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2-アセトアミドフルオレン

2-Acetylaminofluorene

HCID 5897
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
53-96-3
標準SMILES
CC(=O)Nc1ccc2c(c1)Cc1ccccc1-2
InChIKey
CZIHNRWJTSTCEX-UHFFFAOYSA-N
分子式
C15H13NO
平均分子量
223.27 g/mol
単同位体質量
223.09971404

概要

2-Acetylaminofluorene can cause cancer according to an independent committee of scientific and health experts.

名称と識別子

優先名称
2-Acetylaminofluorene
IUPAC
N-(9H-fluoren-2-yl)acetamide
現地名
2-アセトアミドフルオレン
英語名
2-Acetamidofluorene
分子式
C15H13NO
分子量
223.27

名称と別名

2-Acetamidofluorene53-96-3N-(9H-Fluoren-2-yl)acetamide2-AcetylaminofluoreneN-2-Fluorenylacetamide2-AAFN-acetyl-2-aminofluoreneAcetamide, N-9H-fluoren-2-yl-2-FAA2-Acetaminofluorene2-Fluorenylacetamide2-(Acetylamino)fluorene
名称をさらに表示
2-アセトアミドフルオレン2-アセチルアミノフルオレンN-(9H-フルオレン-2-イル)アセトアミドN-アセチル-9H-フルオレン-2-アミン2-アセチルアミノ-9H-フルオレン2-(アセチルアミノ)-9H-フルオレン2-アセトアミドフルオレン標準品2アセチルアミノフルオレンN-2-フルオレニルアセトアミド2‐アセトアミドフルオレン2‐アセトアミドフルオレン標準品N-(2-フルオレニル)アセトアミド2-アセトアミドフルオレン, 100 µg/mL in TolueneN-2-フルオレニルアセタミドN-2-フルオレニルアセタミド標準品AAFaaf[qr]faa[qr]2-faa[qr]2-aaf[qr]NSC 12279
2-AcetoaminofluoreneN-9H-Fluoren-2-ylacetamideAcetoaminofluoreneAzetylaminofluoren2-Acetylamino-fluorenACETYLAMINOFLUORENERCRA waste number U005Acetamide, N-fluoren-2-yl-

物性

構造計算による物性

XLogP
3.3
極性表面積
29.1 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
1
重原子数
17
形式電荷
0
複雑度
301

実験および物理化学的性質

Chemical Classes · 2 件

Hazardous Air Pollutants (HAPs)

Carcinogens

PolymersOther Classes -> Polycyclic Aromatic Hydrocarbons
Color/Form · 2 件

Crystals from alcohol + water

Tan, crystalline powder

Solubility · 4 件

less than 1 mg/mL at 68.9 °F (NTP, 1992)

Soluble in glycols, fat solvents

Soluble in ether, acetic acid

Insoluble

DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Melting Point · 5 件

381 °F (NTP, 1992)

194 °C

381 °F

194 °C

381 °F

Vapor Pressure · 2 件

0.00023 mmHg at 212 °F (NTP, 1992)

0.00023 mmHg

Physical Description · 4 件

2-acetylaminofluorene appears as white powder or light beige solid. (NTP, 1992)

Tan, crystalline powder; [NIOSH]

Tan, crystalline powder.

Tan, crystalline powder.

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Danger

H302 (95.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 71 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 4 件

Chemical: Acetamide, N-9H-fluoren-2-yl-

Hazard Traits - Carcinogenicity

Acetamide, N-9H-fluoren-2-yl-: Does not have an individual approval but may be used under an appropriate group standard

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.)

Other Safety InformationIMAP assessments - Acetamide, N-9H-fluoren-2-yl-: Environment tier I assessment
DOT LabelClass 9
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health HazardsExcerpt from NIOSH Pocket Guide for 2-Acetylaminofluorene:
Hazards Summary · 3 件

2-Acetylaminofluorene is used by scientists to study the carcinogenicity and mutagenicity of aromatic amines. No information is available on the acute (short-term), chronic (long-term), reproductive, or developmental effects of 2-acetylaminofluorene in humans. It has caused a variety of tumors in laboratory animals. EPA has not classified 2-acetylaminofluorene for carcinogenicity.

