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Amiton

HCID 6542
NotizenReaktionen
GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
78-53-5
Standard-SMILES
CCOP(=O)(OCC)SCCN(CC)CC
InChIKey
PJISLFCKHOHLLP-UHFFFAOYSA-N
Summenformel
C10H24NO3PS
Durchschnittliche Molmasse
269,34 g/mol
Monoisotopische Masse
269,1214518

Überblick

Amiton is a liquid. Used as an acaricide and insecticide. (EPA, 1998)

Namen und Bezeichner

Bevorzugter Name
Amiton
IUPAC
2-diethoxyphosphorylsulfanyl-N,N-diethylethanamine
Englischer Name
S-[2-(Diethylamino)ethyl]O,O-diethylphosphorothioate
Summenformel
C10H24NO3PS
Molmasse
269.34

Namen und Synonyme

AMITONMetramacInfernoMetramChipman 6200Rhodia-620078-53-5ENT 24,980-XDiethyl S-2-diethylaminoethyl phosphorothioateEPA Pesticide Chemical Code 0573027SD1SH009VO,O-Diethyl S-(2-diethylaminoethyl) thiophosphate
Weitere Namen anzeigen
DSDPR-5158Brn 1785674Amiton [bsi]Caswell no. 333dPJISLFCKHOHLLP-UHFFFAOYSA-N
R-5,158O,O-Diethyl S-2-diethylaminoethyl phosphorothioateO,O-Diethyl S-2-diethylaminoethyl phosphorothiolateS-(Diethylaminoethyl) O,O-diethyl phosphorothioate(2-Diethylamino)ethylphosphorothioic acid O,O-diethyl esterO,O-Diethyl S-diethylaminoethyl phosphorothiolateS-(2-(Diethylamino)ethyl)phosphorothioic acid O,O-diethyl esterPhosphorothioic acid, S-(2-(diethylamino)ethyl) O,O-diethyl ester

Datenbank-Bezeichner

CAS
78-53-5
PubChem CID
6542
DTXSID
DTXSID6058184
UNII
7SD1SH009V
Nikkaji

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,7
Polarare Oberfläche (TPSA)
64,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
10
Schwere Atome
16
Formalladung
0
Komplexität
202

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesBoiling point
PesticidesPesticides -> Organophosphate Insecticides
Density1.056 @ 20°C
Color/FormColorless liquid
SolubilityHighly soluble in water and most organic solvents
Boiling Point · 4 Einträge

230 °F at 0.2 mmHg (EPA, 1998)

110 °C at 0.2 mm Hg

Bp: 76 °C at 0.01 mm Hg

146 °C @760 [mm Hg]

Melting PointCrystals from isopropanol + ether; Mp: 98-99 °C /Amiton acid oxalate, (amiton hydrogen oxalate)/
Vapor Pressure0.01 mm Hg @ 80 °C
Refractive IndexIndex of refraction: 1.4655 at 27 °C/D
Physical Description · 2 Einträge

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 InformationThe 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.)
DOT LabelPoison
Fire Hazards · 1 Eintrag

When heated to decomposition, can emit toxic fumes of oxides of nitrogen, phosphorus, and sulfur. (Non-Specific -- Organophosphorus Pesticide, Liquid, n.o.s.) Container may explode in heat of fire. Fire may produce irritating or poisonous gases. Runoff from fire control water may give off poisonous gases. Runoff from fire control or dilution water may cause pollution. Avoid extreme heat. (EPA, 1998)

Health HazardsThis material is highly toxic orally. It is a cholinesterase inhibitor. (EPA, 1998)
Hazards Summary · 1 Eintrag

One of the most toxic of the organic phosphorus insecticides. [HSDB] A highly toxic cholinesterase inhibitor; [CAMEO] The average of two baseline respective cholinesterase activity determinations three days apart, with no exposures to enzyme inhibiting pesticides for at least 30 days, is recommended for each worker prior to exposure to cholinesterase inhibitors because of large inter-individual differences in published baseline values. To be established at least once a year. Removal from workplace exposures is recommended until the cholinesterase activity returns to within 20% of baseline. [TLVs and BEIs]

Reactive GroupAmines, Phosphines, and Pyridines
Reactivity Profile · 1 Eintrag

Organothiophosphates, such as AMITON, 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.

