Acridine

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Acridine

Acridine, C₁₃H₉N, is an organic compound

Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
and a nitrogen heterocycle

Heterocyclic compound

Heterocyclic compounds are organic compounds containing at least one atom of carbon, and at least one element other than carbon, such as sulfur, oxygen or nitrogen within a ring structure....
. Acridine is also used to describe compounds containing the C₁₃N tricycle.

Acridine is structurally related to anthracene

Anthracene

Anthracene is a solid polycyclic aromatic hydrocarbon consisting of three fused benzene rings derived from coal-tar or other residues of thermal pyrolysis....
with one of the central CH groups is replaced by nitrogen. Acridine, a colorless solid, was first isolated from coal tar

Coal tar

Coal tar is a brown or black liquid of high viscosity, which smells of naphthalene and aromatic hydrocarbons. Coal tar is among the by-products when coal is...
. It is a raw material used for the production of dye

Dye

A dye can generally be described as a colored substance that has an Chemical affinity to the Wiktionary:substrate to which it is being applied....
s and some valuable drugs. Many acridines, such as proflavine

Proflavine

Proflavine , also called proflavin and diaminoacridine, is an acriflavine derivative, a disinfectant bacteriostatic against many gram-positive bacteria....
, also have antiseptic

Antiseptic

Antiseptics are antimicrobials that are applied to living biological tissue/skin to reduce the possibility of infection, sepsis, or putrefaction....
properties.

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Encyclopedia

Acridine, C₁₃H₉N, is an organic compound

Organic compound

Heterocyclic compound

Anthracene

Coal tar

Dye

Proflavine

Proflavine , also called proflavin and diaminoacridine, is an acriflavine derivative, a disinfectant bacteriostatic against many gram-positive bacteria....
, also have antiseptic

Antiseptic

Antiseptics are antimicrobials that are applied to living biological tissue/skin to reduce the possibility of infection, sepsis, or putrefaction....
properties. Acridine and related derivatives bind to DNA and RNA due to their abilities to intercalate

Intercalation (chemistry)

In chemistry, intercalation is the reversible inclusion of a molecule between two other molecules . Examples include DNA intercalation and in graphite intercalation compounds....
. Acridine orange

Acridine orange

Acridine orange is a nucleic acid selective fluorescent cationic dye useful for cell cycle determination. It is cell-permeable, and interacts with DNA and RNA by Intercalation or electrostatic attractions respectively....
(3,6-dimethylaminoacridine) is a nucleic acid

Nucleic acid

A nucleic acid is a macromolecule composed of chains of monomeric nucleotides. In biochemistry these molecules carry genetic information or form structures within Cell ....
-selective metachromatic stain

Staining (biology)

Staining is an auxiliary technique used in microscopy to enhance contrast in the microscopic image.In biochemistry it involves adding a class-specific dye to a substrate to qualify or quantify the presence of a specific compound....
useful for cell cycle determination. Acridarsine is formally derived from acridine by replacing the nitrogen

Nitrogen

Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
atom with one of arsenic

Arsenic

Arsenic is a well-known chemical element that has the symbol As and atomic number 33. Arsenic was first documented by Albertus Magnus in 1250....
, and acridophosphine by replacing it with one of phosphorus

Phosphorus

Phosphorus is the chemical element that has the symbol P and atomic number 15. The name comes from the and . A Valency nonmetal of the nitrogen group, phosphorus is commonly found in inorganic phosphate minerals....
.

History

Acridine was first isolated in 1871 by Carl Gräbe

Carl Gräbe

Carl Gr?be was a Germany chemist from Frankfurt.Gr?be studied in Frankfurt, Karlsruhe and Heidelberg. Later he worked for the chemical company Meister Lucius und Br?ning ....
and Heinrich Caro

Heinrich Caro

Heinrich Caro , was a Germany Chemist.He started his study of chemistry at the Humboldt University of Berlin and later chemistry and dyeing in Berlin at the Royal Trades Institute....
.

Sources

Acridine occurs naturally in coal tar

Coal tar

Coal tar is a brown or black liquid of high viscosity, which smells of naphthalene and aromatic hydrocarbons. Coal tar is among the by-products when coal is...
. It is separated from coal tar by extracting with dilute sulfuric acid

Sulfuric acid

Sulfuric acid, hydrogen2sulfuroxygen4, is a strong mineral acid. It is soluble in water at all concentrations. Sulfuric acid has many applications, and is one of the top products of the chemical industry....
; addition of potassium dichromate

Potassium dichromate

Potassium dichromate, K2Cr2O7, is a common inorganic compound chemical reagent, most commonly used as an oxidizing agent in various laboratory and industrial applications....
to this solution precipitates acridine bichromate. The bichromate is decomposed

Chemical decomposition

Chemical decomposition or analysis is the separation of a chemical compound into chemical element or smaller compounds. It is sometimes defined as the opposite of a chemical synthesis....
using ammonia

Ammonia

Ammonia is a chemical compound with the chemical formula nitrogenhydrogen. It is normally encountered as a gas with a characteristic pungent odor....
.

