Nornuciferine

Nornuciferine

Clinical data
Other names	15781; 1,2-Dimethoxynoraporphine; N-Nornuciferine
Drug class	Serotonin 5-HT2C receptor agonist
ATC code	None
Identifiers
IUPAC name 1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
CAS Number	54750-04-8
PubChem CID	624491
ChemSpider	542509
UNII	XUR3H4VB7J
CompTox Dashboard (EPA)	DTXSID40203210
Chemical and physical data
Formula	C18H19NO2
Molar mass	281.355 g·mol^−1
3D model (JSmol)	Interactive image
SMILES COC1=C(C2=C3C(CC4=CC=CC=C42)NCCC3=C1)OC
InChI InChI=1S/C18H19NO2/c1-20-15-10-12-7-8-19-14-9-11-5-3-4-6-13(11)17(16(12)14)18(15)21-2/h3-6,10,14,19H,7-9H2,1-2H3 Key:QQKAHDMMPBQDAC-UHFFFAOYSA-N

Nornuciferine, also known as 15781 or as 1,2-dimethoxynoraporphine, is a noraporphine alkaloid found in Nelumbo nucifera and a serotonin 5-HT_2C receptor agonist related to the aporphine alkaloid nuciferine.^[1][2] It is the N-desmethyl analogue of nuciferine.^[1][2] The drug has been found to act as a selective partial agonist of the serotonin 5-HT_2C receptor, with an EC₅₀Tooltip half-maximal effective concentration of 653 nM and an E_maxTooltip maximal efficacy of 66% in terms of G_q signaling.^[1] Conversely, it was inactive as an agonist of the serotonin 5-HT_2A and 5-HT_2B receptors, but did show weak antagonism of these receptors at high concentrations.^[1] The serotonin 5-HT_2C receptor agonism of nornuciferine was described by Bingjie Zhang and colleagues in 2020.^[1]

See also

• Aporphine alkaloid
• Asimilobine
• 11-Chloroasimilobine
• 11-Methoxyasimilobine
• MQ02-439

References

1. Zhang B, Zhao S, Yang D, Wu Y, Xin Y, Cao H, et al. (February 2020). "A Novel G Protein-Biased and Subtype-Selective Agonist for a G Protein-Coupled Receptor Discovered from Screening Herbal Extracts". ACS Central Science. 6 (2): 213–225. doi:10.1021/acscentsci.9b01125. PMC 7047268. PMID 32123739.
2. Ye LH, He XX, You C, Tao X, Wang LS, Zhang MD, et al. (2018). "Pharmacokinetics of Nuciferine and N-Nornuciferine, Two Major Alkaloids From Nelumbo nucifera Leaves, in Rat Plasma and the Brain". Frontiers in Pharmacology. 9 902. doi:10.3389/fphar.2018.00902. PMC 6123365. PMID 30210336.