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Amsacrine

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Identification
Molecular formula
C22H19Cl2N3O·2HCl
CAS number
51264-14-3
IUPAC name
N1,N1-bis(2-chloroethyl)-N4-(6-chloro-2-methoxy-acridin-9-yl)pentane-1,4-diamine;dihydrochloride
State
State

In its pure form, Amsacrine is generally found as a solid at room temperature. Due to its chemical structure and properties, it is typically handled and stored as a solid powder, and it is formulated into injectable solutions for its use in medical treatments.

Melting point (Celsius)
228.00
Melting point (Kelvin)
501.15
Boiling point (Celsius)
460.00
Boiling point (Kelvin)
733.15
General information
Molecular weight
457.82g/mol
Molar mass
457.8180g/mol
Density
2.5000g/cm3
Appearence

Amsacrine is typically encountered as a bright yellow powder or crystalline solid in its pure form. As a dihydrochloride, it may appear as a bright yellow to orange powder that is sensitive to light.

Comment on solubility

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

The solubility of N1,N1-bis(2-chloroethyl)-N4-(6-chloro-2-methoxy-acridin-9-yl)pentane-1,4-diamine; dihydrochloride can be characterized as being moderately soluble in polar solvents such as water. The presence of dihydrochloride enhances solubility due to the ionic nature of the compound, which favors interaction with the solvent.

Key points regarding solubility:

  • The dihydrochloride form increases the solubility in aqueous environments.
  • Polar solvents are preferred for dissolution, with water being the most common solvent.
  • Factors such as temperature and pH can influence solubility; typically, higher temperatures increase solubility.
  • Due to its chlorinated and aromatic structure, solubility may be limited in non-polar solvents.

In conclusion, while this compound exhibits a defined level of solubility in polar solvents, it is essential to consider the solvation dynamics that might arise under varying conditions.

Interesting facts

Interesting Facts about N1,N1-bis(2-chloroethyl)-N4-(6-chloro-2-methoxy-acridin-9-yl)pentane-1,4-diamine; dihydrochloride

N1,N1-bis(2-chloroethyl)-N4-(6-chloro-2-methoxy-acridin-9-yl)pentane-1,4-diamine; dihydrochloride is a compound that presents a fascinating intersection between organic chemistry and medicinal applications. Here are some key points to highlight its significance:

  • Pharmacological Relevance: This compound is linked to notable research in the field of oncology due to its cytotoxic properties. The presence of acridine moieties suggests potential applications in antitumor therapies.
  • Mechanism of Action: Compounds with similar structures often function by interfering with DNA replication processes in cancer cells, thus slowing down or stopping tumor growth.
  • Structural Complexity: The intricate arrangement of both chloroethyl and methoxy groups along with the acridine backbone contributes to the compound's unique pharmacological activities, making it an interesting subject for further study.
  • Derivative Studies: The versatility of this compound allows for the synthesis of various derivatives, which can be tailored to enhance efficacy and reduce toxicity in cancer treatment regimens.
  • Historical Insights: The development of compounds with acridine structures dates back to the early 20th century and continues to inspire research for new therapeutic agents.

As a single entity within a broader category of anticancer compounds, N1,N1-bis(2-chloroethyl)-N4-(6-chloro-2-methoxy-acridin-9-yl)pentane-1,4-diamine; dihydrochloride represents the complexities and potential of synthetic medicinal chemistry. Its ongoing study not only enhances our understanding of cancer treatments but also paves the way for innovative drug discovery.

Synonyms
Quinacrine mustard dihydrochloride
4213-45-0
Atabrine mustard dihydrochloride
ICR 10
CCRIS 1090
RCB69HPY0X
NSC 3424
EINECS 224-140-9
Mepacrine mustard dihydrochloride
AI3-26376
UNII-RCB69HPY0X
DTXSID00884049
NSC-3424
1,4-Pentanediamine, N',N'-bis(2-chloroethyl)-N4-(6-chloro-2-methoxy-9-acridinyl)-, 2HCl
2-Methoxy-6-chloro-9-(3-(ethyl-2-chloroethyl)aminopropylamino)acridine dihydrochloride
2-Methoxy-6-chloro-9-(4-bis(2-chloroethyl)amino-1-methylbutylamino)acridine dihydrochloride
9-(4-Bis(2-chloroethyl)amino-1-methylbutylamino)-6-chloro-2-methoxyacridine dihydrochloride
1,4-Pentanediamine, N1,N1-bis(2-chloroethyl)-N4-(6-chloro-2-methoxy-9-acridinyl)-, hydrochloride (1:2)
Acridine, 9-(4-bis(2-chloroethyl)amino-1-methylbutylamino)-6-chloro-2-methoxy-, dihydrochloride
CHEBI:21182
N(1),N(1)-bis(2-chloroethyl)-N(4)-(6-chloro-2-methoxyacridin-9-yl)pentane-1,4-diamine dihydrochloride
DTXCID301023521
224-140-9
quinacrine mustard
Quinacrine mustard (dihydrochloride)
1,4-Pentanediamine, N1,N1-bis(2-chloroethyl)-N4-(6-chloro-2-methoxy-9-acridinyl)-, dihydrochloride
1-N,1-N-bis(2-chloroethyl)-4-N-(6-chloro-2-methoxyacridin-9-yl)pentane-1,4-diamine;dihydrochloride
Quinacrine mustard (hydrochloride)
MFCD00043254
N1,N1-Bis(2-chloroethyl)-N4-(6-chloro-2-methoxyacridin-9-yl)pentane-1,4-diamine dihydrochloride
SCHEMBL7521593
JETDZFFCRPFPDH-UHFFFAOYSA-N
quin-acrine-mustard dihydrochloride
EAA21345
AKOS024418786
HY-W127705
AS-87087
DA-67072
CS-0185903
NS00048349
G77610
Quinacrine mustard dihydrochloride, >=85% (HPLC)
Q27109376
N4-(6-Chloro-2-methoxyacridin-9-yl)-N1,N1-bis(2-chloroethyl)pentane-1,4-diamine dihydrochloride
N4-(6-Chloro-2-methoxyacridin-9-yl)-N1,N1-bis(2-chloroethyl)pentane-1,4-diaminedihydrochloride