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First recognized in 1957 by Shantz et al. in the butter clam Saxidomus giganteus, saxitoxin is a naturally occurring toxin that is synthesized by various marine dinoflagellates and cyanobacteria. It is used in neurochemical and molecular biology research, but regulatory concerns have focused on its weaponization and potent toxicological effects on animals and humans. Saxitoxin causes paralytic shellfish poisoning (PSP) in humans and other animals; whales having ingested organisms contaminated with the toxin have died just hours after exposure. In humans, PSP can occur as a result of consuming shellfish or other seafood in which saxitoxin has accumulated. While effects have been documented worldwide, the sources of contaminated seafood have been identified as primarily the west and east coasts of the United States. To date, more than 30 different saxitoxin analogs have been identified. These include pure saxitoxin (STX), neosaxitoxin (neoSTX), the gonyautoxins (GTX), and decarbamoylsaxitoxin (dc-STX); of these, STX, 6NeoSTX, GTX1, and dc-STX seem to be the most toxic. The term saxitoxin typically refers to this collection of compounds produced naturally by cyanobacteria. Saxitoxin is far more potent than the classic puffer fish toxin tetrodotoxin, and is one of only two naturally occurring Schedule 1 chemical warfare agents (the other is ricin). In 1970, President Nixon ordered stocks of the toxin destroyed in compliance with U.N. agreements on biological weapons; however, the Central Intelligence Agency revealed in 1975 that there was a remaining supply, which was distributed to research facilities by the National Institutes of Health in order to study neurological diseases.

35523-89-8

35523-89-8 Suppliers

This product is a nationally controlled contraband or patented product, and the Lookchem platform doesn't provide relevant sales information.

35523-89-8 Usage

Chemical Properties

Crystalline solid; soluble in water and me thanol; forms dihydrochloride with HCl.

Uses

Different sources of media describe the Uses of 35523-89-8 differently. You can refer to the following data:
1. As a Schedule 1 controlled substance under the Chemical Weapons Convention of 1993, the use of saxitoxin is extremely limited outside of weaponized forms. Its use as a chemical reagent in research is its other important use, as it has been instrumental in experiments to elucidate the mechanisms involved in sodium channels used in cellular communication.
2. Mussel poison; clam poison; paralytic shellfish poison; gonyaulax toxin. These poisonous shellfish have been connected to instances of toxic”red-tides” where the high concentration of algae discoloring the water were of the Gonyaulax genus. Used as a too
3. Saxitoxin is an alkaloid of nonplant origin.It is the neurotoxic constituent of dinoflagel lates (Gonyaulax catenella and G. excavata)the so-called “red tide” found along the U.S.coast. Shellfish, clams, and scallops consumethis and become extremely poisonous forhuman consumption.

Definition

ChEBI: An alkaloid isolated from the marine dinoflagellates and cyanobacteria that causes paralytic shellfish poisoning.

Health Hazard

Saxitoxin is an extremely toxic substance.It binds to sodium channels and the blocksnerve membrane. In humans, ingestion ofSAXITOXIN can produce tingling andburning in the lip, tongue, face, and thewhole body within an hour. This is fol lowed by numbness, muscular incoordina tion, confusion, headache, and respiratoryfailure. Death may occur within 12 hours.LD50 value intraperitoneal (mice): 0.005mg/kgLD50 value oral (mice): 0.26 mg/kgIntravenous administration of 1 mL of1:2000 solution of prostigmine methylsulfatehas been reported to be effective againstsaxitoxin poisoning (Hodgson et al. 1988).

Environmental Fate

Dinoflagellates (flagellate protists, plankton) are primarily responsible for the biosynthesis of saxitoxin, and bioaccumulation tends to occur in several shellfish such as mussels, clams, scallops, and cockles. Broth made from shellfish can harbor saxitoxin as well due to its stability at normal cooking temperatures. Consumption of the shellfish leads to toxicity in humans, while consumption of other organisms in which saxitoxin has accumulated (up the food chain, for example) has historically affected other animals such as whales. Data describing the environmental fate of saxitoxin is extremely limited. There have been some studies investigating the absorption/desorption capacities of various soils for the compound, but more exhaustive studies are yet to be reported.

