para-Nitrophenylpiperazine

*para*-Nitrophenylpiperazine
Clinical data
Other names	pNPP; 4-NPP; 4-Nitro-PP; PAL-175; PAL175
Drug class	Selective partial serotonin releasing agent
Identifiers
	IUPAC name 1-(4-nitrophenyl)piperazine;
CAS Number	6269-89-2;
PubChem CID	80447;
ChemSpider	72658;
UNII	SE8XST987K;
ChEMBL	ChEMBL165012;
CompTox Dashboard (EPA)	DTXSID40978310 ;
ECHA InfoCard	100.025.858
Chemical and physical data
Formula	C10H13N3O2
Molar mass	207.233 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CN(CCN1)C2=CC=C(C=C2)[N+](=O)[O-];
	InChI InChI=1S/C10H13N3O2/c14-13(15)10-3-1-9(2-4-10)12-7-5-11-6-8-12/h1-4,11H,5-8H2; Key:VWOJSRICSKDKAW-UHFFFAOYSA-N;

para-Nitrophenylpiperazine (pNPP; code name PAL-175) is a monoamine releasing agent of the phenylpiperazine family.^[1]^[2] It acts specifically as a selective partial serotonin releasing agent, with an EC₅₀Tooltip half-maximal effective concentration of 19 to 43 nM and an E_maxTooltip maximal efficacy of 57%.^[1]^[2] The drug was inactive as a releasing agent of dopamine or norepinephrine (EC₅₀ >10,000 nM).^[1]^[2] Its possible activity at serotonin receptors was not reported.^[1]^[2] pNPP was first described in the scientific literature by 2012.^[1]^[2]