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C5366

Sigma-Aldrich

Chlorisondamine diiodide

≥98% (HPLC), white, solid

Synonym(s):

4,5,6,7-Tetrachloro-2,3-dihydro-2-methyl-2-[2-(trimethylammonio)ethyl]-2H-isoindolium diiodide

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About This Item

Empirical Formula (Hill Notation):
C14H20Cl4I2N2
CAS Number:
96750-66-2
Molecular Weight:
611.94
MDL number:
MFCD01074794
UNSPSC Code:
12352116
PubChem Substance ID:
24724443
NACRES:
NA.77

assay

≥98% (HPLC)

form

solid

storage condition

protect from light

color

white

solubility

H2O: ≥2 mg/mL
DMSO: >20 mg/mL

storage temp.

2-8°C

SMILES string

[I-].[I-].C[N+](C)(C)CC[N+]1(C)Cc2c(Cl)c(Cl)c(Cl)c(Cl)c2C1

InChI

1S/C14H20Cl4N2.2HI/c1-19(2,3)5-6-20(4)7-9-10(8-20)12(16)14(18)13(17)11(9)15;;/h5-8H2,1-4H3;2*1H/q+2;;/p-2

InChI key

FPNVAOZHQUJJJQ-UHFFFAOYSA-L

Application

Chlorisondamine diiodide has been used:
  • as a nicotinic receptor antagonist to test its effect on trinitrobenzene sulfonic acid (TNBS)-induced colitis
  • as an irreversible nicotinic acetylcholine(nAChR) blocker to pre-treat brain samples to test its effect on cytochrome P450 2B (CYP2B) induction
  • as a ganglionic blocker to test its effect on regulating corticosterone levels in rat with chronic stress

Biochem/physiol Actions

Chlorisondamine diiodide mediates ganglionic and central blockade.
Irreversible, long-lasting nicotinic acetylcholine receptor antagonist.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Acetylcholine Receptors (Nicotinic) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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G Costa et al.
Brain research, 888(2), 336-342 (2001-01-11)
While the work of several groups has shown the neuroprotective effects of nicotine in vitro, evidences for the same effects in vivo are controversial, mainly regarding neuroprotection in experimental models of Parkinson's disease. In this context, we investigated the capability
T Marenco et al.
British journal of pharmacology, 129(1), 147-155 (2000-02-29)
Chlorisondamine blocks central nicotinic receptors for many weeks via an unknown mechanism. Intracerebroventricular administration of [(3)H]-chlorisondamine in rats results in an anatomically restricted and persistent intracellular accumulation of radioactivity. The initial aim of the present study was to test whether
T Mori et al.
Molecular pharmacology, 59(4), 732-743 (2001-03-22)
Inhalational general anesthetics have recently been shown to inhibit neuronal nicotinic acetylcholine (ACh) receptors (nnAChRs) expressed in Xenopus laevis oocytes and in molluscan neurons. However, drug actions on these systems are not necessarily the same as those seen on native
A Bai et al.
Scandinavian journal of immunology, 66(5), 538-545 (2007-10-24)
Inflammatory bowel diseases (IBD) are characterized by proinflammatory cytokines, tissue damage and loss of neuron in inflamed mucosa, which implies the cholinergic anti-inflammatory pathway may be destroyed during the process of inflammatory response. In the study, we identified the effect
Colin S Cunningham et al.
Pharmacology, biochemistry, and behavior, 179, 27-33 (2019-02-10)
Mecamylamine is a non-competitive nicotinic acetylcholine receptor (nAChR) antagonist that has been prescribed for hypertension and as an off-label smoking cessation aid. Here, we examined pharmacological mechanisms underlying the interoceptive effects (i.e., discriminative stimulus effects) of mecamylamine (5.6 mg/kg s.c.)
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