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Merck
CN

A4109

N-(2-Fluorenyl)acetamide

Synonym(s):

2-AAF, 2-Acetamidofluorene, N-Acetyl-2-aminofluorene

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About This Item

Empirical Formula (Hill Notation):
C15H13NO
CAS Number:
53-96-3
Molecular Weight:
223.27
EC Number:
200-188-6
UNSPSC Code:
12352103
MDL number:
MFCD00001116
Beilstein/REAXYS Number:
2807677

Key Documents

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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)

InChI key

CZIHNRWJTSTCEX-UHFFFAOYSA-N

SMILES string

CC(=O)Nc1ccc-2c(Cc3ccccc-23)c1

mp

192-196 °C (lit.)

Biochem/physiol Actions

A genotoxic carcinogen that is used to model liver carcinogenesis in rat. When N-hydroxylated by cytochrome CYP1A2 in the liver, 2-AAF forms adducts with DNA and is tumorigenic in liver and bladder.

Disclaimer

OSHA-regulated carcinogen − 29 CFR Part 1910.1014

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

hcodes

H302,H350

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
08073BV
05147CV
05923JZ
05839TU
04157CZ

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Yoshifumi Uno et al.
Mutation research. Genetic toxicology and environmental mutagenesis, 786-788, 182-187 (2015-07-28)
The data from the JaCVAM-organized international validation study of the in vivo rat alkaline comet assay were reported and analyzed statistically using the simple means of % tail DNA. However, OECD test guideline TG 489 recommends use of the median
Horacio A Priestap et al.
Journal of natural products, 73(12), 1979-1986 (2010-12-15)
Aristolochic acids are nephrotoxic and carcinogenic natural products that have been implicated both in endemic nephropathy in the Balkan region and in ailments caused by ingestion of herbal remedies. Aristolochic acids are metabolized to active intermediates that bind to DNA.
Keiko Inami et al.
Bioorganic & medicinal chemistry, 16(14), 7070-7077 (2008-07-01)
Oxidation of 2-acetylaminofluorene (AAF), a carcinogen, by a chemical model for cytochrome P450 was investigated to identify an active mutagen and elucidate the oxidation pathway. The oxidation system consisted of a water-insoluble tetrakis(pentafluorophenyl)porphyrinatoiron(III) chloride and tert-butyl hydroperoxide. The mutagen derived
Yoshifumi Uno et al.
Mutation research. Genetic toxicology and environmental mutagenesis, 786-788, 45-76 (2015-07-28)
The in vivo rodent alkaline comet assay (comet assay) is used internationally to investigate the in vivo genotoxic potential of test chemicals. This assay, however, has not previously been formally validated. The Japanese Center for the Validation of Alternative Methods
A R Kraynak et al.
Mutation research. Genetic toxicology and environmental mutagenesis, 786-788, 77-86 (2015-07-28)
As part of the Japanese Center for the Validation of Alternative Methods (JaCVAM) initiative international validation study of the in vivo rat alkaline comet assay (comet assay), we examined the ability of the assay to determine the genotoxicity of 2-acetylaminofluorene
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