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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

Molecular Formula C14H20Cl4N2
Molecular Weight 358.134
Charge 2
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 0
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
Modulation of neuronal nicotinic acetylcholine receptors by halothane in rat cortical neurons.
2001 Apr
Reversal of acute effects of high dose morphine on lymphocyte activity by chlorisondamine.
2001 Apr 1
Dietary soy exerts an antihypertensive effect in spontaneously hypertensive female rats.
2001 Aug
Pharmacological dissection of vascular effects caused by activation of protease-activated receptors 1 and 2 in anesthetized rats.
2001 Jun
Evidence that extrapancreatic GLUT2-dependent glucose sensors control glucagon secretion.
2001 Jun
Depletion of brown fat norepinephrine content by acute cold exposure and adrenoceptor blockade.
2001 Mar
Effects of antihypertensive drugs on ultrasound production and cardiovascular responses in 15-day-old rats.
2002 Apr 1
Influence of cytisine on catecholamine release in isolated perfused rat adrenal glands.
2002 Dec
Rapid elevation of plasma interleukin-6 by morphine is dependent on autonomic stimulation of adrenal gland.
2002 Jan
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
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
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
Role of prostaglandin, endothelin and sympathetic nervous system on the L-NAME-induced pressor responses in spontaneously hypertensive rats.
2003 Sep 5
Effect of a perinatal high-salt diet on blood pressure control mechanisms in young Sprague-Dawley rats.
2004 Apr
Adrenocorticotropin reverses hemorrhagic shock in anesthetized rats through the rapid activation of a vagal anti-inflammatory pathway.
2004 Aug 1
Ganglionic action of angiotensin contributes to sympathetic activity in renin-angiotensinogen transgenic mice.
2004 Feb
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
Brain stem control of arterial pressure in chronic arterial baroreceptor-denervated rats.
2005 Dec
Study of the interaction of chlorisondamine and chlorisondamine analogues with an epitope of the alpha-2 neuronal acetylcholine nicotinic receptor subunit.
2005 Mar-Apr
Localization and analyses of small drug molecules in rat brain tissue sections.
2005 Oct 15
The effect of the cholinergic anti-inflammatory pathway on experimental colitis.
2007 Nov
Chlorisondamine inhibits the nicotine-induced stimulation of c-fos in the pigeon brain for up to 2 weeks.
2007 Sep
Effect of chronic IL-6 infusion on acute pressor responses to vasoconstrictors in mice.
2007 Sep
Nicotine-activated descending facilitation on spinal NMDA-dependent reflex potentiation from pontine tegmentum in rats.
2008 May
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
Increase in locomotor activity after acute administration of the nicotinic receptor agonist 3-bromocytisine in rats.
2010 May 25

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 Fri Dec 15 17:24:39 GMT 2023
Edited
by admin
on Fri Dec 15 17:24:39 GMT 2023
Record UNII
JD3M24F66I
Record Status Validated (UNII)
Record Version
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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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
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