1-(2-Naphthyl)piperazine

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1-(2-Naphthyl)piperazine
2-Naphthylpiperazine.svg
Clinical data
Other names2-Naphthylpiperazine; 2-NP; 1-Deazaquipazine
Drug class Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
Identifiers
  • 1-naphthalen-2-ylpiperazine
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
Formula C14H16N2
Molar mass 212.296 g·mol−1
3D model (JSmol)
  • C1CN(CCN1)C2=CC3=CC=CC=C3C=C2
  • 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]

Contents

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. [3] [2] [4] [5] Conversely, it has negligible affinity for the serotonin 5-HT1D 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-HT2A 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

References

  1. ↑ Glennon RA, Dukat M (2 May 2023). "Quipazine: Classical hallucinogen? Novel psychedelic?". Australian Journal of Chemistry. 76 (5): 288–298. doi:10.1071/CH22256. ISSN   0004-9425.
  2. 1 2 3 4 5 6 de la Fuente Revenga M, Shah UH, Nassehi N, Jaster AM, Hemanth P, Sierra S, et al. (March 2021). "Psychedelic-like Properties of Quipazine and Its Structural Analogues in Mice". ACS Chemical Neuroscience. 12 (5): 831–844. doi:10.1021/acschemneuro.0c00291. PMC   7933111 . PMID   33400504.
  3. 1 2 3 4 Glennon RA, Slusher RM, Lyon RA, Titeler M, McKenney JD (November 1986). "5-HT1 and 5-HT2 binding characteristics of some quipazine analogues". Journal of Medicinal Chemistry. 29 (11): 2375–2380. doi:10.1021/jm00161a038. PMID   3783595.
  4. ↑ Dukat M, Abdel-Rahman AA, Ismaiel AM, Ingher S, Teitler M, Gyermek L, et al. (September 1996). "Structure-activity relationships for the binding of arylpiperazines and arylbiguanides at 5-HT3 serotonin receptors". Journal of Medicinal Chemistry. 39 (20): 4017–4026. doi:10.1021/jm9603936. PMID   8831767.
  5. ↑ Glennon RA, Ismaiel AE, McCarthy BG, Peroutka SJ (September 1989). "Binding of arylpiperazines to 5-HT3 serotonin receptors: results of a structure-affinity study". European Journal of Pharmacology. 168 (3): 387–392. doi:10.1016/0014-2999(89)90802-9. PMID   2583244.
  6. ↑ Glennon RA, Ismaiel AM, Chaurasia C, Titeler M (1991). "5-HT 1D serotonin receptors: Results of a structure-affinity investigation". Drug Development Research. 22 (1): 25–36. doi:10.1002/ddr.430220103. ISSN   0272-4391.
  7. ↑ Sutherland GJ (1961). "The thermal decomposition of some N,N'-diarylethylenediamine hydrobromides". University of Canterbury. Chemistry. Retrieved 13 March 2025.
  8. ↑ Červená I, Dlabač A, Němec J, Protiva M (1975). "Naphthylpiperazines and tetralylpiperazines: Synthesis and pharmacological properties". Collection of Czechoslovak Chemical Communications. 40 (5): 1612–1622. doi:10.1135/cccc19751612. ISSN   0010-0765.
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