.ALPHA.-HEXACHLORCYCLOHEXANE

Details

Stereochemistry	RACEMIC
Molecular Formula	C6H6Cl6
Molecular Weight	290.83
Optical Activity	( + / - )
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of .ALPHA.-HEXACHLORCYCLOHEXANE

Structure Search

SMILES

Cl[C@H]1[C@H](Cl)[C@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl

InChI

InChIKey=JLYXXMFPNIAWKQ-LKPKBOIGSA-N

InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3-,4-,5+,6+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C6H6Cl6
Molecular Weight	290.83
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.atsdr.cdc.gov/toxprofiles/tp43.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2431769

α-Hexachlorcyclohexane a byproduct of a production of insecticide lindane (γ-hexachlorocyclohexane). α-Hexachlorcyclohexane is a major (60-70%) component of technical grade hexachlorocyclohexane. It is a widespread environment pollutant and cause liver tumors in rats and mice.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 203 Target ID: CHEMBL1907607 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1377327	Positive Allosteric Modulator 186

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Carcinogenicity and mode of action evaluation for alpha-hexachlorocyclohexane: Implications for human health risk assessment.	2016-04	26713892
Preferential distribution of alpha-hexachlorocyclohexane into cerebral white matter.	1989-01	2474221
In vivo and in vitro binding of alpha- and gamma-hexachlorocyclohexane to mouse liver macromolecules.	1984-03	6199873
The elevation of rat liver glutathione-S-transferase activity by alpha-hexachlorocyclohexane.	1981-02-15	6163436
Convulsive properties of lindane, lindane metabolites, and the lindane isomer alpha-hexachlorocyclohexane: effects on the convulsive threshold for pentylenetetrazol and the brain content of gamma-aminobutyric acid (GABA) in the mouse.	1978-10	83029

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

GABA-A potentiation was measured usin two-electrode voltage-clamp assay. RNA, encoding GABA-A receptors was extracted from rat cerebral cortec and expression in Xenopus oocytes. Effect of Alpha-HCH was studied by chloride currents elicited by 10uM GABA. Application of 10uM alpha-HCH caused increase in response by 200-300 %.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:26:23 GMT 2025` Edited by `admin` on `Mon Mar 31 21:26:23 GMT 2025`
Record UNII	IVM9A2N49K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(±)-.ALPHA.-HCH

Preferred Name

English

.ALPHA.-HEXACHLORCYCLOHEXANE

Common Name

English

CYCLOHEXANE, 1,2,3,4,5,6-HEXACHLORO-, (1.ALPHA.,2.ALPHA.,3.BETA.,4.ALPHA.,5.BETA.,6.BETA.)-

Common Name

English

.ALPHA.-666

Common Name

English

LINDANE RELATED COMPOUND A [USP-RS]

Common Name

English

.ALPHA.-LINDANE

Common Name

English

.ALPHA.-BENZOHEXACHLORIDE

Common Name

English

.ALPHA.-BENZENEHEXACHLORIDE

Common Name

English

.ALPHA.-HCH

Common Name

English

(±)-.ALPHA.-HEXACHLOROCYCLOHEXANE

Common Name

English

BHC, .ALPHA.-

Common Name

English

.ALPHA.-HEXACHLORAN

Common Name

English

.ALPHA.-1,2,3,4,5,6-HEXACHLOROCYCLOHEXANE

Common Name

English

.ALPHA.-BHC

Common Name

English

.ALPHA.-HEXACHLORANE

Common Name

English

CYCLOHEXANE, 1,2,3,4,5,6-HEXACHLORO-, .ALPHA.-

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID2020684