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Berbérine

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Identification
Molecular formula
C20H20NO4
CAS number
2086-83-1
IUPAC name
1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-isoquinoline
State
State

At room temperature, berbérine is typically found in a solid crystalline form.

Melting point (Celsius)
145.00
Melting point (Kelvin)
418.15
Boiling point (Celsius)
656.00
Boiling point (Kelvin)
929.15
General information
Molecular weight
336.38g/mol
Molar mass
336.3630g/mol
Density
1.3768g/cm3
Appearence

Berbérine is typically a yellow crystalline substance that may appear as a bright yellow powder. It is often used in research and supplement industries and can also be found in its refined form as bright yellow crystals.

Comment on solubility

Solubility of 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-isoquinoline (C20H20NO4)

The solubility of complex organic compounds like 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-isoquinoline is influenced by several factors, including molecular structure, polarity, and the presence of functional groups. In this case, the compound features multiple methoxy groups and an isoquinoline structure, which can significantly impact its solubility characteristics.

Factors Affecting Solubility:

  • Polarity: The presence of methoxy (-OCH3) groups increases the overall polarity, potentially enhancing solubility in polar solvents.
  • Hydrogen Bonding: The methoxy groups can engage in hydrogen bonding with solvents, which can aid in dissolution.
  • Aromatic System: The isoquinoline structure contributes to hydrophobic characteristics, which may limit solubility in highly polar solvents.
  • Temperature: Solubility often increases with temperature, so testing at various temperatures may yield more insights.

In practical terms, this compound may exhibit higher solubility in organic solvents such as ethanol, acetone, or dimethyl sulfoxide (DMSO), while demonstrating lower solubility in water due to its hydrophobic characteristics! Thus, researchers must consider these factors when working with 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-isoquinoline in solution.

Interesting facts

Interesting Facts about 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-isoquinoline

This intriguing compound is a member of the isoquinoline family, which is renowned for its diverse bioactivity and potential medicinal applications. Isoquinolines have been studied extensively due to their presence in various natural products and their ability to function as pharmacophores in drug design.

Structural Features

  • Dimethoxy Group: The presence of two methoxy groups in the isoquinoline structure enhances its lipophilicity and helps in molecular interactions, contributing significantly to its biological activity.
  • Substituted Phenyl Ring: The 3,4-dimethoxyphenyl substitution provides additional electron-donating properties, which can facilitate interactions with biological receptors.

Potential Applications

This compound has garnered attention in various areas of research, including:

  • Pharmacology: Its complex structure suggests potential anti-cancer, anti-inflammatory, and analgesic properties.
  • Neuroscience: Isoquinoline derivatives are often investigated for their neuroprotective effects and possible use in the treatment of neurodegenerative diseases.

Research Insights

Studies indicate that compounds like 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-isoquinoline may function through mechanisms such as:

  • Modulation of neurotransmitter systems
  • Inhibition of specific enzymes related to disease pathways
  • Interference with cell cycle progression in cancer cells

In the words of a researcher exploring isoquinoline derivatives: "The intricate architecture of these compounds opens avenues for novel therapeutic strategies that often extend beyond traditional pharmacology."

Overall, 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-isoquinoline encapsulates the dynamic potential of synthetic organic compounds in contemporary chemical research. Its structural uniqueness and potential applications make it a fascinating subject for ongoing studies in both medicinal chemistry and biochemistry.

