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Malaoxon

Malaoxon structure

Malaoxon 

structure
  • CAS No:

    1634-78-2

  • Formula:

    C10H19O7PS

  • Chemical Name:

    Malaoxon

  • Synonyms:

    Butanedioic acid,2-[(dimethoxyphosphinyl)thio]-,1,4-diethyl ester;Succinic acid,mercapto-,diethyl ester,S-ester with O,O-dimethyl phosphorothioate;Butanedioic acid,[(dimethoxyphosphinyl)thio]-,diethyl ester;Succinic acid,mercapto-,diethyl ester,dimethyl phosphate;Phosphorothioic acid,O,O-dimethyl ester,S-ester with diethyl mercaptosuccinate;Diethyl mercaptosuccinate S-ester with O,O-dimethyl phosphorothioate;Liromat;Malaoxon;Malathion-O-analog;O,O-Dimethyl S-1,2-bis(ethoxycarbonyl)ethyl phosphorothioate;Malaoxone;Oxycarbophos;Diethyl [(dimethoxyphosphino)thio]butanedioate;Malathion oxon;Maloxon;DL-Malaoxon;Malaoxan;35805-20-0

  • Categories:

    Agrochemicals  >  Insecticides

Description

Colorless viscous oily liquid with a weak unpleasant odor.


Malaoxon is a colorless viscous oily liquid with a weak unpleasant odor. (NTP, 1992)


Malaoxon is a colorless viscous oily liquid with a weak unpleasant odor. (NTP, 1992)|Diethyl 2-[(dimethoxyphosphoryl)thio]succinate is a diester that is diethyl succinate in which position 2 is substituted by a (dimethoxyphosphoryl)thio group. It is a diester, an ethyl ester and an organic thiophosphate.

Malaoxon Basic Attributes

314.29

314.29

204-497-7

3018

DTXSID9020790

Characteristics

113

2.07

1.235 at 70° F (NTP, 1992)

<20 °C

114 °C

-18 °C

1.4696 (589.3 nm 25℃)

5 to 10 mg/mL at 72° F (NTP, 1992)

0-6°C

9.8e-06 mm Hg at 68° F ; 0.00032 mm Hg at 122° F (NTP, 1992)

Oral-Rat LD50: 158 mg/kg; Oral-Mouse LD50: 215 mg/kg

Combustion produces toxic phosphorus oxide and sulfur oxide gas

161.98 Ų [M+H]+

Oxygen analog of malathion

This chemical may be sensitive to prolonged exposure to air. (NTP, 1992). Slightly water soluble.

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

A thioorganophosphate, ester. Organophosphates are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Safety Information

III

6.1(b)

3018

3

11-38-50/53-65-67-24/25-43-22

60-61-62-45-36/37/39-46-37-24

WM8410000

F,Xn,N,T

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Missing Phrase - N15.00950417-P262-P280-P302 + P352 + P310-P361 + P364

H301-H310

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|All organic pesticides, whether of botanical or synthetic origin, can be destroyed by incineration. /Organic pesticides/|Manufacturers or formulators of very large amounts of pesticides may find it advantageous to build incinerators adequate to destroy all organic pesticides and equipped with scrubbers to remove acid wastes. /Organic pesticides/

DHEW/NCI; Bioassay of Malaoxon for Possible Carcinogenicity p.v (1979) Technical Rpt Series No. 135 DHEW Pub No. (NIH) 79-1390

This chemical is probably combustible. (NTP, 1992)

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P262, P264, P270, P280, P301+P310, P302+P350, P310, P321, P322, P330, P361, P363, P405, and P501|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere, and store it at refrigerated temperatures. (NTP, 1992)

