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TTX in Nature

  • TTX is a paralytic toxin produced in the liver by some types of fish such as the pufferfish.(5)
  • Poisoning in humans can occur when flesh or organs are not prepared correctly and can be fatal.(5)
  • It is found in the liver and gonads of certain fish, order Tetraodontiformes, such as pufferfish, globefish, and toadfish.(5)

Medical Uses

  • Tetrodotoxin in low doses is used as a treatment for heroin addicts and is being researched as a pain reliever for cancer patients and as an anesthesia. It is used because it has a selective and potent sodium channel blocking abilities.(6)
  • TTX blocks the ability of Na+ to transmit pain. (6)

Stereochemistry

Identification of Tetrodotoxin

Tetrodotoxin has 9 chiral centers which gives us a total of 512 stereoisomers.

Formula: 2^n

Answer: 2^9=512

IUPAC name:

(4R,4aR,5R,6S,7S,8S,8aR,10S,12S)-2-azaniumylidene-4,6,8,12-tetrahydroxy-6-(hydroxymethyl)-2,3,4,4a,5,6,7,8-octahydro-1H-8a,10-methano-5,7-(epoxymethanooxy)quinazolin-10-olate(3)

CAS No: 4368-28-9(4)

Physical Properties

  • Molecular Formula: C11H17N3O8 (1)
  • Molar mass: 319.268 g/mol (1)
  • Melting Point: 220°C (1)
  • Boiling Point: 702.6°C at 760 mmHg (1)
  • Appearance: Colorless Crystalline Solid (1)
  • Structural Formula:

References

TETRODOTOXIN (TTX)

By: Penelope Delong Ashley Mitchell

Enna Diaz Mary Ford

Gideon Odonkor Sharon Shrestha

1. Tetrodotoxin. Material Safety Data Sheet, https://fscimage.fishersci.com/

msds/01139.htm (accessed Feb 5, 2016).

2. TETRODOTOXIN. - National Library of Medicine HSDB Database, http://

toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs hsdb:@term @docno 3543

(accessed Mar 28, 2016).

3. ChemSpider. ChemSpider, http://www.chemspider.com/ (accessed Mar 26,

2016).

4. Tetrodotoxin. Tocris Bioscience, https://www.tocris.com/dispprod.php?

itemid=1906#.vs5pizmricg (accessed Mar 26, 2016).

5. TETRODOTOXIN : Biotoxin. Centers for Disease Control and Prevention, http://www.cdc.gov/niosh/ershdb/emergencyresponsecard_29750019.html (accessed Mar 28, 2016)

6. Result Filters. National Center for Biotechnology Information, http://www.ncbi.nlm.nih.gov/pubmed/19268686 (accessed Mar 28, 2016).

Hazards

  • Tetrodotoxin is a neurotoxin that causes paralysis and respiratory arrest which can lead to death.(2)
  • It is extremely toxic, a fatal dose may be as little as 1-4 mg per person which makes it more poisonous then cyanide.(2)
  • Can enter the body by ingestion, injection, inhalation, or abraded skin. (5)
  • Other symptoms include dizziness, vomiting, extremity numbness, headache and motor dysfunction. (2)
  • The toxin interferes with the transmission of signals from nerves to muscles by blocking sodium channels.(2)

Functional Groups

WHAT I LEARNED IN OCHEM IS.........

3-D Structure

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