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Bupivacaine

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Identification
Molecular formula
C18H28ClN3O
CAS number
2180-92-9
IUPAC name
N-(2-chloro-5-ethyl-phenyl)-4-(diethylamino)butanamide
State
State

At room temperature, Bupivacaine is typically encountered in its solid form, as a white crystalline powder. It is commonly used in a dissolved state within anesthetic formulations, owing to its high solubility in water when in salt form.

Melting point (Celsius)
106.00
Melting point (Kelvin)
379.15
Boiling point (Celsius)
323.50
Boiling point (Kelvin)
596.65
General information
Molecular weight
288.44g/mol
Molar mass
288.4370g/mol
Density
1.0456g/cm3
Appearence

Bupivacaine typically appears as a white crystalline powder. It is odorless and has a slightly bitter taste. The compound is often formulated into a hydrochloride salt for medicinal use, which may influence its physical appearance slightly depending on the pharmaceutical preparation.

Comment on solubility

Solubility of N-(2-chloro-5-ethyl-phenyl)-4-(diethylamino)butanamide

The solubility of N-(2-chloro-5-ethyl-phenyl)-4-(diethylamino)butanamide can be influenced by a number of factors, including its molecular structure and functional groups. This compound appears to be a polar amide due to the presence of the amide functional group (-CONH-).

Here are some key points regarding its solubility:

  • Solvent Interactions: Due to the amide group, this compound might exhibit good solubility in polar solvents such as water or methanol.
  • Effect of Substituents: The presence of the 2-chloro and 5-ethyl substituents could potentially affect solubility. Chlorine, being electronegative, might enhance polar interactions while ethyl groups could provide steric hindrance.
  • Temperature Influence: As with many organic compounds, solubility can increase with temperature, indicating that higher temperatures might facilitate the dissolution of N-(2-chloro-5-ethyl-phenyl)-4-(diethylamino)butanamide.
  • Comparative Solubility: Compared to other organic compounds, this compound's solubility could be considered moderate, primarily due to its polar character stemming from the amide linkage.

As a result, while it is likely to be soluble in a range of polar solvents, the actual solubility would need to be experimentally determined to ascertain its precise behavior. In conclusion, understanding the solubility of N-(2-chloro-5-ethyl-phenyl)-4-(diethylamino)butanamide is crucial, especially for applications in pharmaceuticals, where solubility often dictates bioavailability and efficacy.

Interesting facts

Interesting Facts about N-(2-chloro-5-ethyl-phenyl)-4-(diethylamino)butanamide

N-(2-chloro-5-ethyl-phenyl)-4-(diethylamino)butanamide is a complex molecule that demonstrates both unique structural properties and potential applications in pharmacology. Here are some fascinating aspects to consider:

  • Pharmaceutical Significance: This compound falls under the category of amides, which are often of interest in drug design due to their ability to modify the pharmacological properties of potential drug candidates.
  • Chlorine Substitution: The presence of a chloro group at the 2-position of the phenyl ring may enhance lipophilicity, potentially affecting the compound's ability to cross biological membranes.
  • Ethyl Group Effects: The ethyl substituent at the 5-position contributes to the overall hydrophobic character of the compound, which can influence receptor binding and biological activity.
  • Diethylamino Group: Having a diethylamino moiety is notable since this functional group can strongly influence the basicity and solubility of the compound, thus impacting its reactivity and interaction with various targets.
  • Clinical Research Potential: Compounds akin to this structure are frequently evaluated for their neuroactive properties, making them candidates for numerous therapeutic applications, including analgesics and anesthetics.
  • Structure-Activity Relationship (SAR): Understanding how structural modifications (such as those present in this compound) affect potency and activity can lead to more effective drug development strategies.

In summary, N-(2-chloro-5-ethyl-phenyl)-4-(diethylamino)butanamide showcases the intricate relationship between chemical structure and biological function. As research continues, the intricate design of such compounds could pave the way for novel treatments in modern medicine.

Synonyms
BRN 2698826
BUTYRANILIDE, 2'-CHLORO-4-(DIETHYLAMINO)-5'-ETHYL-
3100-74-1
2'-Chloro-4-(diethylamino)-5'-ethylbutyranilide
gamma-Diaethylamino-3-aethyl-6-chlor-butyranilid [German]
DTXSID10184981
gamma-Diaethylamino-3-aethyl-6-chlor-butyranilid
DTXCID50107472