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Details

Stereochemistry ACHIRAL
Molecular Formula C12H4Cl4O2
Molecular Weight 321.971
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2,3,7,8-TETRACHLORODIBENZO-P-DIOXIN

SMILES

ClC1=CC2=C(OC3=CC(Cl)=C(Cl)C=C3O2)C=C1Cl

InChI

InChIKey=HGUFODBRKLSHSI-UHFFFAOYSA-N
InChI=1S/C12H4Cl4O2/c13-5-1-9-10(2-6(5)14)18-12-4-8(16)7(15)3-11(12)17-9/h1-4H

HIDE SMILES / InChI

Molecular Formula C12H4Cl4O2
Molecular Weight 321.971
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

2,3,7,8-Tetrachlorodibenzo-p-dioxin which is often referred to simply as dioxin and is the reference for a number of compounds which are similar structurally and have dioxin-like toxicity. A substance extremely toxic to mammals, with a wide variation in sensitivity among species. Longer-term exposure of test mammals to lesser amounts can affect reproduction, cause birth defects, damage the liver and suppress the immune system. Several studies suggest that exposure to TCDD increases the risk of several types of cancer in people. Animal studies have also shown an increased risk of cancer from exposure to TCDD. The WHO and the USA DHHS have determined that TCDD is a human carcinogen. TCDD is a persistent environmental contaminant inadvertently produced as a by-product of herbicide and pesticide manufacturing. TCDD is also released during the bleaching process at tree pulp and paper mills, and during burning of municipal solid waste. Dioxins, like TCDD, have a long environmental half-life, bioaccumulate in the food chain, and can be found in human fat tissue, blood serum, breast milk and ovarian follicular fluid. TCDD is an aryl hydrocarbon receptor (AhR) agonist

Approval Year

PubMed

PubMed

TitleDatePubMed
Quantitative analysis of constitutive and 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced cytochrome P450 1B1 expression in human lymphocytes.
1999 Feb
Aryl hydrocarbon receptor imported into the nucleus following ligand binding is rapidly degraded via the cytosplasmic proteasome following nuclear export.
1999 Oct 1
Transcriptional activation of c-fos protooncogene by 17beta-estradiol: mechanism of aryl hydrocarbon receptor-mediated inhibition.
1999 Sep
Endocrine disruptive effects of polychlorinated aromatic hydrocarbons on intestinal cholecystokinin in rats.
2000 Aug
TCDD suppression of tissue transglutaminase stimulation by retinoids in malignant human keratinocytes.
2000 Aug
NRH:quinone oxidoreductase2 (NQO2).
2000 Dec 1
Acute administration of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in pregnant Long Evans rats: association of measured tissue concentrations with developmental effects.
2000 Feb
Serum alters the uptake and relative potencies of halogenated aromatic hydrocarbons in cell culture bioassays.
2000 Feb
Demonstration of 2,3,7,8-tetrachlorodibenzo-p-dioxin attenuation of P450 steroidogenic enzyme mRNAs in rat granulosa cell in vitro by competitive reverse transcriptase-polymerase chain reaction assay.
2000 Jun
Inhibition of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)-stimulated Cyp1a1 promoter activity by hypoxic agents.
2000 Jun 15
Role of p53 tumor suppressor gene in the toxicity of TCDD, endrin, naphthalene, and chromium (VI) in liver and brain tissues of mice.
2000 Mar 15
Inhibition of dioxin effects on bone formation in vitro by a newly described aryl hydrocarbon receptor antagonist, resveratrol.
2000 Oct
Ovarian tumors in rats induced by chronic 2,3,7,8-tetrachlorodibenzo-p-dioxin treatment.
2000 Oct 1
The transcriptional signature of dioxin in human hepatoma HepG2 cells.
2000 Oct 15
Serum levels of TCDD and dioxin-like chemicals in Rhesus monkeys chronically exposed to dioxin: correlation of increased serum PCB levels with endometriosis.
2001 Jan
Anti-CD40 Treatment of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)-exposed C57Bl/6 mice induces activation of antigen presenting cells yet fails to overcome TCDD-induced suppression of allograft immunity.
2001 Jan 1
Patents

