SN-22

SN-22
Clinical data
Other names3-(1-Methyl-4-piperidinyl)indole
Drug classSerotonin receptor modulator
Identifiers
  • 3-(1-methylpiperidin-4-yl)-1H-indole
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H18N2
Molar mass214.312 g·mol−1
3D model (JSmol)
  • CN1CCC(CC1)C2=CNC3=CC=CC=C32
  • InChI=1S/C14H18N2/c1-16-8-6-11(7-9-16)13-10-15-14-5-3-2-4-12(13)14/h2-5,10-11,15H,6-9H2,1H3
  • Key:KYSCKYJNMTUJPA-UHFFFAOYSA-N

SN-22, also known as 3-(1-methyl-4-piperidinyl)indole, is a serotonin receptor modulator of the piperidinylindole group related to the psychedelic drug dimethyltryptamine (DMT). Though it is not technically a tryptamine itself, SN-22 can be regarded as a constrained analogue of DMT.

The drug shows affinity for the serotonin 5-HT1A and 5-HT2A receptors (Ki = 146–514 nM and 19–67 nM, respectively). A deuterated isotopologue of SN-22 is known to be a serotonin 5-HT2A receptor agonist, albeit with lower potency than DMT.

The chemical synthesis of SN-22 has been described. Analogues of SN-22 include MTHPI, RU-24969 (5-MeO-THPI), RU-28253, and MPMI, among others. Derivatives include BRL-54443 (5-hydroxy-SN-22), LY-334370, naratriptan, and sertindole. Many other derivatives of SN-22 are also known, most of which are ligands for serotonin 5-HT1A, 5-HT2A, or 5-HT6 receptors, dopamine D2 receptors, or the serotonin transporter (SERT). Deuterated derivatives of SN-22 have been described as well. SN-22, along with MTHPI, shows some resemblance to MPTP in terms of chemical structure.

SN-22 was first described in the scientific literature by Ethan Will Taylor and colleagues by 1988.

See also

References

  1. 1 2 3 4 5 6 Taylor EW, Nikam SS, Lambert G, Martin AR, Nelson DL (July 1988). "Molecular determinants for recognition of RU 24969 analogs at central 5-hydroxytryptamine recognition sites: use of a bilinear function and substituent volumes to describe steric fit". Molecular Pharmacology. 34 (1): 42–53. doi:10.1016/S0026-895X(25)08646-8. PMID 3393140.
  2. 1 2 3 4 Agarwal A, Pearson PP, Taylor EW, Li HB, Dahlgren T, Herslöf M, et al. (December 1993). "Three-dimensional quantitative structure-activity relationships of 5-HT receptor binding data for tetrahydropyridinylindole derivatives: a comparison of the Hansch and CoMFA methods". Journal of Medicinal Chemistry. 36 (25): 4006–4014. doi:10.1021/jm00077a003. PMID 8258822.
  3. 1 2 Sabnis RW (2025). "Novel Serotonergic Psychedelic Agents as 5‑HT2A Agonists for Treating Psychosis, Mental Illness, and CNS Disorders". ACS Med Chem Lett. 16 (9): 1729–1730. doi:10.1021/acsmedchemlett.5c00484. PMC 12434528. PMID 40959237.
  4. 1 2 "3-cycloamino-indole compounds as serotonergic agents useful for the treatment of disorders related thereto". Google Patents. 19 August 2022. Retrieved 5 October 2026.
  5. ↑ Cole DC, Ellingboe JW, Lennox WJ, Mazandarani H, Smith DL, Stock JR, et al. (January 2005). "N1-arylsulfonyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole derivatives are potent and selective 5-HT6 receptor antagonists". Bioorganic & Medicinal Chemistry Letters. 15 (2): 379–383. doi:10.1016/j.bmcl.2004.10.064. PMID 15603958.
  6. ↑ Deskus JA, Epperson JR, Sloan CP, Cipollina JA, Dextraze P, Qian-Cutrone J, et al. (June 2007). "Conformationally restricted homotryptamines 3. Indole tetrahydropyridines and cyclohexenylamines as selective serotonin reuptake inhibitors". Bioorganic & Medicinal Chemistry Letters. 17 (11): 3099–104. doi:10.1016/j.bmcl.2007.03.040. PMID 17391962.
  7. ↑ Mattsson C, Andreasson T, Waters N, Sonesson C (November 2012). "Systematic in vivo screening of a series of 1-propyl-4-arylpiperidines against dopaminergic and serotonergic properties in rat brain: a scaffold-jumping approach". Journal of Medicinal Chemistry. 55 (22): 9735–9750. doi:10.1021/jm300975f. PMID 23043306.
  8. ↑ "Inhibition of serotonin reuptake". Google Patents. 30 July 1998. Retrieved 5 October 2026.