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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H34O9
Molecular Weight 466.5214
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of T-2 TOXIN

SMILES

CC(C)CC(=O)O[C@H]1C[C@@]2(COC(C)=O)[C@H](O[C@@H]3[C@H](O)[C@@H](OC(C)=O)[C@@]2(C)[C@]34CO4)C=C1C

InChI

InChIKey=BXFOFFBJRFZBQZ-QYWOHJEZSA-N
InChI=1S/C24H34O9/c1-12(2)7-18(27)32-16-9-23(10-29-14(4)25)17(8-13(16)3)33-21-19(28)20(31-15(5)26)22(23,6)24(21)11-30-24/h8,12,16-17,19-21,28H,7,9-11H2,1-6H3/t16-,17+,19+,20+,21+,22+,23+,24-/m0/s1

HIDE SMILES / InChI
Molecular Formula C24H34O9
Molecular Weight 466.5214
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including

Among the naturally occurring trichothecenes in food and feed, T-2 toxin is a cytotoxic fungal secondary metabolite produced by various species of Fusarium. Following ingestion, T-2 toxin causes acute and chronic toxicity and induces apoptosis in the immune system and fetal tissues. T-2 toxin is usually metabolized and eliminated after ingestion, yielding more than 20 metabolites. Consequently, there is a possibility of human consumption of animal products contaminated with T-2 toxin and its metabolites. The molecular mechanism of inhibition of protein synthesis may be the high affinity of T-2 toxin for the 60S ribosomal subunit.

CNS Activity

CNS Penetrant
2588
Curator's Comment: Known to be CNS penetrant in vitro in . Human data not available In general the toxic effects on the BBB in vitro were detected at low nanomolar concentrations. However, when comparing the results to the situation in vivo, it has to be taken into account that the used model system does not include serum which can modify the availability of T-2 and HT-2 toxin under in vivo conditions.

Originator

Bamburg, J.R. et al.
1
Curator's Comment: T-2 Toxin was first isolated by Bamburg et al. (1968) from a culture of Fusarium sporo- trichioides, wrongly identified as F. tricinctum (Marasas et al., 1984).