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: When working with this chemical, wear a NIOSH-approved full face chemical cartridge respirator equipped with the appropriate organic vapor cartridges. If that is not available, a half face respirator similarly equipped plus airtight goggles can be substituted. However, please note that half face respirators provide a substantially lower level of protection than do full face respirators. (NTP, 1992)|Respiratory protection (supplied-air respirator with full facepiece or self-contained breathing apparatus) should be available where these compounds are manufactured or used and should be worn in case of emergency and overexposure. /Phosphorus compounds/|WORKERS HANDLING AND APPLYING ORGANOPHOSPHATE PESTICIDES (OPP) MUST ... BE GIVEN PERSONAL PROTECTIVE EQUIPMENT COMPRISING OVERALLS MADE OF A TIGHT FABRIC OR POLYVINYL CHLORIDE, GLOVES, AND RUBBER BOOTS. THEY MUST WEAR A RESPIRATOR WITH AN ACTIVATED-CARBON GAS FILTER CARTRIDGE AFFORDING PROTECTION FOR A DETERMINED NUMBER OF WORKING HOURS. THE EYES SHOULD BE PROTECTED BY GOGGLES. THE SIGNALMEN FOR AERIAL DUSTING OPERATIONS SHOULD BE EQUIPPED WITH A HAT AND CAPE MADE OF POLYVINYL CHLORIDE OR A FABRIC IMPREGNATED WITH A WATER REPELLENT. /PESTICIDES, ORGANOPHOSPHORUS/

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, liquid, NOS/|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 "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, solid, NOS/

In some situations where personnel may become accidently contaminated ... it is necessary to provide shower bath in addition to the usual washing facilities. Special arrangements for cleaning clothing & overalls may be necessary ... /Pesticides/|Special aircraft should preferably be used for spraying or dusting toxic organophosphorus pesticides. ... aerial spraying or dusting gives rise to clouds which spread over larger surfaces than clouds produced by ground application. Aerial spraying should therefore be carried out on windless days only. Residential areas, water supply sources, etc must be avoided. ... When aircraft approaches, signalmen /guiding the aircraft/ should leave the windward side. ... The local population should be informed about the site & time of aerial pesticide treatment. Access of unauthorized persons & especially children to the area to be treated must be ... forbidden. Warning signs should be placed at the limits of the area. Ground spraying must be carried out with compressed-air spraying equipment towed by tractors with closed cabs. /Organophosphorus pesticides/|Small packages of pesticides are preferable for individual application in order to limit the quantities to be weighed & metered. A special vessel with long stirring rod for dilution & suspension of the poison must be available in order to reduce manual handling to a minimum. The strict observance of hygiene rules--no smoking & no food intake during work. Thorough washing with soap after work, changing protective clothing before going home--is of utmost importance. /Organophosphorus pesticides/|Containers ... should be cleaned with a suspension of bleaching powder in water or with other alkaline soln after soaking for 24 hr and then be rinsed with hot water. /Organophosphorus pesticides/|For more Preventive Measures (Complete) data for MALAOXON (10 total), please visit the HSDB record page.

Toxicity

highly toxic

TOXICITY OF MALATHION IS POTENTIATED BY O-ETHYL O-PARA-NITROPHENYL PHENYLPHOSPHOROTHIOATE, TRI-O-TOLYLPHOSPHATE, & SOME OTHER ORGANOPHOSPHORUS CMPD. IT IS POSTULATED THAT THIS POTENTIATION RESULTS FROM THE INHIBITION OF CARBOXYLESTERASE OR ALIESTERASE ENZYMES RESPONSIBLE FOR DEGRADATION OF MALATHION IN MAMMALS. PRESUMABLY, THIS MECHANISM WOULD LEAD TO INCR FORMATION OF MALAOXON, THE ACTIVATION PRODUCT, BECAUSE THE ENZYMES RESPONSIBLE FOR DEGRADATION OF MALAOXON WOULD BE INHIBITED.|Pretreatment of rats with chloramphenicol (100 mg/kg, ip) 30 min prior to a single oral LD50 dose of malathion at 340 mg/kg completely protected against malathion induced inhibition of cholinesterase. It appears that the inhibition of malathion toxicity by chloramphenicol pretreatment is attributable to inhibition by chloramphenicol of the metabolic activation of malathion to malaoxon.|Some phenothiazines may antagonize & some may potentiate the toxic anticholinesterase effects of ... /organophosphorus insecticides/. /Organophosphate cholinesterase inhibitors/|In long term therapy, adrenocorticoids antagonize the antiglaucoma effects of anticholinesterases (incr ocular pressure). ... Anticholinergics antagonize the miotic (antiglaucoma) & other muscarinic effects of anticholinesterases on the autonomic & central nervous systems. Tricyclic antidepressants (anticholinergic effects) antagonize the antiglaucoma (miotic) effects of anticholinesterases in glaucoma. ... Antihistamines with anticholinergic effects antagonize the miotic (antiglaucoma) & CNS effects of anticholinesterases. Anticholinesterases potentiate tranquilizing & behavioral changes induced by antihistamines. The actions of anticholinesterase agents on autonomic effector cells, & to some extent those on CNS, are antagonized by atropine, an antidote of choice. Barbiturates are potentiated by anticholinesterases. ... Dexpanthenol potentiates the effects of anticholinesterases. Fluorophosphate insecticides potentiate the effects of other anticholinesterases. /Anticholinesterases/|For more Interactions (Complete) data for MALAOXON (6 total), please visit the HSDB record page.

