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Carmustine

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Identification
Molecular formula
C5H9ClN3O2
CAS number
154-93-8
IUPAC name
1-(2-chloroethyl)-3-(2,6-dioxo-3-piperidyl)-1-nitroso-urea
State
State

At room temperature, carmustine is typically a solid.

Melting point (Celsius)
30.50
Melting point (Kelvin)
303.65
Boiling point (Celsius)
250.00
Boiling point (Kelvin)
523.15
General information
Molecular weight
214.60g/mol
Molar mass
214.0590g/mol
Density
1.5000g/cm3
Appearence

Carmustine is a yellow to orange crystalline solid.

Comment on solubility

Solubility of 1-(2-chloroethyl)-3-(2,6-dioxo-3-piperidyl)-1-nitroso-urea

The solubility of 1-(2-chloroethyl)-3-(2,6-dioxo-3-piperidyl)-1-nitroso-urea is an important characteristic that influences its behavior in various chemical and biological environments. Here are some key points regarding its solubility:

  • Nature of the Compound: The presence of multiple functional groups such as nitroso and urea moieties, along with a chloroethyl substituent, impacts its interaction with solvents.
  • Solvents: Typically, this compound may exhibit varying solubility in different solvents:
    • Water: May have limited solubility due to potential hydrophobic regions.
    • Organic Solvents: Better solubility could be observed in polar organic solvents like methanol or dimethyl sulfoxide (DMSO).
  • Temperature Dependence: Solubility can vary significantly with temperature. Generally, increasing temperature tends to improve solubility in solids.
  • pH Influence: The solubility may also be affected by the pH of the solution, which alters the ionization state of the compound's functional groups.

In summary, understanding the solubility of 1-(2-chloroethyl)-3-(2,6-dioxo-3-piperidyl)-1-nitroso-urea is crucial for its application in pharmaceuticals and chemical studies. As the saying goes, “Like dissolves like,” and this compound's solubility characteristics demonstrate the importance of solvent choice in achieving effective dissolution.

Interesting facts

Interesting Facts about 1-(2-chloroethyl)-3-(2,6-dioxo-3-piperidyl)-1-nitroso-urea

The compound 1-(2-chloroethyl)-3-(2,6-dioxo-3-piperidyl)-1-nitroso-urea, often referred to in scientific literature as a member of the nitrosourea family, is noteworthy for its significance in medicinal chemistry, particularly in cancer treatment. Here are some fascinating facts that elucidate its roles and properties:

  • Mechanism of Action: This compound operates as an anticancer agent through the alkylation of DNA, which leads to the inhibition of DNA replication. This is particularly crucial in targeting rapidly dividing cancer cells.
  • Chemotherapy Applications: Due to its DNA-damaging effects, it has been employed in the chemotherapy regimen for various malignancies, including brain tumors and certain types of leukemia.
  • Challenges in Administration: Its clinical use is often tempered by the potential for toxicity. Chemotherapeutic agents like this one can result in side effects that necessitate careful dosage and monitoring.
  • Research Developments: Ongoing studies are investigating modified versions of this compound to enhance its efficacy and reduce side effects. The aim is to create derivatives that better target tumor cells while sparing normal cells.
  • Historical Significance: The discovery of nitrosoureas in the mid-20th century represents a pivotal moment in cancer treatment, leading to more specialized therapies that have transformed patient outcomes.

As a chemical entity charged with dual roles of therapeutic promise and significant risk, 1-(2-chloroethyl)-3-(2,6-dioxo-3-piperidyl)-1-nitroso-urea epitomizes the complex balance that exists in pharmacological science. Scientists continually strive to unlock its full potential while mitigating its adverse effects, making it a fascinating topic within the realms of medicinal chemistry and oncology.

Synonyms
13909-02-9
1-(2-Chloroethyl)-3-(2,6-dioxo-3-piperidyl)-1-nitrosourea
NSC-95,466
NSC-95466
UNII-AZW59V4Q3B
Urea, N-(2-chloroethyl)-N'-(2,6-dioxo-3-piperidinyl)-N-nitroso-
AZW59V4Q3B
NSC 95466
BRN 0431046
N-(2-Chloroethyl)-N'-(2,6-dioxo-3-piperidinyl)-N-nitrosourea
Urea, 1-(2-chloroethyl)-3-(2,6-dioxo-3-piperidyl)-1-nitroso-
AI3-52898
1-(2-Chloroethyl)-3-(2,6-dioxo-3-piperidinyl)-1-nitrosourea
Urea, N-(2-chloroethyl)-N'-(2,6-dioxo-3-piperidinyl)-N-nitroso-(9CI)
PCNU
1-(2-chloroethyl)-3-(2,6-dioxopiperidin-3-yl)-1-nitrosourea
NSC95466
1-(2-Chloroethyl)3-(2,6-dioxo-3-piperidyl)-1-nitrosourea
CHEMBL12200
SCHEMBL845062
DTXSID10864453
KHWIRCOLWPNBJP-UHFFFAOYSA-N
Urea,6-dioxo-3-piperidyl)-1-nitroso-
Urea,6-dioxo-3-piperidinyl)-N-nitroso-
NCI60_042124
NS00122842
Q27274209
1-(2-chloroethyl)-3-(2,6-dioxo-3-piperidyl)-1-nitroso-urea
N-(2-chloroethyl)-N'-(2,6-dioxopiperidin-3-yl)-N-nitrosourea
Urea, N-(2-chloroethyl)-N'-(2, 6-dioxo-3-piperidinyl)-N-nitroso-
3-(((1-(2-Chloroethyl)-2-oxohydrazino)carbonyl)amino)-2,6-piperidinedione
3-(([1-(2-Chloroethyl)-2-oxohydrazino]carbonyl)amino)-2,6-piperidinedione #