Azapride

Azapride
Clinical data
Other names	Azidoclebopride
ATC code	None;
Identifiers
	IUPAC name 4-Azido-5-chloro-2-methoxy-N-[1-(phenylmethyl)piperidin-4-yl]benzamide;
CAS Number	92990-90-4 ;
PubChem CID	3036441 ;
ChemSpider	2300456 ;
UNII	URS8YWT9Q7 ;
CompTox Dashboard (EPA)	DTXSID00239217 ;
Chemical and physical data
Formula	C20H22ClN5O2
Molar mass	399.88 g·mol−1
3D model (JSmol)	Interactive image ;
	SMILES Clc1cc(c(OC)cc1/N=[N+]=[N-])C(=O)NC3CCN(Cc2ccccc2)CC3;
	InChI InChI=1S/C20H22ClN5O2/c1-28-19-12-18(24-25-22)17(21)11-16(19)20(27)23-15-7-9-26(10-8-15)13-14-5-3-2-4-6-14/h2-6,11-12,15H,7-10,13H2,1H3,(H,23,27) ; Key:CKKHIIXHAWWTNP-UHFFFAOYSA-N ;
	(verify)

Last updated September 13, 2025

Azapride is the azide derivative of the dopamine antagonist clebopride synthesized in order to label dopamine receptors.^[1]^[2] It is an irreversible dopamine antagonist.^[2]

References

↑ Niznik HB, Guan JH, Neumeyer JL, Seeman P (February 1985). "A photoaffinity ligand for dopamine D2 receptors: azidoclebopride". Molecular Pharmacology. 27 (2): 193–9. doi:10.1016/S0026-895X(25)12275-X. PMID 3969068.
1 2 Wouters W, Van Dun J, Laduron PM (December 1984). "Photoaffinity labelling of dopamine receptors. Synthesis and binding characteristics of azapride". European Journal of Biochemistry. 145 (2): 273–8. doi: 10.1111/j.1432-1033.1984.tb08548.x . PMID 6548707.

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[1] Niznik HB, Guan JH, Neumeyer JL, Seeman P (February 1985). "A photoaffinity ligand for dopamine D2 receptors: azidoclebopride". Molecular Pharmacology. 27 (2): 193–9. doi:10.1016/S0026-895X(25)12275-X. PMID 3969068.

[Wouters-2] 1 2 Wouters W, Van Dun J, Laduron PM (December 1984). "Photoaffinity labelling of dopamine receptors. Synthesis and binding characteristics of azapride". European Journal of Biochemistry. 145 (2): 273–8. doi: 10.1111/j.1432-1033.1984.tb08548.x . PMID 6548707.

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