LD50 Rat oral 158 mg/kg|LD50 Rat ip 17,500 ug/kg

... Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Negative; Female Mice: Negative.

Young persons under 18 yr, expectant or nursing mothers, /alcoholics/, or persons for whom work with toxic chemicals is contraindicated on account of their state of health /are at elevated risk from the toxic effects of organophosphorus pesticides. Those individuals with/ organic diseases of the CNS, mental disorders & epilepsy, pronounced endocrine & vegetative disorders, pulmonary tuberculosis, bronchial asthma, chronic respiratory diseases, cardiovascular diseases and circulatory disorders, gastrointestinal diseases (peptic ulcer), gastroenterocolitis, diseases of the liver & kidneys, eye diseases (chronic conjunctivitis and keratitis) /are at elevated risk from exposure/. /Organophosphorus pesticides/|Those individuals who are exposed to organophosphorus pesticides with pre-existing/ organic diseases of the central nervous system, mental disorders & epilepsy, pronounced endocrine & vegetative disorders, pulmonary tuberculosis, bronchial asthma, chronic respiratory diseases, cardiovascular diseases & circulatory disorders, gastrointestinal diseases (peptic ulcer), gastroenterocolitis, diseases of liver & kidneys, eye diseases (chronic conjunctivitis & keratitis) /are at elevated risk from exposure/. The blood cholinesterase activity must be determined before work starts. In the event of prolonged work periods, this activity should be determined at intervals of 3-4 days. Persons exhibiting a fall in cholinesterase activity of 25% or more must be transferred to other work where they are not exposed to organophosphorus pesticides until this activity is completely restored. Persons with initial signs of indisposition should cease work with pesticides. /Organophosphorus pesticides/

CRUDE OR TECHNICAL GRADE MALATHION MAY CONTAIN MALAOXON AS IMPURITY ...|Malathion's production and use as an insecticide may result in the release of malaoxon to the environment as malaoxon is the primary oxidation product of malathion(2) produced via ozone or other possible oxidants such as oxides of nitrogen(3). Malathion's use in the control of animal ectoparasites, flies, household insects, human head and body lice and mosquitoes(1) may result in malaoxon's release to the environment.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 46(SRC), determined from an estimated log Kow of 0.52(2,SRC) and a regression-derived equation(3), indicates that malaoxon is expected to have very high mobility in soil(SRC). Volatilization of malaoxon from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.8X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Malaoxon is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1X10-4 mm Hg(5), determined from a fragment constant method(5). If released to soil, malaoxon can be expected to undergo hydrolysis. The half-lives for hydrolysis in sterile soil have been determined to be 7.5, 5.1, and 3.9 days at a pH of 6.2, 7.2, and 8.2, respectively(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 46(SRC), determined from an estimated log Kow of 0.52(2,SRC) and a regression-derived equation(3), indicates that malaoxon is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.8X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from an estimated log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), malaoxon, which has an estimated vapor pressure of 1X10-4 mm Hg at 25 °C(2), is expected to exist solely in the vapor phase. Vapor-phase malaoxon is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 16 hr(SRC), calculated from its estimated rate constant of 24X10-12 cu cm/molecule-sec at 25 °C determined using a structure estimation method(3).

