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Details

Stereochemistry ACHIRAL
Molecular Formula C14H20Cl4N2
Molecular Weight 358.134
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 2

SHOW SMILES / InChI
Structure of CHLORISONDAMINE

SMILES

C[N+](C)(C)CC[N+]1(C)CC2=C(C1)C(Cl)=C(Cl)C(Cl)=C2Cl

InChI

InChIKey=IXWDUZLHWJKVPX-UHFFFAOYSA-N
InChI=1S/C14H20Cl4N2/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/q+2

HIDE SMILES / InChI
CHLORISONDAMINE is a nicotinic acetylcholine receptor antagonist used as a ganglionic blocking agent in animal research. It was used precedently in the prolonged treatment of hypertension.

CNS Activity

Curator's Comment: Known to be CNS active in the rat. Human data not available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.8 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Ecolid chloride

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Influences of the corticotropic axis and sympathetic activity on neurochemical consequences of 3,4-methylenedioxymethamphetamine (MDMA) administration in Fischer 344 rats.
2002 Aug
Influence of cytisine on catecholamine release in isolated perfused rat adrenal glands.
2002 Dec
Isoflurane hyperalgesia is modulated by nicotinic inhibition.
2002 Jul
Cardiovascular and behavioural components of conditioned fear to context after ganglionic and alpha-adrenergic blockade.
2002 Jun 28
Heteromeric nicotinic inhibition by isoflurane does not mediate MAC or loss of righting reflex.
2002 Oct
Subclinical doses of the nerve gas sarin impair T cell responses through the autonomic nervous system.
2002 Oct 15
Effects of nicotine on memory impairment induced by blockade of muscarinic, nicotinic and dopamine D2 receptors in rats.
2003 Aug 8
Effect of intravenous angiotensin II infusion on responses to hypothalamic PVN injection of bicuculline.
2003 Dec
Effect of (+/-)-epibatidine, a nicotinic agonist, on the central pathways controlling voiding function in the rat.
2003 Jul
Peripheral and central sites of action for A-85380 in the spinal nerve ligation model of neuropathic pain.
2003 Jun
Efferent vagal fibre stimulation blunts nuclear factor-kappaB activation and protects against hypovolemic hemorrhagic shock.
2003 Mar 4
Interaction of chlorisondamine with the neuronal nicotinic acetylcholine receptor.
2003 Mar-Apr
An endogenous cannabinoid tone attenuates cholera toxin-induced fluid accumulation in mice.
2003 Sep
Effect of a perinatal high-salt diet on blood pressure control mechanisms in young Sprague-Dawley rats.
2004 Apr
Ganglionic action of angiotensin contributes to sympathetic activity in renin-angiotensinogen transgenic mice.
2004 Feb
Cardiovascular effects of nicotine, chlorisondamine, and mecamylamine in the pigeon.
2004 Jan
The interaction between the cholinergic and dopaminergic system in learning and memory process in rats.
2004 Jan-Jun
Mechanism of action of A-85380 in an animal model of depression.
2004 Jul
Central but not the peripheral action of cholinergic compounds suppresses the immune system.
2004 Mar
Mechanisms and significance of the increased brain uptake of tryptophan.
2005 Dec
Vasodilatation of the hindquarters induced by antagonism of GABA(A) receptors in the freely moving rat.
2005 Feb
Direct tissue analysis of phospholipids in rat brain using MALDI-TOFMS and MALDI-ion mobility-TOFMS.
2005 Feb
Localization and analyses of small drug molecules in rat brain tissue sections.
2005 Oct 15
Intracellular cGMP may promote Ca2+-dependent and Ca2+-independent release of catecholamines from sympathetic nerve terminals.
2006 Aug
Untranslated region-dependent exclusive expression of high-sensitivity subforms of alpha4beta2 and alpha3beta2 nicotinic acetylcholine receptors.
2006 Jul
CCCP enhances catecholamine release from the perfused rat adrenal medulla.
2006 Jul 30
Activation of the cholinergic anti-inflammatory pathway reduces NF-kappab activation, blunts TNF-alpha production, and protects againts splanchic artery occlusion shock.
2006 May
Role of beta-endorphin, corticotropin-releasing hormone, and autonomic nervous system in mediation of the effect of chronic ethanol on natural killer cell cytolytic activity.
2006 Oct
Effect of a diterpenoid from Salvia cinnabarina on arterial blood pressure in rats.
2007 Jul
Long- and short-term changes in the neuroimmune-endocrine parameters following inhalation exposures of F344 rats to low-dose sarin.
2007 May
Nicotine-induced phosphorylation of ERK in mouse primary cortical neurons: evidence for involvement of glutamatergic signaling and CaMKII.
2007 Oct
What's new in Nicotine & Tobacco Research?
2007 Sep
Morphine and ABT-594 (a nicotinic acetylcholine agonist) exert centrally mediated antinociception in the rat cyclophosphamide cystitis model of visceral pain.
2008 Feb
Effects of dipeptidyl peptidase iv inhibition on arterial blood pressure.
2008 Jan
Prenatal high salt programs enhanced sympathoadrenal activation of the cardiovascular response to restraint.
2009 Oct 5
The effect of restraint stress on glucocorticoid receptors in mouse spleen lymphocytes: involvement of the sympathetic nervous system.
2010
Rat brain CYP2B induction by nicotine is persistent and does not involve nicotinic acetylcholine receptors.
2010 Aug 12
Lipid-enriched enteral nutrition controls the inflammatory response in murine Gram-negative sepsis.
2010 Oct

