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:
Molecular Weight:
223.27
EC Number:
200-188-6
UNSPSC Code:
12352103
MDL number:
Beilstein/REAXYS Number:
2807677
mp
192-196 °C (lit.)
SMILES string
CC(=O)Nc1ccc-2c(Cc3ccccc-23)c1
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
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
signalword
Danger
hcodes
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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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