The rate constant for the vapor-phase reaction of malaoxon with photochemically-produced hydroxyl radicals has been estimated as 24X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 49 hr at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 6X10-2 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 4 years and 130 days at pH values of 7 and 8, respectively(2). Malaoxon is expected to undergo hydrolysis in the environment. The half-lives for hydrolysis of malaoxon in sterile soil have been determined to be 7.5, 5.1, and 3.9 days at a pH of 6.2, 7.2, and 8.2, respectively(3). Malathion was shown to produce small amounts of malaoxon in very slow solid phase photolysis under both natural sunlight and laboratory UV photolysis(4). The half-life for hydrolysis of malaoxon at 70 °C in 20% ethanol/water at pH 6 has been reported as 7 hr(5). Hydrolysis of organophosphorus pesticides has been found to be more rapid under basic conditions than under acidic conditions(3,6). The half-life for the gas phase reaction of malaoxon with photochemically produced hydroxyl radicals in the atmosphere can be estimated at 10 hours(7).

1.12|An estimated BCF of 3.2 was calculated for malaoxon(SRC), using an estimated log Kow of 0.52(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

The Koc of malaoxon is estimated as 46(SRC), using an estimated log Kow of 0.52(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that malaoxon is expected to have very high mobility in soil.

The Henry's Law constant for malaoxon is estimated as 1.8X10-12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that malaoxon is expected to be essentially nonvolatile from water surfaces(2). Malaoxon's Henry's Law constant(1) indicates that volatilization from moist soil surfaces will not occur(SRC). Malaoxon is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1X10-4 mm Hg(SRC), determined from a fragment constant method(3).

Exposure to malaoxon may occur through the use of malathion as an insecticide, or via inhalation by working close to the areas where malathion has been applied. The general population may be exposed to malaoxon during the use of malathion for the control of household insects, human head and body lice, or mosquitoes(1).

Drug Information

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)

Eight autopsy samples from an individual who had ingested a large amt of malathion were analyzed for 4 components: intact pesticide, malaoxon, malathion monocarboxylic acid (MCA), and malathion dicarboxylic acid (DCA). Malathion was present in all samples except liver. The highest concn were found in the gastric content (8621 ppm) and adipose tissue (76.4 ppm). Malaoxon was identified in some tissues at very low levels; a significant amt was found only in fat (8.2 ppm). The MCA and DCA were detected in all tissues. The former was found in greater abundance: 221 ppm in bile, 106 ppm in kidney, and 103 ppm in the gastric content.|The fate of malaoxon was studied in a susceptible and a resistant strain of housefly following topical application. Sublethal doses were used: 160 pmol for the S-strain (0.17 times LD50) and 1570 pmol for the R-strain (0.1 times LD50). The penetration rates are dose dependent and semilog plots of the external amt versus time show that these rates are not proportional to this external amt. Internal concn of malaoxon rapidly increase following administration, reach max values between 30 min and 2 hr (depending on dose), and then slowly decrease. The rate of metabolic degradation is highest in the early stage of the intoxication process. A 3 compartment pharmacokinetic model is postulated to explain the experimental data quantitatively. The 1st compartment represents external malaoxon, the other 2 represent internal parent cmpd. Statistical analysis shows that the penetration rate is better described with a sum of 2 exponentials rather than with a single exponential decay. In the model, degradation occurs in the 1st internal compartment and is assumed to be 1st order. Malaoxon is distributed between the 2 internal compartments slowly with 1st order kinetics. Parameter estimations with curve fitting procedures for the internal processes (degradation and exchange) shows that there is not one set of parameter values that can be used for both strains simultaneously. Interstrain differences in degradation capacity studies showed that in vitro the R-strain had a 4-fold higher oxidative breakdown rate. Taking this difference into account, it is possible to explain the 2 sets of data with one kinetic model, although other alternatives cannot be excluded.|... 7% OF TOTAL METABOLITES IN FECES /FROM COW GIVEN MALATHION ORALLY/ WAS CHLOROFORM SOLUBLE, OF WHICH 855 WAS MALATHION & 12% MALAOXON. THE MILK CONTAINED A SMALL AMOUNT OF MALATHION METABOLITES (9.2% OF TOTAL DOSE AFTER 7 DAYS); OF THIS, ONLY 29% WAS EXTRACTABLE OUT OF MILK AND PARTITIONED IN FAVOR OF WATER OVER BENZENE, INDICATING THE ABSENCE OF EITHER MALATHION OR MALAOXON.|Most organophosphate compounds are ... absorbed from skin, conjunctiva, gastrointestinal tract, & lung. /Organophosphate compounds/|For more Absorption, Distribution and Excretion (Complete) data for MALAOXON (10 total), please visit the HSDB record page.

