Iolopride

Base Information

• Chemical Name: Iolopride
• CAS No.: 84226-06-2
• Molecular Formula: C15H21 I N2 O3
• Molecular Weight: 404.248
• UNII: 9J5D4ZN1JK
• DSSTox Substance ID: DTXSID401144235
• Nikkaji Number: J138.630A
• Wikipedia: Iodobenzamide
• Wikidata: Q3801336
• Pharos Ligand ID: CAYVYKDLR85H
• ChEMBL ID: CHEMBL267723
• Mol file: 84226-06-2.mol

Synonyms:123I-IBZM;3-iodo-2-hydroxy-6-methoxy-N-((1-ethyl-2-pyrrolidinyl)methyl)benzamide;3-iodo-2-hydroxy-6-methoxy-N-((1-ethyl-2-pyrrolidinyl)methyl)benzamide, (R)-isomer;3-iodo-2-hydroxy-6-methoxy-N-((1-ethyl-2-pyrrolidinyl)methyl)benzamide, (R)-isomer, 125I labeled;3-iodo-2-hydroxy-6-methoxy-N-((1-ethyl-2-pyrrolidinyl)methyl)benzamide, (S)-isomer, 125I labeled;3-iodo-N-(1-ethyl-2-pyrrolidinyl)methyl-2-hydroxy-6-methoxybenzamide;IBZM;N-((1-ethyl-2-pyrrolidinyl)methyl)-2-hydroxy-3-iodo-6-methoxybenzamide

Chemical Property of Iolopride

Chemical Property:

• Appearance/Colour: dark yellow oil
• Vapor Pressure: 6.88E-08mmHg at 25°C
• Boiling Point: 426.9 °C at 760 mmHg
• Flash Point: 212 °C
• PSA: 61.80000
• Density: 1.51 g/cm³
• LogP: 2.54830
• Storage Temp.: 2-8°C
• Solubility.: H2O: <0.5 mg/mL, slightly soluble
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 404.05969
• Heavy Atom Count: 21
• Complexity: 356

Purity/Quality:

98%Min ^*data from raw suppliers

IBZM ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1CCCC1CNC(=O)C2=C(C=CC(=C2O)I)OC
• Isomeric SMILES: CCN1CCC[C@H]1CNC(=O)C2=C(C=CC(=C2O)I)OC
• Uses: A halogenated benzamide derivative as potential radioligands for non-invasive quantification of D2-like dopamine receptor. The main purpose of a brain study with IBZM is the differentiation of Parkinson disease from other neurodegenerative disease A halogenated benzamide derivative as potential radioligands for non-invasive quantification of D2-like dopamine receptor. The main purpose of a brain study with IBZM is the differentiation of Parkinson’s disease from other neurodegenerative diseases like Lewy Body dementia, multiple system atrophy.

Technology Process of Iolopride

There total 10 articles about Iolopride 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: 84.4%

FLA 981 → [123I]-IBZM (84226-06-2,130383-75-4)

Guidance literature:

With Iodine monochloride; In methanol; dichloromethane; at 50 ℃; for 2h;

Reference yield: 73.0%

N-((S)-1-Ethyl-pyrrolidin-2-ylmethyl)-3-iodo-2,6-dimethoxy-benzamide (96897-88-0) → [123I]-IBZM (84226-06-2,130383-75-4) + 5-Iodo-BZM (132448-74-9)

Guidance literature:

With hydrogenchloride; boron tribromide; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/jm00147a025

Reference yield: 71.0%

(-)-BZM (84226-04-0) → [123I]-IBZM (84226-06-2,130383-75-4)

Guidance literature:

(-)-BZM; With tetrafluoroboric acid; In ethanol; water; at 20 ℃; for 0.5h;

With N-iodo-succinimide; silver(I) triflimide; In dichloromethane; at 20 ℃; for 0.8h; Darkness;

DOI:10.1021/acs.joc.5b02761

upstream raw materials:

N-((S)-1-Ethyl-pyrrolidin-2-ylmethyl)-3-iodo-2,6-dimethoxy-benzamide

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

2-hydroxy-6-methoxybenzoic acid

2-6-dimethoxybenzoic acid

Downstream raw materials:

N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-hydroxy-6-methoxy-3-tri-butylbenzamide

Refernces

• 1、 Racys, Daugirdas T.,Warrilow, Catherine E.,Pimlott, Sally L.,Sutherland, Andrew. "Highly Regioselective Iodination of Arenes via Iron(III)-Catalyzed Activation of N-Iodosuccinimide". supporting information. p. 4782 - 4785. Retrieved 2015/10/12.
• 2、 Kung,Kasliwal,Pan,Kung,Mach,Guo. "Dopamine D-2 receptor imaging radiopharmaceuticals: Synthesis, radiolabeling, and in vitro binding of (R)-(+)- and (S)-(-)-3-iodo-2-hydroxy-6 methoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]benzamide". . p. 1039 - 1043. Retrieved 2007/10/02.