기본 정보
- 표준 SMILES
c1ccc2nc3ccccc3cc2c1- InChIKey
DZBUGLKDJFMEHC-UHFFFAOYSA-N- 분자식
- C13H9N
- 평균 분자량
- 179.22 g/mol
- 단동위원소 질량
- 179.07349929
이름 및 식별자
- 우선 이름
- Acridine
- IUPAC
- acridine
- 현지명
- 아크리딘
- 영어명
- Acridine
- 분자식
- C13H9N
- 분자량
- 179.22
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- 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
물성
구조 계산 물성
- XLogP
- 3.4
- 극성 표면적
- 12.9 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 1
- 회전 가능 결합 수
- 0
- 무거운 원자 수
- 14
- 형식 전하
- 0
- 복잡도
- 181
실험 및 물리화학적 성질
Density
1.2 at 68 °F (approx.) (USCG, 1999) - Denser than water; will sink
1.005 @ 20 °C/4 °C
1.2
Color/Form
RHOMBOHEDRAL NEEDLES OR PRISMS FROM ALCOHOL; MONOCLINIC, ORTHORHOMBIC
SMALL COLORLESS NEEDLES
ORTHORHOMBIC PLATES, NEEDLES FROM DILUTED ALCOHOL
SMALL, COLORLESS OR FAINTLY YELLOW CRYSTALS
Solubility
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
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
655 °F at 760 mmHg (NTP, 1992)
345.5 °C @ 760 mm Hg
655 °F
Decomposition
WHEN HEATED TO DECOMPOSITION, ACRIDINE EMITS TOXIC FUMES.
When heated to decomp ... emits toxic fumes of /nitrogen oxides/.
Melting Point
225 to 230 °F (NTP, 1992)
111 °C; 106 °C (form a); 110 °C (form b)
225-230 °F
Vapor Pressure
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
Physical Description
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.
Pale yellow solid; [Merck Index] Colorless solid; [Hawley] Yellow crystalline powder; [MSDSonline]
Small colorless needle-like crystalline solid.
Ionization Efficiency
Positive
3.91
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
물리화학적 성질
- 녹는점
- 106 · 106-109 °C
- 끓는 점
- 346 °C · 346 °C(lit.)
- 밀도
- 1 · 1,005 g/cm3
- 굴절률
- 1.727 · 1.7270 (estimate)
- 인화점
- 346 °C · 346°C
- 저장 조건
- Refrigerator
- 용해도
- 0.1 g/mL, · 디옥산: 0.1 g/mL, 투명
- 산도 계수 (pKa)
- 5.58 · 5.58(at 20℃)
- 물리적 상태
- 결정성 분말
- 색상
- 노란색에서 황갈색
- 수용성
- 57.35 mg/L · 57.35mg/L(24℃)
- Merck
- 14 · 14,122
- BRN
- 120200 · 120200
- Henry's Law Constant
- 3.3 · 3.3×101 mol/(m3Pa) at 25℃, Mackay et al. (2006)
- 안정성
- 안정적인. 타기 쉬운. 강한 산화제와 호환되지 않습니다.
- 주요 응용
- 유기 발광 다이오드, 포토레지스트, 나노센서, 연료 전지, 메모리 장치, 반도체, 정보 저장 장치, 액정 디스플레이, 제품 위조 감별, 잉크, 접착제, 섬유, 염색약, 유전자 검출 분석법, 세포 염색, 바이오센서, 핵산, 단백질, 항HCV 항체 검출, 항균제, 항아밀로이드제, 상처 드레싱 재료, 감염, 알레르기 및 암 백신
- 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
- EPA
- Acridine (260-94-6)
화학적 성질
colourless to light yellow crystals
안전 및 규제
GHS 분류
GHS Classification
Warning
H302 (94%): Harmful if swallowed [Warning Acute toxicity, oral];H312 (10%): Harmful in contact with skin [Warning Acute toxicity, dermal];H315 (18%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (16%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H332 (10%): Harmful if inhaled [Warning Acute toxicity, inhalation];H335 (22%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
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.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
유해성 정보
Regulatory Information
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.)
Fire Hazards
Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire.;Behavior in Fire: Sublimes before melting (USCG, 1999)
· 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.;· Corrosives in 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.
