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Details

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

SHOW SMILES / InChI
Structure of CHLORISONDAMINE

SMILES

C[N+](C)(C)CC[N+]1(C)CC2=C(Cl)C(Cl)=C(Cl)C(Cl)=C2C1

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

Molecular Formula C14H20Cl4N2
Molecular Weight 358.134
Charge 2
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 2
E/Z Centers 0
Optical Activity NONE

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
Lipid-enriched enteral nutrition controls the inflammatory response in murine Gram-negative sepsis.
2010-10
Rat brain CYP2B induction by nicotine is persistent and does not involve nicotinic acetylcholine receptors.
2010-08-12
Increase in locomotor activity after acute administration of the nicotinic receptor agonist 3-bromocytisine in rats.
2010-05-25
The effect of restraint stress on glucocorticoid receptors in mouse spleen lymphocytes: involvement of the sympathetic nervous system.
2010
Prenatal high salt programs enhanced sympathoadrenal activation of the cardiovascular response to restraint.
2009-10-05
Peripheral and central routes of administration of quaternary ammonium compound IEM-1460 are equally potent in reducing the severity of nicotine-induced seizures in mice.
2008-07
Nicotine-activated descending facilitation on spinal NMDA-dependent reflex potentiation from pontine tegmentum in rats.
2008-05
Morphine and ABT-594 (a nicotinic acetylcholine agonist) exert centrally mediated antinociception in the rat cyclophosphamide cystitis model of visceral pain.
2008-02
Effects of dipeptidyl peptidase iv inhibition on arterial blood pressure.
2008-01
Effects of kappa opioid agonists alone and in combination with cocaine on heart rate and blood pressure in conscious squirrel monkeys.
2007-12-08
Effect of anabasine on catecholamine secretion from the perfused rat adrenal medulla.
2007-12
The effect of the cholinergic anti-inflammatory pathway on experimental colitis.
2007-11
Nicotine-induced phosphorylation of ERK in mouse primary cortical neurons: evidence for involvement of glutamatergic signaling and CaMKII.
2007-10
Chlorisondamine inhibits the nicotine-induced stimulation of c-fos in the pigeon brain for up to 2 weeks.
2007-09
What's new in Nicotine & Tobacco Research?
2007-09
Effect of chronic IL-6 infusion on acute pressor responses to vasoconstrictors in mice.
2007-09
Effect of a diterpenoid from Salvia cinnabarina on arterial blood pressure in rats.
2007-07
Long- and short-term changes in the neuroimmune-endocrine parameters following inhalation exposures of F344 rats to low-dose sarin.
2007-05
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.
2006-10
Intracellular cGMP may promote Ca2+-dependent and Ca2+-independent release of catecholamines from sympathetic nerve terminals.
2006-08
CCCP enhances catecholamine release from the perfused rat adrenal medulla.
2006-07-30
Untranslated region-dependent exclusive expression of high-sensitivity subforms of alpha4beta2 and alpha3beta2 nicotinic acetylcholine receptors.
2006-07
Activation of the cholinergic anti-inflammatory pathway reduces NF-kappab activation, blunts TNF-alpha production, and protects againts splanchic artery occlusion shock.
2006-05
Mechanisms and significance of the increased brain uptake of tryptophan.
2005-12
Brain stem control of arterial pressure in chronic arterial baroreceptor-denervated rats.
2005-12
Localization and analyses of small drug molecules in rat brain tissue sections.
2005-10-15
The interaction between the cholinergic and dopaminergic system in learning and memory process in rats.
2005-06-30
Evaluation in rats and primates of [11C]-mecamylamine, a potential nicotinic acetylcholine receptor radioligand for positron emission tomography.
2005-05
Study of the interaction of chlorisondamine and chlorisondamine analogues with an epitope of the alpha-2 neuronal acetylcholine nicotinic receptor subunit.
2005-04-13
ABT-594 (a nicotinic acetylcholine agonist): anti-allodynia in a rat chemotherapy-induced pain model.
2005-02-10
Vasodilatation of the hindquarters induced by antagonism of GABA(A) receptors in the freely moving rat.
2005-02
Direct tissue analysis of phospholipids in rat brain using MALDI-TOFMS and MALDI-ion mobility-TOFMS.
2005-02
Supraspinal and systemic administration of the nicotinic-cholinergic agonist (+/-)-epibatidine has inhibitory effects on C-fiber reflexes in the rat.
2004-12-15
Salsolinol, an antagonist of prolactoliberine, induces an increase in plasma catecholamine levels in the rat.
2004-09-30
Adrenocorticotropin reverses hemorrhagic shock in anesthetized rats through the rapid activation of a vagal anti-inflammatory pathway.
2004-08-01
Mechanism of action of A-85380 in an animal model of depression.
2004-07
Effect of a perinatal high-salt diet on blood pressure control mechanisms in young Sprague-Dawley rats.
2004-04
Central but not the peripheral action of cholinergic compounds suppresses the immune system.
2004-03
Ganglionic action of angiotensin contributes to sympathetic activity in renin-angiotensinogen transgenic mice.
2004-02
Cardiovascular effects of nicotine, chlorisondamine, and mecamylamine in the pigeon.
2004-01
Effect of intravenous angiotensin II infusion on responses to hypothalamic PVN injection of bicuculline.
2003-12
Role of prostaglandin, endothelin and sympathetic nervous system on the L-NAME-induced pressor responses in spontaneously hypertensive rats.
2003-09-05
An endogenous cannabinoid tone attenuates cholera toxin-induced fluid accumulation in mice.
2003-09
Catecholamine secretory vesicle stimulus-transcription coupling in vivo. Demonstration by a novel transgenic promoter/photoprotein reporter and inhibition of secretion and transcription by the chromogranin A fragment catestatin.
2003-08-22
Effects of nicotine on memory impairment induced by blockade of muscarinic, nicotinic and dopamine D2 receptors in rats.
2003-08-08
Effect of (+/-)-epibatidine, a nicotinic agonist, on the central pathways controlling voiding function in the rat.
2003-07
Different vascular responsiveness to angiotensin II in two normotensive rat strains.
2003-06
Peripheral and central sites of action for A-85380 in the spinal nerve ligation model of neuropathic pain.
2003-06
The role of ionotropic receptors of glutaminic acid in cardiovascular system. A. The influence of ionotropic receptor NMDA agonist - 1R,3R-ACPD and antagonist - DL-AP7 on the systemic pressure in rats.
2003-06
Interaction of chlorisondamine with the neuronal nicotinic acetylcholine receptor.
2003-04-29

