Clamoxyquine

Clamoxyquine

File:Clamoxyquine.svg
Systematic (IUPAC) name
5-Chloro-7-({[3-(diethylamino)propyl]amino}methyl)quinolin-8-ol
Identifiers
CAS Number	2545-39-3
ATC code	none
PubChem	CID: 18029
ChemSpider	17033
UNII	JUN13FZ6RF Y
ChEMBL	CHEMBL2106065
Chemical data
Formula	C17H24ClN3O
Molecular mass	321.846 g·mol−1
SMILES Clc1cc(c(O)c2ncccc12)CNCCCN(CC)CC

Clamoxyquine (INN) or clamoxyquin (former BAN), as the pamoate or hydrochloride salt, is an antiamebic and antidiarrheal drug.

It has been used as a veterinary medicine to treat salmonids for infection with the myxozoan parasite Myxobolus cerebralis.

Synthesis

Antimalarial activity also predominates in a quinoline that bears a diaminoalkyl side chain at a rather different position from the other agents noted.

File:Clamoxyquin synthesis.svg

Clamoxyquin synthesis:

Thus, Mannich condensation of the hydroxyquinoline (1) with formaldehyde and N,N-diethylpropylenediamine affords clamoxyquin (2).