Potential for cancer--see 29 CFR 1910.1003. An animal carcinogen (liver, bladder, and kidneys); [ACGIH]

化学と産業

薬理情報

Mechanism of Action · 5 件

... METABOLIC ACTIVATION OF 2-ACETYLAMINOFLUORENE TO MUTAGENIC & COVALENTLY PROTEIN-BOUND INTERMEDIATES ... /HAVE BEEN STUDIED/ USING HUMAN-LIVER SUB-CELLULAR COMPONENTS. ... IN VITRO MUTAGENICITY OF ... INDIVIDUAL SAMPLES CORRESPONDED WITH THOSE OF 2-AMINOFLUORENE & SO DID THE DEGREE OF N-HYDROXYLATION. N-OH-AAF WAS METABOLIZED INTO MUTAGENS BY HUMAN-LIVER MICROSOMAL & CYTOSOL FRACTIONS, PRESUMABLY BY WAY OF DEACETYLATION.

... METABOLISM OF 2-ACETYLAMINOFLUORENE & ACTIVATION TO COVALENTLY BOUND & MUTAGENIC INTERMEDIATES ... /HAS BEEN STUDIED IN/ RAT-HEPATOCYTE SUSPENSIONS: THE CELL SYSTEM PREDICTABLY AFFORDED OXIDIZED, DEACETYLATED, & CONJUGATED METABOLITES. PRETREATMENT OF ANIMALS WITH BETA-NAPHTHOFLAVONE INCR THE PHENOLIC, CONJUGATED & COVALENTLY BOUND PROTEIN PRODUCTS. SIMILARLY, ADDN OF 4-NITROPHENOL ... INCR CONCN OF FREE PHENOLS & DECR CONJUGATION; AT SAME TIME, RATES OF COVALENT PROTEIN BINDING WERE DIMINISHED. FORMATION OF ALICYCLIC HYDROXYLATED 9-HYDROXY-2-AAF WAS DEMONSTRATED, & THIS PATHWAY WAS NEITHER INDUCED BY PRIOR BETA-NAPHTHOFLAVONE TREATMENT NOR ARRESTED BY THAT WITH 4-NITROPHENOL. THE CELL SYSTEM GENERATED MUTAGENS FROM 2-ACETYLAMINOFLUORENE & 2-AMINOFLUORENE. ADDN OF MICROSOMES INCR MUTAGENICITY OF 2-AAF, PRESUMABLY THROUGH DEACETYLATION OF N-HYDROXY-ACETYLAMINOFLUORENE TO N-HYDROXY-2-AMINOFLUORENE, BUT NOT OF 2-AMINOFLUORENE.

DETAILED BIOCHEMICAL INVESTIGATION IMPLIES THAT 1ST STEP IN MUTAGENIC ACTIVATION OF N-HYDROXY-2-ACETYLAMINOFLUORENE BY ISOLATED MOUSE & RAT LIVER-CELL NUCLEI &/OR CYTOSOL FROM RAT-LIVER HOMOGENATES CONSISTS OF DEACETYLATION BROUGHT ABOUT ... BY MEMBRANE-BOUND AMIDASE OR BY CYTOSOL N,O-ACETYLTRANSFERASE. ACTIVATION OF 2-ACETYLAMINOFLUORENE TO N-HYDROXY-2-AMINOFLUORENE ... BY GUINEA-PIG LIVER (S-9) MIX AFFORDED 2-AMINOFLUORENE (AF) AS WELL AS N-OH-AAF /N-HYDROXY-2-ACETYLAMINOFLUORENE/. MUTAGENICITIES OF AF & N-OH-AAF WERE INHIBITED BY ANTISERA AGAINST NADPH-CYTOCHROME C REDUCTASE & BY PARAOXON. WHILE MUTAGENIC ACTIVITY OF 2-AAF TO N-HYDROXY-2-AMINOFLUORENE CAN BE PRODUCED BY N-HYDROXYLATION OF 2-AMINOFLUORENE OR DEACETYLATION OF N-HYDROXY-2-ACETYLAMINOFLUORENE, THE DATA SUGGESTED THAT DEACETYLATION OF 2-ACETYLAMINOFLUORENE (TO 2-AMINOFLUORENE), FOLLOWED BY N-HYDROXYLATION TO PRODUCE N-HYDROXY-2-AMINOFLUORENE, WAS MAIN PATHWAY FOR MUTAGENIC ACTIVATION OF 2-ACETYLAMINOFLUORENE BY GUINEA-PIG LIVER (S-9) MIX.

