Nuciferine

Last updated
Nuciferine
Nuciferine Structure.svg
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
PubChem CID
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 X mark.svgN
    Key: ORJVQPIHKOARKV-OAHLLOKOSA-N X mark.svgN
  • 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).
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Nuciferine is an alkaloid found within the plants Nymphaea caerulea and Nelumbo nucifera . [1] [2]

Contents

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.

Pharmacology

A 1978 study found that nuciferine acts as a dopamine-receptor blocker producing neuroleptic effects, whereas its Hofmann degradation product atherosperminine stimulates dopamine receptors, producing opposing psychopharmacological effects. [3]

According to a newer study from 2016, Nuciferine acts as an antagonist at 5-HT2A, 5-HT2C, and 5-HT2B receptors, an inverse agonist at the 5-HT7 receptor, a partial agonist at D2, D5, and 5-HT6 receptors, and an agonist at 5-HT1A and 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 morphine analgesia. The median lethal dose in mice is 289 mg/kg. It is structurally related to apomorphine and other aporphine derivatives. [5] [6]

Nuciferine has been reported to have various anti-inflammatory effects, possibly mediated via PPAR delta activation. [7]

See also

References

  1. ↑ Seligman, Sian (2023-01-13). "Blue Lotus Flower: Smoking, Tea & More". DoubleBlind Mag. Retrieved 2023-01-19.
  2. ↑ Farrell, Martilias S.; McCorvy, John D.; Huang, Xi-Ping; Urban, Daniel J.; White, Kate L.; Giguere, Patrick M.; Doak, Allison K.; Bernstein, Alison I.; Stout, Kristen A.; Park, Su Mi; Rodriguiz, Ramona M.; Gray, Bradley W.; Hyatt, William S.; Norwood, Andrew P.; Webster, Kevin A. (2016). "In Vitro and In Vivo Characterization of the Alkaloid Nuciferine". PLOS ONE. 11 (3): e0150602. Bibcode:2016PLoSO..1150602F. doi: 10.1371/journal.pone.0150602 . ISSN   1932-6203. PMC   4786259 . PMID   26963248.{{cite journal}}: CS1 maint: article number as page number (link)
  3. ↑ Bhattacharya, S. K.; Bose, R.; Ghosh, P.; Tripathi, V. J.; Ray, A. B.; Dasgupta, B. (1978-09-15). "Psychopharmacological studies on (--)-nuciferine and its Hofmann degradation product atherosperminine". Psychopharmacology. 59 (1): 29–33. doi:10.1007/bf00428026. ISSN   0033-3158. PMID   100809. S2CID   11847319.
  4. 1 2 Farrell, Martilias S.; McCorvy, John D.; Huang, Xi-Ping; Urban, Daniel J.; White, Kate L.; Giguere, Patrick M.; Doak, Allison K.; Bernstein, Alison I.; Stout, Kristen A.; Park, Su Mi; Rodriguiz, Ramona M.; Gray, Bradley W.; Hyatt, William S.; Norwood, Andrew P.; Webster, Kevin A. (2016-03-10). "In Vitro and In Vivo Characterization of the Alkaloid Nuciferine". PLOS ONE. 11 (3): e0150602. Bibcode:2016PLoSO..1150602F. doi: 10.1371/journal.pone.0150602 . ISSN   1932-6203. PMC   4786259 . PMID   26963248.{{cite journal}}: CS1 maint: article number as page number (link)
  5. ↑ Bhattacharya SK, Bose R, Ghosh P, Tripathi VJ, Ray AB, Dasgupta B (Sep 1978). "Psychopharmacological studies on (—)-nuciferine and its Hofmann degradation product atherosperminine". Psychopharmacology. 59 (1): 29–33. doi:10.1007/BF00428026. PMID   100809. S2CID   11847319.
  6. ↑ Spess, David L. Errors in Alkaloids of Nelumbo and Nymphaea species, 2011, academia.edu
  7. ↑ Zhang, Lina; Gao, Jinghua; Tang, Peng; Chong, Li; Liu, Yue; Liu, Peng; Zhang, Xin; Chen, Li; Hou, Chen (October 2018). "Nuciferine inhibits LPS-induced inflammatory response in BV2 cells by activating PPAR-γ". International Immunopharmacology. 63: 9–13. doi:10.1016/j.intimp.2018.07.015. ISSN   1878-1705. PMID   30056259. S2CID   51894703.
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