Synonyms
papaverine
Papaverin
58-74-2
Papanerine
Robaxapap
Papanerin
Papaverina
Cerespan
Pavabid
1-(3,4-Dimethoxybenzyl)-6,7-dimethoxyisoquinoline
6,7-Dimethoxy-1-veratrylisoquinoline
Papaverine [BAN]
1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinoline
Papaverinum
NSC 136630
Papaverine free base
Isoquinoline, 6,7-dimethoxy-1-veratryl-
Isoquinoline, 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-
UNII-DAA13NKG2Q
DAA13NKG2Q
EINECS 200-397-2
S-M-R
Papaverine (BAN)
1-((3,4-Dimethoxyphenyl)methyl)-6,7-dimethoxyisoquinoline
NSC-136630
BRN 0312930
Isoquinoline, 1-((3,4-dimethoxyphenyl)methyl)-6,7-dimethoxy-
CHEBI:28241
HSDB 3147
1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-isoquinoline
58-74-2 (free base)
CHEMBL19224
4-[(6,7-Dimethoxyisoquinolyl)methyl]-1,2-dimethoxybenzene
DTXSID4023418
5-21-06-00182 (Beilstein Handbook Reference)
NSC136630
Pavacot
Papaverina [Italian]
PAPAVERINE (MART.)
PAPAVERINE [MART.]
Ceraspan
Mesotina
Mesotina (TN)
EV1
NOSCAPINE IMPURITY A (EP IMPURITY)
NOSCAPINE IMPURITY A [EP IMPURITY]
NSC35443
CAS-61-25-6
NCGC00015810-02
Pavadyl
1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-isoquinoline
2wey
RS 47
TNP00305
Spectrum_000071
PAPAVERINE [MI]
Prestwick0_000583
Prestwick1_000583
Prestwick2_000583
Prestwick3_000583
Spectrum2_000978
Spectrum3_000537
Spectrum4_000467
Spectrum5_001188
Lopac-P-3510
PAPAVERINE [VANDF]
PAPAVERINUM [HPUS]
Isoquinoline, 6,7-dimethoxy-1-veratryl-(8Cl)
PAPAVERINE [WHO-DD]
Lopac0_000957
Oprea1_387689
Oprea1_810508
SCHEMBL34702
BSPBio_000426
BSPBio_002153
KBioGR_000914
KBioSS_000471
DivK1c_000321
6,7-Dimethoxy-1-(3,4-dimethoxybenzyl)isoquinoline
SPBio_001015
SPBio_002645
BPBio1_000470
DTXCID603418
MEGxp0_001880
ACon1_000238
ACon1_002094
BDBM14754
GTPL13147
KBio1_000321
KBio2_000471
KBio2_003039
KBio2_005607
KBio3_001653
1-[(3,4-Dimethoxyphenyl)methyl]6,7-dimethoxyisoquinoline
NINDS_000321
HMS3561N11
HMS3746M21
ALBB-010475
1-{[3,4-bis(methyloxy)phenyl]methyl}-6,7-bis(methyloxy)isoquinoline
BBL012345
STK039035
Isoquinoline,7-dimethoxy-1-veratryl-
AKOS000277460
CCG-202821
CS-7800
DB01113
KS-5336
SDCCGMLS-0003037.P003
SDCCGSBI-0050931.P005
IDI1_000321
NCGC00015810-01
NCGC00015810-03
NCGC00015810-04
NCGC00015810-05
NCGC00015810-06
NCGC00015810-07
NCGC00015810-08
NCGC00015810-09
NCGC00015810-13
NCGC00015810-24
NCGC00015810-29
NCGC00024428-03
NCGC00024428-04
HY-18077
NCI60_003183
Papaverine 100 microg/mL in Acetonitrile
SBI-0050931.P004
DB-053252
AB00053515
NS00007287
C06533
D07425
EN300-177755
AB00053515_14
WLN: T66 CNJ B1R CO1 DO1& HO1 IO1
AG-205/03660043
Q410374
6,7-dimethoxy-1-veratryl-isoquinoline;hydrochloride
1-(3,4-Dimethoxybenzyl)-6,7-dimethoxyisoquinoline #
BRD-K15567136-001-01-1
BRD-K15567136-003-06-6
BRD-K15567136-003-18-1
BRD-K15567136-003-27-2
Isoquinoline,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-
SR-01000003098-10
1-((3,4-Dimethoxyphenyl)-methyl)-6,7-dimethoxyisoquinoline
200-397-2
InChI=1/C20H21NO4/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16/h5-8,10-12H,9H2,1-4H