Sample Use Guides

In Vitro Use Guide
In cultured dissociated mesencephalic cells of the fetal rat, chlorisondamine inhibited [3H]-dopamine release evoked by N-methyl-D-aspartate (10^-4 M), but only at high concentrations (IC50 approx. 600 microM). A high concentration of chlorisondamine (10^-3 M) had no effect on responses to quisqualate (10^-5 M) and only slightly reduced responses to kainate (10^-4 M). In adult rat hippocampal slices, chlorisondamine depressed NMDA receptor-mediated synaptically-evoked field potentials, but again only at high concentrations (10^-4-10^-3 M). Synaptic responses that were mediated by non-NMDA excitatory amino acid receptors were less affected.
Name Type Language
CHLORISONDAMINE
WHO-DD  
Common Name English
Chlorisondamine [WHO-DD]
Common Name English
CHLORISONDAMINE ION
Common Name English
ISOINDOLINIUM, 4,5,6,7-TETRACHLORO-2-METHYL-2-(2- (TRIMETHYLAMMONIO)ETHYL)-
Common Name English
1H-ISOINDOLIUM, 4,5,6,7-TETRACHLORO-2,3-DIHYDRO-2-METHYL-2-(2- (TRIMETHYLAMMONIO)ETHYL)-
Common Name English
CHLORISONDAMINE CATION
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66886
Created by admin on Fri Dec 15 17:24:40 GMT 2023 , Edited by admin on Fri Dec 15 17:24:40 GMT 2023
Code System Code Type Description
CAS
7701-62-4
Created by admin on Fri Dec 15 17:24:39 GMT 2023 , Edited by admin on Fri Dec 15 17:24:39 GMT 2023
PRIMARY
FDA UNII
JD3M24F66I
Created by admin on Fri Dec 15 17:24:40 GMT 2023 , Edited by admin on Fri Dec 15 17:24:40 GMT 2023
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EPA CompTox
DTXSID0048395
Created by admin on Fri Dec 15 17:24:39 GMT 2023 , Edited by admin on Fri Dec 15 17:24:39 GMT 2023
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WIKIPEDIA
CHLORISONDAMINE
Created by admin on Fri Dec 15 17:24:40 GMT 2023 , Edited by admin on Fri Dec 15 17:24:40 GMT 2023
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MESH
D002714
Created by admin on Fri Dec 15 17:24:40 GMT 2023 , Edited by admin on Fri Dec 15 17:24:40 GMT 2023
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DRUG CENTRAL
598
Created by admin on Fri Dec 15 17:24:39 GMT 2023 , Edited by admin on Fri Dec 15 17:24:39 GMT 2023
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NCI_THESAURUS
C83619
Created by admin on Fri Dec 15 17:24:40 GMT 2023 , Edited by admin on Fri Dec 15 17:24:40 GMT 2023
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PUBCHEM
6244
Created by admin on Fri Dec 15 17:24:40 GMT 2023 , Edited by admin on Fri Dec 15 17:24:40 GMT 2023
PRIMARY