ACRIDINE

Acridine is an important heteroaromatic intermediate used in the preparation of dyes, fine chemicals, analytical reagents, and advanced functional compounds.
Acridine's fused tricyclic framework provides distinctive optical and electronic characteristics that support applications in fluorescence, molecular design, and specialty material development.
Acridine is also widely used as a precursor for producing diverse acridine derivatives for research and industrial chemistry.

CAS Number: 260-94-6
EC Number: 205-971-6
Molecular Formula: C13H9N
Molecular Weight: 179.22 g/mol

Synonyms: ACRIDINE, 260-94-6, 9-Azaanthracene, 10-Azaanthracene, 2,3-Benzoquinoline, Acrydine, Akridin, Dibenzo[b,e]pyridine, Benzo(b)quinoline, Dibenzo(b,e)pyridine, 2,3,5,6-Dibenzopyridine, Benzo[b]quinoline, Akridin [Czech], NSC 3408, NSC-3408, CCRIS 1636, HSDB 634, EINECS 205-971-6, UNII-42NI1P5Q1X, UN2713, BRN 0120200, 42NI1P5Q1X, CHEBI:36420, AI3-15279, ACRIDINE [MI], 39327-16-7, DTXSID8059766, 5-20-08-00199 (Beilstein Handbook Reference), UN 2713, DIBENZO (B,E) PYRIDINE, DIBENZO [B,E] PYRIDINE, Aceridine, 9Azaanthracene, 10Azaanthracene, 2,3Benzoquinoline, 9-ASAANTHRACENE, RefChem:109388, 2,3,5,6Dibenzopyridine, BENZO (B) QUINOLINE, DIBENZO(B,C)PYRIDINE, DTXCID6037433, 205-971-6, 9,9-dimethyl-2-nitro-9,10-dihydroacridine, BENZOQUINOLINE, DZBUGLKDJFMEHC-UHFFFAOYSA-N, InChI=1/C13H9N/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-9, NSC3408, MFCD00005025, Acridines, acridine acid, ACRIDINE (1,2,3,4,5,6,7,8,9-D9), Coal tar pitch volatiles: acridine, Acridine, 97%, UPCMLD-DP077, SCHEMBL8339, SCHEMBL23981, SCHEMBL24814, SCHEMBL25265, SCHEMBL26373, SCHEMBL27027, CHEMBL39677, SCHEMBL752521, WLN: T C666 BNJ, orb3029221, SCHEMBL1663602, SCHEMBL3922976, SCHEMBL4106752, SCHEMBL9322559, SCHEMBL29352289, UPCMLD-DP077:001, Acridine (purified by sublimation), Acridine [UN2713] [Poison], BDBM50551545, AKOS001568550, EBC-332170, FA17205, MSK001425-100T, Acridine Solution in Toluene, 100ug/mL, MSK001425-1000T, NCGC00161635-01, NCGC00161635-02, AS-42152, Acridine Solution in Toluene, 1000ug/mL, DB-046832, A0129, A0294, A3436, NS00009725, ST50330595, EN300-21156, C20141, AC-907/21098007, F332696, Q342713, J-200084, Acridine, BioReagent, suitable for fluorescence, >=97.0% (HPLC)

Acridine is a polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.
Acridine has a role as a genotoxin.
Acridine is a member of acridines, a mancude organic heterotricyclic parent and a polycyclic heteroarene.

Acridine is a polycyclic aromatic dye with antineoplastic, antimicrobial and imaging activities.
Acridine and its derivatives intercalate within DNA and RNA by forming hydrogen-bonds and stacking between base pairs resulting in DNA crosslinks and strand breaks.

In addition, acridine and its derivatives are a potent inhibitor of topoisomerase II enzyme.
This results in the inhibition of DNA and RNA synthesis, predominantly occurring during S phase of the cell cycle and ultimately leads to cell death.

Acridine is a small cationic and planar dye that mainly binds to RNA and DNA.
These dyes are strongly fluorescent.

Acridine resembles the structure of xanthene except that the heteroatom is nitrogen, not oxygen.
Acridine is a useful dye for biological research purposes.

Acridine is an organic compound and a nitrogen heterocycle with the formula C13H9N.
Acridines are substituted derivatives of the parent ring.

Acridine is a planar molecule that is structurally related to anthracene with one of the central CH groups replaced by nitrogen.
Like the related molecules pyridine and quinoline, acridine is mildly basic.

Acridine is an almost colorless solid, which crystallizes in needles.
There are few commercial applications of acridines; at one time acridine dyes were popular, but they are now relegated to niche applications, such as with acridine orange.
The name is a reference to the acrid odour and acrid skin-irritating effect of Acridine.