Approval Year

Unknown
149124
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Developmental exposure to T-2 toxin reversibly affects postnatal hippocampal neurogenesis and reduces neural stem cells and progenitor cells in mice.
2016-08
Toxic effects of HT-2 toxin on mouse oocytes and its possible mechanisms.
2016-06
Toxicity and oxidative stress induced by T-2 toxin and HT-2 toxin in broilers and broiler hepatocytes.
2016-01
Delay of the onset of puberty in female rats by prepubertal exposure to T-2 toxin.
2015-11-09
Integrated Transcriptional and Proteomic Analysis of Growth Hormone Suppression Mediated by Trichothecene T-2 Toxin in Rat GH3 Cells.
2015-10
T-2 toxin inhibits gene expression and activity of key steroidogenesis enzymes in mouse Leydig cells.
2015-08
T-2 toxin regulates steroid hormone secretion of rat ovarian granulosa cells through cAMP-PKA pathway.
2015-02-03
Differential effects of route of T-2 toxin exposure on hepatic oxidative damage in mice.
2015-01
Toxicity induced by F. poae-contaminated feed and the protective effect of Montmorillonite supplementation in broilers.
2014-12
Toxic effects of dietary exposure to T-2 toxin on intestinal and hepatic biotransformation enzymes and drug transporter systems in broiler chickens.
2013-05
Toxic effects of T-2 toxin and deoxynivalenol on the mitochondrial electron transport system of cardiomyocytes in rats.
2013
T-2 toxin induced skin inflammation and cutaneous injury in mice.
2012-12-16
An in vitro investigation of endocrine disrupting effects of trichothecenes deoxynivalenol (DON), T-2 and HT-2 toxins.
2012-11-15
T-2 toxin enhances catabolic activity of hypertrophic chondrocytes through ROS-NF-κB-HIF-2α pathway.
2012-10
JAK/STAT pathway plays a critical role in the proinflammatory gene expression and apoptosis of RAW264.7 cells induced by trichothecenes as DON and T-2 toxin.
2012-06
T-2 toxin is a cytochrome P450 1A1 inducer and leads to MAPK/p38- but not aryl hydrocarbon receptor-dependent interleukin-8 secretion in the human intestinal epithelial cell line Caco-2.
2011-06-18
T-2 toxin induces apoptosis in ovarian granulosa cells of rats through reactive oxygen species-mediated mitochondrial pathway.
2011-05-10
Cytotoxicity and accumulation of ergot alkaloids in human primary cells.
2011-04-11
Effects of T-2 toxin and selenium on chondrocyte expression of matrix metalloproteinases (MMP-1, MMP-13), α2-macroglobulin (α2M) and TIMPs.
2011-03
Alteration of blood brain barrier permeability by T-2 toxin: Role of MMP-9 and inflammatory cytokines.
2011-02-04
Brain oxidative stress after dermal and subcutaneous exposure of T-2 toxin in mice.
2010-12
Immunopathological effects of ochratoxin A and T-2 toxin combination on broilers.
2010-06
DNA damage and DNA damage responses in THP-1 monocytes after exposure to spores of either Stachybotrys chartarum or Aspergillus versicolor or to T-2 toxin.
2010-05
Oxidative stress induction by T-2 toxin causes DNA damage and triggers apoptosis via caspase pathway in human cervical cancer cells.
2009-08-03
Fusarial toxin-induced toxicity in cultured cells and in isolated mitochondria involves PTPC-dependent activation of the mitochondrial pathway of apoptosis.
2009-08
Oxidative damage and gene expression profile of antioxidant enzymes after T-2 toxin exposure in mice.
2009-06-16
Role of GRP78/BiP degradation and ER stress in deoxynivalenol-induced interleukin-6 upregulation in the macrophage.
2009-06
Metabolism and cytotoxic effects of T-2 toxin and its metabolites on human cells in primary culture.
2009-04-28
Promotion of the articular cartilage proteoglycan degradation by T-2 toxin and selenium protective effect.
2008-01
[Protective effect of selenium against T-2 toxin-induced inhibition of chondrocyte aggrecan and collagen II synthesis].
2006-04
T-2 toxin induces apoptosis, and selenium partly blocks, T-2 toxin induced apoptosis in chondrocytes through modulation of the Bax/Bcl-2 ratio.
2006-04
Effects of trichothecene structure on cytokine secretion and gene expression in murine CD4+ T-cells.
1995-12-15
Direct and reflex cardiovascular effects of trichothecene mycotoxins.
1987
Synthesis of DNA in human fibroblasts treated with T-2 toxin and HT-2 toxin (the trichothecene metabolites of Fusarium species) and the effects of hydroxyurea.
1980-02
T-2 toxin production by Fusarium tricinctum on solid substrate.
1971-04
Patents

