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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)-N'-ethyl-propane-1,3-diamine;dihydrochloride
State
State

At room temperature, Amsacrine exists as a solid.

Melting point (Celsius)
268.00
Melting point (Kelvin)
541.00
Boiling point (Celsius)
427.00
Boiling point (Kelvin)
700.00
General information
Molecular weight
528.46g/mol
Molar mass
528.4550g/mol
Density
1.3820g/cm3
Appearence

Amsacrine is a yellow crystalline solid.

Comment on solubility

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

The solubility of the compound N'-(2-chloroethyl)-N-(6-chloro-2-methoxy-acridin-9-yl)-N'-ethyl-propane-1,3-diamine; dihydrochloride in various solvents can be influenced by its structural characteristics. Understanding its solubility is essential for various applications and uses, particularly in pharmaceutical formulations.

Factors Affecting Solubility

  • Polarity: The presence of specific functional groups, such as the dihydrochloride part, often increases the solubility in polar solvents like water.
  • Hydrogen bonding: The presence of amino groups enhances interactions with water, promoting solubility.
  • Interactions with solvents: Non-polar components in its structure may lead to reduced solubility in non-polar solvents.

General Insights

This compound is likely to exhibit good solubility in aqueous solutions due to its ionic character provided by the dihydrochloride formation. In contrast, non-polar solvents may not dissolve the compound effectively. Experimentation with solvent mixtures could provide insight into optimizing its bioavailability.

Ultimately, the solubility of N'-(2-chloroethyl)-N-(6-chloro-2-methoxy-acridin-9-yl)-N'-ethyl-propane-1,3-diamine; dihydrochloride is influenced by a combination of its chemical structure and the nature of the solvents being used.

Interesting facts

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

This compound belongs to a class of molecules known as anti-cancer agents, highlighting its significance in medicinal chemistry. Here are some noteworthy aspects:

  • Chemical Structure: The complex structural arrangement includes a chloroethyl group, which plays a crucial role in its reactivity and biological activity.
  • Mechanism of Action: This compound is designed to interact with DNA, potentially acting as an alkylating agent. It can form covalent bonds with DNA, which may lead to cancer cell death.
  • Targeted Therapy: Due to its selective targeting mechanisms, it has been studied for its potential application in treating specific types of cancer, enhancing the efficacy of the treatment while minimizing side effects.
  • Research Applications: The compound has been utilized in numerous studies aimed at understanding its pharmacological properties, including its effects on various cancer cell lines.
  • Synthetic Pathways: The synthesis of this compound provides an essential insight into several organic chemistry techniques, including nucleophilic substitutions and coupling reactions.

As a part of ongoing research, the compound's performance in clinical trials is of great interest to chemists and medical professionals alike. Understanding its life cycle—from synthesis to application—provides an extensive learning opportunity for students and practitioners in the field.

In conclusion, N'-(2-chloroethyl)-N-(6-chloro-2-methoxy-acridin-9-yl)-N'-ethyl-propane-1,3-diamine; dihydrochloride showcases the fusion of organic chemistry and medicine, embodying the potential to impact cancer treatment significantly. Its study not only contributes to therapeutic advancements but also enriches our understanding of nitrogen-containing compounds in drug design.