Acridine is defined as a three-ring aromatic molecule consisting of two fused benzene rings and a pyridine ring, serving as the structural backbone for various acridine derivatives that have diverse applications in chemistry and biology.

Acridine Orange is a cell-permeant nucleic acid binding dye that emits green fluorescence when bound to dsDNA and red fluorescence when bound to ssDNA or RNA.
This unique characteristic makes acridine orange useful for cell-cycle studies.
Acridine orange has also been used as a lysosomal dye.

Acridine is a nitrogen-containing polycyclic aromatic heterocycle with the molecular formula C13H9N and a molecular weight of 179.22 g/mol.
Acridine's rigid three-ring structure resembles anthracene, with one central carbon atom replaced by nitrogen, giving acridine characteristic basic and aromatic properties.
Acridine is an important starting material and intermediate for the preparation of dyes, fluorescent compounds, pharmaceuticals, analytical reagents, and other specialized heterocyclic derivatives.

Uses of Acridine:
Acridine is used to make dyes, pharmaceuticals, intermediates, and derivatives (especially acriflavine and proflavine).
Acridine is used as an intermediate in the synthesis of dyes, pigments, and fluorescent compounds.

Acridine is employed in the preparation of pharmaceutical and biologically active heterocyclic derivatives.
Acridine derivatives are widely used in fluorescence studies, molecular probes, and analytical chemistry.

Acridine serves as a building block in organic synthesis for producing nitrogen-containing aromatic compounds.
Acridine-based compounds are also investigated for applications in photochemistry, optoelectronic materials, and functional organic systems.
Acridine is used in research laboratories as a reference compound and precursor for specialized acridine derivatives.

Applications of Acridine:
Acridine is suitable for nucleic acid staining, particularly for cell cycle determination.
Acridines are used as fluorescent materials for visualization of biomolecules, and in laser technologies.

Several dyes and drugs feature the acridine skeleton.
Many acridines, such as proflavine, also have antiseptic properties.

Acridine and related derivatives (such as amsacrine) bind to DNA and RNA due to their abilities to intercalate.
Acridine orange (3,6-dimethylaminoacridine) is a nucleic acid-selective metachromatic stain useful for cell cycle determination.

Dyes:
At one time acridine dyes were commercially significant, but they are now uncommon because they are not lightfast.
Acridine dyes are prepared by condensation of 1,3-diaminobenzene derivatives.
Illustrative is the reaction of 2,4-diaminotoluene with acetaldehyde.

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 gas), a byproduct in the manufacture of rosaniline.
Chrysaniline forms red-coloured salts, which dye silk and wool in 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 o-nitrobenzaldehyde with aniline, the resulting o-nitro-p-diaminotriphenylmethane being reduced to the corresponding o-amino compound, which on oxidation yields chrysaniline.

Benzoflavin, an isomer of chrysaniline, is also a dyestuff, and has been prepared by K. Oehler from m-phenylenediamine and benzaldehyde.
These substances condense to form tetraaminotriphenylmethane, which, on heating with acids, loses ammonia and yields 3,6-diamino-9,10-dihydrophenylacridine, from which benzoflavin is obtained by oxidation.
Acridine is a yellow powder, soluble in hot water.

Molecular biology:
Acridine is known to induce small insertions or deletions in nucleotide sequences, resulting in frameshift mutations.
Acridine was useful to identify the triplet nature of the genetic codes.

Structure of Acridine:
As established by X-ray crystallography, acridine has been obtained in eight polymorphs.
All feature very similar planar molecules with nearly identical bond lengths and bond distances.

Isolation and Synthysis of Acridine:
Carl Gräbe and Heinrich Caro first isolated acridine in 1870 from coal tar.
Acridine is separated from coal tar by extracting with dilute sulfuric acid.

Addition of potassium dichromate to this solution precipitates acridine bichromate.
The bichromate is decomposed using ammonia.

Acridine and its derivatives can be prepared by many synthetic processes.
In the Bernthsen acridine synthesis, diphenylamine is condensed with carboxylic acids in the presence of zinc chloride.

When formic acid is the carboxylic acid, the reaction yields the parent acridine.
With the higher larger carboxylic acids, the derivatives substituted at the meso carbon atom are generated.

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 salicylaldehyde with aniline and zinc chloride or by distilling acridone (9-position a carbonyl group) over zinc dust.
Another classic method for the synthesis of acridones is the Lehmstedt-Tanasescu reaction.

