Nuciferine

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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
SMILES
  • 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).
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Nuciferine is an

Nymphaea caerulea and Nelumbo nucifera.[1][2]

Preliminary psychopharmacological research in 1978 was unable to conclusively determine the compound's classification regarding dopamine-receptor activity.[3] On one hand, investigative studies found evidence of behavior traditionally associated with dopamine-receptor stimulation: stereotypy, increase in spontaneous motor activity, inhibition of conditioned avoidance response, and an increase in pain sensitivity resulting in an inhibition of morphine analgesia.[3] On the other hand, these early investigative studies also found evidence of behavior traditionally associated with dopamine-receptor blockade: decrease of spontaneous motor activity, chills, catalepsy, trance-like states of consciousness.[3]

Nuciferine exhibits a receptor profile similar to atypical

antipsychotics, demonstrating antipsychotic-like effects in rodent models without inducing catalepsy.[4]

Pharmacology

Nuciferine has been reported to have various anti-inflammatory effects, possibly mediated via PPAR delta activation.[5]

According to a newer study from 2016, Nuciferine acts as an

D4 receptors. Additionally, it inhibits the dopamine transporter (DAT).[4]

In rodent models relating to antipsychotic drug effects, Nuciferine has shown various actions such as blocking head-twitch responses and discriminative stimulus effects of a 5-HT2A agonist, enhancing amphetamine-induced locomotor activity, inhibiting phencyclidine (PCP)-induced locomotor activity, and restoring PCP-induced disruption of pre-pulse inhibition without inducing catalepsy.[4]

Nuciferine may also potentiate

analgesia. The median lethal dose in mice is 289 mg/kg. It is structurally related to apomorphine and other aporphine derivatives.[6][7]

See also

References

  1. ^ Seligman, Sian (2023-01-13). "Blue Lotus Flower: Smoking, Tea & More". DoubleBlind Mag. Retrieved 2023-01-19.
  2. PMID 26963248
    .
  3. ^
    S2CID 11847319
    .
  4. ^
    PMID 26963248
    .
  5. S2CID 51894703
    .
  6. S2CID 11847319
    .
  7. ^ Spess, David L. Errors in Alkaloids of Nelumbo and Nymphaea species, 2011, academia.edu
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