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
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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26770351
Curator's Comment: Known to be CNS penetrant in rat. Human data not available
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: map04151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27180984 |
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Target ID: CHEMBL2095200 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26963248 |
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Target ID: Q01959 Gene ID: 6531.0 Gene Symbol: SLC6A3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26963248 |
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Target ID: P08908 Gene ID: 3350.0 Gene Symbol: HTR1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26963248 |
3.2 µM [EC50] | ||
Target ID: P34969 Gene ID: 3363.0 Gene Symbol: HTR7 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26963248 |
150.0 nM [IC50] | ||
Target ID: CHEMBL2095229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28817840 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Psychopharmacological studies on (--)-nuciferine and its Hofmann degradation product atherosperminine. | 1978 Sep 15 |
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Antipoliovirus structure-activity relationships of some aporphine alkaloids. | 1998 Apr |
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In Vitro and In Vivo Characterization of the Alkaloid Nuciferine. | 2016 |
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Identification of the anti-tumor activity and mechanisms of nuciferine through a network pharmacology approach. | 2016 Jul |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27180984
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27180984
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.
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475-83-2
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Nuciferine
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SUBSTANCE RECORD