1-(2-Naphthyl)piperazine

1-(2-Naphthyl)piperazine
Clinical data
Other names	2-Naphthylpiperazine; 2-NP; 1-Deazaquipazine
Drug class	Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
Identifiers
	IUPAC name 1-naphthalen-2-ylpiperazine;
CAS Number	57536-91-1;
PubChem CID	2760172;
ChemSpider	2040919;
ChEMBL	ChEMBL278509;
Chemical and physical data
Formula	C14H16N2
Molar mass	212.296 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CN(CCN1)C2=CC3=CC=CC=C3C=C2;
	InChI InChI=1S/C14H16N2/c1-2-4-13-11-14(6-5-12(13)3-1)16-9-7-15-8-10-16/h1-6,11,15H,7-10H2; Key:LWLBVIFUVSUSAY-UHFFFAOYSA-N;

1-(2-Naphthyl)piperazine (2-NP), also known as 1-deazaquipazine, is a serotonin receptor modulator and putative serotonergic psychedelic of the arylpiperazine family related to quipazine.^[1]^[2]^[3]

Quick Facts Clinical data, Other names ...

It shows affinity for the serotonin 5-HT₁, 5-HT₂, and 5-HT₃ receptors and is known to act as a serotonin 5-HT_2A receptor partial agonist.^[3]^[2]^[4]^[5] Conversely, it has negligible affinity for the serotonin 5-HT_1D receptor.^[6] The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, although it was less efficacious than quipazine.^[2] This effect was absent in serotonin 5-HT_2A receptor knockout mice.^[2] In addition, 2-NP fully generalizes to the psychedelic DOM in animal drug discrimination tests.^[3] Hence, it may have hallucinogenic effects in humans.^[2]

Along with quipazine, the drug is one of a relatively small number of known psychedelics that is distinct from the tryptamine, phenethylamine, and lysergamide families.^[2] It was first described in the scientific literature by at least 1961.^[7]^[8]^[3]

See also