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カコジル酸

Dimethylarsinic Acid

HCID 2513
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
75-60-5
標準SMILES
C[As](C)(=O)O
InChIKey
OGGXGZAMXPVRFZ-UHFFFAOYSA-N
分子式
C2H7AsO2
平均分子量
138 g/mol
単同位体質量
137.966199

概要

Cacodylic Acid can cause cancer according to The Environmental Protection Agency (EPA).

名称と識別子

優先名称
Dimethylarsinic Acid
IUPAC
dimethylarsinic acid
現地名
カコジル酸
英語名
CACODYLIC ACID
分子式
C2H7AsO2
分子量
138

名称と別名

cacodylic acidDimethylarsinic acid75-60-5SilvisarPhytarArsanDIMETHYLARSENIC ACIDEraseAnsar 138Silvisar 510Arsinic acid, dimethyl-Phytar 560
名称をさらに表示
カコジル酸シルビサールアンサール138フィタールヒドロキシジメチルオキソひ素(V)ジメチルアルシン酸アルサンオキソヒドロキシジメチルヒ素(V)ジメチルヒドロキシアルシンオキシドヒドロキシジメチルアルシンオキシドジメチルアルシン酸水溶液 CRM7913‐Aカコジル酸, 98%DIMETHYLARSONIC ACIDAnsarSalvoANSAR(R)
MoncideSylvicorDilicAgent BlueAcide cacodyliqueAlkargenPhytar 138Acide dimethylarsinique

データベース識別子

CAS
75-60-5、917-76-0
PubChem CID
2513
DTXSID
DTXSID7020508
ChEMBL
CHEMBL1231644
ChEBI
CHEBI:48765
UNII
AJ2HL7EU8K
EC Number
200-883-4
Nikkaji
J2.395G

物性

構造計算による物性

極性表面積
37.3 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
0
重原子数
5
形式電荷
0
複雑度
62

実験および物理化学的性質

Chemical Classes · 2 件

Metals -> Arsenic Compounds, Organic

Carcinogens

PesticidesPesticide -> EPA IRIS
OdorOdorless
Densitygreater than 1.1 at 68 °F (est.) (USCG, 1999)
Color/Form · 4 件

Crystals from alcohol and ether

Colorless

TRICLINIC CRYSTALS

White; water solutions may be dyed blue

Solubility · 4 件

Very soluble (NTP, 1992)

Soluble in acetic acid

Soluble in ethanol; insoluble in diethyl ether

In water, 2X10+6 mg/l @ 25 °C.

CorrosivityAll formulations are mildly corrosive.
Boiling Point · 2 件

greater than 392 °F at 760 mmHg (NTP, 1992)

>200 °C

Decomposition · 2 件

When heated to decomposition it emits toxic fumes of /arsenics/.

Decomposed by powerful oxidizing or reducing agents.

Melting Point · 3 件

383 to 385 °F (NTP, 1992)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Danger

H301 (94.2%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P270, P271, P273, P301+P316, P304+P340, P316, P321, P330, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 52 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 4 件

Hazard Traits - Carcinogenicity; Cardiovascular Toxicity; Dermatotoxicity; Developmental Toxicity; Neurotoxicity; Other Toxicological Hazard Traits; Respiratory Toxicity

Restricted substance: Dimethylarsinic acid

Arsinic acid, dimethyl-: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Arsinic acid, dimethyl-: Environment tier I assessment
DOT LabelPoison
Fire Hazards · 2 件

Behavior in Fire: May form toxic oxides of arsenic when heated. (USCG, 1999)

· Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes.

Fire PotentialNonflammable
Health Hazards · 2 件

Chemical is essentially non-irritating in contact with skin or eyes. Ingestion causes arsenic poisoning, but symptoms are delayed. (USCG, 1999)

· Highly toxic, may be fatal if inhaled, ingested or absorbed through skin.

