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Methotrexate

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Identification
Molecular formula
C20H22N8O5
CAS number
59-05-2
IUPAC name
(2S)-2-[[3,5-dichloro-4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]benzoyl]amino]pentanedioic acid
State
State

At room temperature, Methotrexate is a solid compound, typically available as a crystalline powder.

Melting point (Celsius)
195.00
Melting point (Kelvin)
468.00
Boiling point (Celsius)
760.00
Boiling point (Kelvin)
1 033.00
General information
Molecular weight
454.44g/mol
Molar mass
454.4410g/mol
Density
1.0600g/cm3
Appearence

Methotrexate appears as a yellow or orange crystalline powder. It is generally odourless and is light-sensitive, hence it should be stored away from light to prevent degradation.

Comment on solubility

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

The solubility of (2S)-2-[[3,5-dichloro-4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]benzoyl]amino]pentanedioic acid can be described with an extensive focus on various factors that influence its behavior in solution.

Factors Affecting Solubility

  • Polarity: The polar functional groups within the molecule suggest that this compound could have a moderate to high solubility in polar solvents such as water.
  • Hydrogen Bonding: The presence of amine groups may facilitate hydrogen bonding with solvents, potentially enhancing solubility.
  • pH Sensitivity: Given its acidic nature, solubility may vary significantly with the pH of the solution. Under different pH conditions, protonation or deprotonation can alter solubility characteristics.

Additionally, it is important to consider the following points:

  • The compound could exhibit different solubility behaviors at varying temperatures, impacting its overall solubility profiles.
  • Like dissolves like: The molecular structure indicates a likelihood of compatibility with similar polar solvents, with potential limitations in non-polar environments.

In conclusion, the solubility of (2S)-2-[[3,5-dichloro-4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]benzoyl]amino]pentanedioic acid is influenced by its molecular structure, polarity, and the solution's pH. Understanding these factors is critical for predicting its behavior in various chemical contexts.

Interesting facts

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

(2S)-2-[[3,5-Dichloro-4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]benzoyl]amino]pentanedioic acid is a fascinating compound with significant relevance in medicinal chemistry and drug development. Here are some intriguing facts about this compound:

  • Mechanism of Action: This compound plays a crucial role in the inhibition of specific enzymes involved in purine metabolism, making it a potential candidate for targeting certain types of cancers and autoimmune diseases.
  • Structural Insight: The presence of the dichlorobenzoyl group coupled with the pentanedioic acid backbone provides unique chemical properties that enhance biological activity and selectivity.
  • Pharmacological Importance: It serves as a structural framework for various drug analogs, showcasing how modifications can lead to diverse pharmacological profiles, which is pivotal in drug design.
  • Research Potential: Studies into this compound can reveal insights into its interactions at the molecular level, which may open doors for new therapeutic applications.
  • Historical Significance: Compounds with similar structures have historically paved the way for the development of groundbreaking therapies, illustrating the impact of chemical innovation on modern medicine.

As a scientist or chemistry student, understanding the complexities and potentials of such compounds challenges our perception of chemistry's role in real-world applications. The blend of organic chemistry and pharmacology in this compound exemplifies the beauty of molecular design and its implications for human health.

