2-Aminofluorene

Few references, all ~30 years old November 2025 2-Aminofluorene.svg Structure of 2-aminofluorene 9H-Fluoren-2-amine 2-Fluorenamine; 2-fluoreneamine 2-AF 153-78-6 correct CAS 84472 1484 205-817-8 40598 1539 correct FDA 3A69OS195N 2811 c1cccc3c1c2c(cc(N)cc2)C3 1S/C13H11N/c14-11-5-6-13-10(8-11)7-9-3-1-2-4-12(9)13/h1-6,8H,7,14H2 CFRFHWQYWJMEJN-UHFFFAOYSA-N White to tan solid 13 11 1 125-132 <.1 g/100 mL at 19.5 °C Cytotoxic 08 Warning 341 351 201 280 308+313 2-Aminofluorene (2-AF) is a synthetic arylamine. It is a white to tan solid with a melting point of 125-132 °C.Heflich Robert H. Neft Robin E. Genetic toxicity of 2-acetylaminofluorene, 2-aminofluorene and some of their metabolites and model metabolites Mutation Research/Reviews in Genetic Toxicology October 1994 318 2 73–174 10.1016/0165-1110(94)90025-6 7521935 2-AF has only been tested in controlled laboratory settings thus far. There is no indication that it will be tested in industrialized settings. There is evidence that 2-aminofluorene is a carcinogen and an intercalating agent that is extremely dangerous to genomic DNA that potentially can lead to mutation if not death. Furthermore, it has been suggested that 2-aminofluorene can undergo acetylation reactions that causes these reactive species to undergo such reactions in cells. Several experiments have been conducted that have suggested 2-aminofluorene be treated with care and with an overall awareness of the toxicity of this compound.Hoffmann George R. Fuchs Robert P. P. Mechanisms of Frameshift Mutations: Insight from Aromatic Amines Chemical Research in Toxicology 1 April 1997 10 4 347–359 10.1021/tx960128n 9114969 Structure and properties 2-Aminofluorene is used in laboratory research settings, in which it is converted into differentiating substancesNovember 2025 that can be harmful to deoxyribonucleic acids. Reactive species can be formed from its original structure. 2-AF has 3 cyclic rings: a benzene attached to a cyclopentane which is attached to another benzene. The functional group is a primary amine, which can act as a hydrogen donor or acceptor under certain conditions. Therefore, it can become reactive under such laboratory settings. 2-Aminofluorene is a relatively bulky molecule. The average mass is about 181 daltons and its melting point ranges from 125 °C-132 °C. This molecule can be converted to other molecules when metabolized. Therefore, it is mostly used as a model compound that can help researches study carcinogens and the functionality of such compounds that are similar in structure to 2-AF. 2-Acetylaminofluorene (2-AAF) is used similarly to 2-AF because of the nature of these molecules. Uses in research There have been experiments carried out using 2-AF as a possible mutagen that can be introduced into a host species. For example, it has been shown that human leukocytes are able to metabolize 2-AF into a human mutagen.Isola V J Hartman T C Trumble S J Ruzek M C Gentile J M Metabolism of 2-aminofluorene by human polymorphonuclear leukocytes: more evidence for the association between inflammation and cancer. Environmental Health Perspectives October 1993 101 suppl 3 27–31 1521138 10.1289/ehp.93101s327 8143630 When inserted into Salmonella, it was noted that 2-AF was metabolized and created a mutagenic strain of Salmonella.November 2025 In other species, 2-AF was also the cause of mutations in the host genome. The leukocytes, in particular, were able to uptake 2-AF and the researchers were able to conclude that the metabolism of 2-AF was the precursor to the tumor formation. Toxicity and reactions 2-AF can undergo a reaction to become 2-acetylaminofluorene (2-AAF), which is a carcinogen to animals. This compound has been a major research area for cancer-causing agents. 2-AAF is able to cause tumors in mice and other animals in the liver and kidney. This substance can act as a substrate for cytochrome P450 (CYP) which adds a hydroxyl group to the amino group producing N-hydroxy-2-acetylaminofluorene, which is a carcinogen. The addition of these side groups to 2-AF are very dangerous in biological systems. The transferase enzyme cytosolic N-acetyltransferase can act on the hydroxyl group which can also be acetylated. This oxygen acetylation will create the intermediate N-acetyl-N-acetoxyaminofluorene. The side groups of the N-acteyl-N-acetoxyaminofluorene can form the arylamidonium ion and a carbonium ion which can interact directly with DNA.November 2025 Exposure to these carcinogens can increase metabolic rates, if the exposure is repeated several times.November 2025 This is carcinogenic and exposure should be limited. These carcinogens can affect the genome induce mutations. Furthermore, the N-hydroxy derivative can undergo sulfation by the enzyme cytosolic sulfur transferase, which will produce another compound, N-acetyl-N-sulfoxy.N-acetyl-N-sulfoxy is an incomplete chemical name November 2021 Biological interactions 2-AF is able to induce tumors in the livers of male and female rats. Additionally, this chemical can cause mammary gland tumors in female rats. Its carcinogenic nature introduces rare tumors in the ear ducts and small intestines in rats. 2-AF is a mutagen and causes genetic mutations, DNA damage, chromosomal transformations, and sister-chromatid exchanges in animal genomes. In biological systems, the conversion of 2-AF to different formsNovember 2025 can react with DNA. thumb|DNA damaged by 2-aminofluorene In molecular biology, 2-AF is able to induce frameshift mutations, by deleting 2 bases in the DNA. DNA is able to undergo a transition from one conformation form, B-DNA, to another, Z-DNA. B-DNA is the natural state that DNA is found in animals, and shifting the conformation to Z-DNA is especially harmful to biological systems. Z-DNA has less base pairs per turn and in turn, the DNA is more reactive and unable to act under normal conditions. This form of DNA will not be able to interact with enzymes, histone proteins, and other molecules the way it normally would. The implications of this reaction is that site-specific or non-specific interactions with other molecules is severely shifted to be prone to mutations during replication of the genome. If DNA mutations occur during DNA replication, this will ultimately affect the central dogma and every protein that gets translated. Mutations ultimately affect the production of proteins and at times, it can be quite fatal. Applications 2-AF is not common in industrial settings. It is, though, commonly used in laboratory settingsNovember 2025 because of mutagenic nature. The observation of 2-aminofluorene that it is related to genetic mutations, DNA damage, chromosomal aberrations, and sister-chromatid exchanges. References External links http://oehha.ca.gov/prop65/pdf/hid2amin.pdf https://web.archive.org/web/20121018235058/http://www.oehha.ca.gov/prop65/pdf/hid2amin.pdf 2012-10-18 Category:Aromatic amines Category:Fluorenes