化学と産業

薬理情報

Biological Half-Life · 1 件

When administered to rats, cacodylic acid was rapidly absorbed from the lung with a half-time of 2.2 min. Peroral absorption half-time was 248 min. The half-time for clearance from the whole blood after iv, intratracheal and peroral administration as 92, 76 and 90 days, respectively. In pregnant rats cacodylic acid readily crossed the placenta. The small amount of carbon dioxide evolved indicated that only a small fraction of the dose was demethylated.

Metabolism/Metabolites · 6 件

... METAB OF CACODYLIC ACID IN BLACK VALENTINE BEANS /WAS STUDIED/. ANALYSIS OF THE EXTRACT REVEALED AS, PRESUMED TO BE CACODYLIC ACID /CA/, IN THE CHROMATOGRAM WHERE CA SHOULD HAVE BEEN. THE ABSENCE OF AS3+ & MSMA /MONOSODIUM METHANEARSONATE/ WAS DEMONSTRATED. IN SEPARATE EXPT, NO ARSINE ... DETECTED EVEN THOUGH SEVERE TOXICITY DEVELOPED ... . IN CONCLUSION, APPARENTLY NO DEGRADATION OF CACODYLIC ACID OCCURS IN PLANTS BASED ON LIMITED STUDIES. VARIOUS ORGANISMS, HOWEVER, ARE CAPABLE OF REDUCING CACODYLIC ACID TO DI- OR TRIMETHYLARSINE.

INGESTION OF WINE CONTAINING 50 UG AS3+ & 13 UG AS5+ INCR URINE LEVELS OF AS3+, AS5+, & DIMETHYLARSINIC ACID IN HUMAN. AS3+ & 5+ LEVELS WERE NORMAL AFTER 20 HR, BUT DIMETHYLARSINIC ACID LEVELS WERE NOT NORMAL UNTIL 85 HR LATER.

METHANOBACTERIUM SPECIES (STRAIN M.OH) IN AN INCUBATION MIXTURE UNDER ANAEROBIC CONDITIONS REDUCED CACODYLIC ACID TO DIMETHYLARSINE IN ABSENCE OF A C-1 DONOR.

AFTER IV ADMIN OF INORG ARSENIC TO DOGS, METABOLITE DIMETHYLARSINIC ACID APPEARED RAPIDLY IN ERYTHROCYTES, THEN IN PLASMA. WITHIN 6 HR MOST ARSENIC REMAINING WAS DIMETHYLARSINIC ACID. BOTH INORG ARSENIC & DIMETHYLARSINIC ACID WERE RAPIDLY EXCRETED IN URINE.

For more Metabolism/Metabolites (Complete) data for DIMETHYLARSENIC ACID (11 total), please visit the HSDB record page.

Arsenic and its metabolites are primarily excreted in the urine. (L2)

MeSH Pharmacological ClassificationPesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.
Absorption, Distribution and Excretion · 5 件

... ABSORPTION RATES ... FROM RAT SMALL INTESTINE ... WATER PARTITION COEFFICIENT SUGGEST THAT THESE CMPD /INCL CACODYLIC ACID/ MAY BE ABSORBED PREDOMINANTLY BY PASSIVE DIFFUSION.

関連反応

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化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

195 °C

195 °C

Vapor Pressure0.0000001 [mmHg]
Physical Description · 3 件

Cacodylic acid appears as a colorless, odorless crystalline solid. Melting point 195-196 °C. Toxic by ingestion and irritating to skin and eyes.

