Acridine
Chemical name	Acridine
Chemical formula	C13H9N
Molecular mass	179.2 g/mol
Melting point	107 °C
Boiling point	346 °C
CAS number	260-94-6
SMILES	C1(N=C(C=CC=C2)C2=C3) =C3C=CC=C1

Acridine, C₁₃H₉N, is an organic compound and a nitrogen heterocycle. The compound is similar to anthracene with the central benzene ring replaced by a pyridine ring. Acridine is colorless and was first isolated from crude coal tar. It is a raw material for the production of dyes. Many acridines also have antiseptic properties such as Proflavine. Acridine and their derivatives are DNA and RNA binding compounds due to their intercalation abilities. IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass (abbreviated MM) of a substance, called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Image File history File links Acridine_chemical_structure. ... Benzene An organic compound is any member of a large class of chemical compounds whose molecules contain carbon, with the exception of carbides, carbonates, carbon oxides and elementary carbon. ... Pyridine a simple heterocyclic compound Heterocyclic compounds are organic compounds which contain a ring structure containing atoms in addition to carbon, such as sulfur, oxygen or nitrogen, as part of the ring. ... In chemistry, anthracene is a solid polycyclic aromatic hydrocarbon consisting of three benzene rings derived from coal-tar. ... Pyridine is a clear liquid with an odor that is sour, putrid, and fish-like. ... Coal tar is the liquid by-product of the distillation of coal to make coke. ... Yarn drying after being dyed in the early American tradition, at Conner Prairie living history museum. ... An antiseptic (Greek αντι, against, and σηπτικος, putrefactive) is a substance that prevents the growth and reproduction of various microorganisms (such as bacteria, fungi, protozoa, and viruses) on the external surfaces of the body. ... Proflavine (pron. ... Intercalation induces structural distortions. ...

Acridine Orange (3,6-dimethylaminoacridine) is a nucleic acid selective metachromatic stain useful for cell cycle determination. Schematic diagram of a double-stranded nucleic acid. ... Staining is a biochemical technique of adding a class-specific (DNA, proteins, lipids, carbohydrates) dye to a substrate to qualify or quantify the presence of a specific compound. ...

History

Acridine was first isolated in 1890 by Carl Gräbe and Heinrich Caro. 1890 (MDCCCXC) was a common year starting on Wednesday (see link for calendar) of the Gregorian calendar (or a common year starting on Friday of the Julian calendar). ... Carl Gräbe (or Carl Graebe; February 24, 1841 - January 19, 1927), German chemist. ... Heinrich Caro (February 13, 1834 in Poznan - October 11, 1910 in Dresden), was a German Chemist. ...

Sources

Acridine occurs naturally in coal tar. It is separated from coal tar by shaking out with dilute sulfuric acid, and then precipitating the sulfuric acid solution with potassium dichromate, the resulting acridine bichromate is decomposed in the final step by ammonia. Coal tar is the liquid by-product of the distillation of coal to make coke. ... Sulfuric acid (British English: sulphuric acid), H2SO4, is a strong mineral acid. ... Potassium dichromate, K2Cr2O7 is used in oxidation reactions. ... chemical decomposition is the gradual fragmentation of a chemical compound into smaller molecules. ... Ammonia is a compound of nitrogen and hydrogen with the formula NH3. ...

Many synthetic processes are known for the production of acridine and its derivatives. A. Bernthsen condensed diphenylamine with carboxylic acids, in the presence of zinc chloride in the Bernthsen acridine synthesis. With Formic acid as the carboxylic acid the reaction yields acridine itself, and with the higher homologues the derivatives substituted at the meso carbon atom are generated. Diphenyl amine has been used for scald control on apples in the US, it is a fungicide. ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)-OH, usually written as -COOH. In general, the salts and anions... Zinc chloride (ZnCl2) is a colorless or white compound of zinc and chlorine that is extremely hygroscopic. ... The Bernthsen acridine synthesis is a chemical reaction in which a diarylamine is heated with a carboxylic acid (or carboxylic anhydride) and zinc chloride to form a 9-substituted acridine. ... Formic acid (systematically called methanoic acid) is the simplest carboxylic acid. ... The term homologue or homolog has several meanings: In biology, homologues are structures that are alike because of shared ancestry. ... Arene substitution patterns are part of organic chemistry IUPAC nomenclature and pinpoint the position of substituents other than hydrogen in relation to each other on an aromatic hydrocarbon. ...

Other older methods for the organic synthesis of acridines include condensing diphenylamine with chloroform in the presence of aluminium chloride, by passing the vapours of orthoaminodiphenylmethane over heated litharge, by heating salicylic aldehyde with aniline and zinc chloride to 260°C or by distilling acridone (9-position a carbonyl group) over zinc dust. Organic synthesis is the construction of organic molecules via chemical processes. ... Diphenyl amine has been used for scald control on apples in the US, it is a fungicide. ... PEL-TWA (OSHA) 50 ppm (240 mg/m3) IDLH (NIOSH) 500 ppm Flash point non-flammable RTECS number FS9100000 Supplementary data page Structure & properties n, εr, etc. ... Aluminium chloride (AlCl3) is a compound of aluminium and chlorine. ... Litharge is a yellow monoxide of lead created by heating lead in air. ... Aniline, phenylamine or aminobenzene (C6H5NH2) is an organic chemical compound which is a primary aromatic amine consisting of a benzene ring and an amino group. ... Zinc chloride (ZnCl2) is a colorless or white compound of zinc and chlorine that is extremely hygroscopic. ... Carbonyl group In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom. ... General Name, Symbol, Number zinc, Zn, 30 Chemical series transition metals Group, Period, Block 12, 4, d Appearance bluish pale gray Atomic mass 65. ...