... /IT HAS BEEN/ SHOWN THAT ACTIVATION OF 2-ACETYLAMINOFLUORENE TO A MUTAGEN IN VITRO BY MOUSE-LIVER FRACTIONS IS ASSOC WITH GENETIC DIFFERENCES IN THE POLYCYCLIC HYDROCARBON INDUCTIBILITY OF ARYL HYDROCARBON HYDROXYLASE ACTIVITY. ... /IT HAS BEEN SUGGESTED/ THAT THE RATE LIMITING STEP OF 2-ACETYLAMINOFLUORENE MUTAGENESIS IS THE N-HYDROXYLATION BY CYTOCHROME P448. ... EFFECTS OF DETERGENTS UPON RING & N-OXIDATION OF 2-ACETYLAMINOFLUORENE SUGGEST THAT THE TWO REACTIONS ARE CATALYZED BY DIFFERENT ENZYMES.

関連反応

0 件
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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
53-96-3
PubChem CID
5897
DTXSID
DTXSID0039227
ChEMBL
CHEMBL311469
ChEBI
CHEBI:17356
UNII
9M98QLJ2DL
EC Number
200-188-6
Nikkaji
J2.312D
Other Experimental Properties
Needles crystallized from 50% alcohol or 50% acetic acid

物理化学的性質

融点
192 · 192-196 °C(lit.)
沸点
364.56 °C · 364.56°C (rough estimate)
比重(密度)
1.0707 · 1.0707 (rough estimate)
屈折率
1.55 · 1.5500 (estimate)
貯蔵温度
30 °C · Store below +30°C.
溶解性
アセトン、酢酸、アルコール (Weast, 1986)、エチレングリコール、脂肪族溶剤 (Windholze et al., 1983) に可溶
酸解離定数(Pka)
14.89 · 14.89±0.20(Predicted)
外見
結晶性粉末
色
オフホワイトからタン
水溶解度
26.3 °C · 26.3 °C で 10.13 mg/L (Ellington et al., 1987)
Merck
14 · 14,4157
BRN
2807677 · 2807677
Henry's Law Constant
5.2 · 5.2×104 mol/(m3Pa) at 25℃, HSDB (2015)
InChI
1S/C15H13NO/c1-10(17)16-13-6-7-15-12(9-13)8-11-4-2-3-5-14(11)15/h2-7,9H,8H2,1H3,(H,16,17)
InChIKey
CZIHNRWJTSTCEX-UHFFFAOYSA-N
SMILES
CC(=O)Nc1ccc-2c(Cc3ccccc-23)c1
CAS データベース
53 · 53-96-3(CAS DataBase Reference)
EPAの化学物質情報
2 · 2-Acetylaminofluorene (53-96-3)

化学的性質

化学的特性WHITE TO YELLOW-BROWN CRYSTALLINE POWDER

The major hazards encountered in the use and handling of 2-acetylaminofluorene stem from its toxicologic properties. Toxic by inhalation and skin absorption, exposure to this tan, crystalline solid may occur from its use in biomedical research. The major toxic effect from exposure is cancer. OSHA considers 2-acetylaminofluorene to be an occupational carcinogen, and has established strict standards regulating its industrial use. Engineering controls are required to prevent exposure. However, in activities or situations where exposure may occur, wear a self-contained breathing apparatus and personal protective clothing. If contact should occur, immediately wash the affected skin, and remove contaminated clothing at the site. Waste 2-acetylaminofluorene is a candidate for rotary kiln and fluidized bed forms of incineration. Before implementing land disposal of 2-acetylaminofluorene consult with environmental regulatory agencies for guidance.

