1-(2-Naphthyl)piperazine

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]

Other names2-Naphthylpiperazine; 2-NP; 1-Deazaquipazine

Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen

ATC code

• None

CAS Number

• 57536-91-1

Quick facts Clinical data, Other names ...

1-(2-Naphthyl)piperazine

Clinical data
Other names	2-Naphthylpiperazine; 2-NP; 1-Deazaquipazine
Drug class	Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code	None
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

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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]