ALTHOUGH NO METABOLITE FOR MALAOXON WITH HYDROLYZED CARBOETHOXY GROUP HAS BEEN IDENTIFIED, CARBOXYESTERASE HYDROLYSIS OF MALAOXON UNDOUBTEDLY MUST OCCUR IN VIEW OF GREAT DIFFICULTY ENCOUNTERED IN DETECTING MALAOXON IN ANIMAL TISSUE.|IN VITRO STUDIES WITH MOUSE LIVER INDICATED THAT ONLY ABOUT HALF OF TOTAL MALAOXON DETOXIFICATION WAS ACCOUNTED FOR BY CARBOXYESTERASE HYDROLYSIS.|WITH RESISTANT & NON-RESISTANT HOUSEFLY STRAINS, IN VITRO STUDIES SHOWED THAT RESISTANT STRAINS DEGRADED MALAOXON OXIDATIVELY @ RATE 10X HIGHER THAN THAT OF SUSCEPTIBLE STRAIN. THE OXIDATION PRODUCT WAS MALAOXON BETA-MONOCARBOXYLIC ACID WHEN A SUSCEPTIBLE STRAIN WAS USED. THE RESISTANT STRAIN PRODUCED SOME BETA MONOACID BUT THE MALAOXON ALPHA-MONOACID WAS PROBABLY THE MAIN METABOLITE.|A "BINDING" TYPE OF INACTIVATION BY LIVER & OTHER TISSUES HAS BEEN DEMONSTRATED FOR ... MALAOXON. THIS APPEARS TO REPRESENT A LOSS OF THE ACTIVE CHOLINESTERASE INHIBITORS TO NONCRITICAL TISSUE BINDING SITES, THEREBY SPARING CRITICAL ACETYLCHOLINESTERASE OF NERVE TISSUE FROM INHIBITION.|For more Metabolism/Metabolites (Complete) data for MALAOXON (12 total), please visit the HSDB record page.|Maloxon is a known human metabolite of Malathion.

0.09 Days

MALAOXON, ACTIVE ANTICHOLINESTERASE METABOLITE OF MALATHION ... HAS ALIESTERASES INHIBITING ACTIVITY.|MOSQUITO CULEX TARSALIS SHOWS REMARKABLE MALATHION RESISTANCE ORIGINATING FROM (FRESNO, CA,) SO SPECIFIC THAT IT EXTENDS TO NO OTHER ORGANOPHOSPHATE CMPD EXCEPT MALAOXON.|Organophosphorus derivatives act by combining with and inactivating the enzyme acetylcholinesterase (AChE). ... The inactivation of cholinesterase by cholinesterase inhibitor pesticides allows the accumulation of large amounts of acetylcholine, with resultant widespread effects that may be ... separated into 4 categories: (1) Potentiation of postganglionic parasympathetic activity. ... (2) Persistent depolarization of skeletal muscle ... (3) Initial stimulation following depression of cells of central nervous system ... (4) Variable ganglionic stimulation or blockade ... /Cholinesterase inhibitor pesticides/|The characteristic pharmacological effects of the anti-ChE agents are due primarily to the prevention of hydrolysis of ACh by AChE at sites of cholinergic transmission. Transmitter thus accumulates, and the response to ACh that is liberated by cholinergic impulses or that is spontaneously released from the nerve ending is enhanced. With most of the organophosphorus agents ... virtually all the acute effects of moderate doses are attributable to this action. /Anticholinesterase agents/|For more Mechanism of Action (Complete) data for MALAOXON (12 total), please visit the HSDB record page.

Two organophosphorus impurities of technical malathion (insecticide), isomalathion and O,S,S,-trimethyl phosphorodithioate.

