| Identification | Back Directory | [Name]
CHLORISONDAMINE DIIODIDE | [CAS]
96750-66-2 | [Synonyms]
Chlorisondamine (iodide)
4,5,6,7-tetrachloro-2-methyl-2-[2-(trimethylammonium)ethyl]isoindolinium diiodide | [Molecular Formula]
C14Cl4H20I2N2 | [MDL Number]
MFCD01074794 | [MOL File]
96750-66-2.mol | [Molecular Weight]
611.94 |
| Chemical Properties | Back Directory | [storage temp. ]
2-8°C | [solubility ]
H2O: ~3.75 mg/mL | [form ]
solid | [color ]
white | [Water Solubility ]
Soluble to 10 mM in water | [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 | [InChIKey]
FPNVAOZHQUJJJQ-UHFFFAOYSA-L | [SMILES]
[I-].[I-].C[N+](C)(C)CC[N+]1(C)Cc2c(Cl)c(Cl)c(Cl)c(Cl)c2C1 |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,N | [Risk Statements ]
22-50 | [Safety Statements ]
60-61 | [RIDADR ]
UN 3077 9 / PGIII | [WGK Germany ]
2 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Aquatic Acute 1 |
| Hazard Information | Back Directory | [Description]
Chlorisondamine is an antagonist of nicotinic acetylcholine receptors (nAChRs; IC50 = 1.8 μM in rat striatal synaptosomes) and a ganglion blocker. It decreases dopamine release induced by nicotine (Item Nos. 16535 | 20887) in a dose-dependent manner in rat striatal synaptosomes at concentrations ranging from 0-100 μM. The effect of chlorisondamine is long-lasting, with a 10 mg/kg dose blocking nicotine-induced stimulant activity for at least five weeks. Chlorisondamine (5 μg, i.c.v.) prevents rats from acquiring a (–)-nicotine-induced conditioned taste aversion response, a model of the aversive effects of nicotine. It also inhibits autonomic ganglia, providing approximately 50% inhibition of the contractile response in feline superior cervical ganglion nictitating membrane preparations when administered at a dose of 50 mg/kg. | [Uses]
Chlorisondamine diiodide has been used:
- as a nicotinic receptor antagonist to test its effect on trinitrobenzene sulfonic acid (TNBS)-induced colitis
- as an irreversible nicotinic acetylcholine(nAChR) blocker to pre-treat brain samples to test its effect on cytochrome P450 2B (CYP2B) induction
- as a ganglionic blocker to test its effect on regulating corticosterone levels in rat with chronic stress
| [Biochem/physiol Actions]
Chlorisondamine diiodide mediates ganglionic and central blockade. | [in vivo]
Chlorisondamine (0.2, 1.0, 5.0 μg; IV; single dosage) antagonizes the depressant action of nicotine on vertical activity (0-20min) in a dose-dependent way at 1 and 2 weeks[1]. | Animal Model: | Rats (treated once with nicotine 0.4 mg/kg, s.c.)[1] | | Dosage: | 0.2, 1.0, 5.0 μg | | Administration: | IV; single dosage | | Result: | Antagonized the depressant action of nicotine on vertical activity (0-20min) in a dose-dependent way at 1 and 2 weeks. |
| [References]
[1] H. EL-BIZRI P. B S C. Blockade of nicotinic receptor-mediated release of dopamine from striatal synaptosomes by chlorisondamine and other nicotinic antagonists administered in vitro[J]. British Journal of Pharmacology, 1994, 111 2: 406-413. DOI: 10.1111/j.1476-5381.1994.tb14749.x
[2] CLARKE P B. Chronic central nicotinic blockade after a single administration of the bisquaternary ganglion-blocking drug chlorisondamine.[J]. British Journal of Pharmacology, 1984, 83 2: 527-535. DOI: 10.1111/j.1476-5381.1984.tb16517.x
[3] C. REAVILL. Chlorisondamine blocks acquisition of the conditioned taste aversion produced by (?)-nicotine[J]. Neuropharmacology, 1986, 25 9: Pages 1067-1069. DOI: 10.1016/0028-3908(86)90204-2
[4] A J PLUMMER. Ganglionic blockade by a new bisquaternary series, including chlorisondamine dimethochloride.[J]. Journal of Pharmacology and Experimental Therapeutics, 1955, 115 2: 172-184.
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