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MedKoo Cat#: 530109 | Name: SIB-1553A HCl
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

SIB-1553A is a nicotinic acetylcholine receptor agonist potentially for the treatment of Alzheimer’s disease (AD).

Chemical Structure

SIB-1553A HCl
SIB-1553A HCl
CAS#191611-89-9

Theoretical Analysis

MedKoo Cat#: 530109

Name: SIB-1553A HCl

CAS#: 191611-89-9

Chemical Formula: C13H20ClNOS

Exact Mass: 0.0000

Molecular Weight: 273.82

Elemental Analysis: C, 57.02; H, 7.36; Cl, 12.95; N, 5.12; O, 5.84; S, 11.71

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 Weeks
5mg USD 550.00 2 weeks
10mg USD 700.00 2 weeks
50mg USD 1,450.00 2 weeks
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Related CAS #
No Data
Synonym
SIB1553A; SIB 1553A; SIB-1553A
IUPAC/Chemical Name
4-((2-(1-methylpyrrolidin-2-yl)ethyl)thio)phenol hydrochloride
InChi Key
RJSVKPQKXSMZMT-UHFFFAOYSA-N
InChi Code
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
SMILES Code
OC1=CC=C(SCCC2N(C)CCC2)C=C1.[H]Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Related CAS # 191611-76-4(SIB-1553A free base)
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Siamycin I is active against laboratory strains and clinical isolates of HIV-1 (ED50s = 0.05-0.45 and 0.89-5.7 μM, respectively), as well as the CBL-20 strain of HIV-2 (ED50 = 0.45 μM), in vitro. Siamycin I inhibits HIV-induced fusion of C8166 T cells with HIV-1-infected CEM-SS cells with an ED50 value of 0.08 μM.
In vitro activity:
To be determined
In vivo activity:
SIB-1553A, a potential neuronal nicotinic acetylcholine receptor (nAChR) ligand, exhibits selective properties and may contribute to our understanding of cognitive disorders. The compound induces neurotransmitter release in various brain regions, demonstrating partial agonist properties and cognitive-enhancing effects in rodent and primate models. SIB-1553A selectively targets beta4-subunit-containing recombinant nAChRs and displays lower efficacy than nicotine in activating human muscle-type AChRs. Reference: Brain Res. 2003 Aug 15;981(1-2):85-98. https://pubmed.ncbi.nlm.nih.gov/12885429/
Solvent mg/mL mM comments
Solubility
DMF 25.0 91.30
DMSO 20.0 73.04
Ethanol 10.0 36.52
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 273.82 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Rao TS, Reid RT, Correa LD, Santori EM, Gardner MF, Sacaan AI, Lorrain D, Vernier JM. In vivo pharmacological characterization of (+/-)-4-[2-(1-methyl-2-pyrrolidinyl)ethyl]thiophenol hydrochloride (SIB-1553A), a novel cholinergic ligand: microdialysis studies. Brain Res. 2003 Oct 3;986(1-2):71-81. doi: 10.1016/s0006-8993(03)03174-3. PMID: 12965231. 2. Rao TS, Adams PB, Correa LD, Santori EM, Sacaan AI, Reid RT, Suto CM, Vernier JM. In vitro pharmacological characterization of (+/-)-4-[2-(1-methyl-2-pyrrolidinyl)ethyl]thio]phenol hydrochloride (SIB-1553A), a nicotinic acetylcholine receptor ligand. Brain Res. 2003 Aug 15;981(1-2):85-98. doi: 10.1016/s0006-8993(03)02979-2. PMID: 12885429.
In vitro protocol:
To be determined
In vivo protocol:
1. Rao TS, Reid RT, Correa LD, Santori EM, Gardner MF, Sacaan AI, Lorrain D, Vernier JM. In vivo pharmacological characterization of (+/-)-4-[2-(1-methyl-2-pyrrolidinyl)ethyl]thiophenol hydrochloride (SIB-1553A), a novel cholinergic ligand: microdialysis studies. Brain Res. 2003 Oct 3;986(1-2):71-81. doi: 10.1016/s0006-8993(03)03174-3. PMID: 12965231. 2. Rao TS, Adams PB, Correa LD, Santori EM, Sacaan AI, Reid RT, Suto CM, Vernier JM. In vitro pharmacological characterization of (+/-)-4-[2-(1-methyl-2-pyrrolidinyl)ethyl]thio]phenol hydrochloride (SIB-1553A), a nicotinic acetylcholine receptor ligand. Brain Res. 2003 Aug 15;981(1-2):85-98. doi: 10.1016/s0006-8993(03)02979-2. PMID: 12885429.
