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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
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

Curator's Comment: Known to be CNS penetrant in rat. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q01959
Gene ID: 6531.0
Gene Symbol: SLC6A3
Target Organism: Homo sapiens (Human)
Target ID: P08908
Gene ID: 3350.0
Gene Symbol: HTR1A
Target Organism: Homo sapiens (Human)
3.2 µM [EC50]
Target ID: P34969
Gene ID: 3363.0
Gene Symbol: HTR7
Target Organism: Homo sapiens (Human)
150.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Psychopharmacological studies on (--)-nuciferine and its Hofmann degradation product atherosperminine.
1978 Sep 15
Antipoliovirus structure-activity relationships of some aporphine alkaloids.
1998 Apr
In Vitro and In Vivo Characterization of the Alkaloid Nuciferine.
2016
Identification of the anti-tumor activity and mechanisms of nuciferine through a network pharmacology approach.
2016 Jul
Patents

Patents

Sample Use Guides

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
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.
Name Type Language
NUCIFERINE
Common Name English
1,2-DIMETHOXY-6A.BETA.-APORPHINE
Common Name English
SANJOININE E
Brand Name English
4H-DIBENZO(DE,G)QUINOLINE, 5,6,6A,7-TETRAHYDRO-1,2-DIMETHOXY-6-METHYL-, (6AR)-
Systematic Name English
(R)-NUCIFERINE
Common Name English
D-(-)-NUCIFERINE
Common Name English
(R)-1,2-DIMETHOXYAPORPHINE
Systematic Name English
L-NUCIFERINE
Common Name English
(-)-NUCIFERINE
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID40963862
Created by admin on Sat Dec 16 08:01:35 GMT 2023 , Edited by admin on Sat Dec 16 08:01:35 GMT 2023
PRIMARY
CAS
475-83-2
Created by admin on Sat Dec 16 08:01:35 GMT 2023 , Edited by admin on Sat Dec 16 08:01:35 GMT 2023
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PUBCHEM
10146
Created by admin on Sat Dec 16 08:01:35 GMT 2023 , Edited by admin on Sat Dec 16 08:01:35 GMT 2023
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WIKIPEDIA
Nuciferine
Created by admin on Sat Dec 16 08:01:35 GMT 2023 , Edited by admin on Sat Dec 16 08:01:35 GMT 2023
PRIMARY
FDA UNII
W26UEB90B7
Created by admin on Sat Dec 16 08:01:35 GMT 2023 , Edited by admin on Sat Dec 16 08:01:35 GMT 2023
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