Chemie und Industrie

Pharmakologische Informationen

Mechanism of ActionThe main feature of the toxic mechanism of organophosphorus pesticides is inhibition of the esterase enzyme activity, in particular of cholinesterase ... . /Organophosphorus pesticides/
MeSH Pharmacological ClassificationToxic substances from microorganisms, plants or animals that interfere with the functions of the nervous system. Most venoms contain neurotoxic substances. Myotoxins are included in this concept.
Absorption, Distribution and ExcretionOrganophosphorus pesticides are rapidly absorbed into the body through the mucous membrane of the digestive tract, the respiratory system, & the skin, and are conveyed by the blood to various body tissues. /Organophosphorus pesticides/

Verwendung und Herstellung

Uses · 5 Einträge

Used as contact insecticide, miticide, and acaricide; [HSDB]

Farming (Pesticides) [Category: Industry]

Contact insecticide, miticide

Acaricide

A systemic insecticide to control aphids and mites on various species of plants. /Acid oxalate form/

Methods of ManufacturingIt has been produced by the reaction of sodium diethylaminoethylate with diethyl chlorothiophosphate with subsequent rearrangement of the thiono ester to the thiol form
General Manufacturing Information · 2 Einträge

Marketed as the water sol oxalic acid salt (hydrogen oxalate).

Discontinued 1968 by Imperial Chemical Industries, Ltd

Anwendungen

VerwendenInsecticide.

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
J5.507G

Amiton is a liquid. Used as an acaricide and insecticide. (EPA, 1998)

Colorless liquid; [HSDB]

Other Experimental PropertiesIt hydrolyzes comparatively slowly in water

Physikochemische Eigenschaften

Schmelzpunkt
25 °C · 25°C
Siedepunkt
0.01 · bp0.01 76°; bp0.2 110°
Dichte
1.07 · 1.070±0.06 g/cm3(Predicted)
Brechungsindex
27 · nD27 1.4655
Aggregatzustand
liquid
pka
9.39 · 9.39±0.25(Predicted)
Henry's Law Constant
3.5 · 3.5×104 mol/(m3Pa) at 25℃, Bartelt-Hunt et al. (2008)
EPA chemische Informationen
O,O-Diethyl S-(2-(diethylamino)ethyl) phosphorothioate (78-53-5)
Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.
CERCLA Reportable Quantities · 1 Eintrag

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Amiton is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.

DHS Chemicals of Interest (COI) · 4 Einträge

o,o-Diethyl S-[2-(diethylamino)ethyl]phosphorothiolate

30.00

2.2

Chemical Weapons/Chemical Weapons Precursors chemical material that, if stolen or diverted, can be converted into weapons using simple chemistry, equipment, or techniques.

Shipment Methods and Regulations · 3 Einträge

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./

The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.

The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Sicherheit und Schutzausrüstung

Fire Fighting · 1 Eintrag

(Non-Specific -- Organophosphorus Pesticide, Liquid, n.o.s.) Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Wear positive pressure breathing apparatus and special protective clothing. Remove and isolate contaminated clothing at the site. Move container from fire area if you can do so without risk. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material.

First AidWarning: Effects may be delayed up to 12 hours. Caution is advised.
Exposure Control and Personal Protection · 1 Eintrag

Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Butylcholinesterase activity in serum or plasma = 60% of individual's baseline; Sample at end of shift; [TLVs and BEIs]

Nonfire Spill Response · 1 Eintrag

(Non-Specific -- Organophosphorus Pesticide, Liquid, n.o.s.) Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Remove and isolate contaminated clothing at the site. Do not touch spilled material; stop leak if you can do so without risk. Use water spray to reduce vapors.

Disposal Methods · 1 Eintrag

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.

