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Amsacrine

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Identification
Molecular formula
C21H19Cl2N3O
CAS number
51264-14-3
IUPAC name
N1,N1-bis(2-chloroethyl)-N4-(6-chloro-2-methoxy-acridin-9-yl)pentane-1,4-diamine
State
State

At room temperature, amsacrine is typically in a solid state as a crystalline powder.

Melting point (Celsius)
230.00
Melting point (Kelvin)
503.15
Boiling point (Celsius)
399.00
Boiling point (Kelvin)
672.15
General information
Molecular weight
393.90g/mol
Molar mass
393.8970g/mol
Density
1.4870g/cm3
Appearence

Amsacrine is a synthetic compound that appears as a yellow to orange crystalline powder.

Comment on solubility

Solubility of N1,N1-bis(2-chloroethyl)-N4-(6-chloro-2-methoxy-acridin-9-yl)pentane-1,4-diamine

The solubility of N1,N1-bis(2-chloroethyl)-N4-(6-chloro-2-methoxy-acridin-9-yl)pentane-1,4-diamine in various solvents can exhibit notable characteristics due to its complex structure. Understanding its solubility behavior is crucial for applications across various fields, including pharmaceuticals. Here are some key points regarding its solubility:

  • Polar Solvents: This compound is expected to have limited solubility in polar solvents like water due to its hydrophobic alkyl chains and bulky aromatic system.
  • Non-Polar Solvents: Its solubility may significantly increase in non-polar solvents such as hexane or dichloromethane, where the hydrophobic interactions are more favorable.
  • pH Dependence: The solubility might also be influenced by pH. The presence of amine groups can lead to protonation at lower pH levels, which might alter solubility.
  • Temperature Effects: As with many compounds, increasing temperature may enhance solubility, encouraging more kinetic energy in the system.

In summary, the solubility of N1,N1-bis(2-chloroethyl)-N4-(6-chloro-2-methoxy-acridin-9-yl)pentane-1,4-diamine is significantly influenced by the nature of the solvent and environmental conditions. Understanding these factors is essential for its effective use in practical applications.

Interesting facts

Understanding N1,N1-bis(2-chloroethyl)-N4-(6-chloro-2-methoxy-acridin-9-yl)pentane-1,4-diamine

N1,N1-bis(2-chloroethyl)-N4-(6-chloro-2-methoxy-acridin-9-yl)pentane-1,4-diamine is a complex organic compound notable for its involvement in medicinal chemistry and drug development. This compound has garnered interest due to several compelling factors:

  • Targeting Cancer: The compound is modeled to function as a potent chemotherapeutic agent. The incorporation of chloroethyl groups suggests a mechanism that allows for the alkylation of DNA, potentially disrupting cancer cell division.
  • Acridine Derivative: The presence of acridine in its structure may contribute to intercalation between DNA bases, enhancing its antiproliferative activity. Acridine derivatives are widely studied for their ability to inhibit cancer cell growth.
  • Structure-Activity Relationship (SAR): Researchers are keen on analyzing how subtle modifications in its structure can affect the efficacy and selectivity of the compound against various tumor types. This can lead to more effective and less toxic treatment options.
  • Potential Side Effects: While the therapeutic effects are promising, chemotherapeutics often come with significant side effects. Understanding the toxicity profiles is critical as it can inform dosage and administration in clinical settings.
  • Future Research Directions: Ongoing studies are likely to explore the combinatorial use of this compound with other therapies to enhance its anticancer effectiveness while minimizing adverse effects. This aligns with the current trends in personalized medicine.

In summary, N1,N1-bis(2-chloroethyl)-N4-(6-chloro-2-methoxy-acridin-9-yl)pentane-1,4-diamine stands at the intersection of synthetic chemistry and medical application, holding potential as a vital tool in the fight against cancer. As research progresses, it will be fascinating to watch how this compound may evolve within pharmacology and therapeutic design.

Synonyms
quinacrine mustard
64046-79-3
1-N,1-N-bis(2-chloroethyl)-4-N-(6-chloro-2-methoxyacridin-9-yl)pentane-1,4-diamine
8Y3YQP8GW6
1,4-Pentanediamine, N1,N1-bis(2-chloroethyl)-N4-(6-chloro-2-methoxy-9-acridinyl)-
CHEBI:37595
N1,N1-bis(2-Chloroethyl)-N4-(6-chloro-2-methoxy-9-acridinyl)-1,4-pentanediamine
N(1),N(1)-bis(2-chloroethyl)-N(4)-(6-chloro-2-methoxyacridin-9-yl)pentane-1,4-diamine
N4-(6-Chloro-2-methoxyacridin-9-yl)-N1,N1-bis(2-chloroethyl)pentane-1,4-diamine
UNII-8Y3YQP8GW6
BRN 0056337
Acrichine Yperite
9-(4-(Bis-beta-chloroethylamino)-1-methylbutylamino)-6-chloro-2-methoxyacridine
ACRIDINE, 9-(4-(BIS(2-CHLOROETHYL)AMINO)-1-METHYLBUTYLAMINO)-6-CHLORO-2-METHOXY-
4-21-00-06249 (Beilstein Handbook Reference)
SCHEMBL4995822
CHEMBL1190232
DTXSID40982194
DB02240
NCI60_003038
Q27104415
ACRIDINE, 9-((4-(BIS(2-CHLOROETHYL)AMINO)-1-METHYLBUTYL)AMINO)-6-CHLORO-2-METHOXY-
N,N-Bis(2-chloroethyl)-4-[(6-chloro-2-methoxyacridin-9(10H)-ylidene)amino]pentan-1-amine
N1,N1-BIS(2-CHLOROETHYL-N4-(6-CHLORO-2-METHOXY-9-ACRIDINYL)-1,4-PENTANEDIAMINE