Many synthetic processes are known for the production of acridine and its derivatives. A. Bernthsen condensed diphenylamine

Diphenylamine

Diphenylamine is the organic compound with the chemical formula 2NH. It is a colourless solid, but samples are often yellow due to oxidized impurities....
with carboxylic acid

Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
s, in the presence of zinc chloride

Zinc chloride

Zinc chloride is the name of chemical compound with the chemical formula zincchlorine2 and its hydrates. Zinc chlorides, of which nine crystalline forms are known, are colorless or white and highly soluble in water....
in the Bernthsen acridine synthesis

Bernthsen acridine synthesis

The Bernthsen acridine synthesis is the chemical reaction of a diarylamine heated with a carboxylic acid and zinc chloride to form a 9-substituted acridine....
. With formic acid

Formic acid

Formic acid is the simplest carboxylic acid. Its formula is hydrogencarbonoxygenOH or CH2O2. It is an important intermediate in chemical synthesis and occurs naturally, most notably in the venom of bee and ant stingers....
as the carboxylic acid the reaction yields acridine itself, and with the higher homologues

Homologous series

In chemistry, a homologous series is a series of organic compounds with a similar general formula, possessing similar chemical properties due to the presence of the same functional group, and shows a gradation in physical properties as a result of increase in molecular size and mass ....
the derivatives substituted at the meso carbon atom are generated.

Other older methods for the organic synthesis

Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic_chemistry molecules can often contain a higher level of complexity compared to purely Inorganic_chemistry compounds, so the synthesis of organic compounds has developed into one of the most im...
of acridines include condensing diphenylamine

Diphenylamine

Diphenylamine is the organic compound with the chemical formula 2NH. It is a colourless solid, but samples are often yellow due to oxidized impurities....
with chloroform

Chloroform

Chloroform, also known as trichloromethane and methyl trichloride, is a chemical compound with chemical formula CarbonHydrogenChlorine3....
in the presence of aluminium chloride

Aluminium chloride

Aluminium chloride is a chemical compound of aluminium and chlorine. The solid has a low melting and boiling point, and is Covalent bond. It sublimation at 178 ?Celsius....
, by passing the vapours of orthoaminodiphenylmethane over heated litharge

Litharge

Litharge is one of the natural mineral forms of lead oxide, PbO. Litharge is a secondary mineral which forms from the oxidation of galena ores. It forms as coatings and encrustations with internal tetragonal crystal system....
, by heating salicylic aldehyde with aniline

Aniline

Zinc chloride

Acridone

Acridone is an organic compound based on the acridine skeleton, with a carbonyl group at the 9 position. It may be synthesized by the self-condensation of N-Phenylanthranilic acid....
(9-position a carbonyl

Carbonyl

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double bond to an oxygen atom : C=O.The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex ; in this situation, carbon is triple-bonded to oxygen : C=O....
group) over zinc

Zinc

Zinc is a metallic chemical element with the symbol Zn and atomic number 30. It is a first-row transition metal of the group 12 element of the periodic table....
dust.

A general method for acridine synthesis is the cyclisation of N-phenylanthranilic acid or 2-(phenylamino)benzoic acid with phosphoric acid

Phosphoric acid

Phosphoric acid, also known as orthophosphoric acid or phosphoric acid, is a mineral acid having the chemical formula Hydrogen3PhosphorusOxygen4....
.

A classic method for the synthesis of acridones is the Lehmstedt-Tanasescu reaction

Lehmstedt-Tanasescu reaction

The Lehmstedt-Tanasescu reaction is a method in organic chemistry for the organic synthesis of acridone derivatives from a 2-nitrobenzaldehyde and an arene compound :...
.

Physical properties

Acridine and its homologues are stable compounds of weakly basic character. Acridine has a pKa

PKA

PKA or pKa may be:* Protein kinase A, a cAMP activated protein kinase* pKa, the symbol for Acid dissociation constant...
of 5.6, which is similar to that of pyridine

Pyridine

Pyridine is a simple and important heterocyclic aromatic organic compound with the formula CarbonHydrogenNitrogen. This colorless liquid with a distinctive fish-like odor is structurally related to benzene, wherein one CH group in the six-membered ring is replaced by a nitrogen atom....
. It also shares properties with quinoline

Quinoline

Quinoline, also known as 1-azanaphthalene, 1-benzazine, or benzo[b]pyridine, is a heterocyclic aromatic organic compound. It has the formula C9H7N and is a colourless hygroscopic liquid with a strong odour....
which is the single fused homologue. Acridine crystallizes in needles which melt at 110 °C. It is characterized by its irritating action on the skin, and by the blue fluorescence

Fluorescence

Fluorescence is a luminescence that is mostly found as an optical phenomenon in cold bodies, in which the molecular absorption of a photon triggers the emission of a photon with a longer wavelength....
shown by solutions of its salts.

