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Tetrandrine

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Identification
Molecular formula
C38H42N2O6
CAS number
518-34-3
IUPAC name
(6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one
State
State

At room temperature, tetrandrine is a solid. It is stable under normal laboratory conditions and does not spontaneously turn into a liquid or gas at room temperature.

Melting point (Celsius)
213.00
Melting point (Kelvin)
486.15
Boiling point (Celsius)
718.20
Boiling point (Kelvin)
991.35
General information
Molecular weight
622.75g/mol
Molar mass
622.6790g/mol
Density
1.3780g/cm3
Appearence

Tetrandrine is typically a white or off-white crystalline powder. It has a crystalline appearance under a microscope and is often used in its powdered form for study and medical applications.

Comment on solubility

Solubility Characteristics

The compound (6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one exhibits interesting solubility properties that can be understood by examining several influencing factors:

  • Polarity: The presence of various functional groups, such as dioxoles and furo compounds, enhances the molecule's polarity, which could lead to improved solubility in polar solvents.
  • Hydrogen Bonding: The ability to form hydrogen bonds with solvent molecules may significantly contribute to its solubility in protic solvents, such as water.
  • Steric Hindrance: The complex structure may introduce steric hindrances that could affect the overall solubility in less polar organic solvents.

In general, the solubility of this compound can be summarized as follows:

  1. Likely soluble in polar solvents due to the presence of electronegative atoms capable of hydrogen bonding.
  2. Potentially less soluble in non-polar solvents because of its complex and bulky structure.
  3. Solubility can vary significantly with changes in temperature and pH, affecting ionization states and intermolecular interactions.

While precise solubility data are often experimentally determined, it is essential to emphasize that understanding the structure-property relationships within such compounds is crucial for predicting their behavior in various environments.

Interesting facts

Interesting Facts about (6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one

This complex organic compound is a fascinating example of how intricate molecular structures can lead to unique properties and applications in various fields, particularly in medicinal chemistry.

Notable Aspects

  • Diversity of Structure: The compound showcases a rich assembly of functional groups and rings, reflecting the inherent complexity of natural products.
  • Potential Biological Activity: Compounds with similar structures have been known to exhibit a wide range of biological activities, including antioxidant, anti-inflammatory, and even antimicrobial properties.
  • Isoquinoline Motif: The presence of the isoquinoline moiety is notable because many isoquinoline derivatives demonstrate significant pharmacological effects, making them subjects of extensive research.
  • Synthetic Pathways: The synthesis of such compounds often involves multiple steps and sophisticated reaction techniques, showcasing the creativity and skill required in organic chemistry.
  • Applications in Pharmaceuticals: Due to its complexity, this compound may serve as a precursor or model for the development of new therapeutic agents targeting various diseases.

In conclusion, (6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one stands as a testament to the potential of complex organic structures in enhancing our understanding of chemistry and advancing innovation in the pharmaceutical sector.

