SIB 1553A hydrochloride - CAS 191611-89-9
Category: Inhibitor
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Molecular Formula:
C13H19NOS.HCl
Molecular Weight:
273.82
COA:
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Targets:
nAChR
Description:
SIB 1553A hydrochloride is a nicotinic acetylcholine receptor (nAChR) agonist with selectivity for β4 subunit-containing receptors. It stimulates acetylcholine levels and other neurotransmitters relevant for cognitive processes, and acts as a cognitive enhancer potentially used for the treatment of Alzheimer's disease (AD).
Brife Description:
nAChR agonist
Purity:
≥98% by HPLC
Related CAS:
191611-76-4 (free base)
Synonyms:
SIB1553A; SIB 1553A; SIB-1553A; (±)-4-[[2-(1-Methyl-2-pyrrolidinyl)ethyl]thio]phenol hydrochloride
MSDS:
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Application:
potential treatment of Alzheimer's disease
InChIKey:
RJSVKPQKXSMZMT-UHFFFAOYSA-N
InChI:
InChI=1S/C13H19NOS.ClH/c1-14-9-2-3-11(14)8-10-16-13-6-4-12(15)5-7-13;/h4-7,11,15H,2-3,8-10H2,1H3;1H
Canonical SMILES:
CN1CCCC1CCSC2=CC=C(C=C2)O.Cl
1.Cognitive enhancing properties and tolerability of cholinergic agents in mice: a comparative study of nicotine, donepezil, and SIB-1553A, a subtype-selective ligand for nicotinic acetylcholine receptors.
Bontempi B;Whelan KT;Risbrough VB;Lloyd GK;Menzaghi F Neuropsychopharmacology. 2003 Jul;28(7):1235-46. Epub 2003 Apr 2.
Several studies have demonstrated the importance of nicotinic mechanisms in the pathophysiology of neurodegenerative and cognitive disorders, warranting the search and development of novel nicotinic ligands as potential therapeutic agents. The present study was designed to assess whether the subtype-selective nicotinic acetylcholine receptor (nAChR) ligand SIB-1553A [(+/-)-4-([2-(1-methyl-2-pyrrolidinyl)ethyl]thio)phenol hydrochloride], with predominant agonist activity at beta4 subunit-containing human nAChRs, and no activity at muscle nAChR subtypes, could enhance cognitive performance in rodents with a more desirable safety/tolerability profile as compared to the nonselective prototypic nAChR ligand nicotine. SIB-1553A was equi-efficacious to nicotine in improving working memory performance in scopolamine-treated mice as measured by increased alternation in a T-maze, and was more efficacious than nicotine in improving the baseline cognitive performance of aged mice. This effect on working memory was confirmed in a delayed nonmatching to place task using the eight-arm radial maze. SIB-1553A produced dose-dependent side effects (ie motor deficits and seizures), although these effects were observed at doses 12 to 640-fold above those required to increase cognitive performance.
2.Effects of (+/-)-4-[[2-(1-methyl-2-pyrrolidinyl)ethyl]thio]phenol hydrochloride (SIB-1553A), a selective ligand for nicotinic acetylcholine receptors, in tests of visual attention and distractibility in rats and monkeys.
Terry AV Jr;Risbrough VB;Buccafusco JJ;Menzaghi F J Pharmacol Exp Ther. 2002 Apr;301(1):284-92.
Nicotine, a nonselective ligand for nicotinic acetylcholine receptors (nAChRs), has been shown to improve attention and reduce distractibility in humans. Although the numerous side effects induced by nicotine prevent its use as a therapeutic agent, it is hypothesized that subtype-selective nAChR ligands may offer a potential therapeutic benefit to humans with attention deficits. In this study, we evaluated the attention-enhancing properties of (+/-)-4-[[2-(1-methyl-2-pyrrolidinyl)ethyl]thio]phenol hydrochloride (SIB-1553A), a ligand selective for neuronal nAChRs with predominant activity at the human beta 4 subtype. SIB-1553A was evaluated in a test of attention (i.e., five-choice serial reaction time task or SRTT) and distractibility (i.e., delayed matching to sample task with distractor or DMTS-D) in adult rats and monkeys, respectively. SIB-1553A did not improve SRTT performance in normal rats, but reversed deficits induced by the N-methyl-D-aspartate (NMDA) antagonist dizocilpine. In the DMTS-D, SIB-1553A improved accuracy across several doses at the short delay intervals, which were affected most by distracting stimuli in adult monkeys. Subsequent testing with optimal doses for each monkey was also associated with significant improvements in DMTS-D accuracy at short delays, indicating the reproducibility of the drug effect.
3.SIB-1553A, (+/-)-4-[[2-(1-methyl-2-pyrrolidinyl)ethyl]thio]phenol hydrochloride, a subtype-selective ligand for nicotinic acetylcholine receptors with putative cognitive-enhancing properties: effects on working and reference memory performances in aged rodents and nonhuman primates.
Bontempi B;Whelan KT;Risbrough VB;Rao TS;Buccafusco JJ;Lloyd GK;Menzaghi F J Pharmacol Exp Ther. 2001 Oct;299(1):297-306.
Preclinical and clinical data have suggested the potential use of nicotinic acetylcholine receptor (nAChR) ligands for treating cognitive dysfunction associated with neurodegenerative diseases, such as Alzheimer's disease. SIB-1553A, (+/-)-4-[[2-(1-methyl-2-pyrrolidinyl)ethyl]thio]phenol hydrochloride, a novel nAChR ligand with predominant agonist subtype selectivity for beta4 subunit-containing human neuronal nAChRs, was tested in a variety of cognitive paradigms in aged rodents and nonhuman primates after acute and repeated administration. Subcutaneous administration of SIB-1553A improved delayed nonmatching to place performance in aged mice. In aged rhesus monkeys, intramuscular and oral administration of SIB-1553A improved choice accuracy in a delayed matching to sample task. SIB-1553A improved performances in these spatial and nonspatial working memory tasks but was less effective at improving performances in spatial reference memory tasks (i.e., aged rodents exposed to a discrimination task in a T-maze or trained to locate a hidden platform in a water maze). These data suggest that SIB-1553A has a predominant effect on attention/working memory processes. SIB-1553A also induced the release of acetylcholine in the hippocampus of aged rats and was equally effective whether administered acutely or repeatedly (6 weeks of daily subcutaneous administration).
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CAS 191611-89-9 SIB 1553A hydrochloride

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