84225-95-6

Basic information

• Product Name: S(-)-RACLOPRIDE L-TARTRATE
• Synonyms: (2S)-3,5-DICHLORO-N-[(1-ETHYL-2-PYRROLIDINYL)-METHYL]-6- METHOXYSALICYLAMIDE;BENZAMIDE, 3,5-DICHLORO-N-[[(2S)-1-ETHYL-2-PYRROLIDINYL]METHYL]-2-HYDROXY-6-METHOXY-;3,5-Dichloro-N-[(2S)-1-ethyl-2-pyrrolidinyl]-2-hydroxy-6-methoxybenzamide;FLA-870;RAC;3,5-Dichloro-N-[[(2S)-1-ethyl-2-pyrrolidinyl]methyl]-2-methoxy-6-hydroxybenzamide;3,5-Dichloro-N-[[(2S)-1-ethylpyrrolidine-2α-yl]methyl]2-hydroxy-6-methoxybenzamide;(-)-(S)-3,5-Dichlor-N-((1-ethyl-2-pyrrolidinyl)methyl)-6-hydroxy-o-anisamid
• CAS NO: 84225-95-6
• Molecular Formula: C₁₅H₂₀Cl₂N₂O₃
• Molecular Weight: 497.32
• Product Categories: Dopamine receptor;Amines;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Isotope Labelled Compounds;Pharmaceuticals
• Mol File: 84225-95-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 52.0 to 56.0 °C
• Boiling Point: 420.3 °C at 760 mmHg
• Flash Point: 208 °C
• Appearance: white/solid
• Density: 1.288 g/cm³
• Vapor Pressure: 1.17E-07mmHg at 25°C
• Refractive Index: 1.563
• Storage Temp.: Store at RT
• Solubility: H2O: 89 mg/mL
• PKA: 5.93±0.50(Predicted)
• CAS DataBase Reference: S(-)-RACLOPRIDE L-TARTRATE(CAS DataBase Reference)
• NIST Chemistry Reference: S(-)-RACLOPRIDE L-TARTRATE(84225-95-6)
• EPA Substance Registry System: S(-)-RACLOPRIDE L-TARTRATE(84225-95-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: CV3465000
• Hazardous Substances Data: 84225-95-6(Hazardous Substances Data)

Usage

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.

Chemical Properties

Yellowish solid

Uses

Different sources of media describe the Uses of 84225-95-6 differently. You can refer to the following data:
1. A labelled dopamine receptor
2. neuroleptic;selective dopamine D1/D2 receptors antagonist
3. Raclopride is a potent D2DR/D3DR antagonist.

Biological Activity

Selective and potent dopamine D 2 /D 3 receptor antagonist (K i values are 1.8, 3.5, 2400 and 18000 nM for D 2 , D 3 , D 4 and D 1 receptors respectively). Centrally active following systemic administration in vivo .

InChI:InChI=1/C15H20Cl2N2O3/c1-3-19-6-4-5-9(19)8-18-15(21)12-13(20)10(16)7-11(17)14(12)22-2/h7,9,20H,3-6,8H2,1-2H3,(H,18,21)/t9-/m0/s1

Upstream product

• 84225-94-5 (-)-A 32559 
• 73219-91-7 2,6-dimethoxy-3,5-dichlorobenzoic acid 
• 32541-62-1 3,5-dichloro-2,6-dimethoxybenzoic acid chloride 
• 1382903-07-2 4,6‐dichloro‐2‐iodo‐3‐methoxyphenol 
• 22795-99-9 (S)-2-(Aminomethyl)-1-ethylpyrrolidine 
• 13939-06-5 molybdenum hexacarbonyl 
• 119670-11-0 (S)-(-)-3,5-dichloro-N-((1-ethyl-2-pyrrolidinyl)methyl)-2,6-dihydroxybenzamide 
• 74-88-4 methyl iodide 

Downstream Products

• 119670-11-0 (S)-(-)-3,5-dichloro-N-((1-ethyl-2-pyrrolidinyl)methyl)-2,6-dihydroxybenzamide 
• 130305-11-2 S-(-)-3,5-dichloro-2-palmitoyloxy-N[(1-ethyl-2-pyrrolidinyl)methyl]-6-methoxybenzamide 
• 113310-88-6 (S)-(-)-3,5-dichloro-N-((1-ethyl-2-pyrrolidinyl)methyl)-2,6-dihydroxybenzamide hydrobromide 

Relevant articles and documents

Continuous-flow synthesis of [11C]raclopride, a positron emission tomography radiotracer, on a microfluidic chip

11C-labelled radiotracers such as [11C]raclopride are produced in a process that can take between 45 and 60 min to complete. These conventional approaches can consume upwards of 75% of the 11C (t 1/2 = 20 min) due to radioactive decay alone, even more if synthesis losses are considered. To compensate, a large starting quantity of radioactive precursors such as [11C]methyl iodide is required to produce an adequate amount of the tracer for injection. In this investigation, a continuous-flow microchip is explored for the purpose of synthesizing 11C radiotracers in a shorter time by exploiting the favorable reaction kinetics of using smaller reaction volumes. To enhance the mixing of reagents within the microchannel, a micromixer loop design was used in fabricating various polydimethylsiloxane chip styles. With a loop design implemented in an abacus-style chip for the production of nonradioactive raclopride, shorter reaction times, reduced precursor use, and improved yields were possible when compared with the use of a simple serpentine design (no loop-style chip). However, when performing the equivalent radiochemical reaction, the results were not as favorable. Using the loop design in a full loop-style chip, parameters such as premixing the reagents, reducing flow rate, and varying reagent concentrations were explored to improve the yields of [ 11C]raclopride (in terms of relative radioactivity) formed. The full loop chip design produced the best results, and future work will see the polydimethylsiloxane prototype chip design translated into a glass chip for further optimization.

An improved synthesis of PET dopamine D2 receptors radioligand [11c]raclopride

An improved synthesis of [11C]raclopride is reported. The precursor desmethyl-raclopride was synthesized from 3,5-dichloro-2,6-dimethoxybenzoic acid and (S)-(-)-2-aminoethyl-1-ethylpyrrolidine via a straight-forward, four-step synthetic approac

A general method for the synthesis of raclopride, FLB 457 and epidepride and corresponding desmethyl-precursors

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