7744. Primaquine

Nomenclature

CAS number: 90-34-6
N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine; 8-(4-amino-1-methylbutylamino)-6-methoxyquinoline; SN-13272.
C15H21N3O; mol wt 259.35.
C 69.47%, H 8.16%, N 16.20%, O 6.17%.

Description and references

Prepn following the synthesis of pamaquine: Elderfield et al., J. Am. Chem. Soc. 68, 1525 (1946); improved procedure: Elderfield et al., ibid. 77, 4816 (1955). Review: Olenick in Antibiotics vol. 3, J. W. Corcoran, F. E. Hahn, Eds. (Springer-Verlag, New York, 1975) pp 516-520.

Chemical structure

Properties

Viscous liquid, bp0.2 175-179°. Soluble in ether.

Derivative

Diphosphate.

Nomenclature

CAS number: 63-45-6
C15H21N3O.2H3PO4; mol wt 455.34.
C 39.57%, H 5.98%, N 9.23%, O 31.62%, P 13.60%.

Properties

Yellow crystals from 90% ethanol, mp 197-198°. Moderately sol in water.

Derivative

Oxalate.
C15H21N3O.C2H2O4; mol wt 349.38.
C 58.44%, H 6.64%, N 12.03%, O 22.90%.

Properties

Yellow crystals from 80% ethanol, mp 182.5-185°.

Therapeutic Category

Antimalarial.

Keywords

Antimalarial