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Amsacrine

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Identification
Molecular formula
C21H19Cl2N3O
CAS number
51264-14-3
IUPAC name
N-(2-chloroethyl)-N'-(6-chloro-2-methoxy-acridin-9-yl)propane-1,3-diamine
State
State

Amsacrine is a solid at room temperature. It is commonly used in its hydrochloride salt form for medical applications, where it is more stable and soluble.

Melting point (Celsius)
205.00
Melting point (Kelvin)
478.00
Boiling point (Celsius)
410.00
Boiling point (Kelvin)
683.00
General information
Molecular weight
393.85g/mol
Molar mass
393.8470g/mol
Density
1.0400g/cm3
Appearence

Amsacrine typically appears as a yellow to orange crystalline powder. The compound is sensitive to light, which can lead to degradation. It is important to store it in a light-resistant container.

Comment on solubility

Solubility of N-(2-chloroethyl)-N'-(6-chloro-2-methoxy-acridin-9-yl)propane-1,3-diamine

N-(2-chloroethyl)-N'-(6-chloro-2-methoxy-acridin-9-yl)propane-1,3-diamine, characterized by its complex structure, typically exhibits specific solubility behaviors influenced by its functional groups and molecular characteristics.

Solubility Insights

  • Polarity: This compound contains polar functional groups which may enhance its solubility in polar solvents.
  • Hydrogen Bonding: The presence of amino groups can facilitate hydrogen bonding, potentially increasing solubility in protic solvents.
  • Solvent Compatibility: It is likely to be soluble in dimethyl sulfoxide (DMSO) or ethanol, while its solubility in non-polar solvents may be limited.
  • Temperature Effects: As with many organic compounds, solubility may increase with temperature. An increase in kinetic energy can often help overcome lattice energies and promote dissolution.

It's essential to perform solubility tests under varying conditions to obtain definitive results. The intricate nature of the compound suggests that while soluble in favorable environments, its solubility profile may vary with changes in chemical structure or environmental conditions. As always, thorough experimentation remains key to understanding its solubility behavior.

Interesting facts

Interesting Facts about N-(2-chloroethyl)-N'-(6-chloro-2-methoxy-acridin-9-yl)propane-1,3-diamine

N-(2-chloroethyl)-N'-(6-chloro-2-methoxy-acridin-9-yl)propane-1,3-diamine is a unique chemical compound that has garnered interest in both the fields of medicinal chemistry and organic synthesis. Here are some captivating aspects about this intriguing compound:

  • Targeted Activity: This compound has been explored for its potential use in targeted cancer therapies. The acridine moiety is known for its ability to intercalate with DNA, which may help in disrupting the growth of cancerous cells.
  • Structure-Activity Relationship (SAR): The presence of both the chloroethyl and methoxy groups in its structure allows researchers to examine how changes to these substituents can influence biological activity and toxicity.
  • Versatile Synthesis: The synthetic routes leading to this compound often involve complex methodologies. Chemists study these syntheses not just for the compound itself but also for the techniques that can be applied to create other haloacridine derivatives.
  • Pharmaceutical Research: Ongoing studies are investigating the compound’s ability to act as a cytotoxic agent, highlighting its potential in pharmacology. The compound may offer insights into new cancer treatment avenues.
  • Significance in Organocatalysis: Research indicates that certain derivatives of acridines might serve as effective organocatalysts, paving the way for greener synthesis routes in organic chemistry.

As researchers delve deeper into the properties and applications of N-(2-chloroethyl)-N'-(6-chloro-2-methoxy-acridin-9-yl)propane-1,3-diamine, the hope is to unveil new mechanisms of action, improve therapeutic efficacy and safety, and ultimately contribute to better medical treatments in the future.

Synonyms
Acridine half-mustard
17070-44-9
96O8D10RM2
ICR-191 FREE BASE
CHEBI:132980
Acridine, 6-chloro-9-((3-((2-chloroethyl)amino)propyl)amino)-2-methoxy-
1,3-Propanediamine, N-(2-chloroethyl)-N'-(6-chloro-2-methoxy-9-acridinyl)-
N-(2-Chloroethyl)-N'-(6-chloro-2-methoxy-9-acridinyl)-1,3-propanediamine
N1-(2-Chloroethyl)-N3-(6-chloro-2-methoxy-9-acridinyl)-1,3-propanediamine
N-(2-chloroethyl)-N'-(6-chloro-2-methoxyacridin-9-yl)propane-1,3-diamine
BRN 0444928
UNII-96O8D10RM2
SCHEMBL6403098
CHEMBL1088472
SCHEMBL29407194
SCHEMBL30133044
DTXSID10864731
3-(2-chloroethylazaniumyl)propyl-(6-chloro-2-methoxyacridin-9-yl)azaniumdichloride
Q27271916
2-chloro-6-methoxy-9-(3-(2-chloroethyl)aminopropylamino)acridine
2-methoxy-6-chloro-9-(3-(2-chloroethyl)aminopropylamino)acridine
6-chloro-9-[3-(2-chloroethylamino)propylamino]-2-methoxyacridine
1,3-PROPANEDIAMINE, N-(2-CHLOROETHYL)-N'-(6-CHLORO-2-METHOXY-9- ACRIDINYL)-
ACRIDINE, 6-CHLORO-9-((3-((2-CHLOROETHYL)AMINO)PROPYL)AMINO)-2- METHOXY-
N~1~-(2-Chloroethyl)-N~3~-(6-chloro-2-methoxyacridin-9-yl)propane-1,3-diamine