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Details

Stereochemistry ACHIRAL
Molecular Formula C14H20Cl4N2.2Cl
Molecular Weight 429.04
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORISONDAMINE CHLORIDE

SMILES

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

InChI

InChIKey=DXXUGBPKQDTBQW-UHFFFAOYSA-L
InChI=1S/C14H20Cl4N2.2ClH/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

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
Understanding channel blocking in the nicotinic acetylcholine receptor.
2001
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
Nicotine prevents striatal dopamine loss produced by 6-hydroxydopamine lesion in the substantia nigra.
2001 Jan 12
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
Modulation of the leptin-induced white adipose tissue lipolysis by nitric oxide.
2001 Nov
Effects of antihypertensive drugs on ultrasound production and cardiovascular responses in 15-day-old rats.
2002 Apr 1
Central urocortin activation of sympathetic-regulated energy metabolism in Wistar rats.
2002 Mar 15
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
Effect of intravenous angiotensin II infusion on responses to hypothalamic PVN injection of bicuculline.
2003 Dec
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 Jun
An endogenous cannabinoid tone attenuates cholera toxin-induced fluid accumulation in mice.
2003 Sep
Supraspinal and systemic administration of the nicotinic-cholinergic agonist (+/-)-epibatidine has inhibitory effects on C-fiber reflexes in the rat.
2004 Dec 15
Cardiovascular effects of nicotine, chlorisondamine, and mecamylamine in the pigeon.
2004 Jan
Central but not the peripheral action of cholinergic compounds suppresses the immune system.
2004 Mar
Salsolinol, an antagonist of prolactoliberine, induces an increase in plasma catecholamine levels in the rat.
2004 Sep 30
Vasodilatation of the hindquarters induced by antagonism of GABA(A) receptors in the freely moving rat.
2005 Feb
Evaluation in rats and primates of [11C]-mecamylamine, a potential nicotinic acetylcholine receptor radioligand for positron emission tomography.
2005 May
Effect of anabasine on catecholamine secretion from the perfused rat adrenal medulla.
2007 Dec
Long- and short-term changes in the neuroimmune-endocrine parameters following inhalation exposures of F344 rats to low-dose sarin.
2007 May
The effect of the cholinergic anti-inflammatory pathway on experimental colitis.
2007 Nov
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
Effect of chronic IL-6 infusion on acute pressor responses to vasoconstrictors in mice.
2007 Sep
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 Jul

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 CHLORIDE
INN   MI  
INN  
Official Name English
ISOINDOLINIUM, 4,5,6,7-TETRACHLORO-2-METHYL-2-(2-(TRIMETHYLAMMONIO)ETHYL)-, DICHLORIDE
Systematic Name English
CHLORISONDAMONE CHLORIDE
Common Name English
chlorisondamine chloride [INN]
Common Name English
4,5,6,7-TETRACHLORO-2-(2-DIMETHYLAMINOETHYL)-2-METHYLISOINDOLINUM CHLORIDE METHOCHLORIDE
Common Name English
1H-ISOINDOLIUM, 4,5,6,7-TETRACHLORO-2,3-DIHYDRO-2-METHYL-2-(2-(TRIMETHYLAMMONIO)ETHYL)-, DICHLORIDE
Systematic Name English
CHLORISONDAMINE CHLORIDE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66886
Created by admin on Fri Dec 15 15:12:38 GMT 2023 , Edited by admin on Fri Dec 15 15:12:38 GMT 2023
Code System Code Type Description
PUBCHEM
6243
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PRIMARY
CAS
69-27-2
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INN
609
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NCI_THESAURUS
C76788
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MERCK INDEX
m3371
Created by admin on Fri Dec 15 15:12:38 GMT 2023 , Edited by admin on Fri Dec 15 15:12:38 GMT 2023
PRIMARY Merck Index
SMS_ID
100000081562
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FDA UNII
7B58W7756G
Created by admin on Fri Dec 15 15:12:38 GMT 2023 , Edited by admin on Fri Dec 15 15:12:38 GMT 2023
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EVMPD
SUB06182MIG
Created by admin on Fri Dec 15 15:12:38 GMT 2023 , Edited by admin on Fri Dec 15 15:12:38 GMT 2023
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ChEMBL
CHEMBL1398654
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EPA CompTox
DTXSID7046332
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