Clamoxyquine

Clamoxyquine
Clinical data
ATC code	none;
Identifiers
	IUPAC name 5-Chloro-7-({[3-(diethylamino)propyl]amino}methyl)quinolin-8-ol;
CAS Number	2545-39-3;
PubChem CID	18029;
ChemSpider	17033;
UNII	JUN13FZ6RF;
ChEMBL	ChEMBL2106065;
CompTox Dashboard (EPA)	DTXSID50180109 ;
Chemical and physical data
Formula	C17H24ClN3O
Molar mass	321.85 g·mol−1
3D model (JSmol)	Interactive image;
	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.

Clamoxyquin synthesis:[1]

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

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References

Burckhalter, J. H.; Brinigar, W. S.; Thompson, P. E. (1961). "Antiamebic Agents. V.1Promising Basic Amebicides Derived from 5-Chloro-8-quinolinol". The Journal of Organic Chemistry. 26 (10): 4070. doi:10.1021/jo01068a103.

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[1] Burckhalter, J. H.; Brinigar, W. S.; Thompson, P. E. (1961). "Antiamebic Agents. V.1Promising Basic Amebicides Derived from 5-Chloro-8-quinolinol". The Journal of Organic Chemistry. 26 (10): 4070. doi:10.1021/jo01068a103.