In enzymology, an acridone synthase (EC 2.3.1.159) is an enzyme that catalyzes the chemical reaction:
3 malonyl-CoA + N-methylanthraniloyl-CoA ⇌ 4 CoA + 1,3-dihydroxy-N-methylacridone + 3 CO2

Thus, the two substrates of this enzyme are malonyl-CoA and N-methylanthraniloyl-CoA, whereas its three products are CoA, 1,3-dihydroxy-N-methylacridone, and CO2.

Reactions of Acridine:
Acridine displays the reactions expected of an unsaturated N-heterocycle.
Acridine undergoes N-alkylation with alkyl iodides to form alkyl acridinium iodides, which are readily transformed by the action of alkaline potassium ferricyanide to N-alkyl acridones.

Basicity:
Acridine and its homologues are weakly basic.
Acridine is a photobase which has a ground state pKa of 5.1, similar to that of pyridine, and an excited state pKa of 10.6.
Acridine also shares properties with quinoline.

Reduction and oxidation:
Acridines can be reduced to the 9,10-dihydroacridines, sometimes called leucoacridines.
Reaction with potassium cyanide gives the 9-cyano-9,10-dehydro derivative.

On oxidation with potassium permanganate, Acridine yields acridinic acid (C9H5N(CO2H)2) otherwise known as 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.

Stability and Reactivity of Acridine:

Chemical stability:
Acridine is stable under normal ambient temperatures and recommended storage conditions.

Reactivity:
Acridine may react with acids and should be kept away from incompatible reactive materials.

Conditions to avoid:
Avoid excessive heat, ignition sources, dust formation, and prolonged exposure to incompatible substances.

Incompatible materials:
Avoid strong acids, oxidizing agents, peroxides, acid halides, anhydrides, and other highly reactive materials.

Handling and Storage of Acridine:

Safe handling:
Avoid inhalation of dust and unnecessary contact with the skin and eyes.

Storage conditions:
Keep the container tightly closed in a cool, dry, and well-ventilated place away from heat and incompatible materials.

First Aid Measures of Acridine:

Inhalation:
Move the affected person to fresh air and obtain medical attention if symptoms develop.

Skin contact:
Remove contaminated clothing and wash the affected area thoroughly with soap and water.

Eye contact:
Rinse immediately with plenty of water for several minutes and obtain medical attention.

Ingestion:
Rinse the mouth and seek medical advice if discomfort occurs.

Firefighting Measures of Acridine:

Suitable extinguishing media:
Use water spray, dry chemical, carbon dioxide, or suitable foam according to surrounding fire conditions.

Protective equipment:
Firefighters should wear appropriate protective clothing and self-contained breathing apparatus.

Hazardous combustion products:
Thermal decomposition or combustion may produce carbon oxides, nitrogen oxides, and irritating fumes.

Accidental Release Measures of Acridine:

Personal precautions:
Provide adequate ventilation, avoid generating dust, and wear appropriate personal protective equipment.

Cleanup methods:
Carefully collect spilled material into suitable closed containers while minimizing airborne dust.

Environmental precautions:
Prevent significant quantities from entering drains, surface water, or soil.

Exposure Controls/Personal Protection of Acridine:

Engineering controls:
Use adequate general or local exhaust ventilation where dust may be generated.

Eye protection:
Wear suitable chemical safety goggles.

Hand protection:
Wear appropriate chemical-resistant protective gloves.

Body protection:
Use suitable protective work clothing.

Respiratory protection:
Use appropriate particulate respiratory protection when ventilation is insufficient or significant dust is generated.

Identifiers of Acridine:
CAS No.: 260-94-6
Chemical Name: Acridine
CBNumber: CB9853399
Molecular Formula: C13H9N
Molecular Weight: 179.22
MDL Number: MFCD00005025

CAS Number: 260-94-6
3D Model (JSmol): Interactive image
Interactive image
Beilstein Reference: 120200
ChEBI: CHEBI:36420
ChEMBL: ChEMBL39677
ChemSpider: 8860
ECHA InfoCard: 100.005.429
EC Number: 205-971-6
Gmelin Reference: 143403
PubChem CID: 9215
RTECS Number: AR7175000
UNII: 42NI1P5Q1X
UN Number: 2713
CompTox Dashboard (EPA): DTXSID8059766
InChI: InChI=1S/C13H9N/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-9H
Key: DZBUGLKDJFMEHC-UHFFFAOYSA-N
InChI: InChI=1/C13H9N/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-9H
Key: DZBUGLKDJFMEHC-UHFFFAOYAF
SMILES: n1c3c(cc2c1cccc2)cccc3
c1ccc2c(c1)cc3ccccc3n2

