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Indole-3-acetamide

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Identification
Molecular formula
C12H13N2O2
CAS number
771-63-1
IUPAC name
2-acetamido-3-(1H-indol-3-yl)propanamide
State
State

At room temperature, indole-3-acetamide is in a solid state. It maintains stability under normal conditions and is typically handled as a powder or crystalline solid in laboratory settings.

Melting point (Celsius)
143.00
Melting point (Kelvin)
416.15
Boiling point (Celsius)
350.00
Boiling point (Kelvin)
623.15
General information
Molecular weight
202.25g/mol
Molar mass
202.2280g/mol
Density
1.3400g/cm3
Appearence

Indole-3-acetamide is typically observed as a white to off-white crystalline solid. It possesses a distinct aromatic odor, indicative of its indole structure, which is common in compounds containing the indole moiety.

Comment on solubility

Solubility of 2-acetamido-3-(1H-indol-3-yl)propanamide (C12H13N2O2)

The solubility of 2-acetamido-3-(1H-indol-3-yl)propanamide is an intriguing aspect of this compound, reflecting its chemical properties and potential applications. Several factors influence the solubility of this compound:

  • Polarity: The presence of an acetamido functional group enhances its polarity, which favors solubility in polar solvents.
  • Hydrogen Bonding: The ability of the compound to form hydrogen bonds with solvent molecules contributes significantly to its solubility, allowing for interactions with both water and organic solvents.
  • Structural Considerations: The indole moiety introduces a level of complexity; while it may reduce solubility in some aliphatic solvents, it may interact favorably with others due to π-π stacking interactions.

Commonly, this compound exhibits limited solubility in non-polar solvents, while it may dissolve more readily in:

  1. Alcohols (e.g., ethanol and methanol)
  2. Aqueous solutions, particularly with appropriate pH adjustments
  3. Dimethyl sulfoxide (DMSO) and other polar aprotic solvents

In summary, while 2-acetamido-3-(1H-indol-3-yl)propanamide may not be highly soluble in all solvents, its solubility profile highlights the significance of polarity, hydrogen bonding capacity, and structural interactions in determining its behavior in various environments. Understanding this aspect can enable effective utilization in pharmaceuticals and research applications, where solubility plays a crucial role.

Interesting facts

Interesting Facts about 2-Acetamido-3-(1H-Indol-3-yl)propanamide

2-Acetamido-3-(1H-indol-3-yl)propanamide, often referenced in scientific literature, is a compound that bridges traditional medicinal chemistry with modern drug design. This compound stands out due to its structural features, which include:

  • Indole Ring System: The presence of the indole moiety is significant, as indoles are known for their role in several biologically active compounds and have been extensively researched for their pharmacological properties.
  • Potential Therapeutic Applications: This compound has garnered attention for its potential use in treating various conditions. Compounds with similar structures have been investigated for their anti-cancer, anti-inflammatory, and neuroprotective activities.

Moreover, the synthesis of this compound involves intriguing chemical reactions, demonstrating the versatility of amide and acetamide functional groups. As a chemist or a student, it's fascinating to note that:

  • The versatility in synthetic pathways allows for modifications that could enhance its bioactivity or selectivity.
  • Researchers are continually exploring the nuances of its biological mechanisms, offering a rich field for pharmacological research.

As with many compounds featuring intricate nitrogen-containing heterocycles, understanding their interaction with biological systems opens doors to novel therapeutic interventions. Notably, the study of this compound reflects a larger trend in medicinal chemistry, where the focus is on optimizing molecular frameworks to meet safety and efficacy standards for drug development. With ongoing research, compounds like 2-acetamido-3-(1H-indol-3-yl)propanamide continue to reveal exciting possibilities for future medicines.

Synonyms
Ac-Trp-NH2
2-acetamido-3-(1H-indol-3-yl)propanamide
Ac-Trp-NH
NATA
MFCD00005646
2-(Acetylamino)-3-(1H-indol-3-yl)propanamide #
Cambridge id 6888325
Oprea1_140599
Na-Acetyl-L-tryptophan amide
SCHEMBL3202823
HNGIZKAMDMBRKJ-UHFFFAOYSA-
HNGIZKAMDMBRKJ-UHFFFAOYSA-N
N(.alpha.)-Acetyl-dl-tryptophanamine
AKOS003234764
10346-41-5
SY119835
DB-046258
2-(Acetylamino)-3-(1H-indol-3-yl)propanamide
(.+/-.)-2-Acetamido-3-(3-indolyl)propionamide
AG-670/13188013
SR-01000245792
SR-01000245792-1
InChI=1/C13H15N3O2/c1-8(17)16-12(13(14)18)6-9-7-15-11-5-3-2-4-10(9)11/h2-5,7,12,15H,6H2,1H3,(H2,14,18)(H,16,17)