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PZ0146

Sigma-Aldrich

SC-53116 hydrochloride hydrate

≥98% (HPLC)

Synonym(s):

4-Amino-5-chloro-N-[[(1S,7aS)-hexahydro-1H-pyrrolizin-1-yl]methyl]-2-methoxy-benzamide, SC 49518 hydrate

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About This Item

Empirical Formula (Hill Notation):
C16H22ClN3O2 · HCl · xH2O
CAS Number:
141196-99-8
Molecular Weight:
360.28 (anhydrous basis)
UNSPSC Code:
12352200
PubChem Substance ID:
329823731
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

, white to yellow to brown

solubility

H2O: 10 mg/mL, clear

storage temp.

2-8°C

SMILES string

O.Cl.COc1cc(N)c(Cl)cc1C(=O)NC[C@@H]2CCN3CCCC23

InChI

1S/C16H22ClN3O2.ClH.H2O/c1-22-15-8-13(18)12(17)7-11(15)16(21)19-9-10-4-6-20-5-2-3-14(10)20;;/h7-8,10,14H,2-6,9,18H2,1H3,(H,19,21);1H;1H2/t10-,14-;;/m0../s1

InChI key

CZXMPKPHHWPFSI-UROSVOJDSA-N

Biochem/physiol Actions

SC-53116 is a 5-HT4 receptor partial agonist. SC-53116 has been shown to ameliorate scopolamine-induced impairment in learning in rats at a does of 10 μg/rat i.c.v and increase population spike amplitude in the CA1 and CA3 fields of the hippocampus at the same concentration.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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P G McLean et al.
Naunyn-Schmiedeberg's archives of pharmacology, 354(4), 513-519 (1996-10-01)
The effects of chronic infusion with 5-hydroxytryptamine (5-HT, 75 micrograms/kg per hour) for 5 or 10 days in vivo on the responses of rat oesophagus, fundus and jejunum to 5-HT and partial 5-HT receptor agonists in vitro were investigated. In
S S Hegde et al.
Naunyn-Schmiedeberg's archives of pharmacology, 351(6), 589-595 (1995-06-01)
It is well documented that certain substituted benzamides, such as cisapride, and benzimidazolones, such as BIMU 8, enhance gastric emptying in rats. As these compounds possess 5-HT3 antagonistic and 5-HT4 agonistic properties, the precise mechanisms (5-HT3 or 5-HT4) underlying their
Laurie B Schenkel et al.
Organic letters, 6(20), 3621-3624 (2004-09-25)
[reaction: see text] Highly diastereoselective intra- and intermolecular self-condensation reactions of N-tert-butanesulfinyl aldimines have been developed and applied to the rapid, asymmetric synthesis of trans-2-aminocyclopentanecarboxylic acid and the drug candidate SC-53116. Key to both syntheses is a novel microwave-assisted reaction
SC-53116: the first selective agonist at the newly identified serotonin 5-HT4 receptor subtype.
D L Flynn et al.
Journal of medicinal chemistry, 35(8), 1486-1489 (1992-04-17)
P G McLean et al.
British journal of pharmacology, 115(1), 47-56 (1995-05-01)
1. The pharmacological properties of 5-hydroxytryptamine (5-HT), the 5-HT4 receptor agonists, DAU 6236 and SC 53116 and the 5-HT4 receptor antagonist, GR 1130808, were studied in the rat oesophagus, rat ileum and human colon. 2. 5-HT relaxed the longitudinal muscle
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