| Compound Name |
Lindane |
| Stockholm Annex code | I,IV |
| Key |
Annex I to the regulation are subject to prohibition (with specific exemptions) on manufacturing, placing on the market and use; Annex II to the regulation are subject to restriction on manufacturing, placing on the market and use; Annex III to the regulation are subject to release reduction provisions; and Annex IV to the regulation are subject to waste management provisions. Note that for some substances listed in Annex I, specific exemptions on the prohibition of their use, manufacturing and placing on the market may apply. |
| Classification |
Intentional |
| Category |
Listed under Annex A with a specific exemption for use as a human health pharmaceutical for control |
| Year of Listing Decision |
2009 |
| Persistence |
7-8 years |
| Specific exemptions associated with its use |
Production: None |
| Acceptable purposes associated with its use |
Use: Human health pharmaceutical for control of head lice and scabies as second-line treatment Previously used singly as a pesticide active ingredient until phasing out in 2007 Used in the 1970s in a combination with four other hexachlorocyclohexanes (as a pesticide called BHC) |
| Conventions on POPs |
Stockholm Convention Convention on Long-Range Transboundary Air Pollution Rotterdam Convention Basel Convention |
| Name |
Lindane |
| Synonyms |
(1R,2S,3r,4R,5S,6r)-1,2,3,4,5,6-Hexachlorocyclohexane Cyclohexane, 1,2,3,4,5,6-hexachloro-, (1alpha,2alpha,3beta,4alpha,5alpha,6beta)- beta-HCH gamma-HCH gamma-Hexachlorocyclohexane 1,2,3,4,5,6-Hexachlorocyclohexane Hexachlorane Benzene hexachloride (inappropriately referred) BETA-HEXACHLOROCYCLOHEXANE Bexol Aplidal |
| Structure | Cl)Cl)Cl)Cl)Cl.png)
Molecular Formula:
C6H6Cl6
|
| CAS Number | 58-89-9 |
| European Community (EC) Number | 200-401-2 |
| European Chemicals Agency (ECHA) | 200-401-2 |
| PubChem ID | 727 |
| DSSTOX Substance ID | DTXSID2020686 |
| KEGG | C07075 |
| ChemSpider |
10481896 |
| Similarity threshold | Name of Related Compound | DSSTox Substance ID | CAS Number | Molecular weight | Molecular formula |
|---|---|---|---|---|---|
| 1.0 | 1,2,3,5-Tetrachlorocyclohexane | DTXSID80657935 | 95115-16-5 | 221 g/mol | C6H8Cl4 |
| 1.0 | Cyclohexane, 1,2,4,5-tetrachloro- | DTXSID10875660 | 60067-92-7 | 221 g/mol | C6H8Cl4 |
| 1.0 | 1-PENTACHLOROCYCLOHEXANE | DTXSID00875654 | 22138-39-2 | 256 g/mol | C6H7Cl5 |
| 1.0 | alpha-1,2,3,4,5,6-Hexachlorocyclohexane | DTXSID2020684 | 319-84-6 | 290 g/mol | C6H6Cl6 |
| 1.0 | beta-Hexachlorocyclohexane | DTXSID7020685 | 319-85-7 | 290 g/mol | C6H6Cl6 |
| 1.0 | 1,2,3,4,5,6-Hexachlorocyclohexane | DTXSID7020687 | 608-73-1 | 290 g/mol | C6H6Cl6 |
| 1.0 | delta-Hexachlorocyclohexane | DTXSID5024134 | 319-86-8 | 290 g/mol | C6H6Cl6 |
| 1.0 | epsilon-Hexachlorocyclohexane | DTXSID0024135 | 6108 10-7 | 290 g/mol | C6H6Cl6 |
| 0.94 | trans-1,2-Dichlorocyclohexane | DTXSID7022126 | 822-86-6 | 153 g/mol | C6H10Cl2 |
| 0.94 | 1,2,3-Trichlorooctane | DTXSID8010 | 85269-46-1 | 217 g/mol | C8H15Cl3 |
| N/A | Full List of similar compounds | N/A05756 | N/A | N/A g/mol | N/A |
| Description | Reference | Article Link |
|---|---|---|
| Hexachlorobenzene (HCB) is a chlorinated monocyclic aromatic compound in which the benzene ring is fully substituted by chlorine. HCB is a white crystalline solid. It has been used as fungicide, in the formulation of military pyrotechnic products and tracer bullets, for impregnating paper, and as wood preservatives. It shows toxicity in aquatic animals and is a possible human carcinogen. | 1. Boudh et al., 2019. Microbial resources mediated bioremediation of persistent organic pollutants. | Link |
