1-(2-Naphthyl)piperazine

vanc 6 2-Naphthylpiperazine.svg skin-invert-image 225px Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen None correct CAS 57536-91-1 2760172 2040919 correct FDA VT749H8YJE 278509 2-Naphthylpiperazine; 2-NP; 1-Deazaquipazine 1-naphthalen-2-ylpiperazine 14 16 2 C1CN(CCN1)C2=CC3=CC=CC=C3C=C2 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 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. Glennon RA, Dukat M Quipazine: Classical hallucinogen? Novel psychedelic? Australian Journal of Chemistry 76 5 2 May 2023 0004-9425 10.1071/CH22256 288–298 de la Fuente Revenga M, Shah UH, Nassehi N, Jaster AM, Hemanth P, Sierra S, Dukat M, González-Maeso J Psychedelic-like Properties of Quipazine and Its Structural Analogues in Mice ACS Chemical Neuroscience 12 5 831–844 March 2021 33400504 7933111 10.1021/acschemneuro.0c00291 Glennon RA, Slusher RM, Lyon RA, Titeler M, McKenney JD 5-HT1 and 5-HT2 binding characteristics of some quipazine analogues Journal of Medicinal Chemistry 29 11 2375–2380 November 1986 3783595 10.1021/jm00161a038 It shows affinity for the serotonin 5-HT1, 5-HT2, and 5-HT3 receptors and is known to act as a serotonin 5-HT2A receptor partial agonist. Dukat M, Abdel-Rahman AA, Ismaiel AM, Ingher S, Teitler M, Gyermek L, Glennon RA Structure-activity relationships for the binding of arylpiperazines and arylbiguanides at 5-HT3 serotonin receptors Journal of Medicinal Chemistry 39 20 4017–4026 September 1996 8831767 10.1021/jm9603936 Glennon RA, Ismaiel AE, McCarthy BG, Peroutka SJ Binding of arylpiperazines to 5-HT3 serotonin receptors: results of a structure-affinity study European Journal of Pharmacology 168 3 387–392 September 1989 2583244 10.1016/0014-2999(89)90802-9 Conversely, it has negligible affinity for the serotonin 5-HT1D receptor. Glennon RA, Ismaiel AM, Chaurasia C, Titeler M 5-HT 1D serotonin receptors: Results of a structure-affinity investigation Drug Development Research 22 1 1991 0272-4391 10.1002/ddr.430220103 25–36 The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, although it was less efficacious than quipazine. This effect was absent in serotonin 5-HT2A receptor knockout mice. In addition, 2-NP fully generalizes to the psychedelic DOM in animal drug discrimination tests. Hence, it may have hallucinogenic effects in humans. 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. It was first described in the scientific literature by at least 1961. Sutherland GJ The thermal decomposition of some N,N'-diarylethylenediamine hydrobromides University of Canterbury. Chemistry 1961 https://ir.canterbury.ac.nz/items/661a3a34-1f3d-4f89-aac2-685b1d1db7a3 13 March 2025 Červená I, Dlabač A, Němec J, Protiva M Naphthylpiperazines and tetralylpiperazines: Synthesis and pharmacological properties Collection of Czechoslovak Chemical Communications 40 5 1975 0010-0765 10.1135/cccc19751612 1612–1622 See also Substituted piperazine Substituted naphthylethylamine 1-(1-Naphthyl)piperazine (1-NP) CPQ VCU-1012 (3-azaquipazine) References External links 2-NP - Isomer Design Category:5-HT2A agonists Category:2-Naphthyl compounds Category:Psychedelic arylpiperazines Category:Serotonin receptor agonists