S-15535

S-15535 is a phenylpiperazine drug which is a potent and highly selective 5-HT_1A receptor ligand that acts as an agonist and antagonist (weak partial agonist) at the presynaptic and postsynaptic 5-HT_1A receptors, respectively.^[1]^[2]^[3]^[4] It has anxiolytic^[4]^[5] and antiaggressive effects.^[6]

ATC code

none

CAS Number

146998-34-7^Y

PubChem CID

132787

IUPHAR/BPS

Quick facts Clinical data, ATC code ...

S-15535
Clinical data

ATC code	none
Identifiers
IUPAC name 1-(2,3-dihydro-1,4-benzodioxin-8-yl)-4-(2,3-dihydro-1H-inden-2-yl)piperazine
CAS Number	146998-34-7^Y
PubChem CID	132787
IUPHAR/BPS	26
ChemSpider	117196^N
UNII	XE6KA72FCB
ChEMBL	ChEMBL49247^N
CompTox Dashboard (EPA)	DTXSID90163557
ECHA InfoCard	100.150.279
Chemical and physical data
Formula	C₂₁H₂₄N₂O₂
Molar mass	336.435 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1CN(CCN1C2CC3=CC=CC=C3C2)C4=C5C(=CC=C4)OCCO5
InChI InChI=1S/C21H24N2O2/c1-2-5-17-15-18(14-16(17)4-1)22-8-10-23(11-9-22)19-6-3-7-20-21(19)25-13-12-24-20/h1-7,18H,8-15H2^N Key:QJPPEMXOOWNICQ-UHFFFAOYSA-N^N
^NY (what is this?) (verify)

References

[1]
Millan MJ, Rivet JM, Canton H, Lejeune F, Gobert A, Widdowson P, Bervoets K, Brocco M, Peglion JL (1993). "S 15535: a highly selective benzodioxopiperazine 5-HT1A receptor ligand which acts as an agonist and an antagonist (weak partial agonist) at presynaptic and postsynaptic sites respectively". Eur J Pharmacol. 230 (1): 99–102. doi:10.1016/0014-2999(93)90416-F. PMID 8381359.
[2]
Millan MJ, Canton H, Gobert A, Lejeune F, Rivet JM, Bervoets K, Brocco M, Widdowson P, Mennini T, Audinot V, et al. (1994). "Novel benzodioxopiperazines acting as antagonists at postsynaptic 5-HT1A receptors and as agonists at 5-HT1A autoreceptors: a comparative pharmacological characterization with proposed 5-HT1A antagonists". J Pharmacol Exp Ther. 268 (1): 337–352. PMID 8301575.
[3]
Millan MJ, Newman-Tancredi A, Rivet JM, Brocco M, Lacroix P, Audinot V, Cistarelli L, Gobert A (1997). "S 15535, a novel benzodioxopiperazine ligand of serotonin (5-HT)1A receptors: I. Interaction with cloned human (h)5-HT1A, dopamine hD2/hD3 and h alpha2A-adrenergic receptors in relation to modulation of cortical monoamine release and activity in models of potential antidepressant activity". J Pharmacol Exp Ther. 282 (1): 132–147. PMID 9223549.
[4]
Lejeune F, Millan MJ (1998). "Induction of burst firing in ventral tegmental area dopaminergic neurons by activation of serotonin (5-HT)1A receptors: WAY 100,635-reversible actions of the highly selective ligands, flesinoxan and S 15535". Synapse. 30 (2): 172–180. doi:10.1002/(SICI)1098-2396(199810)30:2<172::AID-SYN7>3.0.CO;2-9. PMID 9723787.
[5]
Dekeyne A, Brocco M, Adhumeau A, Gobert A, Millan MJ (2000). "The selective serotonin (5-HT)1A receptor ligand, S15535, displays anxiolytic-like effects in the social interaction and Vogel models and suppresses dialysate levels of 5-HT in the dorsal hippocampus of freely-moving rats. A comparison with other anxiolytic agents". Psychopharmacology. 152 (1): 55–66. doi:10.1007/s002130000449. PMID 11041316. S2CID 2511149.
[6]
de Boer SF, Koolhaas JM (December 2005). "5-HT1A and 5-HT1B receptor agonists and aggression: a pharmacological challenge of the serotonin deficiency hypothesis". Eur J Pharmacol. 526 (1–3): 125–139. doi:10.1016/j.ejphar.2005.09.065. PMID 16310183.

See also

References

External links

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