Reactive GroupAmides and Imides
Special Reports · 1 件

U.S. Department of Health & Human Services/National Toxicology Program; Twelfth Report on Carcinogens (2011). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. 2-Acetylaminofluorene (53-96-3) is listed as reasonably anticipated to be a human carcinogen. First listed in the Second Annual Report on Carcinogens (1981).[Available from, as of March 1, 2012: http://ntp.niehs.nih.gov/?objectid=03C9AF75-E1BF-FF40-DBA9EC0928DF8B15]

RCRA Requirements · 1 件

U005; As stipulated in 40 CFR 261.33, when 2-acetylaminofluorene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

OSHA Standards · 1 件

Workers' exposure to 2-acetylaminofluorene is to be controlled through the required use of engineering controls, work practices, and personal protective equipment, incl respirators. Identified as an occupational carcinogen without establishing a PEL.

Reactivity Profile2-ACETYLAMINOFLUORENE is incompatible with acids, bases and oxidizing agents. Ozone and chlorinating agents oxidize this compound (NTP, 1992).
Atmospheric Standards · 1 件

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. 2-Acetylaminofluorene is included on this list.

安全と保護具

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
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.

(General first aid procedures)

Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: In cleanup of leaks or spills outside the laboratory hood, maintenance or repair operations on contaminated systems or equipment, where direct contact with this compound could result, each person entering that area should be provided with and required to wear, clean impervious garments, including gloves, boots and continuous air supplied hood-style respirator. To perform cleanup FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 3 件

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U005, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.[

A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.

Preventive Measures · 5 件

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.

The worker should immediately wash the skin when it becomes contaminated.

The worker should wash daily at the end of each work shift, and prior to eating, drinking, smoking, etc.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

Isolation and EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Respirator Recommendations(See OSHA respirator requirements for selected chemicals)
Permissible Exposure Limit (PEL) · 2 件

Ca

[1910.1014] See Appendix B

Protective Action Criteria (PAC) · 3 件

2.2 [mg/m3]

25 [mg/m3]

69 [mg/m3]

Recommended Exposure Limit (REL)Ca See Appendix A
Personal Protective Equipment (PPE) · 6 件

Excerpt from NIOSH Pocket Guide for 2-Acetylaminofluorene:

Wear appropriate personal protective clothing to prevent skin contact.

Wear appropriate eye protection to prevent eye contact.

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.

Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]

For more Personal Protective Equipment (PPE) (Complete) data for 2-ACETYLAMINOFLUORENE (6 total), please visit the HSDB record page.

Immediately Dangerous to Life or Health (IDLH) · 3 件

A potential occupational carcinogen. (NIOSH, 2024)

NIOSH considers 2-acetylaminofluorene to be a potential occupational carcinogen.

Ca [N.D.]

毒性情報

Cancer Sites[in animals: tumors of the liver, bladder, lungs, skin & pancreas]
Interactions · 4 件

CONFIRMATORY EVIDENCE FOR INVOLVEMENT OF N-SULFATE IN CARCINOGENESIS WAS DISCOVERY THAT DEPLETION OF INTRACELLULAR GLUTATHIONE LEVEL WITH ACETANILIDE REDUCES CARCINOGENICITY OF 2-ACETYLAMINOFLUORENE.

ETHIONINE COMPLETELY INHIBITS ... HYDROXYLATION OF ACETYLAMINOFLUORENE.

... /It has been/ found that dietary intake of 500 ppm BHT following an initiating treatment with ... 2-acetylaminofluorene appeared to exert a promoting effect, which was ... not as strong as that of phenobarbital. This was subsequently confirmed /in other studies/. ... /In one study it was/ observed that BHT enhanced pulmonary carcinogenesis in mice. In a study on BHT inhibition of liver carcinogenesis ... /it was/ noted that with rats fed 2-acetylaminofluorene, liver carcinogenesis was inhibited, as ... /demonstrated in other studies/, but that, at high levels of BHT, induction of bladder cancer was seen. Probably, metabolic shifts are involved that protect the liver & yields a higher level of excretion of metabolites that could affect the bladder, but a promoting effect may also be involved. The findings ... /in some of these studies/ are consistent with a promoting effect of these antioxidants, but more work needs to be done before assignment can be confidently made.