Health Hazards
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.;· Methyl bromoacetate (UN2643) is an eye irritant/lachrymator (causes flow of tears).;· Contact with molten substance may cause severe burns to skin and eyes.;· Avoid any skin contact.;· Fire may produce irritating, corrosive and/or toxic gases.;· Runoff from fire control or dilution water may be corrosive and/or toxic and cause environmental contamination.
Hazards Summary
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]
See POLYCYCLIC AROMATIC HYDROCARBONS.
Reactivity Profile
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
/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
Acridine
UN2713
Div 6.1 Poisonous materials (49 eCFR § 173.132)
PG III: the degree of danger presented by the material is minor;For more information about the packing group assignment, please visit 49 eCFR § 173
안전 및 보호
Fire Fighting
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:;SMALL FIRE: Dry chemical, CO2 or water spray.;LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. If it can be done safely, move undamaged containers away from the area around the fire. Dike runoff from fire control for later disposal.;FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. (ERG, 2024)
Accidental Release Measures
· 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.;· Keep unauthorized personnel away.;· Stay upwind, uphill and/or upstream.;· Ventilate closed spaces before entering, but only if properly trained and equipped.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from 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.
First Aid
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)
General First Aid:;· Call 911 or emergency medical service.;· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.;· Move victim to fresh air if it can be done safely.;· Administer oxygen if breathing is difficult.;· If victim is not breathing:;-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingested or inhaled the substance.;-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).;-- If no pulse detected or no respiratory medical device available, provide continuous compressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.;· Remove and isolate contaminated clothing and shoes.;· For minor skin contact, avoid spreading material on unaffected skin.;· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.;· For severe burns, immediate medical attention is required.;· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.;· Keep victim calm and warm.;· Keep victim under observation.;· For further assistance, contact your local Poison Control Center.;· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.;Specific First Aid:;· For corrosives, in case of contact, immediately flush skin or eyes with running water for at least 30 minutes. Additional flushing may be required.
Exposure Control and Personal Protection
· Wear positive pressure self-contained breathing apparatus (SCBA).;· Wear chemical protective clothing that is specifically recommended by the manufacturer when there is NO RISK OF FIRE.;· Structural firefighters' protective clothing provides thermal protection but only limited chemical protection.
Fire Fighting Procedures
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
...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 Response
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:;ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from 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, 2024)
Disposal Methods
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
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
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:;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 the immediate precautionary measure distance, in the downwind direction, as necessary.;FIRE: If tank, rail tank car or highway tank 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, 2024)
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;· For highlighted materials: see Table 1 - Initial Isolation and Protective Action Distances.;· For non-highlighted materials: increase the immediate precautionary measure distance, in the downwind direction, as necessary.;Fire;· If tank, rail tank car or highway tank 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.
독성 정보
Environmental Fate
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
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).
Toxicity Summary
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)
Effluent Concentrations
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
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
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).
규제 정보
Regulatory Information
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.)
안전 데이터
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- AR7175000
- ridadr
- UN 2713
- 독성
- LD50 s.c. in mice: 0.40 g/kg (Rubbo)
- HS 번호
- 29333990
- risk_code
- 22-68-36/37/38
- hazard_code
- Xn
- safety_code
- 22-36-45-36/37/39-26
- 포장분류
- III
- 위험 등급
- 6.1
- Hazard Classifications
- Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Skin Irrit. 2STOT SE 3
- 스토리지 클래스
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- 유해 물질 데이터
- 260-94-6(Hazardous Substances Data)
화학 및 산업
약리 정보
Metabolism/Metabolites
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
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.
용도 및 제조
Uses
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
(1972) No Data
(1975) No Data
U.S. Imports
(1972) No Data
(1975) No Data
U.S. Production
(1972) PROBABLY LESS THAN 4.54X10+5 GRAMS
(1975) PROBABLY LESS THAN 4.54X10+5 GRAMS
Methods of Manufacturing
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.
응용 분야
용도manufacture 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.
일반 설명Small 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.
상·하류 제품 정보
상류 원료
하류 제품
공급사50 곳
추가 설명
정의A colorless crystalline heterocyclic compound with three fused rings. Derivatives of acridine are used as dyes and biological stains.
관련 반응
연결된 노트
불러오는 중…