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Arsphenamine

HCID 8774
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
139-93-5
Standard SMILES
Cl.Cl.Nc1cc([As]=[As]c2ccc(O)c(N)c2)ccc1O
InChIKey
VLAXZGHHBIJLAD-UHFFFAOYSA-N
Molecular formula
C12H14As2Cl2N2O2
Average molar mass
439 g/mol
Monoisotopic mass
437.88642

Overview

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.

Names & identifiers

Preferred name
Arsphenamine
IUPAC
2-amino-4-(3-amino-4-hydroxyphenyl)arsanylidenearsanylphenol;dihydrochloride
English name
Arsphenamine
Molecular formula
C12H14As2Cl2N2O2
Molecular weight
439.00096

Names & synonyms

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
Show more names
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

Database identifiers

CAS
139-93-5
PubChem CID
8774
EC Number
205-386-6

Properties

Computed structural properties

Topological polar surface area
92.5 Ų
Hydrogen bond donors
6
Hydrogen bond acceptors
4
Rotatable bonds
2
Heavy atoms
20
Formal charge
0
Complexity
276

Physicochemical properties

Melting point
190 °C · 190°C (rough estimate)
form
solid
REACH Annex XVII Substances List
6 · 6,6'-dihydroxy-3,3'-diarsene-1,2-diyldianilinium dichloride (139-93-5)
FDA UNII
8 BAJ8WP85I · 8BAJ8WP85I
Toxicity
100 i.v · LD100 i.v. in rats: 140 mg/kg (Schamberg)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

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

Safety & protection

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)

Toxicology

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 item

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).

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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.

Uses & manufacturing

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

Suppliers1 total

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

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Exposure Routes
Oral (L2) ; inhalation (L2); dermal (L2)
Toxicity Summary · 1 item

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 item

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)

Safety data

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