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SAXITOXIN

SAXITOXIN Struktur
35523-89-8
CAS-Nr.
35523-89-8
Englisch Name:
SAXITOXIN
Synonyma:
C13757;SAXITOXIN;Mussel poison;Gonyaulax toxin;SAXITOXIN DIACETATE SALT;gonyaulaxcatenellapoison;saxidomusgiganteuspoison;mytiluscalifornianuspoison;Saxitoxin in acetic acid (determination in mussel);hyl)-3a,4,8,9-tetrahydro-,(3as-(3a-alpha,4-alpha,10ar*))
CBNumber:
CB5241547
Summenformel:
C10H17N7O4
Molgewicht:
299.29
MOL-Datei:
35523-89-8.mol

SAXITOXIN Eigenschaften

Siedepunkt:
440.62°C (rough estimate)
Dichte
1.3010 (rough estimate)
Brechungsindex
1.6400 (estimate)
storage temp. 
−20°C
pka
13.32±0.50(Predicted)
Optische Aktivit?t
+13320 (H2O)
EPA chemische Informationen
Saxitoxin (35523-89-8)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher T+
R-S?tze: 26/27/28
S-S?tze: 36/37/39-45
RIDADR  UN 3462 6.1/PG 1
WGK Germany  3
Toxizit?t 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.
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H300 Lebensgefahr bei Verschlucken. Akute Toxizit?t oral Kategorie 2 Achtung GHS hazard pictogramssrc="/GHS06.jpg" width="20" height="20" /> P264, P270, P301+P310, P321, P330,P405, P501
H310 Lebensgefahr bei Hautkontakt. Acute toxicity,dermal Category 1, 2 Achtung GHS hazard pictogramssrc="/GHS06.jpg" width="20" height="20" /> P262, P264, P270, P280, P302+P350,P310, P322, P361, P363, P405, P501
H330 Lebensgefahr bei Einatmen. Akute Toxizit?t inhalativ Kategorie 1 Achtung GHS hazard pictogramssrc="/GHS06.jpg" width="20" height="20" /> P260, P271, P284, P304+P340, P310,P320, P403+P233, P405, P501
Sicherheit
P260 Dampf/Aerosol/Nebel nicht einatmen.
P262 Nicht in die Augen, auf die Haut oder auf die Kleidung gelangen lassen.
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P271 Nur im Freien oder in gut belüfteten R?umen verwenden.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P284 Atemschutz tragen.
P302+P350 BEI KONTAKT MIT DER HAUT: Behutsam mit viel Wasser und Seife waschen.
P304+P340 BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen.
P310 Sofort GIFTINFORMATIONSZENTRUM/Arzt/ anrufen.
P320 Besondere Behandlung dringend erforderlich
P322 Gezielte Ma?nahmen
P361 Alle kontaminierten Kleidungsstücke sofort ausziehen.
P363 Kontaminierte Kleidung vor erneutem Tragen waschen.
P405 Unter Verschluss aufbewahren.
P501 Inhalt/Beh?lter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

SAXITOXIN Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R26/27/28:Sehr giftig beim Einatmen, Verschlucken und Berührung mit der Haut.

S-S?tze Betriebsanweisung:

S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).

Beschreibung

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.

Chemische Eigenschaften

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

Verwenden

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 ofthis compound 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/kg
LD50 value oral (mice): 0.26 mg/kg
Intravenous 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.

Einzelnachweise

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

SAXITOXIN Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


  • 1h,10h-pyrrolo(1,2-c)purine-10,10-diol,2,6-diamino-4-(((amino-carbonyl)oxy)met
  • gonyaulaxcatenellapoison
  • hyl)-3a,4,8,9-tetrahydro-,(3as-(3a-alpha,4-alpha,10ar*))
  • mytiluscalifornianuspoison
  • saxidomusgiganteuspoison
  • [3AS-(3AALPHA,4A,10AR*)]-2,6-DIAMINO-4-[[(AMINOCARBONYL)OXY]METHYL]-3A,4,8,9-TETRAHYDRO-1H,10H-PYRROLO[1,2-C]PURINE-10,10-DIOL
  • SAXITOXIN
  • SAXITOXIN DIACETATE SALT
  • 1H,10H-Pyrrolo1,2-cpurine-10,10-diol, 2,6-diamino-4-(aminocarbonyl)oxymethyl-3a,4,8,9-tetrahydro-, (3aS,4R,10aS)-
  • Saxitoxin in acetic acid (determination in mussel)
  • (3aS,10aS)-2,6-Diamino-4α-(carbamoyloxymethyl)-3aα,4,8,9-tetrahydro-1H,10H-pyrrolo[1,2-c]purine-10,10-diol
  • (3aS,10aS)-2,6-Diamino-4α-[[(aminocarbonyl)oxy]methyl]-3aα,4,8,9-tetrahydro-1H,10H-pyrrolo[1,2-c]purine-10,10-diol
  • Gonyaulax toxin
  • Mussel poison
  • C13757
  • 35523-89-8
  • C14H25N7O8
  • C10H17N7O4
  • Amines
  • Chiral Reagents
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
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