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Mitragynine

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Identification
Molecular formula
C23H30N2O4
CAS number
4098-40-2
IUPAC name
16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,15(20),16,18-heptaen-14-one
State
State

At room temperature, Mitragynine exists as a solid. This compound is typically stable under standard conditions.

Melting point (Celsius)
102.00
Melting point (Kelvin)
375.15
Boiling point (Celsius)
320.00
Boiling point (Kelvin)
593.15
General information
Molecular weight
398.50g/mol
Molar mass
398.4990g/mol
Density
1.1204g/cm3
Appearence
Mitragynine is typically found as a fine white or slightly yellow powder. The appearance can vary slightly depending on the purity and form, such as extracts versus raw powdered form.

This leucine-based compound forms colorless crystals in its pure state.

Comment on solubility

Solubility of 16,17-Dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,15(20),16,18-heptaen-14-one

The solubility of 16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,15(20),16,18-heptaen-14-one in various solvents reflects its complex molecular structure and the presence of multiple functional groups. Understanding solubility is crucial for its applications in chemical research and medicinal chemistry.

Key Points about Solubility:

  • Polar solvents: The presence of methoxy groups generally suggests better solubility in polar solvents such as water and ethanol.
  • Non-polar solvents: Conversely, the rigidity of the pentacyclic structure might limit solubility in non-polar solvents such as hexane or benzene.
  • Influence of pH: The solubility might also be affected by the pH of the medium, particularly if the compound can partake in protonation/deprotonation reactions.
  • Temperature dependence: As with many organic compounds, increasing temperature could enhance solubility in various solvents.

In summary, predicting solubility involves considering both the functional groups present and the overall molecular geometry. As a result, the solubility of this compound can be characterized as moderate to variable depending on the conditions and solvent used.

Interesting facts

Interesting Facts About 16,17-Dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,15(20),16,18-heptaen-14-one

This complex compound is a fascinating example of intricate molecular architectures and showcases the diversity of organic chemistry. Here are some noteworthy aspects:

  • Structural Complexity: This compound features a unique pentacyclic system, which is significant for chemists as it allows for the exploration of a variety of biological activities. Its elaborate structure includes multiple rings interconnected through various atoms.
  • Functional Groups: The presence of methoxy groups enhances the compound's reactivity and solubility, making it valuable for synthetic applications. These groups often play a crucial role in molecular interactions.
  • Potential Applications: Compounds of this nature are often investigated for their potential pharmacological properties, including antimicrobial, antifungal, and anticancer activities. Their structural complexity can contribute to unique biological activities.
  • Synthesis Challenges: The synthesis of such a compound typically involves sophisticated methodologies, often requiring multiple steps and careful control of reaction conditions to ensure yield and purity.

As a chemist or a student, exploring compounds like this one can inspire deeper insights into synthetic strategies and the potential for discovering new therapeutic agents. The study of these types of molecules illustrates the heart of organic chemistry, where creativity meets rigorous scientific inquiry.

In the words of a noted chemist: "The complexity of molecules reflects the ingenuity of nature; understanding them can unlock the secrets of life."

Synonyms
Oxyberberine
Berlambine
549-21-3
8-Oxyberberine
Oxyberberin
Ketoberberine
JKL 1073A
JKL-1073A
8-BERBINONE, 13,13a-DIDEHYDRO-9,10-DIMETHOXY-2,3-(METHYLENEDIOXY)-
NSC93138
9,10-Dimethoxy-2,3-(methylenedioxy)-13,13a-didehydro-8-berbinone
4A04YKB3FT
Berlambine; 8-Oxoberberine; Ketoberberine
NSC-93138
8-Oxoberberine
NSC 93138
UNII-4A04YKB3FT
BRN 0339209
JKL1073A
8H-BENZO(G)-1,3-BENZODIOXOLO(5,6-A)QUINOLIZIN-8-ONE, 5,6-DIHYDRO-9,10-DIMETHOXY-
8H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-8-one, 5,6-dihydro-9,10-dimethoxy-
Prestwick_92
BERBERIN-8-ONE
Oxyberberine (Berlambine)
16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,15(20),16,18-heptaen-14-one
4-27-00-06654 (Beilstein Handbook Reference)
CHEMBL11531
SCHEMBL229912
DTXSID70203389
ZHYQCBCBTQWPLC-UHFFFAOYSA-N
BCP23559
HY-N5027
BDBM50508730
AKOS037514568
FO65468
AC-35010
MS-25426
CS-0032110
NS00094778
E80779
AK-693/43417392
Q27259321
Berbin-8-one, 13,13a-didehydro-9,10-dimethoxy-2,3-(methylenedioxy)-
9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-one
9,10-Dimethoxy-5,6-dihydro-8H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-one
9,10-Dimethoxy-5,6-dihydro-8H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-one #