Hygroscopic solid; [Merck Index] Colorless odorless hygroscopic solid; [CAMEO] White crystalline solid; [MSDSonline]

Solid

物理化学的性質

融点
195 · 195-198 °C
沸点
200 °C · >200 °C
貯蔵温度
Store at RT.
溶解性
Methanol (Slightly), Water (Slightly)
外見
粉体・固形
酸解離定数(Pka)
1.57 · 1.57(at 25℃)
色
白い
水溶解度
水 (50mg/ml)、水 (25°C で 2000)、アルコール、酢酸に可溶。エーテルに不溶。
Merck
14 · 14,1604
BRN
1736965 · 1736965
安定性
水溶液は活性金属と激しく反応します。強酸化剤、強塩基とは相容れない。
InChI
1S/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5)
InChIKey
OGGXGZAMXPVRFZ-UHFFFAOYSA-N
SMILES
C[As](C)(O)=O
CAS データベース
75 · 75-60-5(CAS DataBase Reference)
EPAの化学物質情報
Cacodylic acid (75-60-5)

化学的性質

化学的特性white crystals or powder

Hazards Summary · 1 件

There is sufficient evidence in experimental animals for the carcinogenicity of dimethylarsenic acid. . . . Arsenic in drinking-water is carcinogenic to humans (Group 1). [IARC] A forestry worker injecting trees with silvicide containing cacodylic acid developed anorexia, nausea, and abdominal pain; He had elevated urine arsenic, and symptoms subsided after termination of exposure; [HSDB] Essentially non-irritating in contact with skin and eyes; [CHRIS] Not converted into inorganic arsenic in the body; [Nordberg, p. 590] Most excreted unchanged; [Rosenstock, p. 947]

DOT ID and Guide1572 151
Reactive GroupAcids, Carboxylic
RCRA Requirements · 1 件

U136; As stipulated in 40 CFR 261.33, when cacodylic acid, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

FIFRA Requirements · 4 件

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Cacodylic acid is found on List B. Case No: 2080; Pesticide type: Herbicide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): cacodylic acid; Data Call-in (DCI) Date(s): 06/07/91, 03/03/95, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

Tolerances are established for residues of the defoliant cacodylic acid (dimethylarsenic acid), expressed as As2O3, in or on raw agricultural commodities as follows: in or on cottonseed; in the kidney and liver of cattle; and in meat, fat, and meat byproducts (except kidney and liver) of cattle.

If material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. /Arsenical cmpd, liquid, NOS/

If material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. /Arsenical cmpd, solid, NOS/

OSHA StandardsPermissible Exposure Limit: Table Z-1 8-Hr Time Weighted Avg: 0.5 mg/cu m. /Arsenic, organic cmpd (as As)/

安全と保護具

Fire FightingExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Accidental Release Measures · 2 件

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.

First Aid · 2 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting Procedures · 1 件

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical or carbon dioxide. Keep run-off water out of water sources and sewers.

Storage Conditions · 2 件

KEEP WELL CLOSED.

DO NOT STORE NEAR FERTILIZERS, SEEDS, INSECTICIDES, /OR/ FUNGICIDES.

Nonfire Spill ResponseExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Disposal Methods · 4 件

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number D004, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U136, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

Storage: To convert the gas-cleaning residues obtained during the metallurgical processing of arsenic-containing ores into a portable and less water-soluble form, the metals are precipitated as hydroxides by using an excess of lime water and the arsenic is precipitated as calcium arsenate and calcium arsenite. This "arsenic sludge" is recycled, on the one hand, in order not to lose the valuable metals, and on the other, in order to reduce the problem of arsenic sludge disposal.

A poor candidate for incineration.

Preventive Measures · 2 件

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers.

Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment.

Isolation and Evacuation · 2 件

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

Immediate precautionary measure

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)
Allowable Tolerances · 2 件

Tolerances are established for residues of the defoliant cacodylic acid (dimethylarsenic acid), expressed as As2O3, in or on raw agricultural commodities as follows: 2.8 ppm in or on cottonseed; 1.4 ppm in the kidney and liver of cattle; and 0.7 ppm in meat, fat, and meat byproducts (except kidney and liver) of cattle.

