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Camptothecin

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Identification
Molecular formula
C20H16N2O5
CAS number
7689-03-4
IUPAC name
[(4S,6S,7R,8S)-7,11-dimethoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
State
State

Camptothecin is a solid at room temperature. It maintains its structural integrity in a finely powdered form, which is typical for many organic compounds of similar molecular structure and allows it to be handled easily in standard laboratory conditions.

Melting point (Celsius)
260.00
Melting point (Kelvin)
533.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
348.35g/mol
Molar mass
0.0000g/mol
Density
1.4410g/cm3
Appearence

Camptothecin is a pale yellow crystalline powder. It is visually characterized by its fine, small crystals that are typically light yellow in color. When analyzed under specific conditions, this compound exhibits luminescent properties, which can be one of its distinguishing features in the laboratory.

Comment on solubility

Solubility of the Compound

The solubility of the compound [(4S,6S,7R,8S)-7,11-dimethoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate can be influenced by several factors:

  • Molecular Structure: The presence of multiple functional groups, including methoxy and carbamate, suggests a potential for varied interaction with solvents.
  • Polarity: Given its complex structure, the polarity of the compound could enhance solubility in polar solvents such as water or alcohols, while possibly reducing it in non-polar solvents.
  • Hydrogen Bonding: The ability to form hydrogen bonds with solvents can greatly enhance solubility. The carbamate group can participate in such interactions.

In summary, while specific solubility data may be limited, it is likely that this compound exhibits distinct solubility characteristics due to its intricate molecular configuration. Its behavior in various solvents would need experimental validation to accurately determine its solubility profile. As a rule of thumb, polar compounds tend to dissolve better in polar solvents, and vice versa.

Interesting facts

Interesting Facts about Methyl Carbamate Derivative

This particular compound, which belongs to the class of complex organic molecules known as carbamates, exhibits a fascinating array of properties and potential applications. Here are some intriguing details about it:

  • Structural Complexity: The compound features a unique tetracyclic structure, which is characterized by multiple rings that make the molecular scaffold quite intricate. This complexity can lead to interesting interactions with biological systems.
  • Biological Activity: Many carbamates, including this derivative, are known for their biological activities. They may serve as potential pharmaceutical agents or agricultural chemicals due to their interactions with enzymes and receptors.
  • Symmetric Dimensions: The presence of multiple stereogenic centers (specifically at positions 4, 6, 7, and 8) indicates that the compound can exist in different stereoisomeric forms, which may dramatically influence its reactivity and interactions in biological contexts.
  • Functional Groups: The inclusion of dimethoxy and dioxo functional groups is particularly noteworthy. These moieties could enhance the compound’s solubility and stability, as well as its suitability for synthesis of more complex derivatives.
  • Applications in Research: Due to its unique chemical structure, this carbamate derivative is a candidate for research in fields such as medicinal chemistry and agrochemistry. Scientists are consistently on the lookout for novel compounds that could lead to new therapeutic agents or crop protection options.

In conclusion, the multifaceted characteristics of this methyl carbamate derivative not only make it a subject of academic interest but also open up pathways for innovative applications in various scientific domains. Its intricate structure and potential biological implications exemplify the beauty and complexity of organic chemistry.

Synonyms
Mitomycin A
4055-39-4
HSDB 3418
NSC 75986
UNII-87TMG6FJHV
87TMG6FJHV
CHEBI:85412
NSC-75986
MITOMYCIN A [MI]
Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-6,8a-dimethoxy-5-methyl-, carbamate (ester)
MITOMYCIN IMPURITY B [EP IMPURITY]
[(1as,8s,8ar,8bs)-6,8a-Dimethoxy-5-Methyl-4,7-Dioxo-1,1a,2,4,7,8,8a,8b-Octahydroazireno[2',3':3,4]pyrrolo[1,2-A]indol-8-Yl]methyl Carbamate
Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-6,8a-dimethoxy-5-methyl-, (1aR-(1aalpha,8beta,8aalpha,8balpha))-
NSC75986
[(4S,6S,7R,8S)-7,11-dimethoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
AZIRINO(2',3':3,4)PYRROLO(1,2-A)INDOLE-4,7-DIONE, 8-(((AMINOCARBONYL)OXY)METHYL)-1,1A,2,8,8A,8B-HEXAHYDRO-6,8A-DIMETHOXY-5-METHYL-, (1AS,8S,8AR,8BS)-
Azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione, 1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-6,8a-dimethoxy-5-methyl-, carbamate (ester)
MITOMYCIN IMPURITY B (EP IMPURITY)
((1aS,8S,8aR,8bS)-6,8a-dimethoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno(2',3':3,4)pyrrolo(1,2-a)indol-8-yl)methyl carbamate
((4S,6S,7R,8S)-7,11-dimethoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo(7.4.0.02,7.04,6)trideca-1(9),11-dien-8-yl)methyl carbamate
Azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione, 8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-6,8a-dimethoxy-5-methyl-, [1aR-(1a.alpha.,8.beta.,8a.alpha.,8b.alpha.)]-
mitomycin A, (1aS-(1aalpha,8alpha,8aalpha,8balpha))-isomer
Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-6,8a-dimethoxy-5-methyl-, carbamate
Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-6,8a-dimethoxy-5-methyl-, (1aR-(1aalpha,8beta,8aalpha,8balpha))-(9CI)
AZIRINO(2',3':3,4)PYRROLO(1,2-A)INDOLE-4,7-DIONE, 1,1A,2,8,8A,8B-HEXAHYDRO-8-(HYDROXYMETHYL)-6,8A-DIMETHOXY-5-METHYL-, CAR///
AZIRINO(2',3':3,4)PYRROLO(1,2-A)INDOLE-4,7-DIONE, 8-(((AMINOCARBONYL)OXY)METHYL)-1,1A,2,8,8A,8B-HEXAHYDRO-6,8A-DIMETHOXY-5///
Azirino(2',3':3,4)pyrrolo(1,2a)indole4,7dione, 1,1a,2,8,8a,8bhexahydro8(hydroxymethyl)6,8adimethoxy5methyl, carbamate (ester)
Azirino(2',3':3,4)pyrrolo(1,2a)indole4,7dione, 8(((aminocarbonyl)oxy)methyl)1,1a,2,8,8a,8bhexahydro6,8adimethoxy5methyl, (1aS(1aalpha,8beta,8aalpha,8balpha))
Azirino(2',3':3,4)pyrrolo(1,2a)indole4,7dione, 8(((aminocarbonyl)oxy)methyl)1,1a,2,8,8a,8bhexahydro6,8adimethoxy5methyl, (1aS(1aalpha,8beta,8aalpha,8balpha)) (9CI)
hyfmsafinfjtfh-uhfffaoysa-n
MitomycinA
CHEMBL298359
SCHEMBL13033872
HYFMSAFINFJTFH-NGSRAFSJSA-N
DTXSID201318131
AKOS040755422
AM26018
HY-130332
CS-0107334
C21161
Q22252148
(1aS,8S,8aR,8bS)-8-[[(Aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-6,8a-dimethoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-a]indo le-4,7-dione