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Names | |
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IUPAC name 11-Hydroxychromeno[5,6-c]cinnolin-2-one | |
Other names Necatorine | |
Identifiers | |
3D model (JSmol) | |
PubChem CID | |
CompTox Dashboard (EPA) | |
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Properties | |
C15H8N2O3 | |
Molar mass | 264.240 g·mol−1 |
Melting point | 220–225 °C (428–437 °F; 493–498 K) [1] |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | Mutagenic |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Necatorin is a highly mutagenic chemical compound with the molecular formula C15H8N2O3. It is found in some mushrooms including Lactarius necator (ugly milk-cap), from which it was first isolated and characterized. [2] It tests positive in the Ames test, an assay for mutagenicity. [3] Crude extracts of L. necator are also highly mutagenic in a bacterial test system, and this effect it attributed to necatorin. [4]
Necatorin is present in L. necator at concentrations of 3 to 20 mg/kg, and blanching the mushroom can reduce it to about 25% of its original amount. [5] In boiling water, the chemical compound is stable except under acidic conditions (pH = 5). [5]
The Ames test is a widely employed method that uses bacteria to test whether a given chemical can cause mutations in the DNA of the test organism. More formally, it is a biological assay to assess the mutagenic potential of chemical compounds. A positive test indicates that the chemical is mutagenic and therefore may act as a carcinogen, because cancer is often linked to mutation. The test serves as a quick and convenient assay to estimate the carcinogenic potential of a compound because standard carcinogen assays on mice and rats are time-consuming and expensive. However, false-positives and false-negatives are known.
In genetics, a mutagen is a physical or chemical agent that permanently changes genetic material, usually DNA, in an organism and thus increases the frequency of mutations above the natural background level. As many mutations can cause cancer in animals, such mutagens can therefore be carcinogens, although not all necessarily are. All mutagens have characteristic mutational signatures with some chemicals becoming mutagenic through cellular processes.
Ethidium bromide is an intercalating agent commonly used as a fluorescent tag in molecular biology laboratories for techniques such as agarose gel electrophoresis. It is commonly abbreviated as EtBr, which is also an abbreviation for bromoethane. To avoid confusion, some laboratories have used the abbreviation EthBr for this salt. When exposed to ultraviolet light, it will fluoresce with an orange colour, intensifying almost 20-fold after binding to DNA. Under the name homidium, it has been commonly used since the 1950s in veterinary medicine to treat trypanosomiasis in cattle. The high incidence of antimicrobial resistance makes this treatment impractical in some areas, where the related isometamidium chloride is used instead. Despite its reputation as a mutagen, tests have shown it to have low mutagenicity without metabolic activation.
Gyromitrin is a toxin and carcinogen present in several members of the fungal genus Gyromitra, like G. esculenta. Its formula is C4H8N2O. It is unstable and is easily hydrolyzed to the toxic compound monomethylhydrazine CH3NHNH2. Monomethylhydrazine acts on the central nervous system and interferes with the normal use and function of vitamin B6. Poisoning results in nausea, stomach cramps, and diarrhea, while severe poisoning can result in convulsions, jaundice, or even coma or death. Exposure to monomethylhydrazine has been shown to be carcinogenic in small mammals.
Bruce Nathan Ames was an American biochemist who was a professor of biochemistry and Molecular Biology Emeritus at the University of California, Berkeley, and was a senior scientist at Children's Hospital Oakland Research Institute (CHORI). Ames made contributions to understanding the mechanisms of mutagenesis and DNA repair. He invented the Ames test, a widely used assay for easily and cheaply evaluating the mutagenicity of compounds. The test revolutionized the field of toxicology and has played a crucial role in identifying numerous environmental and industrial carcinogens.
The Russulaceae are a diverse family of fungi in the order Russulales, with roughly 1,900 known species and a worldwide distribution. They comprise the brittlegills and the milk-caps, well-known mushroom-forming fungi that include some edible species. These gilled mushrooms are characterised by the brittle flesh of their fruitbodies.
Anethole is an organic compound that is widely used as a flavoring substance. It is a derivative of the aromatic compound allylbenzene and occurs widely in the essential oils of plants. It is in the class of phenylpropanoid organic compounds. It contributes a large component of the odor and flavor of anise and fennel, anise myrtle (Myrtaceae), liquorice (Fabaceae), magnolia blossoms, and star anise (Schisandraceae). Closely related to anethole is its isomer estragole, which is abundant in tarragon (Asteraceae) and basil (Lamiaceae), and has a flavor reminiscent of anise. It is a colorless, fragrant, mildly volatile liquid. Anethole is only slightly soluble in water but exhibits high solubility in ethanol. This trait causes certain anise-flavored liqueurs to become opaque when diluted with water; this is called the ouzo effect.