Empirical Formula (Hill Notation): C13H9N
CAS Number: 260-94-6
Molecular Weight: 179.22
NACRES: NA.47
PubChem Substance ID: 24890478
eCl@ss: 39210107
UNSPSC Code: 12171500
EC Number: 205-971-6
MDL Number: MFCD00005025
Beilstein/REAXYS Number: 120200

Properties of Acridine:
Melting Point: 106-109 °C
Boiling Point: 346 °C (lit.)
Density: 1,005 g/cm3
Refractive Index: 1.7270 (estimate)
Flash Point: 346°C
Storage Temperature: Refrigerator
Solubility: dioxane: 0.1 g/mL, clear
pKa: 5.58 (at 20℃)
Form: Crystalline Powder
Color: Yellow to yellow-brown
PH Range: Green B uorescence (5.2) to violet B uorescence (6.6)
Water Solubility: 57.35mg/L (24 ºC)
λmax: 358nm, 392nm
Merck: 14,122
BRN: 120200
Henry's Law Constant: 3.3×101 mol/(m3Pa) at 25℃, Mackay et al. (2006)
Exposure Limits: OSHA: TWA 0.2 mg/m3
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
InChI: 1S/C13H9N/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-9H
InChIKey: DZBUGLKDJFMEHC-UHFFFAOYSA-N
SMILES: c1ccc2nc3ccccc3cc2c1 || c1ccc2nc3ccccc3cc2c1
LogP: 3.400
CAS DataBase Reference: 260-94-6 (CAS DataBase Reference)
EWG's Food Scores: 1
FDA UNII: 42NI1P5Q1X
EPA Substance Registry System: Acridine (260-94-6)
UNSPSC Code: 12171500
NACRES: NA.47

Chemical Formula: C13H9N
Molar Mass: 179.222 g·mol−1
Appearance: White powder
Odor: Irritating
Density: 1.005 g/cm3 (20 °C)
Melting Point: 106–110 °C (223–230 °F; 379–383 K)
at standard pressure
Boiling Point: 344.86 °C (652.75 °F; 618.01 K)
at standard pressure
Solubility in Water: 46.5 mg/L
Solubility: Soluble in CCl4, alcohols, (C2H5)2O, C6H6
Log P: 3.4
Vapor Pressure: 0.34 kPa (150 °C)
2.39 kPa (200 °C)
11.13 kPa (250 °C)
Acidity (pKa): 5.58 (20 °C)
UV-vis (λmax): 392 nm
Magnetic Susceptibility (χ): −123.3×10−6 cm3/mol

Molecular Weight: 179.22 g/mol
XLogP3: 3.4
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 0
Exact Mass: 179.073499291 Da
Monoisotopic Mass: 179.073499291 Da
Topological Polar Surface Area: 12.9 Ų
Heavy Atom Count: 14
Complexity: 181
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Product Name: Acridine, ≥96.5% (HPLC)
Quality Segment: 100
Assay: ≥96.5% (HPLC), 96.5-103.5% (perchloric acid titration)
Form: powder or crystals
Technique(s): microbe id | staining: suitable
Color: light beige to beige, light brown to brown, light yellow to very dark yellow
Boiling Point: 346 °C (lit.)
Melting Point: 107-110 °C (lit.)
λmax: 392 nm
Application(s): diagnostic assay manufacturing
hematology
histology
Storage Temperature: room temp
SMILES String: c1ccc2nc3ccccc3cc2c1
InChI: 1S/C13H9N/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-9H
InChI Key: DZBUGLKDJFMEHC-UHFFFAOYSA-N

Specifications of Acridine:
Color: Orange
Detection Method: Fluorescence
Dye Type: Cell-Permeant
Excitation Wavelength Range: 460/650 (RNA)
For Use With (Equipment): Fluorescence Microscope
Quantity: 10 mL
Shipping Condition: Room Temperature
Label Type: Fluorescent Dye
Product Type: Dye
Sub Cellular Localization: Nucleic Acids, Nucleus
Unit Size: Each

Thermochemistry of Acridine:
Heat Capacity (C): 205.07 J/mol·K
Std Molar Entropy (S⦵298): 208.03 J/mol·K
Std Enthalpy of Formation (ΔfH⦵298): 179.4 kJ/mol
Std Enthalpy of Combustion (ΔcH⦵298): 6581.3 kJ/mol

Names of Acridine:

Preferred IUPAC name:
Acridine

Other names:
Dibenzo[b,e]pyridine
2,3-Benzoquinoline