Tolerances for total residues of combined arsenic (calculated as As) in food are established as follows: (a) In edible tissues & in eggs of chickens & turkeys: 0.5 ppm in uncooked muscle tissue; 2 ppm in uncooked edible by-products; & 0.5 ppm in eggs. (b) In edible tissues of swine: 2 ppm in uncooked liver & kidney; 0.5 ppm in uncooked muscle tissue & by-products other than liver & kidney. /Arsenic/

毒性情報

Body Burden · 1 件

Urinary excretion of arsenic has been directly correlated with worker exposure to dimethylarsenic acid(1,2). Blood levels of arsenic does not seem to be correlated with worker exposure to dimethylarsenic acid(1). Herbicide workers using poor handling and application techniques had urine arsenic levels as high as 1.8 ppm which corresponded to an exposure of at least 0.036 mg As/kg body wt/day(2); proper handling techniques and protective gear reduced exposure by an order of magnitude(2). In forestry workers, the urinary dimethylarsenic acid level during an 11 week observation period ranged from 24-172 ug/24 hr compared to a range of 26-73 ug/24 hr for non-exposed workers(1). Urine samples of humans were found to contain an average of 15 ug/l of dimethylarsenic acid which constituted an average of 66% of the total urinary excretion of arsenic(3).

Treatment · 2 件

Arsenic poisoning can be treated by chelation therapy, using chelating agents such as dimercaprol, EDTA or DMSA. Charcoal tablets may also be used for less severe cases. In addition, maintaining a diet high in sulfur helps eliminate arsenic from the body. (L20)

Aggressive decontamination with gastric lavage is recommended if the patient has consumed a potentially life-threatening dose and if the patient is not vomiting. Administer charcoal as a slurry (T36).

Interactions · 1 件

The influence of the methyltransferase inhibitor periodate oxidized adenosine on the metabolism of arsenite was investigated in mice and rabbits. Groups of male NMRI-mice and New Zealand rabbits were given intraperitoneal (ip) injections of 100 um periodate oxidized adenosine per kilogram (kg) 15 min before an intravenous injection of 0.04 mg/kg (74)As labeled arsenite or injections of (74)As labeled arsenite only. These animals were kept for 16 to 72 hr in metabolic cages designed to separate urine and feces. The urinary concn of dimethylarsenic acid (DMA), the major arsenic metabolite, was measured. Other groups of animals were injected with (74)As labeled arsenite and periodate oxidized adenosine or (74)As labeled arsenite only and killed between 1 to 72 hr. Blood, liver, kidney, lung, epididymis, and portions of skin were removed and measured for (74)As content in a gamma scintillation counter. Also, subcellular fractionation of liver tissue was performed and the concentration of (74)As was ascertained. The urinary excretion of (74)As was lower in mice and rabbits treated with periodate oxidized adenosine prior to arsenite administration than in animals treated with arsenite only. Injection of periodate oxidized adenosine prior to arsenite produced a 25 to 70% decrease in the production of dimethylarsenic acid, implying that S-adenosylmethionine was the methyl donor for the methylation of inorganic arsenic in vivo. The fecal excretion of (74)As was less than 4% of the dose, independent of treatment and animal species. Periodate oxidized adenosine treated animals had 2 to 6 times higher concentrations of (74)As in tissues than that in controls, the effect being first observed in liver tissues. The subcellular distribution of (74)As in liver of mice was not affected by periodate oxidized adenosine treatment in that 50% was found in the soluble cytoplasmic fraction and 20 to 30% was found in thenuclear fraction, independent of the treatment.

Health Effects · 2 件

Arsenic poisoning can lead to death from multi-system organ failure, probably from necrotic cell death, not apoptosis. Arsenic is also a known carcinogen, especially in skin, liver, bladder and lung cancers. (T1, L20)

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).

Environmental Fate · 5 件

TERRESTRIAL FATE: ... /CACODYLIC ACID/ REACTS /IN SOIL/ WITH TRIVALENT CHROMIUM, SILVER NITRATE & OTHER METAL IONS ... MAY FORM CYCLIC TYPES OF CMPD UNDER CERTAIN CONDITIONS.