SYMPTOMS: Symptoms of exposure to this type of compound include cholinesterase inhibition, miosis, frontal headache, increased bronchial secretion, nausea, vomiting, sweating, abdominal cramps, diarrhea, lacrimation, increased salivation, bradycardia, cyanosis and muscular twitching of the eyelids, tongue, face and neck, possibly progressing to convulsions. Other symptoms include hyperemia of the conjunctiva, dimness of vision, rhinorrhea, bronchoconstriction, cough, fasciculation, anorexia, incontinence, eye changes, weakness, dyspnea, bronchospasm, hypotension or hypertension due to asphyxia, restlessness, anxiety, dizziness, drowsiness, tremor, ataxia, depression, confusion, neuropathy (rare), coma and death from depression of respiratory or cardiovascular systems. Exposure to this type of compound may result in giddiness, nervousness, blurred vision, discomfort (tightness) in chest, papilledema, muscular weakness, loss of reflexes, loss of sphincter control, cardiac arrhythmias, various degrees of heart block and cardiac arrest. It may also result in spasm of accommodation, aching pain in and about the eye, nystagmus, delayed distal axonopathy and parethesias and paralysis of limbs. A decrease in blood pressure may occur. Respiratory failure may also occur. ACUTE/CHRONIC HAZARDS: This compound is toxic by ingestion. It is a CHOLINESTERASE INHIBITOR. When heated to decomposition it emits toxic fumes of sulfur oxides and phosphorus oxides. (NTP, 1992)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, administer a slurry of activated charcoal in water and simultaneously call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

A comatose patient who is diaphoretic, has pinpoint pupils and the odor of an insecticide on clothing or breath, and is noted to have muscle fasciculations represents the classic presentation of organophosphate poisoning. ... Specific steps in management include the following. 1. Decontamination. ... 2 Airway. Establish an airway if necessary. ... 3. Respiratory Status. Respiratory distress, in fact, is commonly found in these patients from multiple causes. ... 4. Cardiac Monitoring. ... 5. Cholinesterase Level. ... 6. Pralidoxime. Pralidoxime is the treatment of choice for organophosphate poisoning and should be used for nearly all patients with clinically significant orgnophosphate poisoning, particularly whose patients with muscular fasciculations and weakness. ... 7. Atropine. Atropine is the physiologic antidote for organophosphate poisoning. A trial dose of atropine should be instituted on clinical ground when one suspects organophosphate intoxication. /Organophosphate poisoning/|1. INSURE THAT A CLEAR AIRWAY EXISTS BY ASPIRATION OF SECRETIONS IF NECESSARY. ADMIN OXYGEN BY MECHANICALLY ASSISTED PULMONARY VENTILATION IF RESPIRATION IS DEPRESSED. IMPROVE TISSUE OXYGENATION AS MUCH AS POSSIBLE BEFORE ADMIN ATROPINE TO MINIMIZE RISK OF VENTRICULAR FIBRILLATION. IN SEVERE POISONINGS, IT MAY BE NECESSARY TO SUPPORT PULMONARY VENTILATION MECHANICALLY FOR SEVERAL DAYS. 2. ADMIN ATROPINE SULFATE IV, OR IM IF IV INJECTION IS NOT POSSIBLE. ... IN MODERATELY SEVERE POISONING: ADULT DOSAGE AND CHILDREN OVER 12 YR: 0.4-2.0 MG REPEATED EVERY 15 MIN UNTIL ATROPINIZATION IS ACHIEVED. MAINTAIN ATROPINIZATION WITH REPEATED DOSAGE OF 0.02-0.05 MG/KG BODY WEIGHT. /ORGANOPHOSPHATE PESTICIDES/|2. SEVERELY POISONED INDIVIDUALS MAY EXHIBIT REMARKABLE TOLERANCE TO ATROPINE; TWO OR MORE TIMES THE DOSAGES SUGGESTED ABOVE MAY BE NEEDED. THE DOSE OF ATROPINE MAY BE INCREASED AND THE DOSING INTERVAL DECREASED AS NEEDED TO CONTROL SYMPTOMS. CONTINUOUS INTRAVENOUS INFUSION OF ATROPINE MAY BE NECESSARY WHEN ATROPINE REQUIREMENTS ARE MASSIVE. REVERSAL OF MUSCARINIC SYMPTOMS AND SIGNS, NOT AN ARBITRARY DOSE LIMIT, IS THE DESIRED END-POINT. PRESERVATIVE-FREE ATROPINE PRODUCTS SHOULD BE USED WHENEVER POSSIBLE. NOTE: PERSONS NOT POISONED OR ONLY SLIGHTLY POISONED BY ORGANOPHOSPHATES MAY DEVELOP SIGNS OF ATROPINE TOXICITY FROM SUCH LARGE DOSES. FEVER, MUSCLE FIBRILLATIONS, AND DELIRIUM ARE THE MAIN SIGNS OF ATROPINE TOXICITY. IF THESE APPEAR WHILE THE PATIENT IS FULLY ATROPINIZED, ATROPINE ADMINISTRATION SHOULD BE DISCONTINUED, AT LEAST TEMPORARILY, WHILE THE SEVERITY OF POISONING IS REEVALUATED. /ORGANOPHOSPHATE PESTICIDES/|3. DRAW BLOOD SAMPLE (HEPARINIZED) FOR CHOLINESTERASE ANALYSIS BEFORE ADMINISTRATION OF PRALIDOXIME, WHICH TENDS TO REVERSE THE CHOLINESTERASE DEPRESSION. 4. ADMIN PRALIDOXIME (PROTOPAM, 2-PAM) IN CASES OF SEVERE POISONING...IN WHICH RESP DEPRESSION, MUSCLE WEAKNESS & TWITCHINGS ARE SEVERE. ... ADULT DOSAGE AND CHILDREN OVER 12): GIVE 1.0-2.0 G IV @ NO MORE THAN 0.2 G/MIN. CHILD'S DOSE (UNDER 12 YR): GIVE 20-50 MG/KG (DEPENDING ON SEVERITY) IV, INJECTING NO MORE THAN HALF TOTAL DOSE/MIN. DOSAGE...MAY BE REPEATED IN 1-2 HR, THEN @ 10-12 HR INTERVAL IF NEEDED. IN VERY SEVERE POISONINGS, DOSAGE...MAY BE DOUBLED. /ORGANOPHOSPHATE PESTICIDES/|For more Antidote and Emergency Treatment (Complete) data for MALAOXON (14 total), please visit the HSDB record page.

