HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Compound

Acridine

HCID 9215
New noteNew reactionRequest quotes
Print preview
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
260-94-6
Standard SMILES
c1ccc2nc3ccccc3cc2c1
InChIKey
DZBUGLKDJFMEHC-UHFFFAOYSA-N
Molecular formula
C13H9N
Average molar mass
179.22 g/mol
Monoisotopic mass
179.07349929

Overview

Small colorless needle-like crystalline solid. Slightly soluble in hot water. Slightly denser than water. Contact may irritate skin, eyes, and mucous membranes. Sublimes before melting when heated. May be toxic by ingestion.

Names & identifiers

Preferred name
Acridine
IUPAC
acridine
English name
Acridine
Molecular formula
C13H9N
Molecular weight
179.22

Names & synonyms

ACRIDINE260-94-69-Azaanthracene10-Azaanthracene2,3-BenzoquinolineAcrydineAkridinDibenzo[b,e]pyridineBenzo(b)quinolineDibenzo(b,e)pyridine2,3,5,6-DibenzopyridineBenzo[b]quinoline
Show more names
AceridineAcridine >ACRIDINE 97%
Akridin [Czech]NSC 3408NSC-3408CCRIS 1636HSDB 634EINECS 205-971-6UNII-42NI1P5Q1XUN2713

Database identifiers

CAS
260-94-6、39327-16-7
PubChem CID
9215
DTXSID
DTXSID8059766
ChEMBL
CHEMBL39677
ChEBI
CHEBI:36420
UNII
42NI1P5Q1X
EC Number
205-971-6
Nikkaji
J2.978E

Properties

Computed structural properties

XLogP
3.4
Topological polar surface area
12.9 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
14
Formal charge
0
Complexity
181

Experimental & physicochemical properties

Chemical Classes · 2 items

Dyes -> Acridine Dyes

Flammable agents - 3rd degree

PolymersOther Classes -> Polycyclic Aromatic Hydrocarbons
pHA WEAK BASE, COLORS LITMUS PAPER BLUE
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP · 2 items

Log P= 3.40

3.32

Density · 3 items

1.2 at 68 °F (approx.) (USCG, 1999) - Denser than water; will sink

1.005 @ 20 °C/4 °C

1.2

Color/Form · 4 items

RHOMBOHEDRAL NEEDLES OR PRISMS FROM ALCOHOL; MONOCLINIC, ORTHORHOMBIC

SMALL COLORLESS NEEDLES

ORTHORHOMBIC PLATES, NEEDLES FROM DILUTED ALCOHOL

SMALL, COLORLESS OR FAINTLY YELLOW CRYSTALS

Solubility · 5 items

SLIGHTLY SOL IN HOT WATER; VERY SOL IN ALCOHOL, ETHER, BENZENE AND CARBON DISULFIDE

Freely sol in hydrocarbons; slightly soluble in boiling water, liquid ammonia, liguid sulfur dioxide; sparingly soluble in light petroleum

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (94%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 50 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: Acridine

Acridine: HSNO Approval: HSR001561 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelPoison
Fire Hazards · 2 items

Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire.

· Combustible material: may burn but does not ignite readily.

Health Hazards · 2 items

Inhalation irritates respiratory system and causes sneezing, crying, and vomiting. Contact with liquid irritates eyes, skin, and mucous membranes. At high temperature and during sun exposure, damage to the cornea, skin, and mucous membranes may occur following the liberation of acridine vapor. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

Hazards Summary · 2 items

May be the cause of the photoirritant reactions seen after skin contact with pitch, tar, and creosote; A strong skin, eye, and mucous membrane irritant; [HSDB] An irritant; May cause serious eye injury; Can be absorbed through skin; Effects in high-dose animal studies include lacrimation; [MSDSonline]

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 3 items

YIELDS ACRIDONE IN RABBITS: OTAKA, H & HASHIMOTO, Y, NIPPON UNIV J MED, 2, 1, (1960). /FROM TABLE/

... Metabolism of acridine by guinea pig liver enzymes induced by polychlorinated biphenyls ... produced phenolic metabolites. ...

PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (L10)

Absorption, Distribution and Excretion · 2 items

ACRIDINE WAS RAPIDILY ACCUM FROM WATER BY FATHEAD MINNOWS. EQUIL CONCN WITHIN 24 HR @ CONCN FACTOR ((ACRIDINE)FISH,WET WT/(ACRIDINE)WATER) OF 125 +/- 10. DEPURATION WAS RAPID. NET ELIMINATION RATE WAS 0.23/HR (ACRIDINE)FISH @ EQUILIBRIUM.

4 POSSIBLE PATHWAYS FOR UPTAKE ARE DISCUSSED: UPTAKE BY INTERACTION; BY INGESTION OF CONTAMINATED ZOOPLANKTON & INVERTEBRATES; DIRECT UPTAKE.

Uses & manufacturing

Uses · 5 items

Occurs in coal tar; [Merck Index] Used to make dyes, pharmaceuticals, intermediates, and derivatives (especially acriflavine and proflavine); [HSDB]

MFR DYES AND INTERMEDIATES

IN THE SYNTHESIS OF PHARMACEUTICALS

Manufacture of derivatives, especially acriflavine, proflavine; analytical reagent.

PAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and vocanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (L10)

U.S. Exports · 2 items

(1972) No Data

(1975) No Data

U.S. Imports · 2 items

(1972) No Data

Related reactions

32 records
New reaction record
HRID 36385 reaction equation
HRID 36385As productuspto-grants-1995_05
HRID 37029 reaction equation
HRID 37029As productuspto-grants-1995_05
HRID 324169 reaction equation
HRID 324169As productuspto-grants-2001_04
HRID 324170 reaction equation
HRID 324170As productuspto-grants-2001_04
HRID 369524 reaction equation
HRID 369524As productuspto-grants-2000_10
HRID 369525 reaction equation
HRID 369525As productuspto-grants-2000_10
HRID 371694 reaction equation
HRID 371694As reactantuspto-grants-1978_05
HRID 378755 reaction equation
HRID 378755As productuspto-grants-2001_10
Page 1 of 4

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
More actions
New noteNew reactionRequest quotes

Very soluble in carbon disulfide; very soluble in ethanol, ether, benzene; slightly soluble in water

1 gm soluble in <1 ml boiling benzene or alcohol; 5 ml benzene (20 °C); 6 ml alcohol (20 °C); 16 ml of ether (20 °C); 1.8 ml boiling cyclohexane.

In water= 38.4 mg/L at 24 °C.

Boiling Point · 3 items

655 °F at 760 mmHg (NTP, 1992)

345.5 °C @ 760 mm Hg

655 °F

Decomposition · 2 items

WHEN HEATED TO DECOMPOSITION, ACRIDINE EMITS TOXIC FUMES.

When heated to decomp ... emits toxic fumes of /nitrogen oxides/.

Melting Point · 3 items

225 to 230 °F (NTP, 1992)

111 °C; 106 °C (form a); 110 °C (form b)

225-230 °F

Vapor Pressure · 4 items

1 mmHg at 255.9 °F (NTP, 1992)

Vapor pressure= 1.35X10-4 mm Hg at 25 °C /extrapolated from experimentally-derived coefficients/