TERRESTRIAL FATE: CHEM & BIOLOGICAL TRANSFORMATION OF ARSENICAL IN SOIL: IN SOIL CACODYLIC ACID MAY UNDERGO SALT FORMATION, ADSORPTION, ION EXCHANGE, DEMETHYLATION (OXIDATIVE), REDN, & METHYLATION (REDUCTIVE). /FROM TABLE/

TERRESTRIAL FATE: CACODYLIC ACID FORMED INSOL CMPD WITH SOIL.

TERRESTRIAL FATE: Dimethylarsenic acid is expected to have low mobility in soils(1-4). Organoarsenicals, such as dimethylarsinic acid, are adsorbed by clays soils(1). After rapid initial adsorption, changes occur which result in the redistribution of dimethylarsinic acid into a less soluble form associated with aluminum in the soil(1). The dimethylarsinic acid is fixed by iron and aluminum in the soil, although not as strongly as inorganic arsenate(1). Arsenic residues in browse and herbaceous vegetation in Douglas fir, ponderosa pine, and western larch forests in which trees were treated with cacodylic acid, sodium salt for thinning were relatively low(1). Large quantities of arsenic did not move from the forest floor into the soil, indicating that arsenic residues were tightly bound in the foliage(1). Only small amounts of arsenic were detected in streams in forests treated with cacodylic acid or its sodium salt(1). A pKa of 1.57(5) indicates that dimethylarsenic acid will ionize in water(SRC); therefore, dimethylarsenic acid is expected to be essentially nonvolatile from moist soil surfaces(SRC). Dimethylarsenic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.6X10-3 mm Hg(SRC), determined from a fragment constant method(6). Generation of C-14 labeled CO2 from C-14 labeled dimethylarsenic acid in a clay loam soil reached about 13% (over 98 days of incubation) in soil that had been adapted to dimethylarsenic acid, but was less than 2% in unadapted soil(7); the degradation was presumably microbial in nature(7). Incubation of dimethylarsenic acid in two Japanese soils for a period of six weeks resulted in 4-43% degradation(8); 0% degradation occurred in sterile controls(8). In another study in soil, 36% of dimethylarsenic acid was converted to a volatile organoarsenical compound and 47% to carbon dioxide and arsenate within a 24-week period(9).

For more Environmental Fate (Complete) data for DIMETHYLARSENIC ACID (6 total), please visit the HSDB record page.

Adverse EffectsIARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.
Exposure Routes · 2 件

Oral (L2) ; inhalation (L2); dermal (L2)

Oral (L2) ; inhalation (L2); dermal (L2)

Toxicity Summary · 2 件

Arsenic and its metabolites disrupt ATP production through different mechanisms. At the level of the citric acid cycle, arsenic inhibits the pyruvate dehydrogenase and uncouples the oxidative phosphorylation by competing with phosphate. This leads to inhibition of energy-linked reduction of NAD+, mitochondrial respiration, and ATP synthesis. Hydrogen peroxide production is increased, leading to oxidative stress due to the formation of reactive oxygen species. Arsenic's carginogenicity 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)

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)

Plant Concentrations · 1 件

THE DEFOLIANT FORMULATION BOLLS-EYE, WHICH CONTAINS CACODYLIC ACID & ITS SODIUM SALT, & INORGANIC ARSENIC WAS SPRAYED ON COTTON & RESIDUES WERE DETERMINED 2, 4, 8, & 25 DAYS AFTER APPLICATION. TOTAL ARSENIC, METHANEARSINIC ACID & TOTAL CACODYLICS & ARSENATE PEAKED IMMEDIATELY AFTER SPRAYING & DECLINED. BY DAY 8 THE LEVELS WERE NOT SIGNIFICANTLY ABOVE PRE-APPLICATION BACKGROUND LEVELS. COTTON SEED (TOTAL ARSENIC) LEVELS WERE LOW, SUGGESTING NO DETECTABLE TRANSPORT.

