Ambazon

Structural formula
General
Non-proprietary name	Ambazon
other names	p -Benzoquinone-guanylhydrazone- ; thiosemicarbazone; [4- (2- (diaminomethylidene) hydrazinyl) ; phenyl] iminothiourea ( IUPAC ) ;
Molecular formula	C 8 H 11 N 7 S
Brief description	copper brown crystals
External identifiers / databases
EC number	208-713-0
ECHA InfoCard	100.007.922
PubChem	1549158
Wikidata	Q414317
Drug information
ATC code	R02 AA01
Drug class	antiseptic
properties
Molar mass	237.28 g mol −1
Physical state	firmly
Melting point	193 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
Toxicological data	750 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ambazon is a medicine that was used as an antiseptic in the mouth and throat . It was patented by Bayer in 1957 and later sold under the trade name Iversal ^® , but is no longer on the market today.

Chemically speaking, ambazone is a functional derivative of 1,4-benzoquinone ( p -benzoquinone). As a derivative of guanidine, the compound has strongly basic properties.

synthesis

The synthesis of ambazone is carried out starting from 1,4-benzoquinone in two stages by reaction with aminoguanidine and thiosemicarbazide :

Individual evidence

^ ^A ^b Hans Beyer, Wolfgang Walter: Textbook of Organic Chemistry . 20th ed., Hirzel, Stuttgart, 1984. p. 483, ISBN 3-7776-0406-2 .
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Entry on Ambazon in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ Patent DE965723 : Process for the production of condensation products. Registered on January 31, 1953 , published on June 19, 1957 , applicant: Bayer AG , inventor: Siegfried Petersen, Gerhard Domagk . ‌
^ A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2001) Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 .

Web links

Entry to Ambazon. In: Römpp Online . Georg Thieme Verlag, accessed on January 2, 2015.

[BW-1] A ^b Hans Beyer, Wolfgang Walter: Textbook of Organic Chemistry . 20th ed., Hirzel, Stuttgart, 1984. p. 483, ISBN 3-7776-0406-2 .

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[ChemIDplus-3] Entry on Ambazon in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[4] Patent DE965723 : Process for the production of condensation products. Registered on January 31, 1953 , published on June 19, 1957 , applicant: Bayer AG , inventor: Siegfried Petersen, Gerhard Domagk . ‌

[Kleemann-5] A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2001) Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 .