1 MM HG @ 129 °C

varies depending upon the specific compound

Physicochemical properties

Melting point
106 · 106-109 °C
Boiling point
346 °C · 346 °C(lit.)
Density
1 · 1,005 g/cm3
refractive index
1.727 · 1.7270 (estimate)
Flash point
346 °C · 346°C
storage temp.
Refrigerator
solubility
0.1 g/mL, · dioxane: 0.1 g/mL, clear
pka
5.58 · 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
57.35 mg/L · 57.35mg/L(24 ºC)
λmax
358 nm, · 358nm, 392nm
Merck
14 · 14,122
BRN
120200 · 120200
Henry's Law Constant
3.3 · 3.3×101 mol/(m3Pa) at 25℃, Mackay et al. (2006)
Exposure limits
0.2 mg/m3 · OSHA: TWA 0.2 mg/m3
Stability
Stable. Combustible. Incompatible with strong oxidizing agents.
Major Application
Organic light-emitting diode, photoresists, nanosensors, fuel cells, memory device, semiconductors, information storage device, liquid crystal displays, identification of product forgeries, inks, adhesives, textile, hair dyes, gene detection assay, staining cells, biosensors, detecting nucleic acids, proteins, antiHCV antibodies, antibacterial, antiamyloid agents, wound dressing materials, vaccines against infection, allergy and cancer
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
3.4 · 3.400
CAS DataBase Reference
260 · 260-94-6(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
42 NI1P5Q1X · 42NI1P5Q1X
EPA Substance Registry System
Acridine (260-94-6)
UNSPSC Code
12171500 · 12171500
NACRES
47 · NA.47
Symbol(GHS)
7 · GHS07,GHS09
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H410
Precautionary statements
501 · P501-P273-P270-P264-P280-P302+P352-P391-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330
target organs
Respiratory system
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn
Risk Statements
22 · 22-68-36/37/38
Safety Statements
22 · 22-36-45-36/37/39-26
RIDADR
2713 · UN 2713
WGK Germany
3 · 3
RTECS
7175000 · AR7175000
TSCA
TSCA listed
HazardClass
6.1 · 6.1
PackingGroup
III
HS Code
29333990 · 29333990
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
4 OralAquatic · Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Skin Irrit. 2STOT SE 3
Hazardous Substances Data
260 · 260-94-6(Hazardous Substances Data)
Toxicity
50 s.c · LD50 s.c. in mice: 0.40 g/kg (Rubbo)
Limited Quantities
5 kg · 5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

See POLYCYCLIC AROMATIC HYDROCARBONS.

DOT ID and Guide2713 153
Reactive GroupAmines, Phosphines, and Pyridines
Special ReportsA REVIEW WITH 241 REFERENCES DICUSSING MUTAGENIC ACTIVITIES & BIOLOGICAL EFFECTS OF ACRIDINE & ITS DERIV.[NASIM A, BRYCHCY T; GENETIC EFFECTS OF ACRIDINE COMPOUNDS; MUTAT RES 65(4) 261 (1979)]
Reactivity Profile · 1 item

ACRIDINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides. Burns to give toxic oxides of nitrogen.

DOT Emergency Guidelines · 5 items

/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Health: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.

/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.

For more DOT Emergency Guidelines (Complete) data for ACRIDINE (8 total), please visit the HSDB record page.

DOT Hazard Classification · 4 items

Acridine

UN2713

Div 6.1 Poisonous materials (49 eCFR § 173.132)

PG III: the degree of danger presented by the material is minor

Air and Water ReactionsSlightly soluble in hot water.

Safety & protection

Fire FightingExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Accidental Release Measures · 2 items

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 items

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting Procedures · 1 item

If material on fire or involved in fire: Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources.

Storage Conditions · 1 item

...MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMPOSE INTO TOXIC COMPONENTS...SHOULD BE STORED IN A COOL, WELL VENTILATED PLACE, OUT OF THE DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, AND SHOULD BE PERIODICALLY INSPECTED. INCOMPATIBLE MATERIALS SHOULD BE ISOLATED...

Nonfire Spill ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Disposal Methods · 2 items

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Incineration: Dissolve in such combustible solvent as alcohols, benzene, etc. Spray the solvent into a furnace with afterburner and scrubber. Pour into a mixture of sand and Na2CO3 /sodium carbonate/ (9:1). After mixing, put into a paper carton stuffed full with packing paper to serve as fuel. Burn in a furnace.

Preventive Measures · 5 items

WORKERS SHOULD FOLLOW A CONSCIENTIOUS PERSONAL HYGIENE ROUTINE AND SHOULD WASH THOROUGHLY AT THE END OF EACH WORKING PERIOD; ADEQUATE SANITARY FACILITIES SHOULD BE PROVIDED.

WHEN THE TEMPERATURE OF THE PROCESS OR THE CONDITIONS OF WORK ARE SUCH AS TO GIVE RISE TO SIGNIFICANT CONCENTRATIONS OF ACRIDINE VAPOR, LOCAL EXHAUST VENTILATION SHOULD BE PROVIDED TO PREVENT CONTAMINATION OF THE ATMOSPHERE IN THE VICINITY OF THE PROCESS.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers.