TOXICITY OF MALATHION IS PROBABLY DUE TO ITS OXIDATION TO MALAOXON, WHICH IS SOME 1000 TIMES MORE ACTIVE THAN MALATHION AS AN ANTI-CHOLINESTERASE.|Cholinergic toxicity of organophosphate insecticides is regarded as the principle health hazard associated with both human and animal exposures. Recent studies indicate that these pesticides may have important effects on both the immune and hematopoietic systems. In the present study, human bone marrow cells were exposed in vitro to paraoxon and malaoxon (the primary metabolites of parathion and malathion). These compounds produced dose-dependent depression of colony formation by erythrocyte burst-forming units-erythroid and colony-forming units-erythroid and granulocyte-macrophage progenitors (colony-forming units-granulocyte-macrophage). Colony-forming units-erythroid colony formation was reduced 15%-57%, by both paraoxon and malaoxon, in the range of 10-8-10-5 M. No effects were seen at 10-9 and 10-10 M. Colony formation by burst-forming units-erythroid was reduced 15%-75%, at 10-9-10-5 M organophosphate, then returned to normal at 10-10 M organophosphate. In comparison to colony-forming units-erythroid, burst-forming units-erythroid appeared to be more sensitive to the suppressive action of organophosphates. Numbers of colony-forming units-granulocyte-macrophage colonies were reduced 16%-59% in the range of 10-9-10-5 M organophosphate, then returned to normal at 10-10 M organophosphates. Choline chloride added to marrow cultures (final concentration, 10 mM) enhanced colony-forming units-granulocyte-macrophage colony formation at all concentrations of paraoxon and malaoxon.|All the organophosphorus insecticides have a cumulative effect by progressive inhibition of cholinesterase ... /Organophosphorus insecticides/|The symptoms of chronic poisoning due to organophosphorus pesticides include headache, weakness, feeling of heaviness in head, decline of memory, quick onset of fatigue, disturbed sleep, loss of appetite, & loss of orientation. Psychic disorders, nystagmus, trembling of the hands & other nervous system disorders can be observed in certain cases. Sometimes neuritis, paresis & paralysis develop. /Organophosphorus pesticides/|For more Human Toxicity Excerpts (Complete) data for MALAOXON (19 total), please visit the HSDB record page.

malaoxon

Malaoxon Use and Manufacturing

Methods of Manufacturing

OXIDATION OF MALATHION

Uses

An active metabolite of Malathion. It is a widely used anticholinesterase phosphorothioate insecticide

AS SUBSTRATE IN DECARBOXYLATION REACTION FOR CONVENIENT IN VITRO TESTS FOR ACTIVITY OF CERTAIN MICROSOMAL ENZYMES. /FROM TABLE/|NOT PRODUCED COMMERCIALLY IN USA|Malaoxon is ... results from the chemical modification of malathion, an insecticide.|Malaoxon is ... results from the photolytic modification of malathion, an insecticide.|Malaoxon is ... results from the biological modification of malathion, an insecticide.

