Definition
ChEBI: Amiphenazole is a member of thiazoles.
Manufacturing Process
Thiourea reacted with α-bromophenylacetonitrile and as a result of this
reaction 2-(cyanophenylmethyl)isothiourea was obtained.
By cyclisation of the 2-(cyanophenylmethyl)isothiourea 2,4-diamino-5-
phenylthiazole (amiphenazol) was produced.
Therapeutic Function
Respiratory stimulant, Barbiturate antagonist,
Morphine antagonist
Synthesis Reference(s)
Journal of the American Chemical Society, 73, p. 4517, 1951
DOI: 10.1021/ja01154a005
Purification Methods
The thiazole crystallises from aqueous EtOH or water. Store it in the dark under N2. The hydrochloride has m 273-274o(dec) (from MeOH/EtOAc), and the picrate has m 189-191o(dec) (from H2O). [Davies et al. J Chem Soc 3491 1950, Dodson & Turner J Am Chem Soc 73 4517 1951, Beilstein 27 III/IV 5139.]
