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S5321

Sigma-Aldrich

S15535

≥98% (HPLC), solid

Synonym(s):

1-(2,3-Dihydro-1,4-benzodioxin-5-yl)-4-(2,3-dihydro-1h-inden-2-yl)-piperazine

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About This Item

Empirical Formula (Hill Notation):
C21H24N2O2
CAS Number:
146998-34-7
Molecular Weight:
336.43
MDL number:
MFCD00911672
UNSPSC Code:
12352200
PubChem Substance ID:
329824452
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: ~6 mg/mL
H2O: insoluble

storage temp.

2-8°C

SMILES string

C1COc2c(O1)cccc2N3CCN(CC3)C4Cc5ccccc5C4

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

InChI key

QJPPEMXOOWNICQ-UHFFFAOYSA-N

Application

S15535 has been used as a serotonin 1A receptor (5-HT1A) agonist in zebrafish.
S15535 may be used in histamine 5-HT1A-medaited cell signaling studies.

Biochem/physiol Actions

S15535, a benzodioxane, is a selective but partial agonist of histamine serotonin 1A (5-HT1A) receptor. It activates presynaptic 5-HT1A receptors and suppresses the release of hippocampal 5-HT. It acts as an anxiolytic agent and modulates the cholinergic and cognitive function in rodents.
Potent, orally active, partial 5-HT1A receptor agonist

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

S5321-5MG:
S5321-BULK:
S5321-VAR:
S5321-25MG:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mark J Millan et al.
The Journal of pharmacology and experimental therapeutics, 311(1), 190-203 (2004-05-18)
These studies examined the influence of the selective 5-hydroxytryptamine (serotonin) (5-HT)(1A) receptor partial agonist S15535 [4-(benzodioxan-5-yl)1-(indan-2-yl)piperazine] upon cholinergic transmission and cognitive function in rodents. In the absence of acetylcholinesterase inhibitors, S15535 dose-dependently (0.04-5.0 mg/kg s.c.) elevated dialysis levels of acetylcholine
Jean-Louis Peglion et al.
Journal of medicinal chemistry, 45(1), 165-176 (2002-01-05)
S 15535 (1) displays a distinctive profile of agonist and antagonist (weak partial agonist) activity at pre- and postsynaptic 5-HT(1A) receptors, respectively. It has proven to be active in several models predictive of anxiolytic, antidepressant, and procognitive properties. In an
A Newman-Tancredi et al.
Neuropharmacology, 36(4-5), 451-459 (1997-04-01)
Membrane preparations were made from Chinese Hamster Ovary (CHO) cells expressing 1.6 and 4.2 pmol/mg of recombinant human 5-HT1A receptors, as determined by saturation binding with the selective antagonist, [3H]-S 15535 ([3H]-4-(benzodioxan-5-yl)]-(indan-2-yl)piperazine). There was no change in the number of
A Newman-Tancredi et al.
European journal of pharmacology, 307(1), 107-111 (1996-06-20)
In Chinese hamster ovary (CHO) cells expressing cloned human 5-HT1A receptors, S 15535 (4-(benzodioxan-5-yl)1-(indan-2-yl)piperazine) exhibited high affinity (Ki = 0.79 nM), similar to that of 5-HT (0.61 nM), (+/-)-8-hydroxy-3-(di-n-propylamino)tetralin ((+/-)-8-OH-DPAT; 0.58 nM) and N-{2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl}-N- (2-pyridinyl)cyclo-hexanecarboxamide (WAY 100.635; 0.56 nM). In
Jiun Youn et al.
Neuropharmacology, 57(5-6), 567-576 (2009-07-18)
5-HT(1A) receptors are implicated in the modulation of cognitive processes including encoding of fear learning. However, their exact role has remained unclear due to contrasting contributions of pre- vs. postsynaptic 5-HT(1A) receptors. Therefore, their role in fear conditioning was studied
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