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Camptothecin

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Identification
Molecular formula
C20H16N2O4
CAS number
7689-03-4
IUPAC name
(6aR,9R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
State
State
Camptothecin is in a solid state at room temperature.
Melting point (Celsius)
265.00
Melting point (Kelvin)
538.20
Boiling point (Celsius)
622.15
Boiling point (Kelvin)
895.30
General information
Molecular weight
348.35g/mol
Molar mass
348.3520g/mol
Density
1.5140g/cm3
Appearence

Camptothecin is a yellow crystalline powder at room temperature. It is poorly soluble in water but soluble in organic solvents such as dimethyl sulfoxide (DMSO) and ethanol. Its crystalline form can vary in color intensity depending on purity and handling conditions, often requiring careful processing to maintain its integrity for study and use in pharmaceutical applications.

Comment on solubility

Solubility of (6aR,9R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

The solubility of this complex organic compound can vary significantly based on a number of factors. Here are some key points to consider:

  • Polarity: The presence of multiple functional groups, such as hydroxyl groups and carbonyls, can enhance solubility in polar solvents. However, large hydrophobic aromatic components may hinder solubility in polar media.
  • Solvent Effects: This compound may exhibit different solubility in various solvents. Typically, it can be soluble in dimethyl sulfoxide (DMSO) and methanol, while showing limited solubility in non-polar solvents like hexane.
  • Temperature Dependence: Solubility can also be temperature-dependent. Generally, increasing temperature tends to increase solubility for solid solutes.

In summary, the solubility of (6aR,9R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide is influenced by its molecular structure, the choice of solvent, and temperature conditions. Addressing these factors will be crucial for determining the effective use of this compound in various applications.

Interesting facts

Interesting Facts about (6aR,9R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

This fascinating compound represents a remarkable intersection of complex organic chemistry and medicinal science. Its intricate structure reflects a rich tapestry of molecular features, making it an interesting subject for chemical research.

Chemical Characteristics:

  • Stereochemistry: The careful arrangement of stereocenters gives this compound its specific 3D shape which is vital for its biological activity. The stereogenic centers provide insight into how it interacts within biological systems.
  • Diversity of Functional Groups: The compound features various functional groups such as amides and dioxo moieties that play crucial roles in its reactivity and interactions.
  • Tricyclic and Indole Structures: The presence of both tricyclic and indole scaffolds contributes to potential pharmacological properties, often associated with anticancer and antimicrobial activities.

Potential Applications:

This compound is notably significant in the fields of drug development and biochemistry.

  • Pharmacological Research: Its complex structure has prompted investigations into its effectiveness against various diseases, particularly in targeting cancer cells.
  • Mechanistic Studies: Due to its unique structure, researchers are eager to explore its mode of action, which could lead to a deeper understanding of related biochemical processes.

A Growing Interest

As a student or a scientist, you might find the study of such compounds particularly rewarding. The multifaceted nature of this molecule not only challenges conventional synthetic methods but also paves the way for innovative approaches in drug discovery. To quote one renowned chemist, "The complexity of life is mirrored in the complexity of the molecules we study." So dive into the world of this compound and uncover the secrets within its structure!

Synonyms
ERGOTAMINE
Ergotamin
Gynergen
Ergonsvine
Ergotamina
Ergostat
ergotamine tartrate
ergotaminum
Ergomar
113-15-5
Ergotaminum [INN-Latin]
Ergotamina [INN-Spanish]
Rigetamin
HSDB 4076
12'-Hydroxy-2'-methyl-5'alpha-(phenylmethyl)ergotaman-3',6',18-trione
Ergotamine bitartrate
EINECS 204-023-9
NSC 95090
Ergotamine (INN)
UNII-PR834Q503T
BRN 0078890
CHEBI:64318
PR834Q503T
NSC-95090
DTXSID9043774
ergopeptine
ERGOTAMINE [INN]
Ergotaminum (INN-Latin)
Ergotamina (INN-Spanish)
(5'alpha)-12'-Hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione
Ergotamine [INN:BAN]
Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'-alpha)-
Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'alpha)-
(5'alpha)-5'-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxoergotaman
(4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^{2,6}]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
379-79-3
Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'alpha)-, (2R,3R)-2,3-dihydroxybutanedioate (2:1) (salt)
ERM
Ergotaminum (Latin)
Ergotamin; ergotaminum
NSC41869
ERGOTAMINE [MI]
ERGOTAMINE [HSDB]
ERGOTAMINE [VANDF]
CHEMBL442
SCHEMBL1483
ERGOTAMINE [WHO-DD]
GTPL149
DTXCID7023774
N02CA02
XCGSFFUVFURLIX-VFGNJEKYSA-N
Ergotamine tartrate, Avetol, Cornutamin, Ergam, Ergotartrate
HMS2089H22
BDBM50027065
Ergotamine dried down 100 microg/mL
AKOS015896505
DB00696
NCGC00356592-02
D07906
AB01275473-01
Q419186
CODERGOCRINE MESILATE IMPURITY C [EP IMPURITY]
5'alpha-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxoergotaman
(5''alpha)-12''-hydroxy-2''-methyl-5''-(phenylmethyl)ergotoman-3'',6'',18-trione
(5''alpha)-5''-benzyl-12''-hydroxy-2''-methyl-3'',6'',18-trioxoergotaman
(5'alpha)-12'-Hydroxy-2'-methyl-5'-(phenylmethyl)ergotaman-3',6',18-trione
(5alpha,5'beta)-5'-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxoergotaman
12''-hydroxy-2''-methyl-5''alpha-(phenylmethyl)ergotaman-3'',6'',18-trione
1080650-16-3
204-023-9
N-[(2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxo-8,9,10,10a-tetrahydro-5H-oxazolo[[?]]pyrrolo[[?]]pyrazin-2-yl]-methyl-[?]carboxamide