Органохлорные соединения: свойства, применение и экологические аспекты.

Organic compound with at least 1 covalently bonded atom of chlorine
Two representations of chloroform. Organochlorine chemistry is concerned with the properties of organochlorine compounds, or organochlorides, organic compounds containing at least one covalently bonded atom of chlorine. The chloroalkane class (alkanes with one or more hydrogens substituted by chlorine) includes common examples. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties. Organochlorine compounds have wide use in many applications, though some are of profound environmental concern, with TCDD being one of the most notorious. Chlorinated organic compounds are found in nearly every class of biomolecules and natural products including alkaloids, terpenes, amino acids, flavonoids, steroids, and fatty acids. Dioxins, which are of particular concern to human and environmental health, are produced in the high temperature environment of forest fires and have been found in the preserved ashes of lightning ignited fires that predate synthetic dioxins. In addition, a variety of simple chlorinated hydrocarbons including dichloromethane, chloroform, and carbon tetrachloride have been isolated from marine algae. A majority of the chloromethane in the environment is produced naturally by biological decomposition, forest fires, and volcanoes. The natural organochloride epibatidine, an alkaloid isolated from tree frogs, has potent analgesic effects and has stimulated research into new pain medication. However, because of its unacceptable therapeutic index, it is no longer a subject of research for potential therapeutic uses. The frogs obtain epibatidine through their diet which is then sequestered into their skin. Likely dietary sources are beetles, ants, mites, and flies.

Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the Friedel Crafts halogenation, using chlorine and a Lewis acid catalyst.

The two main groups of organochlorine insecticides are the DDT type compounds and the chlorinated alicyclics. Their mechanism of action differs slightly. The DDT like compounds work on the peripheral nervous system. At the axon's sodium channel, they prevent gate closure after activation and membrane depolarization. Sodium ions leak through the nerve membrane and create a destabilizing negative "afterpotential" with hyperexcitability of the nerve. This leakage causes repeated discharges in the neuron either spontaneously or after a single stimulus. Chlorinated cyclodienes include aldrin, dieldrin, endrin, heptachlor, chlordane and endosulfan. A 2 to 8 hour exposure leads to depressed central nervous system (CNS) activity, followed by hyperexcitability, tremors, and then seizures. The mechanism of action is the insecticide binding at the GABAA site in the gamma aminobutyric acid (GABA) chloride ionophore complex, which inhibits chloride flow into the nerve.

Polychlorinated biphenyls (PCBs) were once commonly used electrical insulators and heat transfer agents. Their use has generally been phased out due to health concerns. PCBs were replaced by polybrominated diphenyl ethers (PBDEs), which bring similar toxicity and bioaccumulation concerns.

Some types of organochlorides have significant toxicity to plants or animals, including humans. Dioxins, produced when organic matter is burned in the presence of chlorine, are persistent organic pollutants which pose dangers when they are released into the environment, as are some insecticides (such as DDT). For example, DDT, which was widely used to control insects in the mid 20th century, also accumulates in food chains, as do its metabolites DDE and DDD, and causes reproductive problems (e. g., eggshell thinning) in certain bird species. DDT also posed further issues to the environment as it is extremely mobile, traces even being found in Antarctica despite the chemical never being used there. Some organochlorine compounds, such as sulfur mustards, nitrogen mustards, and Lewisite, are even used as chemical weapons due to their toxicity. However, the presence of chlorine in an organic compound does not ensure toxicity. Some organochlorides are considered safe enough for consumption in foods and medicines. For example, peas and broad beans contain the natural chlorinated plant hormone 4 chloroindole 3 acetic acid (4 Cl IAA); and the sweetener sucralose (Splenda) is widely used in diet products. as of 2004, at least 165 organochlorides had been approved worldwide for use as pharmaceutical drugs, including the natural antibiotic vancomycin, the antihistamine loratadine (Claritin), the antidepressant sertraline (Zoloft), the anti epileptic lamotrigine (Lamictal), and the inhalation anesthetic isoflurane. Rachel Carson brought the issue of DDT pesticide toxicity to public awareness with her 1962 book Silent Spring. While many countries have phased out the use of some types of organochlorides such as the US ban on DDT, persistent DDT, PCBs, and other organochloride residues continue to be found in humans and mammals across the planet many years after production and use have been limited. In Arctic areas, particularly high levels are found in marine mammals. These chemicals concentrate in mammals, and are even found in human breast milk. In some species of marine mammals, particularly those that produce milk with a high fat content, males typically have far higher levels, as females reduce their concentration by transfer to their offspring through lactation.