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Indometacin

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Identification
Molecular formula
C19H16ClNO4
CAS number
53-86-1
IUPAC name
2-[3-(4-chlorobenzoyl)-6-methoxy-2-methyl-indol-1-yl]acetic acid
State
State
At room temperature, Indometacin is in a solid state, specifically a crystalline powder.
Melting point (Celsius)
158.00
Melting point (Kelvin)
431.15
Boiling point (Celsius)
320.90
Boiling point (Kelvin)
594.05
General information
Molecular weight
357.79g/mol
Molar mass
357.7890g/mol
Density
1.3778g/cm3
Appearence

Indometacin is a white to yellow tan crystalline powder. It is odorless and is known for having a bitter taste. The compound is not very soluble in water but dissolves well in alcohol, acetone, and some other organic solvents.

Comment on solubility

Solubility of 2-[3-(4-chlorobenzoyl)-6-methoxy-2-methyl-indol-1-yl]acetic acid

The solubility of 2-[3-(4-chlorobenzoyl)-6-methoxy-2-methyl-indol-1-yl]acetic acid in various solvents can be quite interesting and depends on several factors:

  • Polarity of the Solvent: Generally, this compound is likely to show higher solubility in polar solvents due to the presence of the carboxylic acid functional group which can form hydrogen bonds.
  • Temperature: Solubility tends to increase with temperature, so higher temperatures may enhance the dissolution of this compound in solvents.
  • pH of the Solution: The solubility in aqueous solution can significantly change depending on the pH, given that the carboxylic acid can dissociate under alkaline conditions, potentially increasing its solubility.
  • Structural Influences: The bulky aromatic and methoxy groups may also affect solubility, potentially making it less soluble in extremely nonpolar solvents.

In conclusion, while specific quantitative solubility data may not be readily available for this compound, it is reasonable to anticipate varying solubility across different solvents influenced by the aforementioned factors. Experimentation with different conditions can be essential to fully understand its solubility behavior.

Interesting facts

Interesting Facts about 2-[3-(4-Chlorobenzoyl)-6-methoxy-2-methyl-indol-1-yl]acetic Acid

This compound represents a fascinating intersection of chemical structure and biological activity, specifically within the realm of medicinal chemistry. It belongs to a class known as indole derivatives, molecules that are often found in numerous natural products and pharmaceuticals.

Key Highlights

  • Indole Structure: The indole ring is a core structure in many biologically active compounds, which contributes to various pharmacological properties.
  • Chlorobenzoyl Group: The presence of the 4-chlorobenzoyl moiety enhances the compound’s lipophilicity, potentially improving its ability to cross cell membranes.
  • Methoxy Group: The methoxy substitution plays a critical role in modifying the electronic properties of the indole ring, which can impact its reactivity and interactions with biological targets.
  • Biological Relevance: Compounds like this are of interest in research aimed at developing new therapeutics for a range of conditions, including cancer and inflammation.

The intricate design of this molecule signifies how subtle changes in structure can lead to significant variations in biological activity. As emphasized by researchers, "The relationship between molecular structure and biological function is a key driver in pharmacology."

Furthermore, compounds with such complex scaffolds are often subjected to structure-activity relationship (SAR) studies to fine-tune their efficacy and selectivity. This is crucial for developing safe and effective medications.

In summary, 2-[3-(4-chlorobenzoyl)-6-methoxy-2-methyl-indol-1-yl]acetic acid stands as an example of the innovative chemistry that fuels drug development, highlighting the importance of functional groups in crafting therapeutic agents.

Synonyms
Clometacin
Clometacine
25803-14-9
Clometacina
Clometacinum
MINDOLIC ACID
C 1656
DTXSID7048827
R 3959
L9M34YK25C
DTXCID4028753
C-1656
R-3959
3-(4-Chlorobenzoyl)-6-methoxy-2-methylindole-1-acetic acid
RefChem:127054
247-271-3
CHEMBL13376
Clometazin
Clomethacin
Duperan
C 1656; Duperan; R 3959
NCGC00183863-01
2-(3-(4-chlorobenzoyl)-6-methoxy-2-methyl-1H-indol-1-yl)acetic acid
Clometacin [INN:DCF]
Acidum mindolicum
Clometacine [INN-French]
Clometacinum [INN-Latin]
Clometacina [INN-Spanish]
EINECS 247-271-3
RU 3959
BRN 1552200
UNII-L9M34YK25C
3-(p-Chlorobenzyl)-6-methoxy-2-methyl-1-indoleacetic acid
Carboxymethyl-1 methyl-2 p.chlorobenzoyl-3 indole [French]
CLOMETACIN [MI]
CLOMETACIN [INN]
1H-Indole-1-acetic acid, 3-(4-chlorobenzoyl)-6-methoxy-2-methyl-
2-[3-(4-chlorobenzoyl)-6-methoxy-2-methylindol-1-yl]acetic acid
INDOLE-1-ACETIC ACID, 3-(p-CHLOROBENZOYL)-6-METHOXY-2-METHYL-
CLOMETACIN [MART.]
CLOMETACIN [WHO-DD]
SCHEMBL25275
5-21-12-00658 (Beilstein Handbook Reference)
Carboxymethyl-1 methyl-2 p.chlorobenzoyl-3 indole
SCHEMBL30666020
CHEBI:135512
3-(p-Chlorobenzoyl)-6-methoxy-2-methylindole-1-acetic acid
Tox21_113309
BDBM50009856
STL301885
AKOS016389835
DA-07613
CAS-25803-14-9
NS00027968
Q3680897
[3-(4-Chloro-benzoyl)-6-methoxy-2-methyl-indol-1-yl]-acetic acid
{3-[(4-chlorophenyl)carbonyl]-6-methoxy-2-methyl-1H-indol-1-yl}acetic acid