Chemistry:Piperlongumine

Piperlongumine

Names
Preferred IUPAC name 1-[(2E)-3-(3,4,5-Trimethoxyphenyl)prop-2-enoyl]-5,6-dihydropyridin-2(1H)-one
Other names Piplartine
Identifiers
CAS Number	20069-09-4 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL465843 Y
ChemSpider	553441 Y
PubChem CID	637858
UNII	SGD66V4SVJ Y
InChI InChI=1S/C17H19NO5/c1-21-13-10-12(11-14(22-2)17(13)23-3)7-8-16(20)18-9-5-4-6-15(18)19/h4,6-8,10-11H,5,9H2,1-3H3/b8-7+ Y Key: VABYUUZNAVQNPG-BQYQJAHWSA-N Y
SMILES O=C2\C=C/CCN2C(=O)\C=C\c1cc(OC)c(OC)c(OC)c1
Properties
Chemical formula	C17H19NO5
Molar mass	317.341 g·mol−1
Solubility	DMSO, DMF, ethanol
Hazards
Safety data sheet
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P264, P280
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Piperlongumine (also called piplartine or piperlongumin) is an amide alkaloid constituent of the fruit of the long pepper (Piper longum), a pepper plant found in southern India and southeast Asia. When extracted, piperlongumine may cause skin, eye or respiratory tract irritation.

Traditional medicine and research

Long peppers have been used in Ayurveda and traditional Chinese medicine as a treatment.

Targtex, a biotechnology spin-off of the Portuguese Institute for Molecular Biology, developed a piperlongumine hydrogel that is to be applied after the removal of Glioblastoma tumours, with the goal of neutralizing remaining cancer cells. The hydrogel was effective in laboratory and animal studies and is scheduled for Phase I human clinical trials sometime in 2023.