Clamoxyquine

Chemical compound

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 dataFormulaC₁₇H₂₄ClN₃OMolar mass321.85 g·mol⁻¹3D 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.

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

References

^ Burckhalter JH, Brinigar WS, Thompson PE (1961). "Antiamebic Agents. V.1Promising Basic Amebicides Derived from 5-Chloro-8-quinolinol". The Journal of Organic Chemistry. 26 (10): 4070–4078. doi:10.1021/jo01068a103.