Structure via PubChem · Public domain (PubChem)
lindane
Sign in to saveAlso known as Gexane, Kwell, Gamene, Quellada, Scabene, gamma-BHC, gamma-1,2,3,4,5,6-Hexachlorocyclohexane, Gammaxene
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 as a pharmaceutical treatment for lice and scabies.
Key facts
- Drug.verifiedrevid
- 457117932
- Drug.IUPAC_name
- (1r,2R,3S,4r,5R,6S)-1,2,3,4,5,6-hexachlorocyclohexane
- Drug.image
- Gamma-hexachlorocyclohexane.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 150px
- Drug.image2
- Lindane (chair) molecule ball.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 170
- Drug.alt2
- Ball-and-stick model of the lindane molecule (chair conformation)
- Drug.MedlinePlus
- a682651
- Drug.pregnancy_category
- C
- Drug.legal_status
- Production and agricultural use is banned in the 182 countries that are Parties to the Stockholm Convention, but pharmaceutical use is allowed as a second-line treatment for scabies and lice
- Drug.routes_of_administration
- Topical
- Drug.protein_bound
- 91%
- Drug.metabolism
- Hepatic cytochrome P-450 oxygenase system
- Drug.elimination_half life
- 18 hours
- Drug.CAS_number
- 58-89-9
- Drug.ATC_prefix
- P03
via Wikipedia infobox
Chemical data
- Formula
- C6H6Cl6
- Molecular weight
- 290.8 g/mol
- IUPAC name
- 1,2,3,4,5,6-hexachlorocyclohexane
- SMILES
- C1(C(C(C(C(C1Cl)Cl)Cl)Cl)Cl)Cl
- InChIKey
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N
- XLogP
- 3.8
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Research
7,310 papers- [Lindane].Der Hautarzt; Zeitschrift fur Dermatologie, Venerologie, und verwandte Gebiete · 1995
- Lindane.Reviews of environmental contamination and toxicology · 1988
- Lessons from the genomes of lindane-degrading sphingomonads.Environmental microbiology reports · 2019
- Lindane-induced liver oxidative stress.Free radical biology & medicine · 1990
- Lindane toxicity: a comprehensive review of the medical literature.Pediatric dermatology · 2012
via PubMed
Wikidata facts
- Mass
- 287.8601
Show 12 more facts
- chemical formula
- C₆H₆Cl₆
- NIOSH Pocket Guide ID
- 0370
- density
- 1.85
- immediately dangerous to life or health
- 50
- melting point
- 235
- boiling point
- 614
- vapor pressure
- 0.00001
- solubility
- 0.001
- time-weighted average exposure limit
- 0.5
- isomeric SMILES
- [C@@H]1([C@@H]([C@@H]([C@H]([C@@H]([C@@H]1Cl)Cl)Cl)Cl)Cl)Cl
- canonical SMILES
- C1(C(C(C(C(C1Cl)Cl)Cl)Cl)Cl)Cl
- Commons category
- Lindane
via Wikidata · CC0
~17 min read
Article
16 sectionsContents
- History and use
- United States
- Pharmaceutical uses
- Other uses
- Pest repellent
- Synthesis
- Human health effects
- Cancer risk
- Adverse reactions
- Environmental contamination
- Isomers
- See also
- References
- External links
- Government and organizations
- News stories and opinion articles
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 as a pharmaceutical treatment for lice and scabies.
Lindane is a neurotoxin that interferes with GABA neurotransmitter function by interacting with the GABAA receptor-chloride channel complex at the picrotoxin binding site. In humans, lindane affects the nervous system, liver, and kidneys, and may well be a carcinogen. Whether lindane is an endocrine disruptor is unclear.