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Details

Stereochemistry ACHIRAL
Molecular Formula C6H6ClN
Molecular Weight 127.572
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-CHLOROANILINE

SMILES

NC1=CC=C(Cl)C=C1

InChI

InChIKey=QSNSCYSYFYORTR-UHFFFAOYSA-N
InChI=1S/C6H6ClN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2

HIDE SMILES / InChI

Molecular Formula C6H6ClN
Molecular Weight 127.572
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

4-Chloroaniline (4-ClA) is a chlorinated aromatic amine that is formed as an intermediate during the microbial decomposition of phenylurea and phenylcarbamate. The formation of various oligomers by polymerization of 4-ClA with guaiacol in an aqueous solution containing oxidoreductases has been reported. 4-Chloroaniline is used as an intermediate in the production of a number of products, including agricultural chemicals, azo dyes and pigments, cosmetics, and pharmaceutical products. Reactive metabolites of 4-Chloroaniline bind covalently to haemoglobin and to proteins of liver and kidney. In humans, haemoglobin adducts are detectable as early as 30 min after accidental exposure, with a maximum level at 3 h. Repeated exposure to 4-Chloroaniline leads to cyanosis and methaemoglobinaemia, followed by effects in blood, liver, spleen, and kidneys, manifested as changes in haematological parameters, splenomegaly, and moderate to heavy haemosiderosis in spleen, liver, and kidney, partially accompanied by extramedullary haematopoiesis. The marketing and use of products containing 4-Chloroaniline based azo dyes were banned by the European Union (EU) (EC, 2000).

CNS Activity

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
The lowest-observed-adverse effect levels (LOAELs; no-observed-effect levels, or NOELs, are not derivable) for a significant increase in methaemoglobin levels in rats and mice are, respectively, 5 and 7.5 mg/kg body weight per day for a 13- week oral administration of PCA by gavage (5 days/ week) and 2 mg/kg body weight per day for rats administered PCA by gavage (5 days/week) at 26, 52, 78, and 103 weeks` exposure. Fibrotic changes of the spleen were observed in male rats, with a LOAEL of 2 mg/kg body weight per day, and hyperplasia of bone marrow was observed in female rats, with a LOAEL of 6 mg/kg body weight per day (103-week gavage).
Route of Administration: Oral
In Vitro Use Guide
4-Chloroaniline has transforming activity in the C3H/10T½ cell transformation assay in non-cytotoxic concentrations ranging from 0.8 to 100 ug/ml
Substance Class Chemical
Record UNII
Z553SGH315
Record Status Validated (UNII)
Record Version