Lindane (Ref: OMS 17)

Lindane (Ref: OMS 17)	Last updated: 14/11/2024
(Also known as: gamma-HCH; HCH; gamma-BHC; gamma-HKhTsH; ENT 8601; pesticide 666)

SUMMARY

Lindane in an insecticide and acaricide. It has a low aqueous solubility by is readily soluble in organic solvents. It is quite volatile and has a high potential for leaching to groundwater. It can be very persistent in soil and water systems. Lindane is moderately toxic to mammals and may be a neurotoxin. It is also a recognised irritant. It is highly toxic to fish and honeybees and moderately toxic to most other species.

GENERAL INFORMATION

Description

An obsolete organochlorine antiparasitic topical medication

Availability status

Current but banned in many countries since 2010

Introduction & key dates

1825, first prepared; circa 1945, introduced

Examples of veterinary uses

Once used to treat parasites such as lice, ticks and fleas

Examples of species treated

Livestock; Domestic pets

Approval status

VMR 2013/2033 approval status (GB/UK)

Not approved

EU Regulatory approval status

Not approved

Chemical structure

Isomerism

Lindane is the gamma-isomer of benzene hexachloride which is a chiral molecule

Chemical formula

C₆H₆Cl₆

Canonical SMILES

C1(C(C(C(C(C1Cl)Cl)Cl)Cl)Cl)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

JLYXXMFPNIAWKQ-GNIYUCBRSA-N

International Chemical Identifier (InChI)

InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3-,4+,5+,6+

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
lindane	-

General status

Veterinary substance type

Insecticide, Veterinary hygiene

Substance groups

Organochloride insecticide; Organochloride acaricide; Organochloride rodenticide

Minimum active substance purity

995 g/Kg

Known relevant impurities

Substance origin

Synthetic

Mode of action

Acts as stimulant to the nervous system with contact and stomach action. GABA-gated chloride channel antagonist.

Molecular targets

[Gamma-aminobutyric acid receptor subunit beta-1, Antagonist], [Glycine receptor subunit alpha-1, Antagonist], [Glycine receptor subunit alpha-2, Antagonist], [Glycine receptor subunit alpha-3, Antagonist], [Glycine receptor subunit beta, Antagonist], [Gamma-aminobutyric acid receptor subunit beta-3], [Gamma-aminobutyric acid receptor subunit rho-1], [Progesterone receptor], [Estrogen receptor alpha], [Nuclear receptor subfamily 1 group I member 2]

CAS RN

58-89-9

EC number

210-168-9 / 200-401-2

CIPAC number

488

US EPA chemical code

009001

PubChem CID

727

CLP index number

602-043-00-6

Therapeutic Class

Antiparasitic products, insecticides & repellents: Chlorine containing products; Sensory organs: Antiparasitics

ATCvet Code

QP53AB02 / QS02QA01

Controlled Drug?

Regulation 37/2010 MRL Classification

Molecular mass

290.82

PIN (Preferred Identification Name)

IUPAC name

1α,2α,3β,4α,5α,6β-hexachlorocyclohexane

CAS name

(1α,2α,3β,4α,5α,6β)-1,2,3,4,5,6-hexachlorocyclohexane

Other status information

POP - Stockholm Convention; LRTAP Annex I; PAN Highly Hazardous Chemical; OSPAR pfap; Severe Marine Pollutant; Rotterdam Convention (Class II) - subject to PIC regulations

Relevant Environmental Water Quality Standards

UK Environment Agency non-statutory standard for the protection of shellfish for human consumption in saltwater: 100 mg l⁻¹

Physical state

Colourless crystals

Formulations

Property

Product

Manufacturer

Authorisation Route

Legal Class (GB/UK)

Example products (past and present) using this active

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

8.52

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

435000

Acetone

289000

Benzene

357000

Ethyl acetate

29000

Methanol

Melting point (°C)

112.9

Boiling point (°C)

323.4

Degradation point (°C)

200

Flashpoint (°C)

