The presence of both amino and acid groups allows this compound to participate in various biological processes, mirroring natural amino acids while retaining synthetic modifications.
  • Pharmacological Potential: Structures similar to this compound are often explored for their potential use in treating conditions like cancer, making it a stepping stone for drug discovery and development.
  • Chlorine and Fluorine Leverage: The substitution of chlorine and fluorine atoms can significantly affect the compound’s biological activity and stability, enabling researchers to fine-tune interactions with biological targets.
  • Synthetic Strategies: The complexity of this molecule requires advanced synthetic techniques, often combining multiple steps to achieve the desired final product, which can help students learn about intricate synthetic pathways.
  • Structure-Activity Relationship (SAR): Studying this compound opens discussions on SAR, where small changes in structure lead to significant alterations in biological activity, essential knowledge for aspiring medicinal chemists.

In conclusion, 2-amino-3-[4-[2-chloroethyl(2-fluoroethyl)amino]phenyl]propanoic acid serves as a fascinating subject of study due to its dual functionality, synthetic challenge, and potential pharmaceutical applications. As researchers continue to investigate compounds like this one, the future of targeted therapies and personalized medicine holds promise for innovative treatments.

Synonyms
3-(p-((2-Chloroethyl)(2-fluoroethyl)amino)phenyl)alanine
1222-64-6
ALANINE, 3-(p-((2-CHLOROETHYL)(2-FLUOROETHYL)AMINO)PHENYL)-
NCIOpen2_004469
DTXSID40924110
NSC81715
NSC-81715
4-[(2-Chloroethyl)(2-fluoroethyl)amino]phenylalanine
DL-Phenylalanine, 4-[(2-chloroethyl)(2-fluoroethyl)amino]-
DL-Alanine, 3-[[p-(2-chloroethyl)(2-fluoroethyl)amino]phenyl]-