The synergism of two carcinogenic aromatic amines with different tissue specificities was studied at the level of initiation in Wistar rats. Gamma-glutamyl transpeptidase and glutathione S-transferase P were used as markers for preneoplastic foci in liver. 2-Acetylaminofluorene (AAF) is a complete rat liver carcinogen, whereas trans-4-acetylaminostilbene (AAS) produces ear duct tumors quite selectively, but also acts as a strong initiator in rat liver. When these carcinogens were administered sequentially as two doses of each or simultaneously as four doses of a mixture to neonate animals, which then were treated with phenobarbital in the drinking water for promotion, the initiating activity was additive. When these chemicals were given to young adult animals within 4 weeks in two series of four doses, followed by partial hepatectomy and phenobarbital in the drinking water, the number of preneoplastic foci was greater in groups which had received AAS in both series or in the second series after AAF than in those groups which had received only AAF or AAF in the second series. The average size of foci depended clearly on the sequence in which the two carcinogens were administered. The foci were larger when AAF was given after AAS. The results support the notion that AAS is a strong initiator in rat liver, and that AAF, which is a complete liver carcinogen, has promoting properties under certain circumstances in addition to its initiating properties. The two carcinogens seem to produce the initiating lesions independently but the extent of initiation is additive in this model situation. The simplified neonatal rat liver model appears to be particularly suitable for investigating initiating properties and is proposed for studies of synergistic effects of genotoxic chemicals on the initiation stage, independent of organotropism. It avoids a number of complicating factors related to treatment schedule, forced proliferation rate and toxicity in other models.

Target OrgansLiver, bladder, kidneys, pancreas, skin
Ecotoxicity Values · 2 件

EC50; Species: Xenopus laevis (African Clawed Frog) embryo; Conditions: freshwater, renewal, 23 °C; Concentration: 6900 ug/L for 96 hr (95% confidence interval: 6500-7300 ug/L); Effect: abnormal development, malformations /100% purity formulation/

LC50; Species: Xenopus laevis (African Clawed Frog) embryo; Conditions: freshwater, renewal, 23 °C; Concentration: 87000 ug/L for 96 hr (95% confidence interval: 84000-89000 ug/L) /100% purity formulation/

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), a log Koc value of 3.14(2), corresponding to a Koc of 1380(SRC), indicates that 2-acetylaminofluorene is expected to have moderate mobility in soil(SRC). Volatilization of 2-acetylaminofluorene from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.9X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 2-Acetylaminofluorene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.9X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Utilizing activated sludge, 7-12% of the Theoretical BOD was reached in 6 days(5) indicating that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), a log Koc value of 3.14(2), corresponding to a Koc of 1380(SRC), indicates that 2-acetylaminofluorene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.9X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 53(SRC), from an estimated log Kow of 3.12(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Utilizing activated sludge, 7-12% of the Theoretical BOD was reached in 6 days(8) indicating that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-acetylaminofluorene, which has an estimated vapor pressure of 2.9X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 2-acetylaminofluorene 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 5 hours(SRC), calculated from its rate constant of 2.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2-acetylaminofluorene may be removed from the air by wet or dry deposition(SRC). 2-Acetylaminofluorene absorbs at wavelengths >290 nm(4), and therefore may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsNTP Carcinogen - Reasonably anticipated to be a human carcinogen.
Exposure Routesinhalation, skin absorption, ingestion, skin and/or eye contact
Signs and SymptomsReduced function of liver, kidneys, bladder, pancreas; [potential occupational carcinogen]
Ongoing Test Status · 1 件

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=53-96-3]

Soil Adsorption/Mobility · 1 件

A log Koc of 3.14 has been reported for 2-acetylaminofluorene(1), corresponding to a Koc of 1380(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-acetylaminofluorene is expected to have low mobility in soil.

