13-00376. Ambazone [Archived]

Nomenclature

CAS number: 539-21-9
2-[4-[(Aminoiminomethyl)hydrazono]-2,5-cyclohexadien-1-ylidene]hydrazinecarbothioamide; [(4-oxo-2,5-cyclohexadien-1-ylidene)amino]guanidine thiosemicarbazone; 1-amidinohydrazono-4-thiosemicarbazono-2,5-cyclohexadiene; p-benzoquinone amidinohydrazone thiosemicarbazone; benzoquinone guanylhydrazone thiosemicarbazone; Iversal (Bayer); Primal (Bayer).
C8H11N7S; mol wt 237.28.
C 40.49%, H 4.67%, N 41.32%, S 13.51%.

Description and references

Prepn from p-benzoquinone and aminoguanidine followed by treatment of the reaction product with thiosemicarbazide in acid soln: Petersen, Domagk, Naturwissenschaften 41, 10 (1954); eidem, DE 965723 and GB 774794 (both 1957 to Bayer).

Chemical structure

Derivative

Monohydrate.

Properties

Brown or copper-colored crystals from water, dec 195°. Sparingly soluble in water. Moderately sol in alcohol, acetone. Freely sol in DMF, dilute acids.

Therapeutic Category

Antibacterial.

Keywords

Antiseptic/Disinfectant; Guanidines

Status

This monograph has been retired and is no longer subject to revision or update.