Synonyms
bicuculline
(+)-Bicuculline
485-49-4
NSC 32192
EINECS 207-619-7
UNII-Y37615DVKC
BRN 0098786
CHEBI:3092
Y37615DVKC
BICUCULLINE [MI]
NSC-32192
(6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one
(6R)-6-[(5S)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]furo[3,4-e][1,3]benzodioxol-8(6H)-one
DTXSID3042687
4-27-00-06900 (Beilstein Handbook Reference)
Furo(3,4-e)-1,3-benzodioxol-8(6H)-one, 6-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (R-(R*,S*))-
(6R)-6-((5S)-6-METHYL-5,6,7,8-TETRAHYDRO(1,3)DIOXOLO(4,5-G)ISOQUINOLIN-5-YL)FURO(3,4-E)(1,3BENZODIOXOL-8(6H)-ONE
(6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[4,3-g][1,3]benzodioxol-8-one
Furo(3,4-e)-1,3-benzodioxol-8(6H)-one, 6-((5S)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (6R)-
Furo[3,4-e]-1,3-benzodioxol-8(6H)-one, 6-[(5S)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-, (6R)-
(+)-Bicuculline,1(S),9(R)
(10R)-10-((5S)-6-methyl-2H,5H,6H,7H,8H-(1,3)dioxolo(4,5-g)isoquinolin-5-yl)-3,5,11-trioxatricyclo(7.3.0.02,6)dodeca-1(9),2(6),7-trien-12-one
(10R)-10-[(5S)-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3,5,11-trioxatricyclo[7.3.0.02,6]dodeca-1(9),2(6),7-trien-12-one
(6R)-6-((5S)-6-methyl-5,6,7,8-tetrahydro(1,3)dioxolo(4,5-g)isoquinolin-5-yl)furo(3,4-e)(1,3)benzodioxol-8(6H)-one
(6R)-6-((5S)-6-methyl-7,8-dihydro-5H-(1,3)dioxolo(4,5-g)isoquinolin-5-yl)-6H-furo(3,4-g)(1,3)benzodioxol-8-one
(6R)-6-((5S)-6-methyl-7,8-dihydro-5H-(1,3)dioxolo(4,5-g)isoquinolin-5-yl)-6H-furo(4,3-g)(1,3)benzodioxol-8-one
Furo[3,4-e]-1,3-benzodioxol-8(6H)-one, 6-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [R-(R*,S*)]-
DTXCID1022687
207-619-7
iygymkdqcdomre-uhfffaoysa-n
d-Bicuculline
Bicculine
Bicucullin
Bicuculline (+)
CHEMBL417990
NSC32192
MFCD00005006
(R)-6-((S)-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-[1,3]dioxolo[4,5-e]isobenzofuran-8(6H)-one
SR-01000075252
bicuculline-(+)
Bicuculline,(+)
Prestwick_96
(6R)-6-[(5S)-5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo[4,5-g]lisoquinolin-5-yl]furo[3,4-e]-1,3-benzodioxol-8(6H)-one;Bicuculline;D-Bic uculline
(+)-Bicuculline?
Bicuculline (Standard)
Prestwick0_000589
Prestwick1_000589
Prestwick2_000589
Prestwick3_000589
Biomol-NT_000252
(+)-Bicuculline, 98%
SCHEMBL8222
Lopac0_000234
BSPBio_000438
MLS002153892
DivK1c_000609
SPBio_002657
BPBio1_000482
BPBio1_000794
GTPL2312
HMS501O11
HY-N0219R
KBio1_000609
IYGYMKDQCDOMRE-ZWKOTPCHSA-N
NINDS_000609
GLXC-06284
HMS1569F20
HMS2096F20
HMS2235H18
HMS3266A07
HMS3414D19
HMS3652N20
HMS3678D19
HMS3886N09
BCP04180
HY-N0219
BDBM50000693
HB0896
PDSP2_000138
s7071
(+)-Bicuculline - Bio-X trade mark
AKOS024282673
CCG-204329
CS-5493
DB11562
FB18590
IDI1_000609
NCGC00017385-06
(+)-Bicuculline, >=97.0% (TLC)
(6R)-6-((5S)-6-methyl(5,6,7,8-tetrahydro-2H-1,3-dioxolano[4,5-g]isoquinolin-5- yl))-6-hydro-2H-1,3-dioxoleno[4,5-e]isobenzofuran-8-one
AC-31293
AS-17471
BB164251
SMR001233241
B1890
NS00031807
SW196408-2
B 9130
C09364
Q3639734
SR-01000075252-1
SR-01000075252-4
SR-01000075252-5
WLN: T C566 DO FO KN EH&&TJ K1 J- ET B565 CVO JO LO EH KHJ
(bicuculline) 6-Methyl-5-(8-oxo-6,8-dihydro-furo[3'',4'':3,4]benzo[1,2-d][1,3]dioxol-6-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium
(R)-6-((S)-6-Methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6H-furo[3'',4'':3,4]benzo[1,2-d][1,3]dioxol-8-one
(R)-6-((S)-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)isobenzofuro[5,4-d][1,3]dioxol-8(6H)-one
6-(6-Methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6H-furo[3'',4'':3,4]benzo[1,2-d][1,3]dioxol-8-one
6-(6-Methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6H-furo[3'',4'':3,4]benzo[1,2-d][1,3]dioxol-8-one (Bicuculline)
6-(6-Methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6H-furo[3'',4'':3,4]benzo[1,2-d][1,3]dioxol-8-one(bicuculline)
Furo[3,3-benzodioxol-8(6H)-one, 6-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [R-(R*,S*)]-
H0Z