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6,6'-Dihydroxy-3,3'-diarsen-1,2-diyldianiliniumdichlorid

Arsphenamine

HCID 8774
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Grundinformationen

CAS
139-93-5
Standard-SMILES
Cl.Cl.Nc1cc([As]=[As]c2ccc(O)c(N)c2)ccc1O
InChIKey
VLAXZGHHBIJLAD-UHFFFAOYSA-N
Summenformel
C12H14As2Cl2N2O2
Durchschnittliche Molmasse
439 g/mol
Monoisotopische Masse
437,88642

Überblick

4,4-arsenobis(2-aminophenol) dihydrochloride is an arsenical drug believed to be the first modern chemotherapeutic agent. It was used to treat syphilis and trypanosomiasis.

Namen und Bezeichner

Bevorzugter Name
Arsphenamine
IUPAC
2-amino-4-(3-amino-4-hydroxyphenyl)arsanylidenearsanylphenol;dihydrochloride
Lokaler Name
6,6'-Dihydroxy-3,3'-diarsen-1,2-diyldianiliniumdichlorid
Englischer Name
Arsphenamine
Summenformel
C12H14As2Cl2N2O2
Molmasse
439.00096

Namen und Synonyme

ARSPHENAMINESalvarsanArsenobenzol139-93-58BAJ8WP85ICHEBI:9016Phenol, 4,4'-(1,2-diarsenediyl)bis(2-amino)-, dihydrochloride4,4'-arsenobis(2-aminophenol) dihydrochlorideNSC-30974,4'-(diarsene-1,2-diyl)bis(2-aminophenol) dihydrochlorideArsenobenzol, SodiumRefChem:114216
Weitere Namen anzeigen
3,3'-Diamino-4,4'-Dihydroxyarsenobenzene4,4-ARSENOBIS(2-AMINOPHENOL)DIHYDROCHLORIDE6,6'-dihydroxy-3,3'-diarsene-1,2-diyldianilinium dichloride2-amino-4-(3-amino-4-hydroxyphenyl)arsanylidenearsanylphenol
2-amino-4-(3-amino-4-hydroxy-phenyl)arsanylidenearsanyl-phenol;dihydrochlorideArsabenzosolPhenarsenamineArsaminolDiarsenolEhrlich 606EparsenolKharsivan

Datenbank-Bezeichner

CAS
139-93-5
PubChem CID
8774

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
92,5 Ų
H-Brücken-Donoren
6
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
2
Schwere Atome
20
Formalladung
0
Komplexität
276

Physikochemische Eigenschaften

Schmelzpunkt
190 °C · 190°C (rough estimate)
Aggregatzustand
solid

Sicherheit und Regulatorisches

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

Gefahrenhinweise

Regulatory InformationRestricted substance: 6,6'-dihydroxy-3,3'-diarsene-1,2-diyldianilinium dichloride

Sicherheit und Schutzausrüstung

Minimum Risk LevelAcute Oral: 0.005 mg/kg/day (L134) Chronic Oral: 0.0003 mg/kg/day (L134) Chronic Inhalation: 0.01 mg/m3 (L134)

Toxikologische Informationen

TreatmentAggressive decontamination with gastric lavage is recommended if the patient has consumed a potentially life-threatening dose and if the patient is not vomiting (T36).
Health Effects · 1 Eintrag

Hypovolemia from capillary leakage (third-spacing of fluids) is a common, serious, early effect. Muscle cramps, facial edema, bronchitis, dyspnea, chest pain, dehydration, intense thirst, and fluid-electrolyte disturbances are also common following significant exposures. A garlic-like odor of the breath and feces may also occur. After absorption, arsenic may cause multi-organ failure by inhibiting sulfhydryl-containing enzymes. Encephalopathy, with headache, lethargy, mental confusion, hallucinations, emotional lability, memory loss and delirium may occur; seizures, stupor, convulsions, coma, and death may follow within 24 hours of a severe acute exposure. Dysrhythmias (particularly QTc prolongation and torsade de pointes), cardiomyopathy, ARDS, hepatitis, rhabdomyolysis, hemolysis, and renal failure may develop over several days. The sequence of chronic poisoning involves hyperpigmentation, and eczematoid and allergic dermatitis. muscle fasciculations; gross tremors; ataxia; incoordination; and mental confusion. Muscular weakness, limb tenderness and difficulty walking may follow. The final phase consists of peripheral sensory neuropathy of the hands and feet. That may be associated with a motor neuropathy as well (T36).

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Arsenic is absorbed mainly by inhalation or ingestion, as to a lesser extent, dermal exposure. It is then distributed throughout the body, where it is reduced into arsenite if necessary, then methylated into monomethylarsenic (MMA) and dimethylarsenic acid (DMA) by arsenite methyltransferase. Arsenic and its metabolites are primarily excreted in the urine. Arsenic is known to induce the metal-binding protein metallothionein, which decreases the toxic effects of arsenic and other metals by binding them and making them biologically inactive, as well as acting as an antioxidant. (L20)

MeSH Pharmacological ClassificationAgents used to treat infections with bacteria of the genus TREPONEMA. This includes SYPHILIS & YAWS.

Verwendung und Herstellung

Uses4,4-arsenobis(2-aminophenol) dihydrochloride was used to treat syphilis and trypanosomiasis.

Anbieter1 Anbieter

青岛海智微元生物科技有限公司18317699790 18317699790 · [email protected]

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EC Number
205-386-6
Exposure RoutesOral (L2) ; inhalation (L2); dermal (L2)
Toxicity Summary · 1 Eintrag

Arsenic and its metabolites disrupt ATP production through several mechanisms. At the level of the citric acid cycle, arsenic inhibits pyruvate dehydrogenase and by competing with phosphate it uncouples oxidative phosphorylation, thus inhibiting energy-linked reduction of NAD+, mitochondrial respiration, and ATP synthesis. Hydrogen peroxide production is also increased, which might form reactive oxygen species and oxidative stress. Arsenic's carcinogenicity is influenced by the arsenical binding of tubulin, which results in aneuploidy, polyploidy and mitotic arrests. The binding of other arsenic protein targets may also cause altered DNA repair enzyme activity, altered DNA methylation patterns and cell proliferation. (T1, A17)

Signs and Symptoms · 1 Eintrag

Initial signs and symptoms of arsenic ingestion include burning lips, throat constriction and dysphagia, followed by excruciating abdominal pain, hemorrhagic gastritis, gastroenteritis, severe nausea, projectile voting, profuse "rice water-like" diarrhea, with hypovolemia that may result in hypotension and an irregular pulse. The sequence of chronic poisoning involves weakness, anorexia, hepatomegaly, jaundice, and gastrointestinal complaints, followed by conjunctivitis, irritation of the throat and respiratory tract. ther effects of chronic exposure include conjunctivitis with irritation and lacrimation; hair, skin and nail changes; hyperkeratosis of feet and hands; and melanosis, with pigment spots in corneal and conjunctival epithelium. Peripheral nervous system symptoms may include numbness, burning, and tingling of the hands and feet; pain; paresthesias; tenderness (T36).

Carcinogen Classification3, not classifiable as to its carcinogenicity to humans. (L135)

Sicherheitsdaten

Toxizität
LD100 i.v. in rats: 140 mg/kg (Schamberg)