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Acridine

Acridine structure

Acridine 

structure

Description

colourless to light yellow crystals


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.|Small colorless needle-like crystalline solid.


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

Acridine Basic Attributes

179.22

179.22

120200

205-971-6

42NI1P5Q1X

3408

2713

DTXSID8059766

C203

RHOMBOHEDRAL NEEDLES OR PRISMS FROM ALCOHOL; MONOCLINIC, ORTHORHOMBIC|SMALL COLORLESS NEEDLES|ORTHORHOMBIC PLATES, NEEDLES FROM DILUTED ALCOHOL|SMALL, COLORLESS OR FAINTLY YELLOW CRYSTALS

2933990090

Characteristics

12.9

3.40

Yellow to yellow-brown Crystalline Powder

1.005 g/cm3 @ Temp: 20 °C

108 °C

345.5 °C @ Press: 760 Torr

346°C

1.727

dioxane: 0.1 g/mL, clear

Refrigerator

1 mmHg at 255.9°F

Oral-rat LD50: 2000 mg/kg; Oral-Mouse LD50: 500 mg/kg

Thermal decomposition of toxic nitrogen oxide gas

A WEAK BASE, COLORS LITMUS PAPER BLUE

pKa= 5.45 at 15 °C (conjugate acid)

132 Ų [M*]+

OF THE 5 CRYSTALLINE FORMS OF ACRIDINE, THE 2 STABLE FORMS MELT AT 110 °C AND 106 °C|OF THE 5 CRYSTALLINE FORMS OF ACRIDINE, 3 MELT AT GREATER THAN 110 °C; 109.5 °C AND 109 °C|DILUTE SOLN OF ACRIDINE AND ITS SALTS HAVE A VIOLET AND GREEN FLUORESCENCE, RESPECTIVELY|FORMS YELLOW CRYSTALLINE SALTS WITH MINERAL ACIDS; FORMS COLORED QUATERNARY AMMONIUM COMPOUNDS (ACRIDINIUM COMPD) BY ACTION OF ALKYL AND ARYL HALIDES AND SULFATES|SUBLIMES AT 100 °C

Slightly soluble in hot water.

Amines, Phosphines, and Pyridines

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.

Safety Information

III

6.1

UN 2713 6.1/PG 3

3

22-68-36/37/38

22-36-45-36/37/39-26

AR7175000

Xn

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Stable. Combustible. Incompatible with strong oxidizing agents.

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

H302

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.

A 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)]

Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire. Behavior in Fire: Sublimes before melting (USCG, 1999)|Flammable - 3rd degree

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: 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. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Dust respirator; chemical goggles; rubber gloves (USCG, 1999)|PRECAUTIONS SHOULD BE DIRECTED MAINLY TO PREVENTING THIS SUBSTANCE FROM COMING IN CONTACT WITH THE SKIN AND EYES. THEY SHOULD INCLUDE THE WEARING OF PERSONAL PROTECTIVE EQUIPMENT AND THE APPLICATION OF A PROTECTIVE LAYER OF PETROLEUM JELLY OR LANOLIN--CASTOR OIL OINTMENT HAS BEEN RECOMMENDED.|THE EYES ARE VULNERABLE AND EYE PROTECTION EQUIPMENT SHOULD BE WORN BY WORKERS HANDLING ACRIDINE. PERSONAL PROTECTIVE EQUIPMENT SHOULD BE CHANGED AND CLEANED REGULARLY.|RESPIRATORY PROTECTIVE EQUIPMENT SHOULD BE READILY AVAILABLE FOR USE IN AN EMERGENCY SUCH AS FIRE, WHEN TOXIC FUMES WOULD BE LIABLE TO BE EVOLVED FROM THE DECOMPOSITION OF ACRIDINE. ...IT IS PARTICULARLY IMPORTANT THAT FIRE-FIGHTING EQUIPMENT BE...AVAILABLE.

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.

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.

/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.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Contact with the material may cause irritation to skin, eyes, and mucous membranes.

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).

