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List of IARC Group 2B Agents - Possibly carcinogenic to humans
Furylfuramide
Другие языки:

Furylfuramide

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Furylfuramide
Furylfuramide.svg
Names
Preferred IUPAC name
(2Z)-2-(Furan-2-yl)-3-(5-nitrofuran-2-yl)prop-2-enamide
Other names
(Z)-2-(2-Furyl)-3-(5-nitro-2-furyl)prop-2-enamide
AF-2, Tofuron,
Alpha-2-furyl-5-nitro-2-furanacrylamide,

2-(2-Furyl)-3-(5-nitro-2-furyl)acrylic acid amide,
a-(Furyl)-b-(5-nitro-2-furyl)acrylic amide,
trans-2-(2-Furyl)-3-(5-nitro-2-furyl)acrylamide,
2-(2-furyl)-3-(5-nitro-2-furyl) acrylamide,

2-Furanacetamide, alpha-((5-nitro-2-furanyl)methylene)-,
Identifiers
3D model (JSmol)
Abbreviations AF-2, FF
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C11H8N2O5/c12-11(14)8(9-2-1-5-17-9)6-7-3-4-10(18-7)13(15)16/h1-6H,(H2,12,14)/b8-6- checkY
    Key: LYAHJFZLDZDIOH-VURMDHGXSA-N checkY
  • InChI=1/C11H8N2O5/c12-11(14)8(9-2-1-5-17-9)6-7-3-4-10(18-7)13(15)16/h1-6H,(H2,12,14)/b8-6-
    Key: LYAHJFZLDZDIOH-VURMDHGXBB
  • O=[N+]([O-])c2oc(/C=C(/c1occc1)C(=O)N)cc2
Properties
C11H8N2O5
Molar mass 248.19162
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Furylfuramide (also known as AF-2) is a synthetic nitrofuran derivative which was widely used as a food preservative in Japan since at least 1965, but withdrawn from the market in 1974 when it was observed to be mutagenic to bacteria in vitro and thus suspected of carcinogenicity. This was confirmed later when animal testing found it to cause benign and malignant tumors in the mammary glands, stomachs, esophagi, and lungs of rodents of both sexes, although insufficient evidence exists in human exposure.

This successful use of bacterial mutagenicity as a screen for carcinogenicity confirmed the use of this methodology as a rapid and efficient test, in comparison to animal testing alone, and led to its further development. The availability of such simpler tests in turn gave rise to greater government oversight and testing of compounds to which the public would be exposed.


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