Sample Use Guides

Treatment of pregnant female Sprague-Dawley rats on Gestational Day 15 with a single oral dose of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) (0.5, 1.0, or 2.0 ug/kg) or indole-3-carbinol (I3C, 1.0 or 100 mg/kg), an aryl hydrocarbon (Ah) receptor agonist which is found in cruciferous vegetables, resulted in reproductive abnormalities in the male offspring (three to five litters in each treatment group).
Route of Administration: Oral
In Vitro Use Guide
Treatment of rat hippocampal neuronal cultures with 2,3,7,8-TCDD (10-100 nM) resulted in a rapid concentration-dependent increase in [Ca2+]i associated with a decrease in mitochondrial membrane potential and activation of alpha-protein kinase C (alpha-PKC).
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:44:30 GMT 2025
Edited
by admin
on Mon Mar 31 18:44:30 GMT 2025
Record UNII
DO80M48B6O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
2,3,7,8-TETRACHLORODIBENZO-P-DIOXIN
HSDB  
Common Name English
TCDD
MI  
Preferred Name English
DIBENZO(B,E)(1,4)DIOXIN, 2,3,7,8-TETRACHLORO-
Systematic Name English
2,3,7,8-TETRACHLORODIBENZO-P-DIOXIN [HSDB]
Common Name English
TETRACHLORODIBENZO-P-DIOXIN, 2,3,7,8-
Common Name English
D 48
Common Name English
PCDD 48
Common Name English
2,3,7,8-TETRACHLORODIBENZO(B,E)(1,4)DIOXIN
Systematic Name English
2,3,7,8-TCDD
Common Name English
TCDD [MI]
Common Name English
TCDBD
Common Name English
NCI-C03714
Code English
DIOXIN
Systematic Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 600000
Created by admin on Mon Mar 31 18:44:30 GMT 2025 , Edited by admin on Mon Mar 31 18:44:30 GMT 2025
Code System Code Type Description
PUBCHEM
15625
Created by admin on Mon Mar 31 18:44:30 GMT 2025 , Edited by admin on Mon Mar 31 18:44:30 GMT 2025
PRIMARY
DAILYMED
DO80M48B6O
Created by admin on Mon Mar 31 18:44:30 GMT 2025 , Edited by admin on Mon Mar 31 18:44:30 GMT 2025
PRIMARY
NCI_THESAURUS
C864
Created by admin on Mon Mar 31 18:44:30 GMT 2025 , Edited by admin on Mon Mar 31 18:44:30 GMT 2025
PRIMARY
MERCK INDEX
m10491
Created by admin on Mon Mar 31 18:44:30 GMT 2025 , Edited by admin on Mon Mar 31 18:44:30 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID2021315
Created by admin on Mon Mar 31 18:44:30 GMT 2025 , Edited by admin on Mon Mar 31 18:44:30 GMT 2025
PRIMARY
WIKIPEDIA
2,3,7,8-Tetrachlorodibenzodioxin
Created by admin on Mon Mar 31 18:44:30 GMT 2025 , Edited by admin on Mon Mar 31 18:44:30 GMT 2025
PRIMARY
CHEBI
36682
Created by admin on Mon Mar 31 18:44:30 GMT 2025 , Edited by admin on Mon Mar 31 18:44:30 GMT 2025
PRIMARY
CHEBI
28119
Created by admin on Mon Mar 31 18:44:30 GMT 2025 , Edited by admin on Mon Mar 31 18:44:30 GMT 2025
PRIMARY
CHEBI
134044
Created by admin on Mon Mar 31 18:44:30 GMT 2025 , Edited by admin on Mon Mar 31 18:44:30 GMT 2025
PRIMARY
EVMPD
SUB33620
Created by admin on Mon Mar 31 18:44:30 GMT 2025 , Edited by admin on Mon Mar 31 18:44:30 GMT 2025
PRIMARY
FDA UNII
DO80M48B6O
Created by admin on Mon Mar 31 18:44:30 GMT 2025 , Edited by admin on Mon Mar 31 18:44:30 GMT 2025
PRIMARY
CAS
1746-01-6
Created by admin on Mon Mar 31 18:44:30 GMT 2025 , Edited by admin on Mon Mar 31 18:44:30 GMT 2025
PRIMARY
HSDB
4151
Created by admin on Mon Mar 31 18:44:30 GMT 2025 , Edited by admin on Mon Mar 31 18:44:30 GMT 2025
PRIMARY
ECHA (EC/EINECS)
217-122-7
Created by admin on Mon Mar 31 18:44:30 GMT 2025 , Edited by admin on Mon Mar 31 18:44:30 GMT 2025
PRIMARY
SMS_ID
100000127538
Created by admin on Mon Mar 31 18:44:30 GMT 2025 , Edited by admin on Mon Mar 31 18:44:30 GMT 2025
PRIMARY
Related Record Type Details
METABOLITE -> PARENT