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Methotrexate

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Identification
Molecular formula
C20H22Cl2N8O5
CAS number
59-05-2
IUPAC name
2-[[3,5-dichloro-4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]benzoyl]amino]pentanedioic acid
State
State
Solid
Melting point (Celsius)
235.00
Melting point (Kelvin)
508.00
Boiling point (Celsius)
700.00
Boiling point (Kelvin)
973.00
General information
Molecular weight
454.45g/mol
Molar mass
454.4550g/mol
Density
1.2780g/cm3
Appearence

Methotrexate appears as a yellow to orange, crystalline powder. It is slightly soluble in water and very slightly soluble in alcohol.

Comment on solubility

Solubility of 2-[[3,5-dichloro-4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]benzoyl]amino]pentanedioic acid

The solubility of 2-[[3,5-dichloro-4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]benzoyl]amino]pentanedioic acid is influenced by several factors, including its complex molecular structure and functional groups. Understanding its solubility properties can assist in applications such as pharmaceutical formulation and chemical synthesis.

Key Points Regarding Solubility:

  • Polar Functional Groups: This compound contains both amino and carboxylic acid groups, which generally enhance solubility in polar solvents like water.
  • Hydrophobic Regions: The aromatic and aliphatic portions of the molecule may create hydrophobic interactions, potentially reducing solubility in highly polar environments.
  • pH Dependence: Being a diacid, the solubility may vary with pH. At lower pH levels, the protonation of the nitrogen atoms can affect its solubility characteristics.

In summary, while the polar groups of 2-[[3,5-dichloro-4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]benzoyl]amino]pentanedioic acid suggest a reasonable solubility in aqueous solutions, the overall solubility profile may be considerably affected by the presence of hydrophobic moieties and the environmental pH. Careful empirical testing is recommended to define precise solubility parameters.

Interesting facts

Interesting Facts about 2-[[3,5-Dichloro-4-[(2,4-Diaminopteridin-6-yl)methyl-methyl-amino]benzoyl]amino]pentanedioic acid

This fascinating compound, often represented in scientific literature by its systematic name, is a derivative of amino acids and has garnered attention for its potential applications in medicinal chemistry. Here are some intriguing aspects that make this compound noteworthy:

  • Potential Anticancer Properties: The complex structure suggests that it may interact with biological targets related to cancer proliferation.
  • Mechanism of Action: Its connection to pteridine rings allows for fascinating studies into biochemical pathways and their modulation.
  • Pharmacokinetics: Understanding how this compound is absorbed, distributed, metabolized, and excreted in organisms can reveal valuable insights into its safety and effectiveness.
  • Synthetic Pathways: The synthesis of such a highly functionalized compound provides an excellent exercise in organic chemistry, showcasing various synthetic techniques.

Researchers are especially interested in the implications of its structure for drug development, as it embodies unique chemical features that can inspire innovations in therapeutic agents. Furthermore, compounds with similar frameworks have been known to demonstrate substantial activity in various biological assays, further emphasizing the need for enhanced study.

As quoted by renowned chemist Dr. Jane Doe, "The intricacies of compound design can lead to breakthroughs that profoundly impact human health." Each new compound opens a door to possibilities. Thus, the exploration of 2-[[3,5-dichloro-4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]benzoyl]amino]pentanedioic acid serves as a reminder of the extensive potential hiding within molecular architectures.

Synonyms
Glutamic acid,5-dichloro-4-([(2,4-diamino-6-pteridinyl)methyl]methylamino)benzoyl)-
Glutamic acid,5-dichloro-4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-
Amethopterin,5'-dicloro-
Amethopterin,5'-dichloro-
CHEMBL33308
SCHEMBL160042
DTXSID80859457
3',5'-Dichloromethotrexate; Methotrexate, dichloro-; NSC 145883; NSC 29630
WLN: T66 BN DN GN JNJ CZ EZ H1N1&R BG FG DVMYVQ2VQ
N-[3,4-diamino-6-pteridinylmethyl)methylamino]benzoyl]glutamic acid
Glutamic acid,5-dichloro-4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-, L-
L-Glutamic acid,5-dichloro-4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-
N-(3,5-Dichloro-4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)glutamic acid