Signs and Symptoms · 2 件

Exposure to lower levels of arsenic can cause nausea and vomiting, decreased production of red and white blood cells, abnormal heart rhythm, damage to blood vessels, and a sensation of “pins and needles” in hands and feet. Breathing high levels of inorganic arsenic can provoque sore throat or irritated lungs. Arsenic also affects the brain, causing neurological disturbances such as headaches, confusion, and drowsiness. (A1)

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).

EPA IRIS InformationCacodylic acid
Soil Adsorption/Mobility · 1 件

Organoarsenicals, such as dimethylarsinic acid, are adsorbed by clays soils(1). After rapid initial adsorption, changes occur which result in the redistribution of dimethylarsinic acid into a less soluble form associated with aluminum in the soil(1). The dimethylarsinic acid are fixed by iron and aluminum in the soil, although not as strongly as inorganic arsenate(1). Leaching tests conducted in specially constructed boxes with clay, silt loam, and sandy soils noted strong adsorption to all soils, although a small degree of leaching did occur(2). The adsorption of dimethylarsenic acid to sediments and soil was found to depend on clay content, iron oxide content, and pH(3,4); adsorption increases with increasing clay and iron oxide content and with higher pH(3,4). Herbicidal applications of dimethylarsenic acid that were applied to forest floors in the northwestern US were found to be tightly bound, and did not leach in soil(5).

法規制情報

RCRA Requirements · 1 件

U136; As stipulated in 40 CFR 261.33, when cacodylic acid, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

FIFRA Requirements · 4 件

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Cacodylic acid is found on List B. Case No: 2080; Pesticide type: Herbicide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): cacodylic acid; Data Call-in (DCI) Date(s): 06/07/91, 03/03/95, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

Tolerances are established for residues of the defoliant cacodylic acid (dimethylarsenic acid), expressed as As2O3, in or on raw agricultural commodities as follows: in or on cottonseed; in the kidney and liver of cattle; and in meat, fat, and meat byproducts (except kidney and liver) of cattle.

If material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. /Arsenical cmpd, liquid, NOS/

If material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. /Arsenical cmpd, solid, NOS/

Atmospheric Standards · 4 件

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Dimethylarsenic acid is included on this list.

(a) The owner or operator of an existing glass melting furnace subject to the provisions of this subpart shall comply with either paragraph (a)(1) or (a)(2) of this section ... (1) Uncontrolled total arsenic emissions from the glass melting furnace shall be less than 2.5 Mg (2.7 ton) per year, or ... (2) Total arsenic emissions from glass melting furnace shall be conveyed to a control device and reduced by at least 85%. /Total arsenic/

(b) The owner or operator of a new or modified glass melting furnace subject to the provisions of this subpart shall comply with either paragraph (b)(1) or (b)(2) of this section ... (1) Uncontrolled total arsenic emissions from the glass melting furnace shall be less than 0.4 Mg (0.44 ton) per year, or ... (2) Total arsenic emissions from glass melting furnace shall be conveyed to a control device and reduced by at least 85%. /Total arsenic/

The owner or operator of each copper converter subject to the provisions of this subpart shall reduce inorganic arsenic emissions to the atmosphere by meeting the following design, equipment, work practice, and operational requirements: (1) Install, operate, and maintain a secondary hood system on each copper converter. Each secondary hood system shall consist of a hood enclosure, air curtain fan(s), exhaust system fan(s), and ductwork that conveys the captured emission to a control device ... (2) Optimize the capture of secondary inorganic arsenic emission by operating the copper converter and secondary hood systems at all times ... . /Inorganic arsenic/

CERCLA Reportable Quantities · 1 件

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1 lb or 0.454 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Clean Water Act Requirements · 3 件

Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Arsenic & cmpd/

For the maximum protection of human health from the potential carcinogenic effects due to exposure of arsenic through ingestion of contaminated water & contaminated aquatic organisms, the ambient water concn should be zero based on the nonthreshold assumption for this chemical. However, zero level may not be attainable at the present time. Therefore, the levels which may result in incremental increase of cancer risk over the lifetime are estimated at 1X10-5, 1X10-6, & 1X10-7. The corresponding criteria are 22 ng/l, 2.2 ng/l, & .22 ng/l, respectively .... For consumption of aquatic organisms only, excluding consumption of water, the levels are 175 ng/ml, 17.5 ng/l, & 1.75 ng/l, respectively. /Arsenic/

D004; A solid waste containing arsenic may or may not become characterized as a hazardous waste when subjected to the Toxicity Characteristic Leaching Procedure listed in 40 CFR 261.24, and if so characterized, must be managed as a hazardous waste.

State Drinking Water Guidelines · 2 件

(AZ) ARIZONA 10 ug/L /Arsenic/

(CT) CONNECTICUT 10 ug/l /Arsenic/

Federal Drinking Water Standards10 ug/l /Arsenic/

安全データ

F
3-10
wgk
3
tsca
TSCA listed
rtecs
CH7525000
ridadr
UN 1572
毒性
LD50 orally in rats: 1350 mg/kg (Bailey, White)
hs_code
29310099
risk_code
23/25-50/53
化審法
(2)-3432
安衛法
特化則 特定化学物質(管理第2類)
hazard_code
T,N
safety_code
20/21-28-45-60-61
hazard_class
6.1
packing_group
II
毒劇物取締法
毒物
Hazard Classifications
Acute Tox. 3 InhalationAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Carc. 1B
ストレージクラス
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
有毒物質データの
75-60-5(Hazardous Substances Data)

IN 5 HEALTHY FOREST WORKERS EXPOSED TO CACODYLIC ACID DURING 2 MO PERIOD, URINARY ARSENIC WAS USED AS INDEX OF EXPOSURE.

... ROOT ABSORPTION OF THE MONOSODIUM SALT OF METHANEARSONIC ACID (MSMA), CACODYLIC ACID, ARSENATE, & ARSENITE FROM NUTRIENT SOLN (1X10-4 M) /WAS STUDIED/. THE ORDER OF CONCN IN ROOTS WAS ARSENATE /HIGHEST, THEN/ ARSENITE, METHANEARSONIC ACID, CACODYLIC ACID. HOWEVER ... IF THE RATIO OF ARSENICAL CONCN IN TOPS TO THAT IN THE ROOTS WAS A MEASURE OF TRANSPORT, CACODYLIC ACID WAS TRANSPORTED TO THE TOPS 5 TO 10 TIMES MORE RAPIDLY THAN METHANEARSONIC ACID, ARSENITE, OR ARSENATE. TOXICITY OF ARSENICALS WAS DIRECTLY PROPORTIONAL TO ROOT CONCN.

CACODYLIC ACID HAS ERYTHROCYTE AFFINITIES AS FOLLOWS: RAT HIGHEST, THEN RABBIT, THEN HUMAN.

For more Absorption, Distribution and Excretion (Complete) data for DIMETHYLARSENIC ACID (12 total), please visit the HSDB record page.

用途と製造

Uses · 6 件

Used as a herbicide; [Sullivan, p. 981] Used as a drug (dermatological and veterinarian); [Merck Index] Used as a preharvest desiccant, a soil sterilant, a chemical warfare agent, a timber thinning defoliant, and a sugarcane ripener; [HSDB] Used as a defoliant and herbicide registered to control weeds under non-bearing citrus trees, around buildings, and for lawn renovation; [Reference #1]

Farming (Pesticides) [Category: Industry]

For Dimethylarsenic Acid (USEPA/OPP Pesticide Code: 012501) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

PREHARVEST DESSICANT

Herbicide; soil sterilant; chemical warfare; timber thinning.

Cacodylic acid is a contact herbicide which defoliates or desiccates a large variety of plants.