Synonyms
DICHLOROMETHOTREXATE
Dichloroamethopterin
3',5'-Dichloromethotrexate
Methotrexate, dichloro-
3',5'-Dichloroamethopterin
Amethopterin, 3',5'-dichloro-
NCI-C04875
NSC-29630
CCRIS 4602
BRN 0073523
3988 B 129-4
3988-B-129-4
29NS58S465
3',5'-Dichloro-4-amino-4-deoxy-N(sup10)-methylpteroglutamic acid
N-(3,5-Dichloro-4-((2,4-diamino-6-pteridinylmethyl)methylamino)benzoyl)glutamic acid
DTXSID3024996
UNII-29NS58S465
3',5'-Dichloro-4-amino-4-deoxy-N(sup 10)-methylpteroglutamic acid
4-26-00-03834 (Beilstein Handbook Reference)
NSC29630
Glutamic acid, N-(3,5-dichloro-4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-
Glutamic acid, N-(3,5-dichloro-4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-, L-
L-Glutamic acid, N-(3,5-dichloro-4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-
L-Glutamic acid, N-[3,5-dichloro-4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-
Glutamic acid, N-[3,5-dichloro-4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-, L-
Glutamic acid, N-[3,5-dichloro-4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-
Glutamic Acid, N-{3,5-dichloro-4-{[(2,4-diamino-6-pteridinyl)methyl]methylamino}benzoyl}-
N-(3,5-Dichloro-4-((2, 4-diamino-6-pteridinylmethyl)methylamino)benzoyl)glutamic acid
N-(3,5-Dichloro-4-((2,4-diamino-6-pteridinylmethyl)methylamino)benzoyl) Glutamic Acid
N-[3,5-Dichloro-4-[(2, 4-diamino-6-pteridinylmethyl)methylamino]benzoyl]glutamic acid
N-[3,5-dichloro-4-[(2,4-diamino-6-pteridinylmethyl)methylamino]benzoyl] glutamic acid
Glutamic acid, N-(3,5-dichloro-4-(((2, 4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-
Glutamic acid, N-(3,5-dichloro-4-([(2, 4-diamino-6-pteridinyl)methyl]methylamino)benzoyl)-
Glutamic acid, N-[3,5-dichloro-4-[[(2, 4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-
L-Glutamic acid, N-(3,5-dichloro-4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-(9CI)
L-Glutamic Acid, N-{3,5-dichloro-4-{[(2,4-diamino-6-pteridinyl)methyl]methylamino}benzoyl}-(9CI)
Methotrexate, Dichloro
3'-5'-Dichloromethotrexate
3', 5'-Dichloroamethopterin
Amethopterin, 3',5'-dichloro
DTXCID304996
4-AMINO-10-METHYL-3',5'-DICHLOROPTEROYLGLUTAMIC ACID
Glutamic acid, N-(3,5-dichloro-4-(((2, 4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-, L-
Glutamic acid, N-(3,5-dichloro-4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-, L-(8CI)
Glutamic Acid, N-(3,5-dichloro-4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-L-
Glutamic acid, N-[3,5-dichloro-4-[[(2, 4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-, L-(8CI)
Glutamic Acid, N-{3,5-dichloro-4-{[(2,4-diamino-6-pteridinyl)methyl]methylamino}benzoyl}-L-(8CI)
L-Glutamic acid, N-(3,5-dichloro-4-(((2, 4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-
L-Glutamic acid, N-[3,5-dichloro-4-[[(2, 4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-(9CI)
N-(3,5-DICHLORO-4-(((2,4-DIAMINO-6-PTERIDINYL)METHYL)METHYLAMINO)BENZOYL)-GLUTAMIC ACID
N-(3,5-DICHLORO-4-((2,4-DIAMINO-6-PTERIDINYLMETHYL)METHYLAMINO)-BENZOYL)GLUTAMIC ACID
mcehfixeknksrw-lbprgkrzsa-n
nsc 145883
528-74-5
NSC 29630
3,5-Dichloromethotrexate
(2S)-2-[[3,5-dichloro-4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid
(3,5-dichloro-4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzoyl)-L-glutamic acid
N-(3,5-dichloro-4-((2,4-diamino-6-pteridinyl)methyl)methyl)methylaminobenzoylglutamic acid
CHEMBL3137680
SCHEMBL10653854
3',5'-Dichloromethotrexate; Methotrexate, dichloro-; NSC 145883; NSC 29630
AKOS040746763
HY-105969
(2S)-2-[[3,5-dichloro-4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]benzoyl]amino]pentanedioic acid
2-[[3,5-dichloro-4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid
L-Glutamic acid, N-[[(2,4-diamino-6-pteridinyl)methyl][methyl]amino]-3,5-dichlorobenzoyl]-
N-(3,5-dichloro-4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)- L-Glutamic acid
N-(3,5-Dichloro-4-[[(2,4-diamino-6-pteridinyl)methyl](methyl)amino]benzoyl)glutamic acid #