1: Decamp E, Schneider JS. Interaction between nicotinic and dopaminergic therapies on cognition in a chronic Parkinson model. Brain Res. 2009 Mar 25;1262:109-14. doi: 10.1016/j.brainres.2009.01.028. Epub 2009 Feb 7. PMID: 19368843; PMCID: PMC2706019. 2: Sobrio F, Quentin T, Dhilly M, Bourdier T, Tymciu S, Debruyne D, Barré L. Radiosynthesis and ex vivo evaluation of [11C]-SIB-1553A as a PET radiotracer for beta4 selective subtype nicotinic acetylcholine receptor. Nucl Med Biol. 2008 Apr;35(3):377-85. doi: 10.1016/j.nucmedbio.2007.11.011. Epub 2008 Jan 30. PMID: 18355694. 3: Sunyer B, Patil S, Frischer C, Hoeger H, Lubec G. Strain-dependent effects of cognitive enhancers in the mouse. Amino Acids. 2008 Apr;34(3):485-95. doi: 10.1007/s00726-007-0511-6. Epub 2007 Aug 10. PMID: 17690951. 4: Decamp E, Schneider JS. Effects of nicotinic therapies on attention and executive functions in chronic low-dose MPTP-treated monkeys. Eur J Neurosci. 2006 Oct;24(7):2098-104. doi: 10.1111/j.1460-9568.2006.05077.x. PMID: 17067307. 5: Nikolov R. Alzheimer's disease therapy - an update. Drug News Perspect. 1998 May;11(4):248-55. PMID: 15616667. 6: Rao TS, Reid RT, Correa LD, Santori EM, Gardner MF, Sacaan AI, Lorrain D, Vernier JM. In vivo pharmacological characterization of (+/-)-4-[2-(1-methyl-2-pyrrolidinyl)ethyl]thiophenol hydrochloride (SIB-1553A), a novel cholinergic ligand: microdialysis studies. Brain Res. 2003 Oct 3;986(1-2):71-81. doi: 10.1016/s0006-8993(03)03174-3. PMID: 12965231. 7: Rao TS, Adams PB, Correa LD, Santori EM, Sacaan AI, Reid RT, Suto CM, Vernier JM. In vitro pharmacological characterization of (+/-)-4-[2-(1-methyl-2-pyrrolidinyl)ethyl]thio]phenol hydrochloride (SIB-1553A), a nicotinic acetylcholine receptor ligand. Brain Res. 2003 Aug 15;981(1-2):85-98. doi: 10.1016/s0006-8993(03)02979-2. PMID: 12885429. 8: Schneider JS, Tinker JP, Menzaghi F, Lloyd GK. The subtype-selective nicotinic acetylcholine receptor agonist SIB-1553A improves both attention and memory components of a spatial working memory task in chronic low dose 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-treated monkeys. J Pharmacol Exp Ther. 2003 Jul;306(1):401-6. doi: 10.1124/jpet.103.051912. Epub 2003 Apr 29. PMID: 12721323. 9: Bontempi B, Whelan KT, Risbrough VB, Lloyd GK, Menzaghi F. 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. Neuropsychopharmacology. 2003 Jul;28(7):1235-46. doi: 10.1038/sj.npp.1300150. Epub 2003 Apr 2. PMID: 12700710. 10: Terry AV Jr, Risbrough VB, Buccafusco JJ, Menzaghi F. 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. J Pharmacol Exp Ther. 2002 Apr;301(1):284-92. doi: 10.1124/jpet.301.1.284. PMID: 11907185. 11: Grottick AJ, Wyler R, Higgins GA. A study of the nicotinic agonist SIB-1553A on locomotion and attention as measured by the five-choice serial reaction time task. Pharmacol Biochem Behav. 2001 Dec;70(4):505-13. doi: 10.1016/s0091-3057(01)00639-6. PMID: 11796150. 12: Bontempi B, Whelan KT, Risbrough VB, Rao TS, Buccafusco JJ, Lloyd GK, Menzaghi F. 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. J Pharmacol Exp Ther. 2001 Oct;299(1):297-306. PMID: 11561092. 13: Vernier JM, El-Abdellaoui H, Holsenback H, Cosford ND, Bleicher L, Barker G, Bontempi B, Chavez-Noriega L, Menzaghi F, Rao TS, Reid R, Sacaan AI, Suto C, Washburn M, Lloyd GK, McDonald IA. 4-[[2-(1-Methyl-2-pyrrolidinyl)ethyl]thio]phenol hydrochloride (SIB-1553A): a novel cognitive enhancer with selectivity for neuronal nicotinic acetylcholine receptors. J Med Chem. 1999 May 20;42(10):1684-6. doi: 10.1021/jm990035d. PMID: 10346920. 14: Lloyd GK, Menzaghi F, Bontempi B, Suto C, Siegel R, Akong M, Stauderman K, Velicelebi G, Johnson E, Harpold MM, Rao TS, Sacaan AI, Chavez-Noriega LE, Washburn MS, Vernier JM, Cosford ND, McDonald LA. The potential of subtype- selective neuronal nicotinic acetylcholine receptor agonists as therapeutic agents. Life Sci. 1998;62(17-18):1601-6. doi: 10.1016/s0024-3205(98)00114-3. PMID: 9585143.