483. Amiphenazole

Nomenclature

CAS number: 490-55-1
5-Phenyl-2,4-thiazolediamine; 2,4-diamino-5-phenylthiazole; DAPT; phenamizole; Dizol; Daptazole (Nicholas); Daptazile; Fenamizol.
C9H9N3S; mol wt 191.25.
C 56.52%, H 4.74%, N 21.97%, S 16.77%.

Description and references

Prepd by the interaction of thiourea and α-bromobenzyl cyanide in alcohol: Davies et al., J. Chem. Soc. 1950, 3491; from thiourea and α-cyanobenzyl benzenesulfonate in acetone: Dodson, Turner, J. Am. Chem. Soc. 73, 4517 (1951).

Chemical structure

Properties

Flakes from water or dilute alcohol, dec 163-164°. Turns brown on exposure to light and air.

Derivative

Hydrobromide.
C9H9N3S.HBr; mol wt 272.16.
C 39.72%, H 3.70%, N 15.44%, S 11.78%, Br 29.36%.

Properties

Prisms from alc, dec >250°. Freely sol in hot water, moderately in cold water.

Derivative

Benzenesulfonate.
C15H15N3O3S2; mol wt 349.43.
C 51.56%, H 4.33%, N 12.03%, O 13.74%, S 18.35%.

Properties

Crystals from alcohol + ether, dec 261-262°. Practically insol in water, most organic solvents. Slightly sol in alcohol.

Therapeutic Category

Narcotic antagonist.

Therapeutic Category (Veterinary)

Barbiturate and morphine antagonist.

Keywords

Narcotic Antagonist