TSCA Test Submissions · 1 件

The mutagenicity of N-2-fluorenylacetamide (NFA) was evaluated in Salmonella tester strains TA98, TA100, TA1535, TA1537 and TA1538 (Ames Test), both in the presence and absence of added metabolic activation by Aroclor-induced rat liver S9 fraction. Based on the results of preliminary bacterial toxicity determinations, NFA, diluted with DMSO, was tested for mutagenicity at concentrations up to 1 mg/plate using the plate incorporation assay. NFA caused a positive response in strains TA1535, TA100, and TA98 following metabolic activation.

Artificial Pollution Sources2-Acetylaminofluorene's production and use in cancer research(1) may result in its release to the environment through various waste streams(SRC).

法規制情報

RCRA Requirements · 1 件

U005; As stipulated in 40 CFR 261.33, when 2-acetylaminofluorene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Atmospheric Standards · 1 件

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. 2-Acetylaminofluorene is included on this list.

CERCLA Reportable Quantities · 1 件

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1 lb or 0.454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

安全データ

wgk
3
tsca
TSCA listed
rtecs
AB9450000
ridadr
UN 3077 9/PG 3
毒性
Acute oral LD50 for mice 1,020 mg/kg (quoted, RTECS, 1985).
hs_code
2924 29 70
risk_code
45-22-51/53
hazard_code
T,N
safety_code
53-36/37/39-45
hazard_class
6.1(b)
packing_group
III
Hazard Classifications
Acute Tox. 4 OralCarc. 1B
ストレージクラス
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
有毒物質データの
53-96-3(Hazardous Substances Data)

The tumor promoting properties of carcinogenic 2-acetylaminofluorene in rat liver are essentially unknown. We proposed that mitochondria are a target for the cytotoxic effects of 2-nitrosofluorene (NOF), a metabolite of 2-acetylaminofluorene, since NOF induces a redox-cycle at complex I and complex III of the respiratory chain, and impairs respiration and oxidative phosphorylation. /It was/ demonstrated that NOF is a potent inducer of the mitochondrial permeability transition pore (PTP) in isolated mitochondria. In the presence of Ca2+, NOF induced rapid swelling of mitochondria in a dose-dependent manner and depolarized the mitochondrial membrane. Permeability transition as well as depolarization were abolished completely by pre-incubation with the PTP inhibitor cyclosporin A. To study whether the PTP is involved in in vivo toxicity, rats were fed a diet containing 2-acetylaminofluorene (0.04%) for 2 weeks. After isolation of mitochondria, permeability transition was induced by high Ca2+ concentrations (150-400 uM) or phosphate plus Ca2+. Swelling was determined as maximal rate of absorption decrease at 540 nm (delta A/delta t). Surprisingly, delta A/delta t-values of mitochondria from 2-acetylaminofluorene-fed rats were significantly lower (16.3 +/- 4.8 x 10(3)/min) than of mitochondria from control animals (32.7 +/- 4.1 x 10(3)/min; P < 0.02). In the presence of phosphate (15 mM), delta A/delta t-values of mitochondria from 2-acetylaminofluorene-fed rats were even lower (10% of control). Moreover, the membrane potential which was dissipated rapidly by the PTP-inducer NOF (30 uM) at a Ca2+ concentration of 80 uM in mitochondria from control animals, remained constant in mitochondria of 2-acetylaminofluorene-treated rats. ... The regulation of the PTP is altered on chronic 2-acetylaminofluorene-feeding. The increased resistance of mitochondria against permeability transition may alter the threshold for apoptosis and thus suppress apoptosis.

Biological Half-LifeNo reports found; [TDR, p. 31]
Metabolism/Metabolites · 6 件

... Metabolism of 2-acetylaminofluorene & activation to covalently bound and mutagenic intermediates ... /has been studied in/ rat-hepatocyte suspensions: the cell system predictably afforded oxidized, deacetylated, and conjugated metabolites. Pre treatment of animals with beta-naphthoflavone increased the phenolic, conjugated and covalently bound protein products. Similarly, the addition of 4-nitrophenol ... increased concn of free phenols and decr conjugation: at same time rates of covalent protein binding were diminished. Formation of alicyclic hydroxylated 9-hydroxy-2-aaf was demonstrated. ... .

