Raclopride

Base Information

• Chemical Name: Raclopride
• CAS No.: 84225-95-6
• Deprecated CAS: 104953-11-9
• Molecular Formula: C15H20Cl2N2O3
• Molecular Weight: 347.241
• UNII: 430K3SOZ7G
• DSSTox Substance ID: DTXSID9045687
• Nikkaji Number: J329.221E
• Wikipedia: Raclopride
• Wikidata: Q7279814
• NCI Thesaurus Code: C152139
• Pharos Ligand ID: FHNTZFPKRM1Y
• Metabolomics Workbench ID: 153493
• ChEMBL ID: CHEMBL8809
• Mol file: 84225-95-6.mol

Synonyms:C11, Raclopride;FLA 870;FLA-870;FLA870;FLB 472;FLB-472;FLB472;Raclopride;Raclopride C11

Chemical Property of Raclopride

Chemical Property:

• Vapor Pressure: 1.17E-07mmHg at 25°C
• Melting Point: 52.0 to 56.0 °C
• Refractive Index: 1.563
• Boiling Point: 420.3 °C at 760 mmHg
• PKA: 5.93±0.50(Predicted)
• Flash Point: 208 °C
• PSA: 61.80000
• Density: 1.288 g/cm³
• LogP: 3.25050
• Storage Temp.: Store at RT
• Solubility.: H2O: 89 mg/mL
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 346.0850979
• Heavy Atom Count: 22
• Complexity: 386

Purity/Quality:

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

Raclopride ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1CCCC1CNC(=O)C2=C(C(=CC(=C2OC)Cl)Cl)O
• Isomeric SMILES: CCN1CCC[C@H]1CNC(=O)C2=C(C(=CC(=C2OC)Cl)Cl)O
• Recent ClinicalTrials: The Role of Dopamine in Motor Learning in Healthy Subjects and Patients With Parkinson's Disease
• Recent EU Clinical Trials: Cognitieve en emotionele controle: gelijkenissen en verschillen in neuraal substraat - 11C-Raclopride
• Recent NIPH Clinical Trials: Effect of transcranial direct current stimulation on the dopamine-GABA systems in healthy subjects
• Description: Raclopride is a selective dopamine D2/D3 receptor antagonist with Ki values of 1.8, 3.5, 2,400, and 18,000 nM for D2, D3, D4, and D1 receptors, respectively. It passes the blood brain barrier and can be used in in vivo binding and autoradiography studies of the dopamine system under normal and pathological conditions such as Huntington’s disease.
• Uses: A labelled dopamine receptor neuroleptic;selective dopamine D1/D2 receptors antagonist Raclopride is a potent D2DR/D3DR antagonist.

Technology Process of Raclopride

There total 6 articles about Raclopride 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: 91.0%

(S)-(-)-3,5-dichloro-N-((1-ethyl-2-pyrrolidinyl)methyl)-2,6-dimethoxybenzamide hydrochloride → raclopride (84225-95-6)

Guidance literature:

With boron tribromide; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1002/(SICI)1099-1344(199912)42:12<1183::AID-JLCR274>3.0.CO;2-Z

Reference yield: 71.0%

(-)-A 32559 (84225-94-5) → raclopride (84225-95-6)

Guidance literature:

With boron tribromide; In dichloromethane; at -20 - 20 ℃;

DOI:10.1081/SCC-120034174

Reference yield: 64.0%

4,6‐dichloro‐2‐iodo‐3‐methoxyphenol (1382903-07-2) + (S)-2-(Aminomethyl)-1-ethylpyrrolidine (22795-99-9) + molybdenum hexacarbonyl (13939-06-5,199620-15-0) → raclopride (84225-95-6)

Guidance literature:

4,6‐dichloro‐2‐iodo‐3‐methoxyphenol; (S)-2-(Aminomethyl)-1-ethylpyrrolidine; With triethylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; sealed tube; Inert atmosphere;

molybdenum hexacarbonyl; With pyridine; In tetrahydrofuran; at 70 ℃; for 19h; sealed tube; Inert atmosphere;

upstream raw materials:

(-)-A 32559

2,6-dimethoxy-3,5-dichlorobenzoic acid

3,5-dichloro-2,6-dimethoxybenzoic acid chloride

4,6‐dichloro‐2‐iodo‐3‐methoxyphenol

Downstream raw materials:

S-(-)-3,5-dichloro-2-palmitoyloxy-N[(1-ethyl-2-pyrrolidinyl)methyl]-6-methoxybenzamide

(S)-(-)-3,5-dichloro-N-((1-ethyl-2-pyrrolidinyl)methyl)-2,6-dihydroxybenzamide hydrobromide

(S)-(-)-3,5-dichloro-N-((1-ethyl-2-pyrrolidinyl)methyl)-2,6-dihydroxybenzamide

Refernces

• 1、 -. "SYSTEM PROVIDING CONTROLLED DELIVERY OF GASEOUS CO FOR CARBONYLATION REACTIONS". Page/Page column 95; 96. . Retrieved 2012/06/30.
• 2、 Langer, Oliver,Nagren, Kjell,Dolle, Frederic,Lundkvist, Camilla,Sandell, Johan,Swahn, Carl-Gunnar,Vaufrey, Francoise,Crouzel, Christian,Maziere, Bernard,Halldin, Christer. "Precursor synthesis and radiolabelling of the dopamine D2 receptor ligand [11C]raclopride from [11C]methyl triflate". . p. 1183 - 1193. Retrieved 2007/10/03.