Furylfuramide

Furylfuramide

Names
IUPAC name (Z)-2-(2-furyl)-3-(5-nitro-2-furyl)prop-2-enamide
Other names AF-2,[1] 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)-,[2][3]
Identifiers
CAS Registry Number	3688-53-7 Y
ChEBI	CHEBI:15660 Y
ChEMBL	ChEMBL259747 Y
ChemSpider	4444292 Y
InChI 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- Y Key: LYAHJFZLDZDIOH-VURMDHGXSA-N Y 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
Jmol-3D images	Image
KEGG	D02528 Y
PubChem	5280707
SMILES O=[N+]([O-])c2oc(/C=C(/c1occc1)C(=O)N)cc2
UNII	054NR2135Y Y
Properties
Chemical formula	C11H8N2O5
Molar mass	248.19162
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Furylfuramide (also known as AF-2)^[1] is a synthetic nitrofuran derivative which was widely used as a food preservative in Japan since at least 1965, but withdrawn from the market in 1974 when it was observed to be mutagenic to bacteria in vitro and thus suspected of carcinogenicity.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^[4] 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.^[3]

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.^[5]

References