ANALYTE: MALAOXON: PROCEDURE: THIN LAYER CHROMATOGRAPHY; ADSORBENT: N-HEXANE & ETHYL ACETATE (3:1); DETECTION REAGENT: NBP SPRAY (RAGAB, MTH, BULL ENVIRON CONT TOXICOL 2, 285 (1967). /FROM TABLE/|MALATHION & MALAOXON ARE EXTRACTABLE FROM AQ SUSPENSIONS BY BENZENE ISOBUTANOL. ALIQUOTS OF THE EXTRACT ARE EVAPORATED AT 110-120 °C, THE RESIDUE IS DISSOLVED IN METHANOL, & THE TOTAL FERRIC HYDROXAMATE COLOR IS DETERMINED. EXTRACTION OF A SECOND ALIQUOT WITH CYCLOHEXANE REMOVES MALATHION & SOME MALAOXON. MALAOXON IS SELECTIVELY PARTITIONED FROM CYCLOHEXANE INTO ALKALINE HYDROXYAMINE, LEAVING MALATHION IN THE CYCLOHEXANE PHASE. AFTER EVAPORATION, THE AMT OF MALATHION CAN BE EST BY THE FERRIC HYDROXAMATE METHOD. THE DIFFERENCE IN THE COLOR FOR THE BENZENE-ISOBUTANOL EXTRACT & THE CYCLOHEXANE EXTRACT REPRESENTS THAT DUE TO MALAOXON; THE AMT OF MALAOXON MAY BE CALCULATED FROM A STANDARD CURVE. THE METHOD, SENSITIVE TO ABOUT 0.2 UMOLE MALAOXON, IS USEFUL FOR MONITORING THE LAB PREPN OF MALAOXON FROM MALATHION.|A METHOD FOR MONITORING PRESENCE OF MALATHION & ITS METABOLITES IN AQUATIC ENVIRONMENT IS DESCRIBED. MALATHION, MALAOXON, MALATHION MONOACID & DIACID WERE DETERMINED IN FISH, OYSTER, & SHRIMP TISSUES BY GAS LIQUID CHROMATOGRAPHY USING PHENTHOATE & PHENTHOATE ACID AS INTERNAL STANDARDS. GLC ANALYSES WERE PERFORMED WITHOUT CLEANUP, USING A FLAME PHOTOMETRIC DETECTOR OPERATING IN THE PHOSPHORUS MODE.

A MULTIRESIDUE METHOD OF ANALYSIS FOR ORGANOPHOSPHORUS PESTICIDE WAS DEVELOPED. PESTICIDES & THEIR METABOLITES WERE SEMIQUANTITATIVELY ESTIMATED IN MUSCLES, LIVER & WHOLE BLOOD OF ANIMALS ANALYZED WITH AID OF TLC & ENZYMATIC DETECTION. USING THE SWEEP CODISTILLATION METHOD, THE AVG YIELD FOR CLEANUP OF MALATHION EXTRACTS FROM BLOOD, MUSCLES, & LIVER WAS 87%. RF VALUE OF MALAOXON IN SOLVENT SYSTEMS 1 (CHLOROFORM/ACETATE (93:3 VOL/VOL) & II (HEXANE/ACETONE (70:30 VOL/VOL) WAS 0.63. AVG RECOVERY WAS 78% FOR MALAOXON. EST SENSITIVITY FOR MALAOXON WAS 0.01 PPM.

Pharmaceuticals

Computed Properties

Molecular Weight:314.29
XLogP3:0.6
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:11
Exact Mass:314.05891111
Monoisotopic Mass:314.05891111
Topological Polar Surface Area:113
Heavy Atom Count:19
Complexity:339
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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