... N-HYDROXY-2-FLUOROACETYLAMINE ... A METABOLITE OF 2-FLUORENYLACETYLAMINE ...

DETAILED BIOCHEMICAL INVESTIGATION IMPLIES THAT 1ST STEP IN MUTAGENIC ACTIVATION OF N-HYDROXY-2-ACETYLAMINOFLUORENE BY ISOLATED MOUSE & RAT LIVER-CELL NUCLEI &/OR CYTOSOL FROM RAT-LIVER HOMOGENATES CONSISTS OF DEACETYLATION BROUGHT ABOUT ... BY MEMBRANE-BOUND AMIDASE OR BY CYTOSOL N,O-ACETYLTRANSFERASE. ACTIVATION OF 2-ACETYLAMINOFLUORENE TO N-HYDROXY-2-AMINOFLUORENE ... BY GUINEA-PIG LIVER (S-9) MIX AFFORDED 2-AMINOFLUORENE (AF) AS WELL AS N-OH-AAF /N-HYDROXY-2-ACETYLAMINOFLUORENE/. MUTAGENICITIES OF AF & N-OH-AAF WERE INHIBITED BY ANTISERA AGAINST NADPH-CYTOCHROME C REDUCTASE & BY PARAOXON. WHILE MUTAGENIC ACTIVITY OF 2-AAF TO N-HYDROXY-2-AMINOFLUORENE CAN BE PRODUCED BY N-HYDROXYLATION OF 2-AMINOFLUORENE OR DEACETYLATION OF N-HYDROXY-2-ACETYLAMINOFLUORENE, THE DATA SUGGESTED THAT DEACETYLATION OF 2-ACETYLAMINOFLUORENE (TO 2-AMINOFLUORENE), FOLLOWED BY N-HYDROXYLATION TO PRODUCE N-HYDROXY-2-AMINOFLUORENE, WAS MAIN PATHWAY FOR MUTAGENIC ACTIVATION OF 2-ACETYLAMINOFLUORENE BY GUINEA-PIG LIVER (S-9) MIX.

... /IT HAS BEEN/ SHOWN THAT ACTIVATION OF 2-ACETYLAMINOFLUORENE TO A MUTAGEN IN VITRO BY MOUSE-LIVER FRACTIONS IS ASSOC WITH GENETIC DIFFERENCES IN THE POLYCYCLIC HYDROCARBON INDUCTIBILITY OF ARYL HYDROCARBON HYDROXYLASE ACTIVITY. ... /IT HAS BEEN SUGGESTED/ THAT THE RATE LIMITING STEP OF 2-ACETYLAMINOFLUORENE MUTAGENESIS IS THE N-HYDROXYLATION BY CYTOCHROME P448. ... EFFECTS OF DETERGENTS UPON RING & N-OXIDATION OF 2-ACETYLAMINOFLUORENE SUGGEST THAT THE TWO REACTIONS ARE CATALYZED BY DIFFERENT ENZYMES.

For more Metabolism/Metabolites (Complete) data for 2-ACETYLAMINOFLUORENE (9 total), please visit the HSDB record page.

2-Acetylaminofluorene has known human metabolites that include 5-hydroxy-AFF, 1-hydroxy-AFF, and N-Hydroxy-2-acetamidofluorene.

MeSH Pharmacological ClassificationSubstances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.
Absorption, Distribution and Excretion · 1 件

REPEATED EXPOSURE TO AROMATIC AMINE CARCINOGEN CAN SOMETIMES INCR METABOLIC RATE. IF RATS ARE EXPOSED REPEATEDLY TO 2-FLUORENYLACETYLAMINE, THERE IS GRADUAL INCR IN RATE OF N-HYDROXY-N-2-FLUORENYLACETYLAMINE EXCRETION IN URINE UNTIL BY 18 WK QUANTITY HAS INCR NINE FOLD. ... AS MUCH AS 22-30% OF DOSE OF FLUORENYLACETYLAMINE IS EXCRETED IN URINE /OF RABBIT/ AS GLUCURONIDE CONJUGATE OF N-HYDROXYL-N-2-FLUORENYLACETYLAMINE.

