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Lobeline

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Identification
Molecular formula
C22H27NO2F
CAS number
90-69-7
IUPAC name
2-(diethylamino)ethyl 2-(4-fluorophenoxy)acetate
State
State

At room temperature, lobeline is typically solid. It is provided as a crystalline or an amorphous powder and does not readily volatilize into the atmosphere under normal room conditions.

Melting point (Celsius)
135.00
Melting point (Kelvin)
408.15
Boiling point (Celsius)
300.00
Boiling point (Kelvin)
573.00
General information
Molecular weight
323.36g/mol
Molar mass
323.3570g/mol
Density
1.1230g/cm3
Appearence

Lobeline typically appears as a white or off-white crystalline powder. It is an alkaloid derived from Lobelia plants and can also be found in an amorphous form. The crystalline form is more purified and has better-defined melting properties than its amorphous form.

Comment on solubility

Solubility of 2-(diethylamino)ethyl 2-(4-fluorophenoxy)acetate

The solubility of 2-(diethylamino)ethyl 2-(4-fluorophenoxy)acetate can be quite intriguing due to its unique structure and the presence of polar and nonpolar functional groups. Here are some noteworthy insights regarding its solubility:

  • Polarity Factors: The diethylamino group contributes to the molecule's polarity, enhancing its interaction with polar solvents such as water.
  • Phenoxy Influence: The 4-fluorophenoxy moiety, while adding some hydrophobic character, can still participate in hydrogen bonding, which might aid in solubility under certain conditions.
  • Solvent Compatibility: This compound is likely to exhibit good solubility in organic solvents like ethanol, methanol, and acetone, while its solubility in water may be limited due to the bulky nature of the diethylamino group.

In summary, the solubility of this compound varies significantly with changes in the solvent system used. Understanding these solubility characteristics is crucial for applications in pharmaceuticals, where solubility plays a vital role in bioavailability and therapeutic efficacy.

Interesting facts

Interesting Facts about 2-(diethylamino)ethyl 2-(4-fluorophenoxy)acetate

2-(diethylamino)ethyl 2-(4-fluorophenoxy)acetate is a fascinating compound that showcases the intricate interplay of organic chemistry and medicinal applications. Here are some intriguing aspects of this compound:

  • Pharmacological Relevance: This compound belongs to a class of pharmaceuticals known for their potential in both anesthetic and analgesic therapies. Its diethylamino group is crucial in influencing the compound's interaction with biological systems.
  • Electron Distribution: The presence of the 4-fluorophenoxy moiety enhances the compound's lipophilicity, offering improved absorption and distribution. This fluorine substitution often leads to better metabolic stability compared to its non-fluorinated counterparts.
  • Bioactivity: With modifications of the phenoxy group, similar compounds have shown significant activity against various types of pain and inflammation. The potential for developing new analgesics based on this structure offers promising therapeutic pathways.
  • Synthetic Versatility: The synthesis of this compound typically involves several key reactions, including amination, esterification, and selective substitutions—highlighting the fascinating strategies chemists employ to construct complex molecules.
  • Research Implications: Studies on this compound can lead to advancements in drug design, as its structure may facilitate the understanding of how chemical modifications can alter pharmacokinetics and pharmacodynamics.

As chemists continue to explore the properties and applications of 2-(diethylamino)ethyl 2-(4-fluorophenoxy)acetate, it remains a remarkable example of how organic compounds can play vital roles in health sciences. The interplay of functional groups and their effects on biological activity make this compound a key subject in ongoing chemical research!

Synonyms
2-(diethylamino)ethyl (4-fluorophenoxy)acetate
STL145831
AKOS003648253