Personnel protection: Keep upwind. Avoid breathing dusts, and fumes from burning material. ... Do not handle broken packages unless wearing appropriate personal protective equipment.

Isolation and Evacuation · 2 items

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Immediate precautionary measure

Threshold Limit Values (TLV)0.2 mg/m³ [1984]
Permissible Exposure Limit (PEL)0.2 mg/m³ as Coal tar pitch volatiles (benzene soluble fraction)

Toxicology

TreatmentThere is no know antidote for PAHs. Exposure is usually handled with symptomatic treatment. (L10)
Health EffectsPAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. (L10)
Environmental Fate · 4 items

TERRESTRIAL FATE: Based on a recommended classification scheme(1), measured Koc values of 14 soil and sediment samples, ranging from 5500 to 30,909 with an average value of 12,910(2), indicate that acridine will be immobile in soil(SRC). Higher sorption was reported for acidic subsoils compared with more neutral subsoils, consistent with compound ionization (pKa of acridine= 5.45(3)) and preferential retention of the organic cation over the neutral compound(4). Volatilization of acridine should not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 4.0X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Volatilization of acridine from dry soil surfaces should not be a major fate process for this compound(SRC) based on an extrapolated vapor pressure of 1.35X10-4 mm Hg(SRC), calculated from experimentally-derived coefficients(6). Acridine is expected to be resistant to aerobic biodegradation and to readily biodegrade under anaerobic conditions(SRC). Acridine, at 500 mg/kg, was completely biodegraded within 83 days in soil samples(7). Norman aquifer materials, taken from two strictly anaerobic zones, also supported extensive degradation of acridine with 92, 96, and 97% degradation reported after 3 weeks for fermentative, denitrifying, and sulfate-reducing incubations, respectively(8). 2-Methylquinoline, phenyl-2-pentenoic acid, hexylbenzene, and benzoic acid were reported as products of the initial ring cleavage of acridine under anaerobic conditions(8).

AQUATIC FATE: Based on a recommended classification scheme(1), measured Koc values of 14 soil and sediment samples, ranging from 5500 to 30,909 with an average value of 12,910(2), indicate that acridine should adsorb to suspended solids and sediment in water(SRC). Acridine is not expected to volatilize from water surfaces(1,SRC) based on an estimated Henry's Law constant of 4.0X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). According to a classification scheme(4), BCF values of 30, 125-126, and 1300, measured in daphnia(5), fathead minnows(6,7), and guppies(8) suggest that bioconcentration in aquatic organisms ranges from low to very high, depending on the aquatic organism(SRC); depuration of this compound has been reported to occur(5,7,8).

AQUATIC FATE: Acridine is expected to be resistant to aerobic biodegradation and to readily biodegrade under anaerobic conditions(SRC). No significant biodegradation of acridine at concentrations from 0.1 to 20 mg/l in river die-away tests, using Green River water, was seen over 11 days(1). Norman aquifer materials, taken from two strictly anaerobic zones, also supported extensive degradation of acridine with 92, 96, and 97% degradation reported after 3 weeks for fermentative, denitrifying, and sulfate-reducing incubations, respectively(2). 2-Methylquinoline, phenyl-2-pentenoic acid, hexylbenzene, and benzoic acid were reported as products of the initial ring cleavage of acridine under anaerobic conditions(2).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acridine, which has an extrapolated vapor pressure of 1.35X10-4 mm Hg at 25 °C(SRC), determined from experimentally-derived coefficients(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase acridine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 14 hours(3,SRC). Particulate-phase acridine may be physically removed from the air by dry deposition(SRC).

Food Survey Values · 1 item

Acridine was measured in Finnish butter, 2 of 8 table margarines, cold pressed sunflower oil, corn oil, and coconut fat at 0.43, 0.18-0.32, 0.89, 0.05, and 0.25 ug/kg, respectively(1). Four of fifteen Finnish leaf lettuce samples, which had been grown in the open air in September 1984, contained acridine at concentrations of 0.05-0.13 ug/kg fresh weight(2).