Lactarius is a genus of mushroom-producing, ectomycorrhizal fungi, containing several edible species. The species of the genus, commonly known as milk-caps, are characterized by the milky fluid ("latex") they exude when cut or damaged. Like the closely related genus Russula, their flesh has a distinctive brittle consistency. It is a large genus with over 500 known species, mainly distributed in the Northern hemisphere. Recently, the genus Lactifluus has been separated from Lactarius based on molecular phylogenetic evidence.
Brilliant blue FCF is a synthetic organic compound used primarily as a blue colorant for processed foods, medications, dietary supplements, and cosmetics. It is classified as a triarylmethane dye and is known under various names, such as FD&C Blue No. 1 or acid blue 9. It is denoted by E number E133 and has a color index of 42090. It has the appearance of a blue powder and is soluble in water and glycerol, with a maximum absorption at about 628 nanometers. It is one of the oldest FDA-approved color additives and is generally considered nontoxic and safe.
Erythrosine, also known as E127 and Red No. 3, is an organoiodine compound, specifically a derivative of fluorone. It is a red-pink dye used for food coloring, cosmetics, hair coloring, pet products, and diverse industrial colorings. It is the disodium salt of 2,4,5,7-tetraiodofluorescein.
Propylparaben is the n-propyl ester of p-hydroxybenzoic acid. It occurs as a natural substance found in many plants and some insects. Additionally, it can be manufactured synthetically for use in cosmetics, pharmaceuticals, and foods. It is a member of the class of parabens and can be used as a preservative in many water-based cosmetics, such as creams, lotions, shampoos, and bath products. As a food additive, it has an E number, which is E216.
Lactarius deterrimus, also known as false saffron milkcap or orange milkcap, is a species of fungus in the family Russulaceae. The fungus produces medium-sized fruit bodies (mushrooms) with orangish caps up to 12 centimetres wide that develop green spots in old age or if injured. Its orange-coloured latex stains maroon within 30 minutes. Lactarius deterrimus is a mycorrhizal fungus that associates with Norway spruce and bearberry. The species is distributed in Europe, but has also found in parts of Asia. A visually similar species in the United States and Mexico is not closely related to the European species. Fruit bodies appear between late June and November, usually in spruce forests. Although the fungus is edible—like all Lactarius mushrooms from the section Deliciosi—its taste is often bitter, and it is not highly valued. The fruit bodies are used as source of food for the larvae of several insect species. Lactarius deterrimus can be distinguished from similar Lactarius species by difference in the mycorrhizal host or latex colour.
Lactarius turpis is a Eurasian species of fungus, commonly known as the ugly milk-cap in English.
Lactarius torminosus, commonly known as the woolly milkcap or the bearded milkcap, is a large species of agaric fungus. A common and widely distributed species, it is found in North Africa, northern Asia, Europe, and North America. It was first described scientifically by Jacob Christian Schäffer in 1774 as an Agaricus, and later transferred to the genus Lactarius in 1821 by Samuel Frederick Gray. A variety, L. torminosus var. nordmanensis, is known from the United States, Canada, and Switzerland. L. torminosus officially became the type species of Lactarius in 2011 after molecular studies prompted the taxonomic reshuffling of species between several Russulaceae genera.
The fixed-dose procedure (FDP), proposed in 1992 by the British Toxicology Society, is a method to assess a substance's acute oral toxicity.
Methysticin is one of the six major kavalactones found in the kava plant. Research suggests that methysticin and the related compound dihydromethysticin have CYP1A1 inducing effects which may be responsible for their toxicity. Additionally, methysticin has been shown to potentiate GABAA receptor activity, contributing to the overall anxiolytic profile of the kava plant.
Up-and-down procedure (or method) for toxicology tests in medicine is an alternative to the LD50 test, in which animals are used for acute toxicity testing. It requires fewer animals to achieve similar accuracy as the LD50 test because animals are dosed one at a time. If the first animal survives, the dose for the next animal is increased; if it dies, the dose is decreased. It is usual to observe each animal for 1 or 2 days before dosing the next animal, however, surviving animals should be monitored for 7 days in case of delayed death. The up-and-down method is not recommended where deaths beyond 2 days are the norm. The U.S. Food and Drug Administration has begun to approve non-animal alternatives.
Methyl isoeugenol (isomethyleugenol) is a phenylpropanoid, the methyl ether of isoeugenol, found in certain essential oils. It can occur as both (E)- and (Z)-isomers.
N,N’-Dibutylhexamethylenediamine (dibutylhexanediamine) is a chemical compound used in the production of polymers. It is highly toxic upon inhalation, and is listed as an extremely hazardous substance as defined by the U.S. Emergency Planning and Community Right-to-Know Act.
Antimutagens are the agents that interfere with the mutagenicity of a substance. The interference can be in the form of prevention of the transformation of a promutagenic compound into actual active mutagen, inactivation, or otherwise the prevention of Mutagen-DNA reaction.