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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:46:01 GMT 2025
Edited
by admin
on Mon Mar 31 18:46:01 GMT 2025
Record UNII
JD3M24F66I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1H-ISOINDOLIUM, 4,5,6,7-TETRACHLORO-2,3-DIHYDRO-2-METHYL-2-(2- (TRIMETHYLAMMONIO)ETHYL)-
Preferred Name English
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
CHLORISONDAMINE CATION
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66886
Created by admin on Mon Mar 31 18:46:01 GMT 2025 , Edited by admin on Mon Mar 31 18:46:01 GMT 2025
Code System Code Type Description
CAS
7701-62-4
Created by admin on Mon Mar 31 18:46:01 GMT 2025 , Edited by admin on Mon Mar 31 18:46:01 GMT 2025
PRIMARY
FDA UNII
JD3M24F66I
Created by admin on Mon Mar 31 18:46:01 GMT 2025 , Edited by admin on Mon Mar 31 18:46:01 GMT 2025
PRIMARY
EPA CompTox
DTXSID0048395
Created by admin on Mon Mar 31 18:46:01 GMT 2025 , Edited by admin on Mon Mar 31 18:46:01 GMT 2025
PRIMARY
WIKIPEDIA
CHLORISONDAMINE
Created by admin on Mon Mar 31 18:46:01 GMT 2025 , Edited by admin on Mon Mar 31 18:46:01 GMT 2025
PRIMARY
MESH
D002714
Created by admin on Mon Mar 31 18:46:01 GMT 2025 , Edited by admin on Mon Mar 31 18:46:01 GMT 2025
PRIMARY
DRUG CENTRAL
598
Created by admin on Mon Mar 31 18:46:01 GMT 2025 , Edited by admin on Mon Mar 31 18:46:01 GMT 2025
PRIMARY
NCI_THESAURUS
C83619
Created by admin on Mon Mar 31 18:46:01 GMT 2025 , Edited by admin on Mon Mar 31 18:46:01 GMT 2025
PRIMARY
PUBCHEM
6244
Created by admin on Mon Mar 31 18:46:01 GMT 2025 , Edited by admin on Mon Mar 31 18:46:01 GMT 2025
PRIMARY
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