Chemistry:Zacopride

Short description: Chemical compound

Zacopride

Clinical data
ATC code	none
Identifiers
IUPAC name 4-amino-5-chloro-2-methoxy-N-(quinuclidin-3-yl)benzamide
CAS Number	90182-92-6 Y
PubChem CID	108182
IUPHAR/BPS	245
ChemSpider	97262 N
UNII	9GN3OT4156
ChEMBL	ChEMBL18041 N
Chemical and physical data
Formula	C15H20ClN3O2
Molar mass	309.79 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC(=C(C=C1C(=O)NC2CN3CCC2CC3)Cl)N
InChI InChI=1S/C15H20ClN3O2/c1-21-14-7-12(17)11(16)6-10(14)15(20)18-13-8-19-4-2-9(13)3-5-19/h6-7,9,13H,2-5,8,17H2,1H3,(H,18,20) N Key:FEROPKNOYKURCJ-UHFFFAOYSA-N N
NY (what is this?)  (verify)

Zacopride is a potent antagonist at the 5-HT₃ receptor and an agonist at the 5-HT₄ receptor. It has anxiolytic and nootropic effects in animal models, with the (R)-(+)-enantiomer being the more active form. It also has antiemetic and pro-respiratory effects, both reducing sleep apnea and reversing opioid-induced respiratory depression in animal studies. Early animal trials have also revealed that administration of zacopride can reduce preference for and consumption of ethanol.

Zacopride was found to significantly increase aldosterone levels in human subjects for 180 minutes at a dose of 400 micrograms. It is thought to do this by stimulating the 5-HT₄ receptors on the adrenal glands. Zacopride also stimulated aldosterone secretion when applied to human adrenal glands in vitro. No significant changes were observed in renin, ACTH, or cortisol levels.

Zacopride has been tested in clinical trials for the treatment of schizophrenia, but was found unsuccessful.