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Raclopride

HCID 3033769
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Basic information

CAS
84225-95-6
Standard SMILES
CCN1CCC[C@H]1CNC(=O)c1c(O)c(Cl)cc(Cl)c1OC
InChIKey
WAOQONBSWFLFPE-VIFPVBQESA-N
Molecular formula
C15H20Cl2N2O3
Average molar mass
347.2 g/mol
Monoisotopic mass
346.0850979

Overview

3,5-dichloro-N-[[(2S)-1-ethyl-2-pyrrolidinyl]methyl]-2-hydroxy-6-methoxybenzamide is a member of salicylamides.

Names & identifiers

Preferred name
Raclopride
IUPAC
3,5-dichloro-N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-2-hydroxy-6-methoxybenzamide
English name
S(-)-RACLOPRIDE L-TARTRATE
Molecular formula
C15H20Cl2N2O3
Molecular weight
347.24

Names & synonyms

RACLOPRIDE84225-95-6RaclopridaRaclopridumDTXSID9045687Raclopridum [Latin]Racloprida [Spanish]Raclopride [INN:BAN]S-raclopride430K3SOZ7GRACLOPRIDE [INN]RACLOPRIDE [MART.]
Show more names
RACSKL202FLA-870Raclopride >Raclopridum [latin]Raclopride84225-95-6
RACLOPRIDE [WHO-DD]DTXCID7025687Raclopridum (Latin)RACLOPRIDE (MART.)raclopride c11 injectionRefChem:389259Benzamide, 3,5-dichloro-N-((1-ethyl-2-pyrrolidinyl)-methyl)-2-hydroxy-6-methoxy-(S)-3,5-dichloro-N-((1-ethylpyrrolidin-2-yl)methyl)-2-hydroxy-6-methoxybenzamide

Database identifiers

CAS
84225-95-6
PubChem CID
3033769
DTXSID
DTXSID9045687
ChEMBL
CHEMBL8809
ChEBI
CHEBI:92070
UNII
430K3SOZ7G
Nikkaji
J329.221E

Properties

Computed structural properties

XLogP
2.9
Topological polar surface area
61.8 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
5
Heavy atoms
22
Formal charge
0
Complexity
386

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Physicochemical properties

Melting point
52 to · 52.0 to 56.0 °C
Boiling point
420.3 · 420.3±45.0 °C(Predicted)
Density
1.288 · 1.288±0.06 g/cm3(Predicted)
storage temp.
2 · Keep in dark place,Sealed in dry,2-8°C
solubility
2 O: · H2O: 89 mg/mL
form
solid
pka
5.93 · 5.93±0.50(Predicted)
color
white
InChI
1S/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-/m1/s1
InChIKey
WAOQONBSWFLFPE-SECBINFHSA-N
SMILES
Clc1c(c(c(c(c1)Cl)O)C(=O)NC[C@@H]2N(CCC2)CC)OC
FDA UNII
430 K3SOZ7G · 430K3SOZ7G

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
3
rtecs
CV3465000
hs_code
2933.99.8290
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
22-24/25
Storage Class
11 - Combustible Solids

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus.

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME.

Applications · 4 items

DescriptionRaclopride 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.

UsesA labelled dopamine receptor

Usesneuroleptic;selective dopamine D1/D2 receptors antagonist

UsesRaclopride is a potent D2DR/D3DR antagonist.

Additional notes

DefinitionChEBI: 3,5-dichloro-N-[[(2S)-1-ethyl-2-pyrrolidinyl]methyl]-2-hydroxy-6-methoxybenzamide is a member of salicylamides.

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Compound notes

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UNSPSC Code
12352200 · 12352200
NACRES
77 · NA.77
Symbol(GHS)
7 · GHS07
Signal word
Warning
Safety Statements
22 · 22-24/25
WGK Germany
3 · 3
RTECS
3465000 · CV3465000
HS Code
2933.99 · 2933.99.8290
Storage Class
11 · 11 - Combustible Solids