Acridine was detected in sediments from Eagle Harbor, Puget Sound, Washington at a concentration of 6.8 ug/g(1). Sediment from a relatively rural reference site, West Beach, Deception Pass, WA did not contain acridine (detection limit= 10 ng/g)(1). Surface sediments from Lake Zurich and Lake Lucerne contained acridine at concentrations of 27 and 0.1 ng/g, respectively(2). Soil samples from Tokyo contained acridine(3). Sediment samples collected from the Kitakyushu area in Japan contained acridine at unreported concentrations(4). Aquatic sediments influenced by coal transport, collected near the Puyallup River delta in Puget Sound, Washington, tentatively contained acridine at unreported concentrations(5). 35 of 42 sediment samples collected from 7 locations in Puget Sound (September 1978), Washington contained acridine at concentrations ranging from 52 to 820 ng/g organic carbon(6).|Over 80% of the surficial sediments collected in the St. Mary's River (connecting Lake Superior with Lake Huron) in 1985, contained acridine at concentrations of <0.02 (detection limit= 0.02 mg/kg dry weight) to 8.70 mg/kg dry weight(1). Acridine was not detected in Black River sediments (in 1984, unreported method detection limit)(1). Black River sediments, collected downstream of the outfall of steel plant coking ovens, contained acridine(2). Sediment samples collected from the Dokai Bay in north Kyushu, Japan contained acridine at unreported concentrations(3).

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).

Street dust, collected from an unknown site, contained acridine at 32 ng/g(1).

Toxicity

moderately toxic

Acridine's production and use as a chemical intermediate, in the manufacture of dyes(1) and in the synthesis of pharmaceuticals(2) may result in its release to the environment through various waste streams(SRC). Acridine may be produced by incomplete combustion at municipal incinerators; propane gas, heavily spiked with hydrochloric acid and then combusted, produced measurable concentrations of acridine(3). Acridine is emitted directly to the environment through diesel exhaust(4), in coal-burning effluent from residential furnaces(5), in catalyst regeneration flue gas from a gas-oil stock of an oil refinery(5), in coal tar emissions, and coke-oven emissions(5). Acridine was detected a former coal tar distillation and wood-treatment site(6)and in streamwater collected from an abandoned creosote works(7).

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).

The rate constant for the vapor-phase reaction of acridine with photochemically-produced hydroxyl radicals has been estimated as 2.7X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 14 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).

125.89|In a static bioconcentration test, a BCF value of 1300 was measured in the guppy, Poecilia reticulata(1). Rate constants for uptake and depuration were 40.8 and 0.031/hour, respectively(1). An equilibrium BCF of 30 was measured for acridine in Daphnia pulex; rate constants for uptake and depuration were 109.6 and 0.47/hour, respectively(2). A BCF value of 126 was measured in fathead minnows(3). Fathead minnows, exposed to 100 ug/L acridine in a flow-through spring water system, rapidly accumulated acridine directly from the water with concentrations of about 12 ug/g wet attained in the fish after 24 hours giving a BCF of 125(4). Further exposure did not result in higher levels of acridine in these fish(4). Rate constants for uptake and depuration were 14 and 0.112/hour, respectively(4). Uncontaminated water rapidly contained measurable concentrations of acridine once minnows containing this compound were added to the water; this suggests that acridine can be eliminated without metabolic alteration as well as through metabolic degradation(4). Minnows exposed to acridine-contaminated sediment and a low level of dissolved acridine did not accumulate much acridine from the sediment(4). According to a classification scheme(5), these BCF values suggest that bioconcentration in aquatic organisms is low to very high depending on the aquatic organism studied(SRC); however, this compound appears to be readily depurated in several organisms. Mussels, Elliptio complanata, did not accumulate detectable concentrations of acridine following three weeks exposure to contaminated sediments in the St. Mary's River in 1985 (detection limit= 1 ug/kg wet weight)(6).

1.51e+04 L/kg|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).

The Henry's Law constant for acridine is estimated as 4.0X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that acridine will be essentially nonvolatile from water surfaces(2,SRC). Acridine's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces should not occur(SRC). 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(3). Volatilization of acridine from a contaminated surface soil (80% quartz sand, pH= 7.1, 1% creosote/PCP by weight) and a surficial sediment (>80% quartz sand, pH= 10.1, 7.0% creosote/PCP by weight) was measured in a bench-scale biotreatability study; over 12 weeks, 1.9 ug and 0.2 ug acridine were lost, respectively(4). Initially a 1 g total mixture of 43 compounds was added to both the soil and sediment chambers(4).

GROUNDWATER: Light non-aqueous phase liquid (LNAPL) and dense non-aqueous phase liquid (DNAPL) samples collected from groundwater beneath the Sydney Steel Corporations's facilities at Sydney, Nova Scotia, Canada contained acridine at concentrations of 0.17 and 1,480 ppm, respectively(1). Groundwater collected beneath an abandoned creosote works in Pensacola, Florida, contained acridine at concentrations ranging from 0.00 to 0.11 mg/l(2). Acridine was detected at the St. Louis Park, Minnesota, a former coal tar distillation and wood-treatment site, at unreported concentrations(3). Groundwater samples collected in 1986 from Pensacola, FL and in St. Louis Park, MN contained acridine at concentrations of 55 ug/l and 11.7 ng/l, respectively(4). A groundwater sample collected from the St. Louis Park, MN site contained acridine at 106 ug/l(5).|SURFACE WATER: Streamwater collected from the abandoned creosote works in Pensacola, Florida, contained acridine at 0.0046 mg/l(1). Acridine was detected in water collected from the Waal River at Brakel, The Netherlands(2).