Chemical properties

Acridine combines readily with alkyl iodides to form alkyl acridinium iodides, which are readily transformed by the action of alkaline potassium ferricyanide

Potassium ferricyanide

Potassium ferricyanide is the chemical compound with the formula K3[Fe6]. This bright red salt consists of the coordination compound ferricyanide....
to N-alkyl acridones. On oxidation with potassium permanganate

Potassium permanganate

Potassium permanganate is the inorganic chemical compound potassiummanganeseoxygen4, a water soluble salt consisting of equal Mole amounts of potassium and permanganate ions....
it yields acridinic acid C₉H₅N(COOH)₂ or quinoline-1,2-dicarboxylic acid. Acridine is easily oxidized by peroxymonosulfuric acid

Peroxymonosulfuric acid

Peroxymonosulfuric acid, also known as persulfuric acid, peroxysulfuric acid, or as Caro's acid, is H2SO5, a colorless solid melting at 45 ?C....
to the acridine amine oxide

Amine oxide

An amine oxide, also known as amine-N-oxide and N-oxide, is a chemical compound that contains the functional group R3N+-O− ....
. The carbon 9-position of acridine is activated for addition reaction

Addition reaction

An addition reaction, in organic chemistry, is in its simplest terms an organic reaction where two or more molecules combine to form a larger one....
s. The compound is reduced to the 9,10-dehydroacridine and reaction with potassium cyanide

Potassium cyanide

Potassium cyanide is an inorganic compound with the chemical formula KCN. This colorless crystalline compound, similar in appearance to sugar, is highly soluble in water....
gives the 9-cyano-9,10-dehydro derivative.

Numerous derivatives of acridine are known and may be prepared by methods analogous to those used for the formation of the parent base. 9-Phenylacridine is the parent base of chrysaniline or 3,6-diamino-9-phenylacridine, which is the chief constituent of the dyestuff phosphine (not to be confused with phosphine

Phosphine

Phosphine is the common name for phosphorus trihydride , also known by the IUPAC name phosphane and, occasionally, phosphamine....
gas), a by-product in the manufacture of rosaniline.

Chrysaniline forms red-coloured salts, which dye silk

Silk

Silk is a natural protein fiber, some forms of which can be weaving into textiles. The best-known type of silk is obtained from Pupa#Cocoons made by the larvae of the mulberry silkworm Bombyx mori reared in captivity ....
and wool

Wool

Wool is the fiber derived from the specialized skin cells, called follicles, of animals in the Caprinae family, principally domestic sheep, but the hair of certain species of other Mammalia such as cashmere goat, llamas, rabbits and keeshonds may also be called wool....
a fine yellow; and the solutions of the salts are characterized by their fine yellowish-green fluorescence. Chrysaniline was synthesized by O. Fischer and G. Koerner by condensing ortho-nitrobenzaldehyde with aniline

Aniline

Aniline, phenylamine or aminobenzene is an organic compound with the Chemical formula C6H7N. It is the simplest and one of the most important aromatic amines, being used as a precursor to more complex chemicals....
, the resulting ortho-nitro-para-diamino-triphenylmethane being reduced to the corresponding orthoamino compound, which on oxidation yields chrysaniline.

Benzoflavin, an isomer of chrysaniline, is also a dye-stuff, and has been prepared by K. Oehler from meta-phenylenediamine and benzaldehyde

Benzaldehyde

Benzaldehyde is a chemical compound consisting of a benzene ring with an aldehyde substituent. It is the simplest representative of the aromatic aldehydes and one of the most industrially used members of this family of compounds....
. These substances condense to form tetra-aminotriphenylmethane, which, on heating with acids, loses ammonia and yields 3,6-diamino-9,10-dihydrophenylacridine, from which benzoflavin is obtained by oxidation. It is a yellow powder, soluble in hot water.

Cancer link

Acridine is a known human carcinogen

Carcinogen

The term carcinogen refers to any substance, radionuclide or radiation that is an agent directly involved in the promotion of cancer or in the increase of its propagation....
. It causes mutations in incorporating into the DNA

DNA

Deoxyribonucleic acid is a nucleic acid that contains the genetics instructions used in the development and functioning of all known living organisms and some viruses....
, and doing so creating an additional base on the opposite strand. If that mutation occurs in a coding sequence, it almost always leads to inactivation of the protein

Protein

Proteins are organic compounds made of amino acids arranged in a linear chain and joined together by peptide bonds between the carboxyl and amino groups of adjacent amino acid Residue ....
it encoded.

External links

Synthesis of acridone in Organic Syntheses
Organic Syntheses

Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds....
19:6; Coll. Vol. 2:15 from o-chlorobenzoic acid and aniline in a Goldberg reaction.
Synthesis of 9-aminoacridine in Organic Syntheses
Organic Syntheses

Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds....
22:5; Coll. Vol. 3:53. from N-phenylanthranilic acid.