Acriflavinium chloride

from Wikipedia, the free encyclopedia
Structural formula
Structure of diaminomethylacridinium chloride Structure of diaminoacridine hydrochloride
General
Non-proprietary name Acriflavinium chloride
other names
  • Trypaflavin
  • Neutroflavin
  • Euflavine
Molecular formula Mixture of
  • C 13 H 12 ClN 3 and
  • C 14 H 14 ClN 3
Brief description

reddish brown, crystalline powder

External identifiers / databases
CAS number
  • 69235-50-3
  • 8063-24-9 (old, deleted CAS number; hydrochloride)
EC number 685-466-9
ECHA InfoCard 100.211.047
PubChem 443101
Wikidata Q225854
Drug information
ATC code

R02 AA13

Drug class

Antiseptics

properties
Molar mass Mixture of substances
Physical state

firmly

Melting point

260 ° C (decomposition from 130 ° C)

solubility

good in water (300 g l −1 at 20 ° C)

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
05 - Corrosive 07 - Warning

danger

H and P phrases H: 302-318
P: 280-305 + 351 + 338
Toxicological data

1048 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 .

Acriflavinium chloride is a mixture of substances that is used as a medicinal substance ( antiseptic in the mouth and throat). It was patented by IG Farben in 1929.

From a chemical point of view, it is a mixture of about two thirds of 3,6-diamino-10-methylacridinium chloride (C 14 H 14 ClN 3 ) and about one third of 3,6-diaminoacridine hydrochloride (C 13 H 12 ClN 3 ), of which the former is a quaternary ammonium compound . Both compounds are derivatives of acridine .

Acriflavinium Chloride: A reddish brown, crystalline powder

effect

Acridine derivatives are effective against gram-positive bacteria . Acriflavinium chloride intercalates in nucleic acids and thereby inhibits the reproduction of bacteria and viruses . However, according to a study by the International Agency for Research on Cancer (IARC) , it may be carcinogenic .

Other uses

Acriflavinium chloride is also used for vital staining . In the past, 3,6-diamino-10-methylacridinium chloride was also used under the name trypaflavin as an agent against African trypanosomiasis ("sleeping sickness"), the pathogen of which is one of the trypanosomes .

Individual evidence

  1. ↑ a b c H. PT Ammon (Ed.): Hunnius. Pharmaceutical Dictionary . 9th edition. Walter de Gruyter, Berlin a. New York 2004.
  2. ↑ a b c data sheet Acriflavine hydrochloride from Sigma-Aldrich , accessed on March 20, 2011 ( PDF ).
  3. ↑ a b Data sheet acriflavinium chloride (PDF) from Merck , accessed on January 19, 2011.
  4. ↑ CJ Estler (Ed.): Pharmacology and Toxicology . 4th edition. Schattauer, Stuttgart a. New York 1995, p. 601.
  5. ↑ J. Falbe, M. Regitz (Ed.): Römpp Lexikon Chemie . 10th edition. Thieme, Stuttgart a. New York 1996-1999, p. 46.
  6. ↑ H. Beyer, W. Walter: Textbook of organic chemistry . 20th edition. Hirzel, Stuttgart 1984, p. 741.