Octanol-water partition coefficient at pH 7, 20 °C

3.16 X 10⁰³

Calculated

Log P

3.50

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.88

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

4.4

Low volatility. If applied directly to plants or soil, drift is a concern & mitigation is advisable

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

1.483 X 10^-06

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

No absorption above 290nm in neutral medium

Surface tension (mN m⁻¹)

72.1

Refractive Index

Environmental release

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

980

Very persistent

DT₅₀ (lab at 20 °C)

980

Very persistent

DT₅₀ (field)

148

Persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

523

Note

EU dossier Field studies DT₉₀ range 42-390 days, DT₉₀ range 75-971 days; Other sources: DT₅₀ 400 days (DW4)

Manure DT₅₀ (days)

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Slow

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

732

at 25°C

Very persistent

Note

DT₅₀ 752 days at pH 5, 182 days at pH 9 all at 25°C

Water-sediment DT₅₀ (days)

394

Stable

Water phase only DT₅₀ (days)

Slow

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

Slightly mobile

K_oc (mL g⁻¹)

1270

Notes and range

EU dossier K_oc range 871-1671 mL g⁻¹

Freundlich

K_f (mL g⁻¹)

15.9

Moderately mobile

K_foc (mL g⁻¹)

477

¹/_n

0.957

Notes and range

Literature data: K_f range 1.4-48.4 mL g⁻¹, K_foc range 46.2-866.2 mL g⁻¹, ¹/_n range 0.85-1.02, Soils=6

pH sensitivity

None

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.87

Calculated

High leachability

Bio-concentration factor

BCF (l kg⁻¹)

1300

(Other literature values log BCF range 1.6-3.1 (R3))

Threshold for concern

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

alpha-HCH

Bioaccumulates

DDE (Ref: HSDB 1625)

Toxic, persistent

1,2,3,5-tetrachlorobenzene

Highly toxic, highly persistent

Known groundwater metabolites

None

Other known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

163

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

0.3

Rat

High

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

122

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

695 mg kg feed⁻¹

Anas platyrhynchos

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

Eisenia foetida

Moderate

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

0.23

Apis mellifera

High

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

0.011

Apis mellifera

High

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Chronic

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

0.133

Trigona spinipes

High

Mode of exposure

Contact

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Harmless

Chrysoperla carnea

Beneficial insects (Parasitic wasps)

Beneficial insects (Predatory mites)

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0029

Oncorhynchus mykiss

High

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

2.9

Oncorhynchus mykiss

Moderate

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.07

Danio rerio

High

Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

1.6

Daphnia magna

Moderate

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

54.0

Daphnia magna

Low

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

> 0.025

Ceriodaphnia dubia

High

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0063

Americamysis bahia

High

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

0.04

Chironomus riparius

High

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

0.027

Lemna gibba

Moderate

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

2.5

Scenedesmus abundans

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

1.9

Unknown species

Low

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀, development (mg l⁻¹)

3.85

Crassostrea gigas Larva

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

163

Rat

Moderate

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

900

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

1.56

Rat 4 hr

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

None allocated

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

None allocated

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

None allocated

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

List I; List II

Exposure Routes

Public

Occupational

PPE and PPC should be worn

Mammalian dose elimination route and rate

Metabolized in the liver by microsomal enzymes and rapidly eliminated via urine

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

Highly toxic
May cause dermatitis
May cause abdominal pain, nausea, vomiting, seizures, muscle tremors and hyperreflexia
US EPA - weak evidence to suggest possible human carcinogen; US NTP - suspected carcinogen; OSHA - anticipated human carcinogen
Endocrine issues - Reduction of oestrous cycles

Handling issues

Property

Value and interpretation

General

Not explosive
Not expected to auto-ignite; Not highly flammable
IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H301, H312, H332, H362, H373
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

UN2761

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

lindane

French

Gamma-HCH

German

gamma-HCH

Danish

lindan

Italian

lindano

Spanish

lindano

Greek

Polish

gamma-HCH

Swedish

Hungarian

Dutch

lindaan

Norwegian

Record last updated:	14/11/2024
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242