Toxicity evaluation

Saxitoxin interrupts nerve transmissions by binding to voltagegated sodium channels. Positively charged guanidinium groups of saxitoxin interact with negatively charged carboxyl groups at a site on the sodium channel (in a one-to-one ratio) of neurons and muscle cells, resulting in blocked action potentials and interrupted transmissions. The inactivation of vasomotor nerves along with vascular smooth-muscle relaxation follows and hypotension can additionally occur. When muscles in the respiratory or cardiovascular system are affected, death can result. Intraperitoneal inoculation with STX extract in the freshwater fish Hoplias malabaricus resulted in a variety of systemic effects culminating in oxidative stress observed in the brain, leading to lipid, protein, and DNA damage. Although the exposure in this study was subchronic, apoptotic cellular processes were implicated.

References

Schantz et al., J. Arner. Chern. Soc., 97, 1238 (1975)

Check Digit Verification of cas no

The CAS Registry Mumber 35523-89-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,5,5,2 and 3 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 35523-89:
(7*3)+(6*5)+(5*5)+(4*2)+(3*3)+(2*8)+(1*9)=118
118 % 10 = 8
So 35523-89-8 is a valid CAS Registry Number.
InChI:InChI=1/C11H18N6O4/c12-7-4-1-2-10(19,20)11(4)6(16-8(13)17-11)5(15-7)3-21-9(14)18/h4-6,19-20H,1-3H2,(H2,12,15)(H2,14,18)(H3,13,16,17)/p+2/t4?,5?,6-,11+/m0/s1

35523-89-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name saxitoxin

1.2 Other means of identification

Product number -
Other names Saxitoxin in acetic acid (determination in mussel)

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:35523-89-8 SDS

35523-89-8Relevant academic research and scientific papers

Confirmation of the Structures of Gonyautoxins I - IV by Correlation with Saxitoxin

Shimizu, Yuzuru,Hsu, Chien P.

, p. 314 - 315 (1981)

The structures of four paralytic shellfish poisons have been unequivocally established by interconversion and ultimate correlation with saxitoxin.

C-H Hydroxylation in Paralytic Shellfish Toxin Biosynthesis

Lukowski, April L.,Ellinwood, Duncan C.,Hinze, Meagan E.,Deluca, Ryan J.,Du Bois,Hall, Sherwood,Narayan, Alison R. H.

, p. 11863 - 11869 (2018)

The remarkable degree of synthetic selectivity found in Nature is exemplified by the biosynthesis of paralytic shellfish toxins such as saxitoxin. The polycyclic core shared by saxitoxin and its relatives is assembled and subsequently elaborated through the installation of hydroxyl groups with exquisite precision that is not possible to replicate with traditional synthetic methods. Here, we report the identification of the enzymes that carry out a subset of C-H functionalizations involved in paralytic shellfish toxin biosynthesis. We have shown that three Rieske oxygenases mediate hydroxylation reactions with perfect site- and stereoselectivity. Specifically, the Rieske oxygenase SxtT is responsible for selective hydroxylation of a tricyclic precursor to the famous natural product saxitoxin, and a second Rieske oxygenase, GxtA, selectively hydroxylates saxitoxin to access the oxidation pattern present in gonyautoxin natural products. Unexpectedly, a third Rieske oxygenase, SxtH, does not hydroxylate tricyclic intermediates, but rather a linear substrate prior to tricycle formation, rewriting the biosynthetic route to paralytic shellfish toxins. Characterization of SxtT, SxtH, and GxtA is the first demonstration of enzymes carrying out C-H hydroxylation reactions in paralytic shellfish toxin biosynthesis. Additionally, the reactions of these oxygenases with a suite of saxitoxin-related molecules are reported, highlighting the substrate promiscuity of these catalysts and the potential for their application in the synthesis of natural and unnatural saxitoxin congeners.