4368-28-9 Usage
Description
Different sources of media describe the Description of 4368-28-9 differently. You can refer to the following data:
1. Tetraodotoxin is a kind of extremely potent toxin which exists in the liver and sex organs of some fishes including pufferfish, porcupine fish, ocean sunfish, and toadfish as well as some kind of amphibian, octopus and shellfish species. It is also produced by some bacteria such as Pseudomonas and Vibrio. Tetraodotoxin is extremely toxic to human, interfering with the transmission of signals of nerves to muscles and further causing paralysis of the body muscle. It can be fatal in some cases. Its mechanism of action is inhibiting the firing of action potentials in nerves through binding to the voltage-gated sodium channels in nerve cell membrane and blocking the passages of sodium ions into the nerve cell. People should wear proper protective equipment upon operations and should be subject to proper treatment upon suffering from it. However, it has been under investigation on the treatment of chronic and breakthrough pain in advanced cancer patients.
2. Tetrodotoxin (TTX) is a selective sodium channel blocker
nonprotein heat-stable toxin. The mechanism of toxicity is
through the blockage of fast voltage-gated sodium channels.
The consumption of toxic amounts of TTX results primarily in
neurologic and gastrointestinal signs and symptoms. TTX is
widely distributed in marine taxa such as pufferfish and
porcupine fish (suborders of the Tetraodontiformes order),
salamanders of the family Salamandridae, Central American
frogs (genus Atelopus), shellfish, starfish, crabs, and some
species of ribbonworm and octopus. However, in terrestrial
taxa, it is limited to a single class of vertebrates (Amphibia).
TTX is now known to be produced not by puffer but by
bacteria, and reaches various species of animals via food chain.
References
https://www.cdc.gov/niosh/ershdb/emergencyresponsecard_29750019.html
https://en.wikipedia.org/wiki/Tetrodotoxin
Chemical Properties
white powder
Uses
Different sources of media describe the Uses of 4368-28-9 differently. You can refer to the following data:
1. Tetrodotoxin is a highly selective, reversible sodium channel blocker.
2. TTX is an extremely popular chemical tool in the physiological
and pharmacological laboratories since discovery of its channel
blocking action in the early 1960s. Some potential therapeutic
uses include suppressing pain in cancer patients, preventing
ischemic damage of the brain that follows stroke, relieving the
symptoms of withdrawal in opiate addicts, and using it as
anesthetic agent.
Definition
ChEBI: A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.
Biological Activity
Selective inhibitor of Na + channel conductance. Binding is reversible and of high affinity (K d = 1-10 nM). Blocks in a use-dependent manner.
Safety Profile
Poison by ingestion,
intraperitoneal, subcutaneous, and
intravenous routes. When heated to
decomposition it emits toxic fumes of Nox.
Toxicity evaluation
TTX is a selective sodium channel blocker that can block nerve
and muscle conductions; action potentials are blocked while
resting membrane potentials and resting membrane resistance
are not affected. TTX blocks axonal transmission by lowering
the conductance of sodium at nodes of Ranvier. Vomiting
occurs because the toxin can act directly at or near the
chemoreceptor trigger zone. Respiratory depression is caused
by either a specific action of tetrodotoxin on the brain’s respiratory
center or because paralysis of respiratory nerves and
muscles occurs.
Check Digit Verification of cas no
The CAS Registry Mumber 4368-28-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,3,6 and 8 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 4368-28:
(6*4)+(5*3)+(4*6)+(3*8)+(2*2)+(1*8)=99
99 % 10 = 9
So 4368-28-9 is a valid CAS Registry Number.
InChI:InChI=1/C11H17N3O8/c12-8-13-6(17)2-4-9(19,1-15)5-3(16)10(2,14-8)7(18)11(20,21-4)22-5/h2-7,15-20H,1H2,(H3,12,13,14)/t2-,3-,4-,5+,6-,7+,9+,10-,11+/m1/s1
4368-28-9Relevant articles and documents
Total Synthesis of (?)-Tetrodotoxin and 11-norTTX-6(R)-ol
Maehara, Tomoaki,Motoyama, Keisuke,Toma, Tatsuya,Yokoshima, Satoshi,Fukuyama, Tohru
supporting information, p. 1549 - 1552 (2017/02/05)
The enantioselective total synthesis of (?)-tetrodotoxin [(?)-TTX] and 4,9-anhydrotetrodotoxin, which are selective blockers of voltage-gated sodium channels, was accomplished from the commercially available p-benzoquinone. This synthesis was based on efficient stereocontrol of the six contiguous stereogenic centers on the core cyclohexane ring through Ogasawara's method, [3,3]-sigmatropic rearrangement of an allylic cyanate, and intramolecular 1,3-dipolar cycloaddition of a nitrile oxide. Our synthetic route was applied to the synthesis of the tetrodotoxin congeners 11-norTTX-6(R)-ol and 4,9-anhydro-11-norTTX-6(R)-ol through late-stage modification of the common intermediate. Neutral deprotection at the final step enabled easy purification of tetrodotoxin and 11-norTTX-6(R)-ol without competing dehydration to their 4,9-anhydro forms.
First asymmetric total synthesis of tetrodotoxin
Ohyabu, Norio,Nishikawa, Toshio,Isobe, Minoru
, p. 8798 - 8805 (2007/10/03)
Tetrodotoxin, a toxic principle of puffer fish poisoning, is one of the most famous marine natural products because of the complex structure having many functional groups and its potent biological activity leading to death. Since the structure elucidation in 1964, this toxin has been recognized as a formidable target molecule for total synthesis. We have recently achieved the first asymmetric total synthesis from 2-acetoxy-tri-O-acetyl-D-glucal as a chiral starting material. The highly hydroxylated cyclohexane ring was constructed by Claisen rearrangement and regioselective hydroxylations of an acetone moiety and an intramolecular directed aldol condensation of the precursor having methyl ketone with dihydroxyacetone, which was synthesized through Sonogashira coupling. Installation of nitrogen functionality was unsuccessful through an attempted Overman rearrangement. We, therefore, employed a new intramolecular conjugate addition strategy between the carbamate and unsaturated ester groups. The α-hydroxyl lactone moiety was synthesized through an intramolecular epoxide opening by the Z-enolate of aldehyde, which was followed by oxidation - reduction of the resulting cyclic vinyl ether. The lactone was then converted to a protected ortho ester, and then gunanidinylation was followed by cleavage of the 1,2-glycol to give the fully protected tetrodotoxin. Selection of the protective groups has finally led us to accomplish the total synthesis of tetrodotoxin in an enantiomerically pure form. All the stereogenic centers were controlled with high selectivity, and the hydroxyl groups were differently protected to discriminate for the future analogue synthesis of a bioorganic program. The synthetic tetrodotoxin was purifed by ion exchange chromatography and characterized to be identifical with the natural compound.
