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nuciferine

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EntityQ7067904· pop 7· linked from 463 articles

nuciferine

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Also known as (R)-1,2-dimethoxyaporphine

Nuciferine is an alkaloid found within the plants Nymphaea caerulea and Nelumbo nucifera.

Chemical data

Formula
C19H21NO2
Molecular weight
295.4 g/mol
IUPAC name
(6aR)-1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
SMILES
CN1CCC2=CC(=C(C3=C2[C@H]1CC4=CC=CC=C43)OC)OC
InChIKey
ORJVQPIHKOARKV-OAHLLOKOSA-N
XLogP
3.4
Polar surface area
21.7 Ų
H-bond donors
0
H-bond acceptors
3
Formal charge
0

via PubChem

Drug data · ChEMBL

Molecule type
Small molecule

via ChEMBL · EBI

Wikidata facts

Mass
295.157228912
Show 4 more facts
found in taxon
Nelumbo nucifera
canonical SMILES
CN1CCC2=CC(=C(C3=C2C1CC4=CC=CC=C43)OC)OC
chemical formula
C₁₉H₂₁NO₂
isomeric SMILES
CN1CCc2cc(c(c-3c2[C@H]1Cc4c3cccc4)OC)OC
Sources (2)

via Wikidata · CC0

~2 min read

Encyclopedic overview

3 sections
Contents
  • Pharmacology
  • See also
  • References

Nuciferine is an alkaloid found within the plants Nymphaea caerulea and Nelumbo nucifera.

Nuciferine, an aporphine derivative structurally related to apomorphine, exhibits complex pharmacological effects: early studies show it had effect demonstrating dopamine blockade, producing neuroleptic effects, while its degradation product, atherosperminine, stimulates dopamine receptors. More recent research indicates nuciferine acts on multiple serotonin and dopamine receptors (as an antagonist, partial agonist, inverse agonist, or full agonist depending on the receptor) and inhibits the dopamine transporter. In rodent models, it demonstrates antipsychotic-like effects, modulates locomotor activity, restores PCP-induced sensory gating deficits, and may enhance morphine analgesia without causing catalepsy. It also shows potential anti-inflammatory effects, possibly through PPAR delta activation, with a reported median lethal dose of 289 mg/kg in mice.

Excerpted from Wikipedia’s “nuciferine” article, available under the CC BY-SA 4.0 licence.

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