A general method for acridine synthesis is the cyclisation of N-phenylanthranilic acid or 2-(phenylamino)benzoic acid with Phosphoric acid. R-phrases S-phrases , , Supplementary data page Structure and properties n, εr, etc. ...

Physical properties

Acridine and its homologues are very stable compounds of feebly basic character. Acridine has a pKa of 5.6 which is similar to that of pyridine. It also shares properties with quinoline 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 shown by solutions of its salts. In chemistry and biochemistry, acid dissociation constant, the acidity constant, or the acid-ionization constant () is a specific type of equilibrium constant that indicates the extent of dissociation of hydrogen ions from an acid. ... Pyridine is a clear liquid with an odor that is sour, putrid, and fish-like. ... Quinoline, also known as 1-azanaphthalene, 1-benzazine, or benzo[b]pyridine, is a heterocyclic aromatic organic compound. ... Fluorescence induced by exposure to ultraviolet light in vials containing various sized Cadmium selenide (CdSe) quantum dots. ...

Chemical properties

Acridine combines readily with alkyl iodides to form alkyl acridinium iodides, which are readily transformed by the action of alkaline potassium ferricyanide to N-alkyl acridones. On oxidation with potassium permanganate it yields acridinic acid C₉H₅N(COOH)₂ or quinoline-1,2-dicarboxylic acid. Acridine is easily oxidized by peroxymonosulfuric acid to the acridine amine oxide. The carbon 9-position of acridine is activated for addition reactions. The compound is reduced to the 9,10-dehydroacridine and reaction with potassium cyanide gives the 9-cyano-9,10-dehydro derivative. The haloalkanes are a group of chemical compounds, consisting of alkanes, such as methane or ethane, with one or more halogens linked, such as chlorine or fluorine, making them a type of organic halide. ... Potassium ferricyanide (K3[Fe(CN)6]) also known as red prussiate, Prussian red or potassium hexacyanoferrate(III), is a coordination compound that is stable at room temperature and pressure and forms ruby red crystals and powder. ... Potassium permanganate (KMnO4) is an inorganic chemical compound composed of potassium (K+) and permanganate (MnO4−) ions. ... Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. ... Peroxymonosulfuric acid, also known as Caros acid, is a strong oxidizing agent. ... An amine oxide, also known as amine-N-oxide and N-oxide, is a chemical compound that contains the functional group R3N+-O− (sometimes written as R3N=O or R3N→O). ... An addition reaction, in chemistry, is in its simplest terms a organic reaction where two or more molecules combine to form a larger one. ... Potassium cyanide or KCN is the potassium salt of hydrogen cyanide or hydrocyanic acid. ...

Numerous derivatives of acridine are known and may be prepared by methods analogous to those used for the formation of the parent base. Phenylacridine (9-phenyl-acridine) 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 gas), a by-product in the manufacture of rosaniline. R-phrases , , , , S-phrases , , , , , Flash point flammable gas Autoignition temperature 38 °C (see text) Explosive limits 1. ... Fuchsine Fuchsine, fuchsin, rosanilin, or rosaniline hydrochloride is a magenta dye with chemical formula C19H17N3·HCl. ...

Chrysaniline forms red-coloured salts, which dye silk and 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, the resulting ortho-nitro-para-diamino-triphenylmethane being reduced to the corresponding orthoamino compound, which on oxidation yields chrysaniline. Silk weaver Silk is a natural protein fiber that can be woven into textiles. ... Wool in a shearing shed Long and short hair wool at the South Central Family Farm Research Center in Boonesville, AR Wool sheep, Royal Melbourne Show Wool is the fibre derived from the fur of animals of the Caprinae family, principally sheep and goats, but the hair of other mammals... Aniline, phenylamine or aminobenzene (C6H5NH2) is an organic chemical compound which is a primary aromatic amine consisting of a benzene ring and an amino group. ...

Benzoflavin, an isomer of chrysaniline, is also a dye-stuff, and has been prepared by K. Oehler from meta-phenylenediamine and benzaldehyde. 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. The chemical compound benzaldehyde (C6H5CHO) consists of a benzene ring with an aldehyde group attached to one carbon. ...

Cancer link

Acridine is a known human carcinogen. In pathology, a carcinogen is any substance or agent that promotes cancer. ...

External links

• Synthesis of acridone in Organic Syntheses 19:6; Coll. Vol. 2:15 [1] from o-chlorobenzoic acid and aniline in a Goldberg reaction.
• Synthesis of 9-aminoacridine in Organic Syntheses 22:5; Coll. Vol. 3:53. [2] from N-phenylanthranilic acid.

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. ... The Goldberg reaction is a variation of the Ullmann reaction in which a primary aromatic amine is coupled to an aryl halide to a secondary amine in the presence of a copper compound. ... 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. ...

References

• Synthesis of Acridine-based DNA Bis-intercalating Agents Gerard P. Moloney, David P. Kelly, P. Mack Molecules 2001, 6, 230-243 [3] open source

This article incorporates text from the Encyclopædia Britannica Eleventh Edition, a publication now in the public domain. Open source refers to projects that are open to the public and which draw on other projects that are freely available to the general public. ... Encyclopædia Britannica, the 11th edition The Encyclopædia Britannica Eleventh Edition (1910–1911) is perhaps the most famous edition of the Encyclopædia Britannica. ... The public domain comprises the body of all creative works and other knowledge—writing, artwork, music, science, inventions, and others—in which no person or organization has any proprietary interest. ...