β-Hexachlorocyclohexane
   HOME

TheInfoList



OR:

β-Hexachlorocyclohexane (β-HCH) is an
organochloride An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalent bond, covalently bonded atom of chlorine. The chloroalkane class (alkanes with one or more hydrogens subst ...
which is one of the isomers of hexachlorocyclohexane (HCH).Toxicological Profile for Alpha-, Beta-, Gamma-, and Delta-Hexachlorocyclohexane
U.S. Department of Health and Human Services, Agency for Toxic Substances and Disease Registry, August 2005
It is a byproduct of the production of the
insecticide Insecticides are substances used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed to b ...
lindane Lindane, also known as ''gamma''-hexachlorocyclohexane (γ-HCH), gammaxene, Gammallin and benzene hexachloride (BHC), is an organochlorine chemical and an isomer of hexachlorocyclohexane that has been used both as an agricultural insecticide and ...
(γ-HCH). It is typically constitutes 5–14% of technical-grade lindane, though it has not been produced or used in the United States since 1985. As of 2009, the
Stockholm Convention on Persistent Organic Pollutants Stockholm Convention on Persistent Organic Pollutants is an international environmental treaty, signed on 22 May 2001 in Stockholm and effective from 17 May 2004, that aims to eliminate or restrict the production and use of persistent organic ...
classified α-hexachlorocyclohexane and β-HCH as persistent organic pollutants (POPs), due to the chemical's ability to persist in the environment,
bioaccumulative Bioaccumulation is the gradual accumulation of substances, such as pesticides or other chemicals, in an organism. Bioaccumulation occurs when an organism absorbs a substance at a rate faster than that at which the substance is lost or eliminated ...
, biomagnifying, and long-range transport capacity. This pesticide was widely used during the 1960s and 1970s, particularly on
cotton plant ''Gossypium'' () is a genus of flowering plants in the tribe Gossypieae of the mallow family, Malvaceae, from which cotton is harvested. It is native to tropical and subtropical regions of the Old and New Worlds. There are about 50 ''Gossypiu ...
s. Although banned as a pesticide more than 30 years ago, traces of beta-HCH can still be found in water and soil. Animal studies show that organochlorine pesticides, including beta-HCH, are
neurotoxic Neurotoxicity is a form of toxicity in which a biological, chemical, or physical agent produces an adverse effect on the structure or function of the central and/or peripheral nervous system. It occurs when exposure to a substance – specificall ...
, cause
oxidative stress Oxidative stress reflects an imbalance between the systemic manifestation of reactive oxygen species and a biological system's ability to readily Detoxification, detoxify the reactive intermediates or to repair the resulting damage. Disturbances ...
, and damage the brain's
dopaminergic system Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. Dopamine constitutes about 80% o ...
. Human studies show that exposure to beta-HCH is linked to
Parkinson's Parkinson's disease (PD), or simply Parkinson's, is a long-term degenerative disorder of the central nervous system that mainly affects the motor system. The symptoms usually emerge slowly, and as the disease worsens, non-motor symptoms becom ...
and
Alzheimer's disease Alzheimer's disease (AD) is a neurodegeneration, neurodegenerative disease that usually starts slowly and progressively worsens. It is the cause of 60–70% of cases of dementia. The most common early symptom is difficulty in short-term me ...
. β-HCH was present in elevated levels in some patients as recently as 2009. It was manufactured by exhausting chlorination of
benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...
and for this reason was called erroneously β-BHC. This synonym still persists. In March 2005, the Italian National Monitoring System on Chemical Residuals in Food of Animal Origin detected levels of the pesticide β-HCH that were 20 times higher than the legal limit of 0.003 mg/kg in bulk milk from a dairy farm in the
Sacco River The Sacco is a river of central Italy, a right tributary of the Liri. It flows between the Metropolitan City of Rome Capital and the province of Frosinone in Lazio. Territory The river originates from the Prenestini Mountains, formed by the ...
valley. β-HCH, a lindane
isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...
and possible human
carcinogen A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive substan ...
, was subsequently found in milk from several neighboring farms. A study was therefore undertaken to evaluate the extent and risk factors for contamination.


See also

*
α-Hexachlorocyclohexane α-Hexachlorocyclohexane (α-HCH) is an organochloride which is one of the isomers of hexachlorocyclohexane (HCH).beta-Hexachlorocyclohexane (beta-HCH) - Integrated Risk Information System
US EPA The Environmental Protection Agency (EPA) is an independent executive agency of the United States federal government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it be ...

Cyclohexane, 1,2,3,4,5,6-hexachloro-, (1α,2β,3α,4β,5α,6β)-
NIST The National Institute of Standards and Technology (NIST) is an agency of the United States Department of Commerce whose mission is to promote American innovation and industrial competitiveness. NIST's activities are organized into physical sci ...
{{DEFAULTSORT:Hexachlorocyclohexane, Beta- Organochlorides Persistent organic pollutants under the Stockholm Convention Persistent organic pollutants under the Convention on Long-Range Transboundary Air Pollution