C5366

Chlorisondamine diiodide

Name: Chlorisondamine diiodide
Brand: SIGMA

≥98% (HPLC), nicotinic acetylcholine receptor antagonist, 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

UNSPSC Code:

12352116

PubChem Substance ID:

24724443

NACRES:

NA.77

MDL number:

MFCD01074794

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

200

Storage condition:

protect from light

Key Documents

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Product Name

Chlorisondamine diiodide, ≥98% (HPLC), white, solid

SMILES string

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

InChI key

FPNVAOZHQUJJJQ-UHFFFAOYSA-L

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

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

Quality Level

200

Related Categories

Bioactive Small Molecules

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Show Differences

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This Item	SML1402	A9605	N8914
Sigma-Aldrich C5366 Chlorisondamine diiodide	Sigma-Aldrich SML1402 TCID	Sigma-Aldrich A9605 AC-93253 iodide	Sigma-Aldrich N8914 NSC308848
form solid	form powder	form solid	form powder
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C
solubility H₂O: ≥2 mg/mL, DMSO: >20 mg/mL	solubility DMSO: 5 mg/mL, clear	solubility DMSO: >10 mg/mL, H₂O: insoluble	solubility DMSO: >20 mg/mL
storage condition protect from light	storage condition -	storage condition desiccated	storage condition protect from light
color white	color white to light brown	color dark purple	color yellow

Application

Chlorisondamine diiodide has been used:

as a nicotinic receptor antagonist to test its effect on trinitrobenzene sulfonic acid (TNBS)-induced colitis[1]
as an irreversible nicotinic acetylcholine(nAChR) blocker to pre-treat brain samples to test its effect on cytochrome P450 2B (CYP2B) induction[2]
as a ganglionic blocker to test its effect on regulating corticosterone levels in rat with chronic stress[3]

Biochem/physiol Actions

Chlorisondamine diiodide mediates ganglionic and central blockade.[4]

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

GHS07,GHS09

signalword

Warning

hcodes

H302,H400

pcodes

P273 - P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Discriminative stimulus effects of mecamylamine and nicotine in rhesus monkeys: Central and peripheral mechanisms.

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.)

The effect of the cholinergic anti-inflammatory pathway on experimental colitis.

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

Sympathetic nervous system contributes to enhanced corticosterone levels following chronic stress.

Steven A Lowrance et al.

Psychoneuroendocrinology, 68, 163-170 (2016-03-15)

Exposure to chronic stress often elevates basal circulating glucocorticoids during the circadian nadir and leads to exaggerated glucocorticoid production following exposure to subsequent stressors. While glucocorticoid production is primarily mediated by the hypothalamic-pituitary-adrenal (HPA) axis, there is evidence that the

Cardiovascular effects of nicotine, chlorisondamine, and mecamylamine in the pigeon.

Kathryn K Chadman et al.

The Journal of pharmacology and experimental therapeutics, 308(1), 73-78 (2003-10-21)

Chlorisondamine and mecamylamine are nicotinic antagonists that produce both ganglionic and central blockade. Chlorisondamine, when administered as a large systemic dose, produces a persistent central block, despite being charged. The present study evaluated the cardiovascular effects of chlorisondamine. Shortly after

Rat brain CYP2B induction by nicotine is persistent and does not involve nicotinic acetylcholine receptors.

Jibran Y Khokhar et al.

Brain research, 1348, 1-9 (2010-07-06)

CYP2B is a drug-metabolizing enzyme expressed in the liver and brain that metabolizes a variety of centrally acting drugs (e.g. propofol, bupropion and nicotine), endogenous neurochemicals (e.g. serotonin and testosterone) and toxins (e.g. chlorpyrifos). Human CYP2B6 is found at higher

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