Synonyms
Acridine mustard
146-59-8
Icr-170
ICR 170
CCRIS 1091
EINECS 205-675-7
UNII-0I3A3407T2
0I3A3407T2
6-chloro-9-[3-n-(2-chloroethyl)ethylamino]propylamino-2-methoxyacridine dihydrochloride
ICR-170H
DTXSID8073893
CHEBI:21183
1,3-Propanediamine, N-(2-chloroethyl)-N'-(6-chloro-2-methoxy-9-acridinyl)-N-ethyl-, 2HCl
6-Chloro-9-((3-((2-chloroethyl)ethylamino)propyl)amino)-2-methoxyacridine dihydrochloride
6-Chloro-9-(3-(ethyl-2-chloroethyl)aminopropylamino)-2-methoxyacridine dihydrochloride
9-(3-(Ethyl(2-chloroethyl)amino)propylamino)-6-chloro-2-methoxyacridine dihydrochloride
N-(2-chloroethyl)-N'-(6-chloro-2-methoxyacridin-9-yl)-N-ethylpropane-1,3-diamine dihydrochloride
N'-(2-chloroethyl)-N-(6-chloro-2-methoxyacridin-9-yl)-N'-ethylpropane-1,3-diamine;dihydrochloride
1,3-Propanediamine, N-(2-chloroethyl)-N'-(6-chloro-2-methoxy-9-acridinyl)-N-ethyl-, dihydrochloride
Acridine, 6-chloro-9-(3-(N-(2-chloroethyl)-N-ethylamino)propylamino)-2-methoxy-, dihydrochloride
6-chloro-9-[[3-[(2-chloroethyl)ethylamino]propyl]amino]-2-methoxyacridine dihydrochloride
N-(2-chloroethyl)-N'-(6-chloro-2-methoxy-9-acridinyl)-N-ethyl-1,3-propanediamine dihydrochloride
ACRIDINE, 6-CHLORO-9-((3-((2-CHLOROETHYL)ETHYLAMINO)PROPYL)AMINO)-2-METHOXY, DIHYDROCHLORIDE MONOHYDRATE
ACRIDINE, 6-CHLORO-9-[[3-[(2-CHLOROETHYL)ETHYLAMINO]PROPYL]AMINO]-2-METHOXY, DIHYDROCHLORIDE MONOHYDRATE
ICR170
SCHEMBL5341589
DTXCID7034751
PWGOWIIEVDAYTC-UHFFFAOYSA-N
DB-042850
NS00041518
Q26840876
1,3Propanediamine, N(2chloroethyl)N'(6chloro2methoxy9acridinyl)Nethyl, 2HCl
1,3Propanediamine, N(2chloroethyl)N'(6chloro2methoxy9acridinyl)Nethyl, dihydrochloride
2-Methoxy-6-chloro-9-[3-[ethyl(2-chloroethyl)amino]propylamino]acridine dihydrochloride
6Chloro9((3((2chloroethyl)ethylamino)propyl)amino)2methoxyacridine dihydrochloride
6Chloro9(3(ethyl2chloroethyl)aminopropylamino)2methoxyacridine dihydrochloride
9(3(Ethyl(2chloroethyl)amino)propylamino)6chloro2methoxyacridine dihydrochloride
Acridine, 6chloro9(3(N(2chloroethyl)Nethylamino)propylamino)2methoxy, dihydrochloride
1,3-PROPANEDIAMINE, N-(2-CHLOROETHYL)-N'-(6-CHLORO-2-METHOXY-9-ACRIDINYL)-N-ETHYL-, DIHYDROCHLORIDE, HYDRATE
1,3-PROPANEDIAMINE, N1-(2-CHLOROETHYL)-N3-(6-CHLORO-2-METHOXY-9-ACRIDINYL)-N1-ETHYL-, HYDROCHLORIDE (1:2)
6-CHLORO-9-((3-((2-CHLOROETHYL)ETHYLAMINO)PROPYL)AMINO)-2-METHOXYACRIDINE 2HCL HYDRATE
ACRIDINE, 6-CHLORO-9-((3-((2-CHLOROETHYL)ETHYLAMINO)PROPYL)AMINO)-2-METHOXY-,2HCL,HYDRATE
N1-(6-Chloro-2-methoxyacridin-9-yl)-N3-(2-chloroethyl)-N3-ethylpropane-1,3-diamine dihydrochloride
N1-(6-Chloro-2-methoxyacridin-9-yl)-N3-(2-chloroethyl)-N3-ethylpropane-1,3-diaminedihydrochloride