Nuciferine

Nuciferine
Names
	Preferred 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
CAS Number	475-83-2 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL464529 ;
ChemSpider	9740 ;
PubChem CID	10146;
UNII	W26UEB90B7 ;
CompTox Dashboard (EPA)	DTXSID40963862 ;
	InChI 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 Key: ORJVQPIHKOARKV-OAHLLOKOSA-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
Chemical formula	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). verify (what is ?) Infobox references

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

Preliminary psychopharmacological research in 1978 was unable to conclusively determine the compound's classification in regards to dopamine-receptor activity.^[1] 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.^[1] 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.^[1]

Nuciferine may also potentiate morphine analgesia. The median lethal dose in mice is 289 mg/kg. It is structurally related to apomorphine.^[2]^[3]

Nuciferine has been reported to have various anti-inflammatory possibly via PPAR delta activation^[4] Nuciferine suppresses the SOX2-AKT/STAT3 signaling pathway in animal models. Targeting SOX-2 pathways in human models with Nuciferine may offer a novel therapeutic approach for cancer treatment.^[5]

References

^ ^a ^b ^c 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.
^ 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.
^ Spess, David L. Errors in Alkaloids of Nelumbo and Nymphaea species, 2011, academia.edu
^ 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.
^ Li, Zizhuo; Chen, Yaodong; An, Tingting; Liu, Pengfei; Zhu, Jiyuan; Yang, Haichao; Zhang, Wei; Dong, Tianxiu; Jiang, Jian; Zhang, Yu; Jiang, Maitao (2019-03-29). "Nuciferine inhibits the progression of glioblastoma by suppressing the SOX2-AKT/STAT3-Slug signaling pathway". Journal of Experimental & Clinical Cancer Research. 38 (1): 139. doi:10.1186/s13046-019-1134-y. ISSN 1756-9966. PMC 6440136. PMID 30922391.{{cite journal}}: CS1 maint: unflagged free DOI (link)

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[:0-1] 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.

[2] 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.

[3] Spess, David L. Errors in Alkaloids of Nelumbo and Nymphaea species, 2011, academia.edu

[4] 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.

[5] Li, Zizhuo; Chen, Yaodong; An, Tingting; Liu, Pengfei; Zhu, Jiyuan; Yang, Haichao; Zhang, Wei; Dong, Tianxiu; Jiang, Jian; Zhang, Yu; Jiang, Maitao (2019-03-29). "Nuciferine inhibits the progression of glioblastoma by suppressing the SOX2-AKT/STAT3-Slug signaling pathway". Journal of Experimental & Clinical Cancer Research. 38 (1): 139. doi:10.1186/s13046-019-1134-y. ISSN 1756-9966. PMC 6440136. PMID 30922391.{{cite journal}}: CS1 maint: unflagged free DOI (link)

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See also

References