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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

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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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
L Oosterbosch et al.
Gut, 34(6), 794-798 (1993-06-01)
The aim was to investigate the action of serotonin (5HT) on function of the ileocolonic junction (ICJ) in vivo. In anaesthetised rats, models were developed to study the effects of intra-aortic (ia) serotonin on ileocolonic and colonic transit, and the
Daniel P Becker et al.
Bioorganic & medicinal chemistry letters, 14(12), 3073-3075 (2004-05-20)
Pyrrolizidine benzamide (+/-)-2, the bridgehead-methyl analog of SC-53116, was prepared and evaluated for 5-HT(4) agonism activity in the rat tunica muscularis (TMM) mucosae assay. Compound (+/-)-2 has an EC(50) of 449 nM in the TMM assay, as compared to 23
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
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