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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H21NO2
Molecular Weight 295.3755
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NUCIFERINE

SMILES

[H][C@]12CC3=CC=CC=C3C4=C(OC)C(OC)=CC(CCN1C)=C24

InChI

InChIKey=ORJVQPIHKOARKV-OAHLLOKOSA-N
InChI=1S/C19H21NO2/c1-20-9-8-13-11-16(21-2)19(22-3)18-14-7-5-4-6-12(14)10-15(20)17(13)18/h4-7,11,15H,8-10H2,1-3H3/t15-/m1/s1

HIDE SMILES / InChI

Molecular Formula C19H21NO2
Molecular Weight 295.3755
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Nuciferine is an aporphine alkaloid extracted from lotus leaves, which is a raw material in Chinese medicinal herb for weight loss. Nuciferine was studied as an anti-tumor agent against human neuroblastoma and mouse colorectal cancer, through inhibiting the PI3K-AKT signaling pathways and IL-1 levels. In addition, was suggested, that nuciferine had atypical antipsychotic-like actions. Nuciferine was an antagonist at 5-HT2A, 5-HT2C, and 5-HT2B, an inverse agonist at 5-HT7, a partial agonist at D2, D5 and 5-HT6, an agonist at 5-HT1A and D4 receptors, and inhibited the dopamine transporter. In addition, was shown, that that nuciferine had a therapeutic effect on respiratory diseases associated with the aberrant contraction of airway smooth muscles and/or bronchospasm through the blockade of voltage-dependent L-type Ca2+ channels and/or nonselective cation channels.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
3.2 µM [EC50]
150.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
tumor-bearing mice: Mice in the nuciferine (1) group were immediately administered nuciferine (ip) after tumor implantation, and mice in the nuciferine (2) group were administered nuciferine (ip) when the tumor xenografts reached a size of 100 mm3. Mice in the nuciferine (1) group and nuciferine (2) group were administered nuciferine (ip) three times a week at a dosage of 9.5 mg/kg.
Route of Administration: Oral
In Vitro Use Guide
Cells (A549, NCI-H1650, HT29, CT26, HCT116 and SY5Y) were treated with nuciferine (0, 0.05, 0.1, 0.2, 0.4, 0.8, and 1.0 mg/mL) for 24 h. Nuciferine, at 0.8 mg/mL, elicited a more significant inhibitory effect on the proliferation of CT26 and SY5Y cells than on other cancer cells.
Substance Class Chemical
Record UNII
W26UEB90B7
Record Status Validated (UNII)
Record Version