Muzolimine

Muzolimine is a high-ceiling loop diuretic.^[1] It is a pyrazole diuretic which was used for treatment of hypertension but was withdrawn worldwide because of severe neurological side effects.^[2]

Muzolimine

Clinical data
ATC code	C03CD01 (WHO)
Legal status
Legal status	Withdrawn
Identifiers
IUPAC name 5-amino-2-[1-(3,4-dichlorophenyl)ethyl]-4H-pyrazol-3-one
CAS Number	55294-15-0 N
PubChem CID	41386
ChemSpider	37766 N
UNII	07Z36289ZX
KEGG	D05093 Y
CompTox Dashboard (EPA)	DTXSID50866476
ECHA InfoCard	100.054.139
Chemical and physical data
Formula	C11H11Cl2N3O
Molar mass	272.13 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C1CC(N)=NN1C(C)c2cc(Cl)c(Cl)cc2
InChI InChI=1S/C11H11Cl2N3O/c1-6(16-11(17)5-10(14)15-16)7-2-3-8(12)9(13)4-7/h2-4,6H,5H2,1H3,(H2,14,15) N Key:RLWRMIYXDPXIEX-UHFFFAOYSA-N N
NY (what is this?)  (verify)

Synthesis

Muzolimine synthesis:^[3][4]

Rxn of (1-(3,4-dichlorophenyl)ethyl)hydrazine (1) with ethyl 3-amino-3-ethoxyacrylate (2) leads to a ring-forming two-site reaction and formation of the pyrazoline diuretic agent, muzolimine (3).