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).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 70 workers are potentially exposed to acridine in the US(1). Occupational exposure will be through the inhalation of acridine dust and vapor and dermal contact with this compound at workplaces where acridine is produced or used(2). One of three air samples taken at the solvent refined pilot plant in Fort Lewis, WA from the coal preparation area contained acridine; personal air samples taken from a welder and operator in a solvent refined coal pilot plant worker in the coal preparation area contained small amounts of acridine(3). Air samples collected in the potroom of a Soderberg aluminum reduction plant contained acridine at unreported concentrations(4). The general population will be exposed to acridine via inhalation of ambient air, ingestion of food, and dermal contact with food and other products containing this compound(SRC).

Drug Information

3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB).

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.

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. ...

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)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

...ACRIDINE IN INGESTED CREOSOTE HAS BEEN SUSPECTED AS THE CAUSE OF CERTAIN SYMPTOMS OF SYSTEMIC ILLNESS INCLUDING VOMITING, RESPIRATORY DIFFICULTIES, HYPOTHERMIA AND CYANOSIS; DEATH FROM LARGE DOSES HAS APPARENTLY BEEN DUE TO CARDIOVASCULAR COLLAPSE.|THE PHOTOSENSITIZATION OF THE SKIN OF WORKERS HANDLING PITCH, TAR OILS, CREOSOTE, ETC, HAS BEEN ATTRIBUTED TO THE PRESENCE OF ACRIDINE IN THESE COAL-TAR PRODUCTS...|ALTHOUGH ACRIDINE IS NOT CONSIDERED TO BE AN EXCESSIVELY DANGEROUS MATERIAL IT IS NEVERTHELESS A POWERFUL IRRITANT WHICH, IN CONTACT WITH THE SKIN OR MUCOUS MEMBRANE, CAUSES ITCHING, BURNING, VIOLENT SNEEZING, LACRIMATION AND IRRITATION OF THE CONJUNCTIVA.|IT IS REGARDED AS THE EFFECTIVE IRRITANT IN TAR AND CREOSOTE OR PITCH, ETC, WHICH CAN SENSITIZE THE SKIN TO LIGHT.|The ability to bind to melanin and other pigments may contribute to the retinal toxicity occasionally seen when antimalarial agents are used. /Antimalarial agents/

Acridine

Acridine Use and Manufacturing

Methods of Manufacturing

Made from acridinone. Acridone is obtained from the dicyclic aniline-2-carboxylic acid combined with sulfuric acid, and then reduced to 9, 10-dioxacridine with amyl alcohol and sodium and then oxidized to obtain acridine. For laboratory preparation, acridine ketone and zinc powder can also be mixed and heated. The acridine sublimation product produced by the reaction is dissolved in hydrochloric acid, and then alkalized with sodium hydroxide solution, and a precipitate is precipitated and filtered to obtain a crude product. Recrystallized with methanol can obtain high-quality melting point of 110 ℃.

Uses

manufacture 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.

Production

(1972) PROBABLY LESS THAN 4.54X10+5 GRAMS|(1975) PROBABLY LESS THAN 4.54X10+5 GRAMS

Acridine: ACTIVE

DETERMINATIONS WERE MADE BY GLC OR HIGH-PRESSURE LIQ CHROMATOGRAPHY.|SEPARATION OF AZAARENES BY HIGH-PRESSURE LIQ CHROMATOGRAPHY. DETECTION LIMIT FOR MOST AZAARENES WAS 1 NG WITH A 254 NM UV DETECTOR.|Acridine present in urban atmospheric particulate matter was analyzed by HPLC coupled with on-line fluorescence detection after a preseparation of the aza heterocyclic hydrocarbon fraction by one-dimensional dual-band TLC.|Acridine was measured in marine sediments following an acid-base partitioning scheme combined with gel permeation-size exclusion chromatography and analysis by glass capillary GC combined with nitrogen-selective detection.|For more Analytic Laboratory Methods (Complete) data for ACRIDINE (6 total), please visit the HSDB record page.

Fire Hazards -> Flammable - 3rd degree

Computed Properties

Molecular Weight:179.22
XLogP3:3.4
Hydrogen Bond Acceptor Count:1
Exact Mass:179.073499291
Monoisotopic Mass:179.073499291
Topological Polar Surface Area:12.9
Heavy Atom Count:14
Complexity:181
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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