Raclopride

Raclopride
Clinical data
ATC code	none;
Pharmacokinetic data
Elimination half-life	20 min
Identifiers
	IUPAC name 3,5-dichloro-N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-2-hydroxy-6-methoxybenzamide;
CAS Number	84225-95-6 ;
PubChem CID	3033769;
IUPHAR/BPS	94;
ChemSpider	2298373 ;
UNII	430K3SOZ7G;
ChEMBL	ChEMBL8809 ;
CompTox Dashboard (EPA)	DTXSID9045687 ;
Chemical and physical data
Formula	C15H20Cl2N2O3
Molar mass	347.24 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1c(O)c(c(OC)c(Cl)c1)C(=O)NC[C@H]2N(CC)CCC2;
	InChI 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-/m0/s1 ; Key:WAOQONBSWFLFPE-VIFPVBQESA-N ;
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Raclopride is a synthetic compound that acts as a selective antagonist on D₂ dopamine receptors.[1]

Its selectivity to the cerebral D₂ receptors is characterized by its respective K_i-values, which are as follows: 1.8, 3.5, 2400 and 18000 nM for D₂, D₃, D₄ and D₁ receptors respectively.

It can be radiolabelled with radioisotopes, e.g. ³H or ¹¹C and used as a tracer for in vitro imaging (autoradiography) as well as in vivo imaging positron emission tomography (PET). Images obtained by cerebral PET scanning (e.g. PET/CT or PET/MRI) allow the non-invasive assessment of the binding capacity of the cerebral D₂ dopamine receptor, which can be useful for the diagnosis of movement disorders. In particular, cerebral D₂ receptor binding as measured by carbon-11-raclopride (¹¹C-raclopride) has shown to reflect disease severity of Huntington's disease, a genetical disease characterized by selective degeneration of cerebral D₂ receptors.[2]

Other studies have investigated the relationship of D₂ receptor binding capacity and personality disorders. For example, one study found decreased binding in the detachment personality trait.[3] Radiolabelled raclopride is also commonly used to determine the efficacy and neurotoxicity of dopaminergic drugs.

References

Köhler C, Hall H, Ogren SO, Gawell L (1985). "Specific in vitro and in vivo binding of 3H-raclopride. A potent substituted benzamide drug with high affinity for dopamine D-2 receptors in the rat brain". Biochemical Pharmacology. 34 (13): 2251–9. doi:10.1016/0006-2952(85)90778-6. PMID 4015674.
Antonini A, Leenders KL, Spiegel R, Meier D, Vontobel P, Weigell-Weber M, Sanchez-Pernaute R, de Yébenez JG, Boesiger P, Weindl A, Maguire RP (1996). "Striatal glucose metabolism and dopamine D2 receptor binding in asymptomatic gene carriers and patients with Huntington's disease". Brain. 119 (6): 2085–95. doi:10.1093/brain/119.6.2085. PMID 9010012.
Farde L, Gustavsson JP, Jönsson E (1997). "D2 dopamine receptors and personality traits". Nature. 385 (6617): 590. doi:10.1038/385590a0. PMID 9024656. S2CID 4235650.

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[1] Köhler C, Hall H, Ogren SO, Gawell L (1985). "Specific in vitro and in vivo binding of 3H-raclopride. A potent substituted benzamide drug with high affinity for dopamine D-2 receptors in the rat brain". Biochemical Pharmacology. 34 (13): 2251–9. doi:10.1016/0006-2952(85)90778-6. PMID 4015674.

[2] Antonini A, Leenders KL, Spiegel R, Meier D, Vontobel P, Weigell-Weber M, Sanchez-Pernaute R, de Yébenez JG, Boesiger P, Weindl A, Maguire RP (1996). "Striatal glucose metabolism and dopamine D2 receptor binding in asymptomatic gene carriers and patients with Huntington's disease". Brain. 119 (6): 2085–95. doi:10.1093/brain/119.6.2085. PMID 9010012.

[3] Farde L, Gustavsson JP, Jönsson E (1997). "D2 dopamine receptors and personality traits". Nature. 385 (6617): 590. doi:10.1038/385590a0. PMID 9024656. S2CID 4235650.