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6,6'-디히드록시-3,3'-디아세네-1,2-디일디아닐리늄디클로라이드

Arsphenamine

HCID 8774
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
139-93-5
표준 SMILES
Cl.Cl.Nc1cc([As]=[As]c2ccc(O)c(N)c2)ccc1O
InChIKey
VLAXZGHHBIJLAD-UHFFFAOYSA-N
분자식
C12H14As2Cl2N2O2
평균 분자량
439 g/mol
단동위원소 질량
437.88642

개요

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.

이름 및 식별자

우선 이름
Arsphenamine
IUPAC
2-amino-4-(3-amino-4-hydroxyphenyl)arsanylidenearsanylphenol;dihydrochloride
현지명
6,6'-디히드록시-3,3'-디아세네-1,2-디일디아닐리늄디클로라이드
영어명
Arsphenamine
분자식
C12H14As2Cl2N2O2
분자량
439.00096

이름 및 동의어

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
이름 더 보기
6,6'-디히드록시-3,3'-디아세네-1,2-디일디아닐리늄디클로라이드3,3'-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

데이터베이스 식별자

CAS
139-93-5
PubChem CID
8774

물성

구조 계산 물성

극성 표면적
92.5 Ų
수소 결합 공여자 수
6
수소 결합 수용자 수
4
회전 가능 결합 수
2
무거운 원자 수
20
형식 전하
0
복잡도
276

물리화학적 성질

녹는점
190 °C · 190°C (rough estimate)
물리적 상태
고체

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

유해성 정보

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

안전 및 보호

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)

독성 정보

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 · 1건

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).

Exposure RoutesOral (L2) ; inhalation (L2); dermal (L2)

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

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.

용도 및 제조

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

공급사1 곳

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

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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
EC Number
205-386-6
Toxicity Summary · 1건

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 · 1건

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)

안전 데이터

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