Adverse EffectsDermatotoxin - PICD (photoirritant contact dermatitis).
Exposure RoutesOral (L10) ; inhalation (L10)
Toxicity Summary · 1 item

The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (L10, L23, A27, A32)

Plant ConcentrationsTwo of twelve vegetation samples collected from areas surrounding the Urx chemical factory, Valasske Mezirici, Czechoslovakia in 1989 contained acridine at concentrations of 789.5 and 2319.4 ng/g(1).
Signs and SymptomsAcute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (A10)
Effluent Concentrations · 1 item

Acridine was detected in creosote-PCP wood preservative wastewater at a concentration of 55 mg/kg(1). Acridine was identified in a commercial coal tar leachate sample at unreported concentrations(2). Diesel exhaust collected from a 1979 Caterpillar Model 3208 contained acridine at unreported concentrations(3). Acridine was measured in coal-burning effluent from a residential furnace, in catalyst regeneration flue gas from a gas-oil stock of an oil refinery, and in air polluted with coal-tar pitch at 111, 3.3-65, and 0.870 ug/cu m, respectively(4). Coal tar emissions, and coke-oven emissions samples contained acridine at concentrations of 297 ug/cu m and 0.032-0.172 mg/g, respectively(4). A maltuned convective kerosene space heater emitted 0.2 ng/kJ acridine(5). Fine particle emissions from the combined exhaust of a vented natural gas-fired residential space heater plus a water heater contained acridine at 7.4 pg/kJ(6).

Soil Adsorption/Mobility · 1 item

Fourteen soil and sediment samples, collected from the Ohio, Missouri, Mississippi, and Illinois rivers and their watersheds had a wide range in pH (4.54-8.34), total clay (6.8 to 69.1%), organic carbon (0.11 to 2.38%), and expanding clay (2.0 to 60.0%). Koc values for acridine added to these soils/sediments ranged from 5500 to 30,909 with an average value of 12,910(1). According to a recommended classification scheme(2), these measured Koc values suggest that acridine will be immobile in soil(SRC). Adsorption of acridine to silica was measured in a continuous-flow column. The extent of adsorption was greater when the solution pH was below the pKa of acridine(pKa= 5.68(3)) than when it was above(4). Therefore, mobility should be greater in a sand soil when the pH is above the pKa of acridine and adsorption is greatest when the solution pH equals acridine's pKa(4). Sorption of acridine to two low organic carbon subsurface materials with similar properties but different equilibrium pH values when saturated with water was measured(5). Higher sorption was reported for the Loring subsoil (0.24% organic carbon, pH 4.85) than the Anvil Points subsoil (0.58% organic carbon, pH 8.15), consistent with compound ionization and preferential retention of the organic cation over the neutral compound(5).

Atmospheric Concentrations · 3 items

SOURCE DOMINATED: Ambient air samples collected near a Horizontal Stud Soderberg plant in Jonquiere, Quebec, Canada in 1982, contained acridine at unreported concentrations(1). 7 of 8 air samples collected in the surroundings of the Urx chemical factory, Valasske Mezirici, Czechoslovakia in 1989, contained acridine at concentrations of 42.5 to 467.7 ng/cu m(2).

URBAN/SUBURBAN: Acridine was measured in New York City and Antwerp, Belgium air at concentrations from 0.040-0.041 to 1.0 ng/cu m, respectively(1). Airborne particulate matter from the Upper Silesia region contained acridine(2). The average concentration of acridine in atmospheric particulate matter collected above an urban street in Tokyo, Japan was 3.5 ug/g particulates(3). Acridine was detected on aerosols collected over the southern North Atlantic Ocean at 0.02 ng/cu m(4). Particulate samples obtained from the urban atmospheric environment of several cities in Southern Ontario contained acridine at unreported concentrations(5). Acridine was detected in airborne particulate matter collected in Duisburg, Germany at unreported concentrations(6).

URBAN/SUBURBAN: Ambient air samples collected from Kokkola, Finland contained acridine in the vapor phase at concentrations from <0.1 to 1.5 ng/cu m; this compound was also detected in particulate matter samples at concentrations from 0.4 to 0.6 ng/cu m(1).

