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92-62-6

Basic Information
CAS No.: 92-62-6
Name: PROFLAVINE
Article Data: 16
Molecular Structure:
Molecular Structure of 92-62-6 (PROFLAVINE)
Formula: C13H11 N3
Molecular Weight: 209.25
Synonyms: Acridine,3,6-diamino- (8CI); 3,6-Diaminoacridine; 3,7-Diamino-5-azaanthracene; Isoflavbase; Proflavin; Proflavine
EINECS: 202-172-4 (Proflavine)
Density: 1.346 g/cm3
Melting Point: 260 C
Boiling Point: 506.9 °C at 760 mmHg
Flash Point: 292.9 °C
Solubility: Slightly soluble SOLVENT
Appearance: orange to brown powder
Hazard Symbols: 9 (Packing Group: III) UN NO.
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).
Transport Information: 307
PSA: 64.93000
LogP: 3.71480
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
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Chemistry

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:

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.

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.

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.

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).

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.