| Lindane - is a gamma isomer of hexachlorocyclohexane, the only isomer with insecticidal properties. It is a highly chlorinated, saturated and cyclic insecticide used for crop protection and control of vector-borne diseases, such as malaria. Its low water solubility and its chlorinated nature contribute to its persistence and resistance to microbial degradation. | 2. Ortiz-Hernández et al., 2018. Strategies for Bioremediation of Organic and Inorganic Pollutants. | Link |
| All HCH isomers are acutely toxic to mammals, due to their mutagenic, teratogenic and carcinogenic properties. Although nowadays its use is restricted or completely banned, it continues posing serious environmental and health concerns. This is because gamma-HCH was widely used as insecticide, which added to its high persistence, ensures lindane residues are found all over the world reaching aquatic environments through effluent release, atmospheric deposition, and runoff, among other ways. The inclusion of the alpha, beta and gamma-HCH isomers in the Stockholm Convention list of POPs renewed the interest in these contaminants and the sanitation of polluted sites. | 3. Simón-Solá et al., 2018. Hexachlorocyclohexane Sources, Harmful Effects and Promising Bacteria for its Bioremediation. | Link |
| HCCH is a synthetic chemical that exists in eight chemical forms called isomers; one of these forms, commonly called lindane (gamma-HCCH), has been widely used as an insecticide. HCCH does nor occur as a natural substance. HCCH present in soil can leach to groundwater, adsorb to soil particulates or volatilize to atmosphere. Owing to the persistence of HCCH, rapid bioconcentration takes place in invertebrates, fish, birds, and humans. Gamma-HCCH can be detected in air, water, soil, sediment, aquatic, and terrestrial organisms and food throughout the world, although the concentrations in these different compartments are generally low and are gradually decreeasing. Humans are exposed daily through food, and gamma-HCCH can has been found in blood, adipose tissue, and breast milk (Health Risks of Persistent Organic Pollutants from Long-Range Transboundary Air Pollution, 2003). More than 90% of human of exposure to all HCCH isomers originates from food sources, particularly those that are animal-based (WHO, 1991). Historically, the largest source of HCCH released to the air was agricultural use of the pesticide lindane (gamma-HCCH). In the early 1980s, mean concentrations of gamma-HCCH in human adipose tissue were very high due to high exposure form different sources. Anyway, more than 90% of human exposure to all HCCH isomers originates from food sources, particular those that are animal-based (WHO, 1991). The intake of lindane in food decreased significantly in the 1990s. HCCH is absorbed following oral exposure in humans and animals. Various studies have demonstrated the rapid absorption of gamma-HCCH from the gastrointestinal tract. The distribution of HCCH isomers in humans and animals is primarily in the adipose tissue but also in the brain, kidney, muscle, lungs, heart, spleen, liver and blood (Siddiqui et al., 1981). Placental transfer of HCCH in humans has been well documented (Saxena et al., 1981). Numerous studies have demonstrated hepatic (Oldiges et al., 1983), neurotoxic (Muller et al., 1981), immunotoxic (Banergee et al., 1996), and reproductive (Dalsenter, 1997) effects of lindane. | 4. Opopol., 2008. Impact of POPs on the Republic of Moldova: Environment and Public Health. (In) Mehmetli and Koumanova (eds.), 2008. The Fate of Persistent Organic Pollutants in the Environment, 405–424. Springer. | Link |
| Lindane information | Wikipedia: Lindane accessed on 05 October 2020 | Link |