Chlorisondamine diiodide

Base Information

• Chemical Name: Chlorisondamine diiodide
• CAS No.: 96750-66-2
• Molecular Formula: C₁₄H₂₀Cl₄N₂*2I
• Molecular Weight: 611.947
• Hs Code.: 2933990090
• European Community (EC) Number: 635-559-5,692-525-2
• DSSTox Substance ID: DTXSID70582020
• Mol file: 96750-66-2.mol

Synonyms:Chlorisondamine diiodide;96750-66-2;Chlorisondamine (diiodide);trimethyl-[2-(4,5,6,7-tetrachloro-2-methyl-1,3-dihydroisoindol-2-ium-2-yl)ethyl]azanium;diiodide;4,5,6,7-Tetrachloro-1,3-dihydro-2-methyl-2-[2-trimethylammonium)ethyl]-2H-isoindolium diiodide;DTXSID70582020;FPNVAOZHQUJJJQ-UHFFFAOYSA-L;HMS3267M11;HMS3414J07;HMS3678J05;WDA75066;3-[[4-(Chlorophenyl)piperazin-1-yl]methyl-1H-pyrrolo[2,3-b]pyridine diiodide;AKOS024456328;HY-101347;CS-0021190;SR-01000597963;SR-01000597963-1;Chlorisondamine diiodide, >=98% (HPLC), white solid;4,5,6,7-Tetrachloro-2-methyl-2-(2-(trimethylammonio)ethyl)isoindolin-2-ium iodide;4,5,6,7-Tetrachloro-2-methyl-2-(2-(trimethylammonio)ethyl)isoindolin-2-iumiodide;4,5,6,7-tetrachloro-2-methyl-2-(2-(trimethylammonio)ethyl)isoindolinium iodide;4,5,6,7-Tetrachloro-2-methyl-2-[2-(trimethylazaniumyl)ethyl]-2,3-dihydro-1H-isoindol-2-ium diiodide

Chemical Property of Chlorisondamine diiodide

Chemical Property:

• PSA: 0.00000
• LogP: -1.56660
• Storage Temp.: 2-8°C
• Solubility.: H2O: ~3.75 mg/mL
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 611.84405
• Heavy Atom Count: 22
• Complexity: 336

Purity/Quality:

98%,99%, ^*data from raw suppliers

Chlorisondamine diiodide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,N
• Statements: 22-50
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[N+]1(CC2=C(C1)C(=C(C(=C2Cl)Cl)Cl)Cl)CC[N+](C)(C)C.[I-].[I-]
• 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 colitisas an irreversible nicotinic acetylcholine(nAChR) blocker to pre-treat brain samples to test its effect on cytochrome P450 2B (CYP2B) inductionas a ganglionic blocker to test its effect on regulating corticosterone levels in rat with chronic stress

Technology Process of Chlorisondamine diiodide

There total 6 articles about Chlorisondamine diiodide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 58.0%

4,5,6,7-tetrachloro-2-[2-(trimethylammonium)ethyl]isoindoline iodide (96649-82-0) + methyl iodide (74-88-4) → chlorisondamine diiodide (96750-66-2)

Guidance literature:

In N,N-dimethyl-formamide; at 100 ℃; for 24h;

DOI:10.1002/jlcr.1069

Reference yield:

4,5,6,7-tetrachloro-2-(2-dimethylaminoethyl)isoindoline (95467-71-3) + methyl iodide (74-88-4) → chlorisondamine diiodide (96750-66-2)

Guidance literature:

With N,N-dimethyl-formamide;

DOI:10.1021/ja01569a048

Reference yield:

4,5,6,7-tetrachloro-2-(2-dimethylaminoethyl)isoindole-1,3-dione (91346-02-0) → chlorisondamine diiodide (96750-66-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 43 percent / LiAlH₄ / diethyl ether / 3 h / Heating

2: 76 percent / ethanol / 48 h / 20 °C

3: 58 percent / dimethylformamide / 24 h / 100 °C

With lithium aluminium tetrahydride; In diethyl ether; ethanol; N,N-dimethyl-formamide;

DOI:10.1002/jlcr.1069

upstream raw materials:

4,5,6,7-tetrachloro-2-(2-dimethylaminoethyl)isoindoline

methyl iodide

4,5,6,7-tetrachloro-2-[2-(trimethylammonium)ethyl]isoindoline iodide

tetrachlorophthalic anhydride

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