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Saxitoxin

HCID 56947150
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Grundinformationen

CAS
35523-89-8
Standard-SMILES
NC(=O)OC[C@@H]1N=C(N)N2CCC(O)(O)[C@@]23NC(N)=N[C@@H]13
InChIKey
RPQXVSUAYFXFJA-HGRQIUPRSA-N
Summenformel
C10H17N7O4
Durchschnittliche Molmasse
299,291 g/mol
Monoisotopische Masse
299,13420202

Namen und Bezeichner

Bevorzugter Name
Saxitoxin
IUPAC
[(3aS,4R,10aS)-10,10-Dihydroxy-2,6-diiminooctahydro-1H,8H-pyrrolo[1,2-c]purin-4-yl]methyl carbamate
Englischer Name
SAXITOXIN
Summenformel
C10H17N7O4
Molmasse
299.29

Namen und Synonyme

C13757SAXITOXINMussel poisonGonyaulax toxinSAXITOXIN DIACETATE SALTgonyaulaxcatenellapoisonsaxidomusgiganteuspoisonmytiluscalifornianuspoisonSaxitoxin in acetic acid (determination in mussel)hyl)-3a,4,8,9-tetrahydro-,(3as-(3a-alpha,4-alpha,10ar*))

Datenbank-Bezeichner

CAS
35523-89-8、73603-72-2
PubChem CID
56947150
DTXSID
DTXSID3074313
ChEMBL
CHEMBL501134
ChEBI
CHEBI:34970
UNII
Q0638E899B
EC Number
632-220-3
Nikkaji
J365.643H

Eigenschaften

Physikochemische Eigenschaften

Siedepunkt
440.62 °C · 440.62°C (rough estimate)
Dichte
1.301 · 1.3010 (rough estimate)
Brechungsindex
1.64 · 1.6400 (estimate)
storage temp.
20 °C · −20°C
pka
13.32 · 13.32±0.50(Predicted)
EPA chemische Informationen
Saxitoxin (35523-89-8)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Sicherheitsdaten

wgk
3
ridadr
UN 3462 6.1/PG 1
risk_code
26/27/28
Toxizität
During seasons when dinoflagellates “bloom,” filter-feeding shellfish become contaminated with accumulated toxin and are toxic when eaten. STX blocks nerve membrane sodium channels in nanomolar concentrations when applied externally. STX competes with tetrodotoxin (TTX) for binding to sodium channels. The mechanism of action on nerves is the same as that of TTX, although recovery from STX block occurs slightly faster than that after TTX block. The i.p. LD50 in mice is 10 μg/kg. Symptoms in humans within 30 min of ingestion include tingling and burning in face, lips, tongue, and eventually the whole body, parathesia followed by numbness, ataxia, general motor incoordination, confusion, and headache. Death due to respiratory paralysis occurs within 12 h. Treatment is restricted to symptoms. There is no antidote, and emesis is advisable. Artificial respiration is given if neces_x0002_sary. Prostigmine methylsulfate (1 mL of 1:2000 solution, i.v.) is helpful.
hazard_code
T+
safety_code
36/37/39-45

Chemie und Industrie

Anwendungen · 2 Einträge

BeschreibungFirst 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.

VerwendenSaxitoxin 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.

Ergänzende Hinweise

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

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