ImpuritiesDimethylarsinic acid is available as a technical grade, containing 65% active ingredient and the following possible impurities: sodium chloride, sodium sulfate, methylarsonic acid and arsenic acid.
U.S. Production · 2 件

(1978) 1.27X10+9 G

(1981) PROBABLY GREATER THAN 2.27X10+6 G

Consumption PatternsCOTTON USES, 25%; INDUSTRIAL/COMMERCIAL USES-EG, WEED CONTROL ON UTILITY & RAILROAD COMPANY RIGHTS-OF-WAY, 75% (1978)
Methods of Manufacturing · 4 件

ALKYLATION OF DISODIUM METHANEARSONATE WITH METHYL CHLORIDE FOLLOWED BY ADDITION OF HYDROCHLORIC ACID.

MOST CACODYLIC ACID IS MADE COMMERCIALLY BY REACTING THE MONOSODIUM SALT OF METHANEARSONIC ACID WITH METHYL CHLORIDE @ 5 PSI & 80 °C ... .

By distilling a mixture of arsenic trioxide and potassium acetate, and oxidizing the resulting product with mercuric oxide.

... Prepared commercially by the alkylation of methanearsonic acid, disodium salt with methyl chloride, followed by addition of hydrochloric acid ... .

Formulations/Preparations · 5 件

USEPA/OPP Pesticide Code 012501; Trade Names: Silvisar 510; Arsan; Phytar 560, component of (with 012502); Rad-E-Cate 35.

PHYTAR 560 (2.48 LB/GAL CACODYLIC ACID EQUIVALENT AS SODIUM SALT); PHYTAR 138 (65% CADODYLIC ACID); PHYTAR 160 (3.25 LB/GAL CACODYLIC ACID EQUIV).

Fisher purified cacodylic acid contains 95.5% cacodylic acid.

Concentrated solution

For more Formulations/Preparations (Complete) data for DIMETHYLARSENIC ACID (9 total), please visit the HSDB record page.

Household ProductsInformation on 2 consumer products that contain Dimethylarsinic acid in the following categories is provided:
General Manufacturing Information · 3 件

Arsinic acid, As,As-dimethyl-: ACTIVE

CACODYLIC ACID WAS KNOWN PRIOR TO 1900 & WAS USED MEDICALLY. ... CACODYLIC ACID PROVED TO BE A BETTER SOIL STERILIZER THAN METHANEARSONIC ACID, SODIUM ARSENITE, & SEVERAL OTHER ... & /WITH/ DALAPON SPRAYS CONTROLLED ORCHARDGRASS & KENTUCKY BLUEGRASS.

Used as a directed spray, postemergence. Rates: 3 to 10 lb/acre. Mix with water plus 2 qt surfactant per 100 gal of solution and apply at 40 gallons per acre. All formulations are 100% water soluble.

応用分野 · 4 件

解説dimethylarsinic acid.C2H7O2As(138.00).カコジル酸は,酸化カコジルを過酸化水素などで酸化すると得られる.潮解性の固体.融点195~196 ℃.エタノールに易溶,水に可溶.両性化合物で,金属水酸化物,ハロゲン化水素とも塩をつくる.毒性が強い.森北出版「化学辞典(第2版)

用途薬理研究用、カコジル酸塩合成原料。

使用Cacodylic acid is used for dermatologic treatment in cronic eczema, anemia and as a tonic.

一般的な説明A colorless, odorless crystalline solid. Melting point 195-196°C. Toxic by ingestion and irritating to skin and eyes.

調製方法

純化方法Recrystallise it from warm EtOH (3mL/g) by cooling and filtering. Dry it in a vacuum desiccator over CaCl2. It has also been recrystallised twice from propan-2-ol. [Koller & Hawkridge J Am Chem Soc 107 7412 1985, Beilstein 4 IV 3681.]

上流・下流製品情報

上流原料

二酸化イオウメチルアルソン酸二ナトリウム塩酸クロロメタン

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補足説明

定義ChEBI: The organoarsenic compound that is arsenic acid substituted on the central arsenic atom with two methyl groups.