Acridine

HCID 9215CAS 260-94-6

基本情報

標準SMILES
c1ccc2nc3ccccc3cc2c1
InChIKey
DZBUGLKDJFMEHC-UHFFFAOYSA-N
分子式
C13H9N
平均分子量
179.22 g/mol
単同位体質量
179.07349929

名称と識別子

優先名称
Acridine
IUPAC
acridine
現地名
アクリジン
英語名
Acridine
分子式
C13H9N
分子量
179.22

名称と別名

ACRIDINE260-94-69-Azaanthracene10-Azaanthracene2,3-BenzoquinolineAcrydineAkridinDibenzo[b,e]pyridineBenzo(b)quinolineDibenzo(b,e)pyridine2,3,5,6-DibenzopyridineBenzo[b]quinoline
名称をさらに表示
アクリジンアクリジン標準品アクリジン, 98+%アクリジン, 50 µg/mL in TolueneAceridineAcridine >ACRIDINE 97%
Akridin [Czech]NSC 3408NSC-3408CCRIS 1636HSDB 634EINECS 205-971-6UNII-42NI1P5Q1XUN2713

データベース識別子

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

物性

構造計算による物性

XLogP
3.4
極性表面積
12.9 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
0
重原子数
14

実験および物理化学的性質

pHA WEAK BASE, COLORS LITMUS PAPER BLUE
LogPLog P= 3.40
Density · 3 件

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

1.005 @ 20 °C/4 °C

1.2

Color/Form · 4 件

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 件

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 · 3 件

655 °F at 760 mmHg (NTP, 1992)

345.5 °C @ 760 mm Hg

655 °F

物理化学的性質

融点
106 · 106-109 °C
沸点
346 °C · 346 °C(lit.)
比重(密度)
1 · 1,005 g/cm3
屈折率
1.727 · 1.7270 (estimate)
闪点
346 °C · 346°C
貯蔵温度
Refrigerator

化学的性質

化学的特性colourless to light yellow crystals

安全と法規制

GHS分類

GHS Classification · 5 件

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.

危険有害性情報

Regulatory Information · 3 件

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 件

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 · 2 件

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 · 2 件

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.

DOT ID and Guide2713 153

安全と保護具

Fire Fighting · 1 件

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 · 2 件

· 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 · 2 件

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 · 1 件

· 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 · 1 件

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 件

...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...

毒性情報

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 件

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 件

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)

法規制情報

Regulatory Information · 3 件

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.)

安全データ

wgk
3
tsca
TSCA listed
rtecs
AR7175000
ridadr
UN 2713
毒性
LD50 s.c. in mice: 0.40 g/kg (Rubbo)
hs_code
29333990

化学と産業

薬理情報

Metabolism/Metabolites · 3 件

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 件

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.

用途と製造

Uses · 5 件

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 件

(1972) No Data

(1975) No Data

U.S. Imports · 2 件

(1972) No Data

(1975) No Data

U.S. Production · 2 件

(1972) PROBABLY LESS THAN 4.54X10+5 GRAMS

(1975) PROBABLY LESS THAN 4.54X10+5 GRAMS

Methods of Manufacturing · 5 件

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
応用分野 · 4 件

解説アクリジン.コールタールから得られるアントラセン油に少量含まれる.ジフェニルアミンとギ酸を塩化亜鉛とともに加熱するか,ジフェニルアミン-2-カルボン酸に硫酸または塩化ホスホリルを作用させたのち,還元すると得られる.無色の針状結晶.融点109~110 ℃,沸点346 ℃.pKa 5.6(20 ℃).100 ℃ で昇華しはじめる.水蒸気蒸留ができる.熱水にわずかに溶け,アルカリ性を示す.アルコール類,エーテル,炭化水素に易溶.希薄溶液は紫色の蛍光を出すが,アクリジンと酸から得られる黄色の塩は緑色の蛍光を出す.ハロゲン化アルキルまたはハロゲン化アリールと反応して,アクリジニウム塩をつくる.光の照射により二量化する.硫酸または水酸化カリウムと処理しても変化しない.二クロム酸カリウムで酸化するとアクリドンとなる.ニッケル触媒で還元するとアクリダン(9,10-ジヒドロアクリジン)となる.合成染料·殺菌剤(トリパフラピン)の原料,金属分析試薬として用いられる.皮膚や粘膜を強く刺激する性質がある.

用途アントラセンの1つの炭素が窒素に置換した構造を持っている。色素や他の化合物の原料となる。プロフラビンなどアクリジン誘導体の多くは殺菌作用を持っている。アクリジンやその誘導体はDNAやRNAにインターカレートし、結合することができる。アクリジンオレンジ(N,N,N',N'-テトラメチルアクリジン-3.6-ジアミン)は核酸を選択的に染色する。

使用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.

一般的な説明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.

調製方法 · 1 件

純化方法Acridine has been crystallised twice from *benzene/cyclohexane, or from aqueous EtOH, then sublimed, removing and discarding the first 25% of the sublimate. The remainder is again crystallised and sublimed, discarding the first 10-15% [Wolf & Anderson J Am Chem Soc 77 1608 1955]. Acridine can also be purified by crystallisation from n-heptane and then from ethanol/water after pre-treatment with activated charcoal, or by chromatography on alumina with pet ether in a darkened room. Alternatively, acridine can be precipitated as the hydrochloride from *benzene solution by adding HCl, after which the base is regenerated, dried at 110o/50mm, and recrystallised to constant melting point from pet ether [Cumper et al. J Chem Soc 4518 1962]. The regenerated free base may be recrystallised, chromatographed on basic alumina, then vacuum-sublimed and zone-refined. [Williams & Clarke, J Chem Soc, Faraday Trans 1 73 514 1977, Albert, The Acridines Arnold Press 1966.] It can exist in five crystalline forms and is steam volatile. It is a strong IRRITANT to skin and mucous membranes and can become a chronic irritant— handle it with CARE. [Beilstein 20/8 V 199.]

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補足説明

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

関連反応

32 件

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