File:Tetrodotoxin.svg · Wikimedia Commons · See Wikimedia Commons
tetrodotoxin
Sign in to saveAlso known as Fugu poison, Maculotoxin, Spheroidine, Tarichatoxin, Tetrodontoxin, TTX
Tetrodotoxin (TTX) is a potent neurotoxin. Its name derives from Tetraodontiformes, an order that includes pufferfish, porcupinefish, ocean sunfish, and triggerfish; several of these species carry the toxin. Although tetrodotoxin was discovered in these fish, it is found in several other animals (e.g., in blue-ringed octopuses, rough-skinned newts, and moon snails). It is also produced by certain infectious or symbiotic bacteria like Pseudoalteromonas, Pseudomonas, and Vibrio as well as other species found in symbiotic relationships with animals and plants.
Chemical data
- Formula
- C11H17N3O8
- Molecular weight
- 319.27 g/mol
- IUPAC name
- (1R,5R,6R,7R,9S,11S,12R,13S,14S)-3-amino-14-(hydroxymethyl)-8,10-dioxa-2,4-diazatetracyclo[7.3.1.17,11.01,6]tetradec-3-ene-5,9,12,13,14-pentol
- SMILES
- C([C@@]1([C@H]2[C@@H]3[C@H](N=C(N[C@@]34[C@H]([C@@H]1O[C@]([C@H]4O)(O2)O)O)N)O)O)O
- InChIKey
- CFMYXEVWODSLAX-QYIGHCJRSA-N
- XLogP
- -5.9
- Polar surface area
- 190 Ų
- H-bond donors
- 8
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Research
20,466 papers- Tetrodotoxin poisoning.Advances in food and nutrition research · 2007
- Tetrodotoxin: chemistry, toxicity, source, distribution and detection.Toxins · 2014
- Tetrodotoxin.Current biology : CB · 2016
- Total Synthesis of Tetrodotoxin.Angewandte Chemie (International ed. in English) · 2020
- Tetrodotoxin.Trends in biochemical sciences · 1988
via PubMed
~24 min read
Encyclopedic overview
21 sectionsContents
- Sources in nature
- Biochemistry
- Biosynthesis
- Resistance
- Chemical synthesis
- Poisoning
- Toxicity
- History
- Symptoms and treatment
- Worldwide distribution of toxicity
- Statistical factors
- Fugu as a food
- Food analysis
- Detection in body fluids
- Modern therapeutic research
- Regulation
- Popular culture
- See also
- References
- Further reading
- External links
Tetrodotoxin (TTX) is a potent neurotoxin. Its name derives from Tetraodontiformes, an order that includes pufferfish, porcupinefish, ocean sunfish, and triggerfish; several of these species carry the toxin. Although tetrodotoxin was discovered in these fish, it is found in several other animals (e.g., in blue-ringed octopuses, rough-skinned newts, and moon snails). It is also produced by certain infectious or symbiotic bacteria like Pseudoalteromonas, Pseudomonas, and Vibrio as well as other species found in symbiotic relationships with animals and plants.
Although it produces thousands of intoxications annually and several deaths, it has shown efficacy for the treatment of cancer-related pain in phase II and III clinical trials.
Excerpted from Wikipedia’s “tetrodotoxin” article, available under the CC BY-SA 4.0 licence.