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Proflavine

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Name

Proflavine

EINECS 202-172-4 (Proflavine)
CAS No. 92-62-6 Density 1.346 g/cm3
PSA 64.93000 LogP 3.71480
Solubility Slightly soluble SOLVENT Melting Point 260 C
Formula C13H11 N3 Boiling Point 506.9 °C at 760 mmHg
Molecular Weight 209.25 Flash Point 292.9 °C
Transport Information 307 Appearance orange to brown powder
Safety Poison by intravenous, intraperitoneal, and subcutaneous routes. Questionable carcinogen. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also 2,6-DIAMINOACRIDINE; 3,6-DIAMINOACRIDINE HYDROCHLORIDE HEMIHYDRATE; 3,6-DIAMINOACRIDINE SULFATE (1:1). Risk Codes N/A
Molecular Structure Molecular Structure of 92-62-6 (PROFLAVINE) Hazard Symbols 9 (Packing Group: III) UN NO.
Synonyms

Acridine,3,6-diamino- (8CI); 3,6-Diaminoacridine; 3,7-Diamino-5-azaanthracene; Isoflavbase; Proflavin; Proflavine

Article Data 16

Proflavine Synthetic route

64-18-6

formic acid

541-69-5

m-phenylenediamine dihydrochloride

A

92-62-6

proflavine

B

9,10-dihydro-9,9'-oxy-bis-acridine-3,6-diyldiamine

Conditions
ConditionsYield
With glycerol at 155℃;
42832-87-1

3,6-diaminoacridin-9(10H)-one

92-62-6

proflavine

Conditions
ConditionsYield
With sodium hydroxide; sodium amalgam; water
26946-33-8

4,4'-methylenebis(m-nitroaniline)

92-62-6

proflavine

Conditions
ConditionsYield
With hydrogenchloride; tin at 135 - 140℃;
181189-62-8

4,4'-methanediyl-bis-m-phenylenediamine

92-62-6

proflavine

Conditions
ConditionsYield
With hydrogenchloride at 170℃;
144-62-7

oxalic acid

108-45-2

m-phenylenediamine

5435-44-9, 22243-66-9

(E)-3-Ureido-but-2-enoic acid ethyl ester

56-81-5

glycerol

92-62-6

proflavine

Conditions
ConditionsYield
at 190℃;
64-18-6

formic acid

108-45-2

m-phenylenediamine

5435-44-9, 22243-66-9

(E)-3-Ureido-but-2-enoic acid ethyl ester

56-81-5

glycerol

92-62-6

proflavine

Conditions
ConditionsYield
at 190℃;
108-45-2

m-phenylenediamine

92-62-6

proflavine

Conditions
ConditionsYield
With oxalic acid; zinc(II) chloride at 190℃; Glycerin;
With formic acid; zinc(II) chloride at 190℃; Glycerin;
64-18-6

formic acid

541-69-5

m-phenylenediamine dihydrochloride

56-81-5

glycerol

A

92-62-6

proflavine

B

9,10-dihydro-9,9'-oxy-bis-acridine-3,6-diyldiamine

Conditions
ConditionsYield
at 155℃;
6262-24-4

formic acid-(3-amino-anilide)

541-69-5

m-phenylenediamine dihydrochloride

5435-44-9, 22243-66-9

(E)-3-Ureido-but-2-enoic acid ethyl ester

56-81-5

glycerol

92-62-6

proflavine

Conditions
ConditionsYield
at 155℃;
219853-08-4

(3,3'-bisamino)diphenylamine

56-81-5

glycerol

92-62-6

proflavine

Conditions
ConditionsYield
With hydrogenchloride; formic acid; water

Proflavine Chemical Properties

Chemistry informtion about Proflavine (CAS NO.92-62-6) is:
IUPAC Name: Acridine-3,6-Diamine
Synonyms: Proflavine ; 3,6-Acridinediamine ; 3,6-Aiaminoacridine ; Isoflabase
MF: C13H11N3 
MW: 11209.2465
Density: 1.346 g/cm3
Flash Point: 292.9 °C
Boiling Point: 506.9 °C at 760 mmHg
Vapour Pressure: 2.14E-10 mmHg at 25°C
 Enthalpy of Vaporization: 77.69 kJ/mol
Following is the molecular structure of Proflavine (CAS NO.92-62-6) is:

Proflavine Uses

3,6-Diaminoacridinium (CAS NO.92-62-6) has been used in the form of the dihydrochloride and hemisulfate salts as a topical antiseptic, and was formerly used as a urinary antiseptic.

Proflavine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 11111ug/kg (11.111mg/kg) sense organs and special senses: other changes: olfaction sense organs and special senses: other: eye lungs, thorax, or respiration: other changes Lancet. Vol. 196, Pg. 838, 1919.
mouse LD50 intraperitoneal 50mg/kg (50mg/kg)   Chemotherapy Vol. 16, Pg. 371, 1971.
mouse LD50 oral > 1gm/kg (1000mg/kg)   Journal of Medicinal Chemistry. Vol. 18, Pg. 320, 1975.
mouse LD50 subcutaneous 140mg/kg (140mg/kg)   British Journal of Experimental Pathology. Vol. 28, Pg. 1, 1947.

Proflavine Consensus Reports

IARC Cancer Review: Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 24 (1980),p. 195.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Proflavine Safety Profile

Poison by intravenous, intraperitoneal, and subcutaneous routes. Questionable carcinogen. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also 2,6-DIAMINOACRIDINE; 3,6-DIAMINOACRIDINE HYDROCHLORIDE HEMIHYDRATE; 3,6-DIAMINOACRIDINE SULFATE (1:1).

Proflavine Specification

 Proflavine (CAS NO.92-62-6), also called proflavin and diaminoacridine, is an acriflavine derivative, a disinfectant bacteriostatic against many gram-positive bacteria. Proflavine is also known to have a mutagenic effect on DNA by intercalating between nucleic acid base pairs. It differs from most other mutagenic components by causing basepair-deletions or basepair-insertions and not substitutions. Proflavine absorbs strongly in the blue region at 445nm (in water at pH 7) with molar extinction coefficient of c. 40,000.

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