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
AR7175000
ridadr
UN 2713
hs_code
29333990
Toxicity
LD50 s.c. in mice: 0.40 g/kg (Rubbo)
risk_code
22-68-36/37/38
Signal word
Warning
Symbol(GHS)
GHS07,GHS09
hazard_code
Xn
safety_code
22-36-45-36/37/39-26
hazard_class
6.1
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group
III
target organs
Respiratory system
Hazard statements
H302-H315-H319-H410
Limited Quantities
5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements
P501-P273-P270-P264-P280-P302+P352-P391-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330
Hazardous Substances Data
260-94-6(Hazardous Substances Data)

(1975) No Data

U.S. Production · 2 items

(1972) PROBABLY LESS THAN 4.54X10+5 GRAMS

(1975) PROBABLY LESS THAN 4.54X10+5 GRAMS

Methods of Manufacturing · 5 items

EXTRACTION FROM ANTHRACENE FRACTION OF COAL TAR WITH SULFURIC ACID, ADDITION OF POTASSIUM DICHROMATE TO PRECIPITATE ACRIDINE CHROMATE, FOLLOWED BY TREATMENT WITH AMMONIA

...FROM N-PHENYLANTHRANILIC ACID: PERKIN, CLEMO, BRITISH PATENT 214,756 (1923); FROM CA-ANTHRANILATE: KOLLER, KRAKAUER, MONATSH 50, 51 (1928); BY PASSING BENZYLANILINE VAPOR OVER RED-HOT PLATINUM WIRE: MEYER, HOFMANN, MONATSH 37, 698 (1916)...

ACRIDINE IS PRESENT IN THE CRUDE ANTHRACENE OF COAL TAR, FROM WHICH IT CAN BE EXTRACTED WITH DILUTE SULFURIC ACID IN WHICH THE CHROMATE IS PRECIPITATED BY POTASSIUM DICHROMATE AND RECRYSTALLIZED FROM HOT WATER. IT CAN ALSO BE OBTAINED BY THE REDUCTION OF ACRIDONE.

OCCURS IN COAL TAR. ISOLATION: GRAEBE, CARO, ANN, 158, 265 (1871); FROM HIGH BOILING TAR OILS: WIRTH, GERMAN PATENT 440,771 (1926).

For more Methods of Manufacturing (Complete) data for ACRIDINE (6 total), please visit the HSDB record page.

General Manufacturing InformationAcridine: ACTIVE
Applications · 4 items

UsesAcridine is a compound occurring in coal tar that has been used in the manufacture of dyes and intermediates. Derivatives are used as antiseptics (e.g., proflavine). Acridine is a strong irritant to mucous membranes and skin, and it causes sneezing on inhalation.

UsesA quinoline derivative used as manufacturing dyes and as intermediate for antileishmanial agents. A catabolic product of carbamazepine (C175840) metabolite.

Usesmanufacture of dyes and intermediates; some dyes derived from it are used as antiseptics, e.g. 9-aminoacridine, acriflavine and proflavine. The hydrochloride has been used as reagent for cobalt, iron and zinc.

General DescriptionSmall colorless needle-like crystalline solid. Slightly soluble in hot water. Slightly denser than water. Contact may irritate skin, eyes, and mucous membranes. Sublimes before melting when heated. May be toxic by ingestion.

Upstream & downstream products

Upstream raw materials

ZINCN-Phenylanthranilic acid9(10H)-ACRIDONEBenzaldehyde, 2-(phenylamino)-2-Azidobenzaldehyde10-Oxylatoacridine-10-iumCARBAZINE9-Acridinecarboxylic acid2-Ethylphenol2,2'-methylenedianilineDiphenyliodonium trifluoromethanesulfonate2-NitrobenzaldehydePhenylboronic acid

Downstream products

Carbazole9-Chloroacridine9-Phenylacridine9-BroMoacridine
Additional notes · 3 items

Definitionacridine: A colourless crystallineheterocyclic compound, C12H9N; m.p.110°C. The ring structure is similarto that of anthracene, with threefused rings, the centre ring containinga nitrogen heteroatom. Severalderivatives of acridine (such as acridineorange) are used as dyes or biologicalstains.

DefinitionA colorless crystalline heterocyclic compound with three fused rings. Derivatives of acridine are used as dyes and biological stains.

DefinitionChEBI: A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.