Nuciferine

Nuciferine
Names
IUPAC name
1,2-Dimethoxy-6aβ-aporphine
Systematic IUPAC name
(6aR)-1,2-Dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
Other names
(R)-1,2-Dimethoxyaporphine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • 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 N
    Key: ORJVQPIHKOARKV-OAHLLOKOSA-N N
  • InChI=1/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
    Key: ORJVQPIHKOARKV-OAHLLOKOBA
  • CN(CC1)[C@]2([H])CC3=CC=CC=C3C4=C2C1=CC(OC)=C4OC
Properties
C19H21NO2
Molar mass 295.376 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox 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.