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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

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Certificates of Analysis (COA)

Lot/Batch Number
0000128580
0000088862
033M4611V
128K46002
128K46001

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S M Jankovic et al.
Methods and findings in experimental and clinical pharmacology, 26(2), 87-91 (2004-04-09)
The Fallopian tubes are sparsely innervated with cholinergic nerve fibers. Acetylcholine is released from these nerves and contracts the smooth muscles of the tubes. The aim of our study was to investigate the effect of acetylcholine on the isthmic segment
M R Ruggieri et al.
Autonomic & autacoid pharmacology, 26(3), 311-325 (2006-08-02)
1 The M3 muscarinic receptor subtype is widely accepted as the receptor on smooth muscle cells that mediates cholinergic contraction of the normal urinary bladder and other smooth muscle tissues, however, we have found that the M2 receptor participates in
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
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
M T de la Vega et al.
Archives of medical research, 28(4), 493-497 (1997-01-01)
In this study, the authors set out to determine the presence of M3 muscarinic receptors in rat striatum by examining the binding of [3H]N-methylscopolamine ([3H]NMS) to striatal membranes and its displacement by antagonists with different affinity for M1 and M3
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