Patents

WO2001001968A2
1

Sample Use Guides

In Vivo Use Guide
in mice toxic effect: Groups of 50 male and 50 female CD-1 mice, six weeks of age, were fed a semi-synthetic diet containing 0, 1.5 or 3.0 mg/kg T-2 toxin for 71 weeks. in rats toxic effect: 40 weanling male and female Wistar- Porton rats were administered one to eight doses of 0.2-4 mg/kg bw T-2 toxin intragastrically at approximately monthly intervals (duration unspecified).
Route of Administration: Other
In Vitro Use Guide
Embryos were cultured in media supplemented with 0.5, 0.75 and 1 ng/ml T-2. Different exposure times were applied [96 h (treatment I) or 24 h following 72 h in toxin-free media (treatment II)]. Blastomere number, nuclear chromatin status and blastocoel formation were investigated in blastocysts. After 24 h of exposure applied following a 72-h culture, blastomeres had a higher level of chromatin damage, although their developmental potential was the same as in the control embryos. In both cases, decreased mitotic rate was found, which resulted in decreased blastomere number even at low toxin concentration.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:55:40 GMT 2025
Edited
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on Mon Mar 31 19:55:40 GMT 2025
Record UNII
I3FL5NM3MO
Record Status Validated (UNII)
Record Version
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Name Type Language
FUSARIOTOXIN T-2
Preferred Name English
T-2 TOXIN
HSDB   MI  
Common Name English
TRICHOTHEC-9-ENE-3.ALPHA.,4.BETA.,8.ALPHA.,15-TETROL, 12,13-EPOXY-, 4,15-DIACETATE 8-ISOVALERATE
Common Name English
T 2 TOXIN
Common Name English
T2-TRICHOTHECENE
Common Name English
TOXIN T 2
Common Name English
T2-TRICHOTHECENE [IARC]
Common Name English
MYCOTOXIN T-2
Brand Name English
T-2 TOXIN [HSDB]
Common Name English
NSC-138780
Code English
T 2 MYCOTOXIN
Common Name English
T-2 LIENOMYCIN
Common Name English
T-2 TOXIN [MI]
Common Name English
4.BETA.,15-DIACETOXY-8.ALPHA.-(3-METHYLBUTYRYLOXY)-12,13-EPOXYTRICHOTHEC-9-EN-3.ALPHA.-OL
Common Name English
8.ALPHA.-(3-METHYLBUTYRYLOXY)-4.BETA.,15-DIACETOXYSCIRP-9-EN-3.ALPHA.-OL
Common Name English
INSARIOTOXIN
Brand Name English
Code System Code Type Description
NSC
138780
Created by admin on Mon Mar 31 19:55:40 GMT 2025 , Edited by admin on Mon Mar 31 19:55:40 GMT 2025
PRIMARY
CHEBI
9381
Created by admin on Mon Mar 31 19:55:40 GMT 2025 , Edited by admin on Mon Mar 31 19:55:40 GMT 2025
PRIMARY
HSDB
3544
Created by admin on Mon Mar 31 19:55:40 GMT 2025 , Edited by admin on Mon Mar 31 19:55:40 GMT 2025
PRIMARY
ECHA (EC/EINECS)
244-297-7
Created by admin on Mon Mar 31 19:55:40 GMT 2025 , Edited by admin on Mon Mar 31 19:55:40 GMT 2025
PRIMARY
PUBCHEM
5284461
Created by admin on Mon Mar 31 19:55:40 GMT 2025 , Edited by admin on Mon Mar 31 19:55:40 GMT 2025
PRIMARY
WIKIPEDIA
T-2 mycotoxin
Created by admin on Mon Mar 31 19:55:40 GMT 2025 , Edited by admin on Mon Mar 31 19:55:40 GMT 2025
PRIMARY
CAS
21259-20-1
Created by admin on Mon Mar 31 19:55:40 GMT 2025 , Edited by admin on Mon Mar 31 19:55:40 GMT 2025
PRIMARY
MESH
D013605
Created by admin on Mon Mar 31 19:55:40 GMT 2025 , Edited by admin on Mon Mar 31 19:55:40 GMT 2025
PRIMARY
EPA CompTox
DTXSID6021298
Created by admin on Mon Mar 31 19:55:40 GMT 2025 , Edited by admin on Mon Mar 31 19:55:40 GMT 2025
PRIMARY
FDA UNII
I3FL5NM3MO
Created by admin on Mon Mar 31 19:55:40 GMT 2025 , Edited by admin on Mon Mar 31 19:55:40 GMT 2025
PRIMARY
MERCK INDEX
m11251
Created by admin on Mon Mar 31 19:55:40 GMT 2025 , Edited by admin on Mon Mar 31 19:55:40 GMT 2025
PRIMARY Merck Index
NIH
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