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Loperamide

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Identification
Molecular formula
C29H33ClN2O2
CAS number
53179-11-6
IUPAC name
2-[2-(dimethylamino)ethyl]-2-(4-isopropylphenyl)-3-methyl-butanamide
State
State
Solid at room temperature.
Melting point (Celsius)
218.00
Melting point (Kelvin)
491.15
Boiling point (Celsius)
420.20
Boiling point (Kelvin)
693.35
General information
Molecular weight
476.04g/mol
Molar mass
476.5600g/mol
Density
1.1470g/cm3
Appearence

Loperamide appears as a white to off-white crystalline powder. It is almost odorless and has a slight bitter taste.

Comment on solubility

Solubility of 2-[2-(dimethylamino)ethyl]-2-(4-isopropylphenyl)-3-methyl-butanamide

The solubility of 2-[2-(dimethylamino)ethyl]-2-(4-isopropylphenyl)-3-methyl-butanamide is influenced by its molecular structure, functional groups, and the presence of hydrophobic and hydrophilic regions. Generally, compounds with polar functional groups tend to have better solubility in polar solvents, while those with larger hydrophobic portions are more soluble in non-polar solvents. In this compound:

  • Polar Features: The dimethylamino group introduces some polar characteristics, which can enhance solubility in water and other polar solvents.
  • Hydrophobic Interactions: The isopropylphenyl group contributes significant hydrophobicity, which could limit solubility in polar solvents.

As a result, the solubility profile can be summarized as follows:

  • Moderate solubility in polar solvents (e.g., water, methanol) due to the presence of polar groups.
  • Higher solubility in non-polar solvents (e.g., hexane, toluene) owing to the hydrophobic regions of the molecule.

When predicting solubility, it's also essential to consider factors such as temperature, pH, and the presence of other solutes. Understanding the balance between hydrophilic and hydrophobic interactions is key to assessing the solubility of such complex compounds.

Interesting facts

Interesting Facts about 2-[2-(dimethylamino)ethyl]-2-(4-isopropylphenyl)-3-methyl-butanamide

This compound is an interesting example of a pharmaceutical agent known for its unique structure and properties. It belongs to the class of amides and features a complex architecture that contributes to its biological activity.

Chemical Structure Highlights

  • The presence of a dimethylamino group enhances the compound's ability to interact with biological systems, often increasing its potency as a drug.
  • The isopropylphenyl moiety is significant for its lipophilicity, which can facilitate membrane penetration in biological settings.
  • The branched isobutyl backbone provides steric hindrance, potentially influencing the compound's interaction with target proteins or receptors.

Biological Significance

This compound has garnered interest for various pharmacological applications, particularly in:

  • Neuropharmacology: Its structure may impart these compounds with **central nervous system** effects, providing insights into neuronal modulation.
  • Analgesic Activity: Some derivatives of similar compounds have been explored for pain relief, showcasing their therapeutic potential.
  • Antidepressant Research: Compounds with dimethylamino groups are often investigated for their influence on mood-regulating neurotransmitters.

Synthesis and Research

The synthesis of this compound involves intricate multi-step reactions, reflecting the importance of synthetic organic chemistry in developing complex molecules. Researchers focus on optimizing yield and purity to harness the full potential of this compound in pharmaceutical studies.

As a student or scientist, it's important to appreciate the nuances of such molecules, as their structural variations can lead to vastly different biological outcomes. As stated, "The devil is in the details," especially when discerning the pharmacological efficacy of various compounds.

This compound symbolizes the intersection of chemistry, biology, and medicinal research, reinforcing the importance of multidisciplinary approaches in drug discovery.

Synonyms
BRN 2132654
2-(p-Cumenyl)-4-(dimethylamino)-2-isopropylbutyramide
14780-18-8
BUTYRAMIDE, 2-(p-CUMENYL)-4-(DIMETHYLAMINO)-2-ISOPROPYL-
DTXSID20933220
2-[2-(Dimethylamino)ethyl]-3-methyl-2-[4-(propan-2-yl)phenyl]butanimidic acid