Skip to main content

Vincristine

ADVERTISEMENT
Identification
Molecular formula
C46H56N4O10
CAS number
57-22-7
IUPAC name
(6aR,9R,10aR)-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,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
State
State

Vincristine is typically encountered as a solid at room temperature, often provided in a lyophilized form which needs to be reconstituted into a solution for medicinal use.

Melting point (Celsius)
218.00
Melting point (Kelvin)
491.00
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
824.99g/mol
Molar mass
825.0070g/mol
Density
1.4000g/cm3
Appearence

Vincristine appears as a white to off-white crystalline powder. It is usually administered in solution form for intravenous use and is soluble in water and methanol but practically insoluble in ethanol and chloroform.

Comment on solubility

Solubility of (6aR,9R,10aR)-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,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

The solubility of this complex compound is influenced by its intricate molecular structure. Several factors determine its solubility properties:

  • Polarity: The presence of multiple functional groups, including hydroxyl (-OH) and amide (C=O-NH2), suggests that the compound may exhibit some degree of polarity, enhancing its solubility in polar solvents like water.
  • Steric Hindrance: The bulky benzyl and hexahydroindole groups can impede solubility in certain solvents, potentially leading to limited solubility in non-polar environments.
  • Hydrogen Bonding: The ability to form hydrogen bonds with solvents can significantly improve solubility. The hydroxyl group may facilitate interactions with water molecules.

Despite these influencing factors, the solubility of this compound in practical applications may present challenges:

  • It may show variable solubility across different temperature ranges.
  • Aqueous solubility can greatly differ from organic solvent solubility.
  • Complex interactions may occur due to its bulky nature, potentially leading to precipitation in certain conditions.

In summary, while the structure hints at some solubility in polar solvents, the exact solubility characteristics require careful evaluation through empirical testing to determine how it behaves in practical formulations.

Interesting facts

Interesting Facts about (6aR,9R,10aR)-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,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

This complex chemical compound showcases a fascinating interplay of structural elements that highlight the intricacies of organic chemistry. Here are some intriguing aspects:

  • Structural Diversity: The compound features a unique multi-cyclic framework that incorporates both indole and quinoline structures, illustrating the rich structural diversity found in organic chemistry.
  • Biological Relevance: Compounds like this one are often investigated for their potential biological activity. Their complex structures may lead to interactions with biological molecules, making them candidates for pharmaceutical research.
  • Stereochemistry: The presence of multiple chiral centers adds layers of stereochemical complexity, emphasizing the significance of three-dimensional molecular arrangements in determining a compound's functionality and reactivity.
  • Oxidative Features: With dioxo groups present in the structure, this compound might exhibit interesting oxidative properties, which are essential for understanding its reactivity in various chemical reactions.
  • Route to Synthesis: The synthesis of such compounds often involves intricate synthetic pathways that can incorporate various reaction mechanisms, showcasing the skill level and creativity involved in organic synthesis.

As a student or scientist delving into this compound, it is crucial to appreciate not only its chemical composition but also the potential applications and the challenges in its study. It reflects the beauty and complexity of chemistry, where every atom has a purpose and every bond tells a story.

Synonyms
dihydroergotamine
9,10-Dihydroergotamine
511-12-6
Dihidroergotamina
Levadex
Dehydroergotamine
Dihydroergotaminum
Neomigran
Diidroergotamina
Dihydroergotaminum [INN-Latin]
Dihidroergotamina [INN-Spanish]
MAP0004
Ergotamine, 9,10-dihydro-
MAP-0004
EINECS 208-123-3
UNII-436O5HM03C
BRN 5720196
CHEBI:4562
DTXSID6045614
436O5HM03C
MAP 0004
DTXCID4025614
5'-Benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman
9,10-Dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione
(10alphaH)-5'alpha-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman
Ergotaman-3',6',18-trione, 9,10-dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'alpha,10alpha)-
Dihydroergotaminum (INN-Latin)
Dihidroergotamina (INN-Spanish)
DIHYDROERGOTAMINE (MART.)
DIHYDROERGOTAMINE [MART.]
Dihydroergotamin
(2R,4R,7R)-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)-6-methyl-6,11-diazatetracyclo(7.6.1.02,7.012,16)hexadeca-1(16),9,12,14-tetraene-4-carboxamide
(2R,4R,7R)-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]-6-methyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),9,12,14-tetraene-4-carboxamide
N02CA01
208-123-3
Agit
Dihydroergotamine (INN)
Dihydroergotamine [INN]
CHEMBL1732
NCGC00017400-05
Diidroergotamina [DCIT]
(6aR,9R,10aR)-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,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
9,10-dihydro-ergotamine
DHE
Neomigran (TN)
(2R,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),9,12,14-tetraene-4-carboxamide
(6aR,9R,10aR)-N-((2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-8H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
CAS-511-12-6
Dihydroergotamine [INN:BAN]
NCGC00017400-10
Spectrum_001057
Spectrum2_001188
Spectrum3_000395
Spectrum4_000958
Spectrum5_000905
Lopac0_000357
SCHEMBL44931
BSPBio_002209
GTPL121
KBioGR_001576
KBioSS_001537
BIDD:GT0120
DIHYDROERGOTAMINE [MI]
DivK1c_000592
SPBio_001235
DIHYDROERGOTAMINE [VANDF]
KBio1_000592
KBio2_001537
KBio2_004105
KBio2_006673
KBio3_001429
NINDS_000592
DIHYDROERGOTAMINE [WHO-DD]
7-Methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid ((2R,5S,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxo-octahydro-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-amide
Tox21_110821
BDBM50295557
Tox21_110821_1
CCG-204452
DB00320
SDCCGSBI-0050345.P005
IDI1_000592
NCGC00017400-06
NCGC00017400-07
NCGC00017400-08
SBI-0050345.P004
C07798
D07837
AB00053458_03
EN300-26508628
Q421336
BRD-K72166146-066-02-1
BRD-K72166146-066-03-9
BRD-K72166146-066-04-7
BRD-K72166146-066-05-4
CODERGOCRINE MESILATE IMPURITY D [EP IMPURITY]
(10alpha)-5'alpha-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman
(2R,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(15),9,12(16),13-tetraene-4-carboxamide
(5'alpha,10alpha)-9,10-Dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotaman-3',6',18-trione
(5alpha,5'beta,10alpha)-5'-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman
2GM
7-Methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (5-benzyl-10b-hydroxy-2-methyl-3,6-dioxo-octahydro-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-amide