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H127

Sigma-Aldrich

p-Fluorohexahydro-sila-difenidol hydrochloride

powder, ≥98% (HPLC)

Synonym(s):

Cyclohexyl-(4-fluorophenyl)-(3-N-piperidinopropyl)silanol hydrochloride, P-F-HHSiD hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C20H32FNOSi · HCl
CAS Number:
116679-83-5
Molecular Weight:
386.02
MDL number:
MFCD00078582
UNSPSC Code:
12352200
PubChem Substance ID:
24277841
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H2O: slightly soluble 1.5 mg/mL
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: >14 mg/mL
ethanol: soluble

SMILES string

Cl[H].O[Si](CCCN1CCCCC1)(C2CCCCC2)c3ccc(F)cc3

InChI

1S/C20H32FNOSi.ClH/c21-18-10-12-20(13-11-18)24(23,19-8-3-1-4-9-19)17-7-16-22-14-5-2-6-15-22;/h10-13,19,23H,1-9,14-17H2;1H

InChI key

JMTYYLMGSBSPPK-UHFFFAOYSA-N

Gene Information

human ... CHRM3(1131)

Application

p-Fluorohexahydro-sila-difenidol hydrochloride (pFHHSid) has been used:
  • as the M3/muscarinic acetylcholine receptor antagonist to study its involvement in carbachol induced Egr-1 biosynthesis using human neuroblastoma cells
  • as M3 receptor antagonist to test its involvement on N,N-diethyl-m-toluamide (DEET)-induced angiogenesis in human umbilical venous endothelial cells (HUVEC)
  • in a study to examine the role of aclidinium on human fibroblast to myofibroblast

Biochem/physiol Actions

High affinity M3 muscarinic acetylcholine receptor antagonist.

Features and Benefits

This compound is featured on the Acetylcholine Receptors (Muscarinic) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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

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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Kunrong Cheng et al.
American journal of physiology. Gastrointestinal and liver physiology, 295(3), G591-G597 (2008-07-26)
Most colon cancers overexpress M3 muscarinic receptors (M3R), and post-M3R signaling stimulates human colon cancer cell proliferation. Acetylcholine (ACh), a muscarinic receptor ligand traditionally regarded as a neurotransmitter, may be produced by nonneuronal cells. We hypothesized that ACh release by
Anthony D Miller et al.
The European journal of neuroscience, 21(7), 1837-1846 (2005-05-05)
Laterodorsal (LDT) and pedunculopontine (PPT) tegmental nuclei in the mesopontine project cholinergic inputs to the midbrain ventral tegmental area (VTA) and substantia nigra pars compacta (SNc), respectively, to directly and indirectly influence the activity of dopamine neuronal cells via actions
Oliver G Rössler et al.
Archives of biochemistry and biophysics, 470(1), 93-102 (2007-12-07)
Carbachol-mediated activation of type M(3) muscarinic acetylcholine receptors induces the biosynthesis of the transcription factor Egr-1 in human SH-SY5Y neuroblastoma cells involving an activation of extracellular signal-regulated protein kinase. Carbachol triggered the phosphorylation of the ternary complex factor Elk-1, a
Javier Milara et al.
Thorax, 67(3), 229-237 (2011-10-01)
Fibroblast to myofibroblast transition is believed to contribute to airway remodelling in lung diseases such as asthma and chronic obstructive pulmonary disease. This study examines the role of aclidinium, a new long-acting muscarinic antagonist, on human fibroblast to myofibroblast transition.
Dora E Benavides-Haro et al.
Naunyn-Schmiedeberg's archives of pharmacology, 368(4), 309-315 (2003-09-10)
The effect of the cholinomimetic agent, bethanechol on macroscopic membrane currents was studied in dispersed cat atrial myocytes, using the whole-cell patch-clamp technique. Bethanechol activated an inward rectifying potassium current similar to I(K(ACh)), and a delayed rectifying-like outward current, similar
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