用途と製造

Uses · 5 件

2-Acetylaminofluorene is frequently used in the laboratory by biochemists and technicians as a positive control in the study of liver enzymes and the carcinogenesis and mutagenicity of aromatic amines.

Used in the study of liver enzymes and the carcinogenicity and mutagenicity of aromatic amines as a positive control. [HSDB]

See 29CFR1910.1003 (Code of Federal Regulations pertaining to the manufacturing, processing, repackaging, releasing, handling, and storing of this chemical);

As a positive control to study the carcinogenicity and mutagenicity of aromatic amines.

Used in the study of liver enzymes and the carcinogenicity and mutagenicity of aromatic amines as a positive control

Formulations/Preparations/Prepared for Sigma with/ min purity of 95-97%
General Manufacturing Information · 3 件

Acetamide, N-9H-fluoren-2-yl-: ACTIVE

Acetylaminofluorene is distributed by several companies that deal in specialty chemicals. Information obtained from these distributors indicates that acetylaminofluorene is imported from Europe. A typical chemical distributor keeps approx 9 lb of acetylaminofluorene in stock. The chemical is usually sold in 1, 5, or 25 g quantities. Based on this information, it is estimated that the total USA usage is less than 20 lb per year.

2-Acetylaminofluorene was intended to be used as a pesticide, but it was never /used/ because this chemical was found to be carcinogenic.

応用分野 · 3 件

用途有機合成原料。

使用N-(2-Fluorenyl)acetamide (2-Acetamidofluorene, 2-AAF), a genotoxic carcinogen, is used to induce liver cancer in animal models such as the 2-AAF/partial hepatectomy rat. 2-AAF may be used to study the mechanism of liver carcinogenesis and as a reference material during its identification or quantitation.

一般的な説明White powder or light beige solid.

調製方法 · 2 件

2-Acetylaminofluorene is produced for research purposes only with an estimated U.S. annual usage of less than 20 lb. It was originally developed as a possible insecticide but has never been used for this purpose after discovery of its carcinogenicity. It is now almost exclusively used in the laboratory studies as a model carcinogen and mutagen.

純化方法Recrystallise it from toluene (1.3mg in 100mL). Its solubility in H2O is 1.3mg/L at 25o, UV: max nm(log ) : 288(4.43), 313(4.13). [Sawicki J Org Chem 21 271 1956.] It can also be recrystallised from 50% AcOH. [Diels et al. Chem Ber 35 3285 1902]. 9-14C and -14C 2-acetamidofluorene were recrystallised from aqueous EtOH and had m 194-195o and 194o respectively. Potent CARCINOGEN. [Miller et al. Cancer Res 9 504 1949, 10 616 1950, Sadin et al. J Am Chem Soc 74 5073 1952, Beilstein 12 H 3287, 12 IV 3373.]

上流・下流製品情報

上流原料

N-(9H-フルオレン-2-イル)-N-スルホオキシアセトアミドN-Acetyl-N-9H-fluoren-2-yl-hydroxylamine-O-sulfonic Acid Potassium Salt2-アミノフルオレンアデノシン3'-りん酸5'-[二りん酸P2-[2,2-ジメチル-3-ヒドロキシ-3-[[2-[[2-(アセチルチオ)エチル]アミノカルボニル]エチル]アミノカルボニル]プロピル]]2-ニトロフルオレングルタチオン

下流製品

N-アセチル-N-アセトキシ-9H-フルオレン-2-アミン

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補足説明

定義ChEBI: The parent of the class of 2-acetamidofluorenes, being an ortho-fused polycyclic arene that consists of 9H-fluorene bearing an acetamido substituent at position 2. It is a carcinogenic and mutagenic derivative of fluorene.