Isolation and EvacuationExcerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:
Protective Action Criteria (PAC) · 3 Einträge

0.0099 [mg/m3]

0.11 [mg/m3]

0.65 [mg/m3]

Personal Protective Equipment (PPE) · 1 Eintrag

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)

Toxikologische Informationen

Adverse EffectsOther Poison - Organophosphate
Human Toxicity Excerpts · 5 Einträge

SYMPTOMATOLOGY: 1. Nausea is often the first symptom, followed by vomiting, abdominal cramps, diarrhea, and excessive salivation (sialorrhea). Hypothermia has been reported in animals and at least once in man as an early sign. 2. Headache, giddiness, vertigo, and weakness. 3. Rhinorrhea and a sensation of tightness in the chest are common in inhalation exposures. 4. Blurring or dimness of vision, miosis (with fixed pinpoint pupils), tearing, ciliary muscle spasm, loss of accommodation, and ocular pain. None of these eye effects are diagnostically dependable except in primary ocular exposures. Indeed, mydriasis is sometimes seen, probably due to sympatho-adrenal discharge. /Parathion/

SYMPTOMATOLOGY: 5. Bradycardia or tachycardia. Varying degrees of AV heart block are described, as well as atrial arrhythmias. 6. Loss of muscle coordination, slurring of speech, fasciculations and twitching of muscles (particularly of the tongue and eyelids), and generalized profound weakness. 7. Mental confusion, disorientation, and drowsiness. 8. Difficulty in breathing, excessive secretion of saliva and of respiratory tract mucus, oronasal frothing, cyanosis, pulmonary rales and rhonchi, and hypertension presumably due to asphyxia. 9. Random jerky movements, incontinence, convulsions, and coma. 10. Death primarily due to respiratory arrest arising from failure of the respiratory muscles, intense bronchoconstriction, or all three. /Parathion/

Exposure to the vapor or to particulate material may cause miosis, sometimes unequal, hyperanemia of the conjunctiva, dimness of vision, rhinorrhoea, frontal headache, bronchoconstrction, incr bronchial secretion, cough, nausea, vomiting, and fasciculation and sweating at the site of contact. Toxic effects may incl anorexia, abdominal cramps, nausea, vomiting, diarrhea, incontinence, eye changes, weakness, dyspnea, bronchospasm, lachrymation, incr salivation and sweating, bradycardia, hypotension or hypertension due to asphyxia, cyanosis, and muscular twitching of the eyelids, tongue, face, and neck, possibly progressing to convulsions. CNS symptoms incl restlessness, anxiety, dizziness, drowsiness, tremor, ataxia, depression, confusion, and coma. Death may occur from depression of the resp or cardiovascular system. /Organophosphorus insecticides/

Chromosome abnormalities were temporarily incr in patients with organophosphorus poisoning. /Organophosphorus insecticides/

For more Human Toxicity Excerpts (Complete) data for AMITON (6 total), please visit the HSDB record page.

Antidote and Emergency Treatment · 5 Einträge

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/

4. BE PREPD TO ASSIST PULMONARY VENTILATION MECHANICALLY IF RESP ... DEPRESSED ... . 5. IN PATIENTS WHO HAVE BEEN POISONED BY ORGANOPHOSPHATE CONTAMINATION OF SKIN, CLOTHING, HAIR, AND/OR EYES, DECONTAMINATION MUST PROCEED CONCURRENTLY WITH WHATEVER RESUSCITATIVE AND ANTIDOTAL MEASURES ARE NECESSARY TO PRESERVE LIFE. ... 6. IF ... INGESTED IN QUANTITY PROBABLY SUFFICIENT TO CAUSE POISONING, THE STOMACH AND INTESTINE MUST BE EMPTIED. A. EMPTY THE STOMACH BY INTUBATION, ASPIRATION, AND LAVAGE, USING SLURRY OF ACTIVATED CHARCOAL IN ISOTONIC SALINE. RIGOROUS PRECAUTIONS MUST BE TAKEN TO PROTECT THE AIRWAY FROM ASPIRATION OF REGURGITATED. IF VICTIM IS UNCONSCIOUS OR OBTUNDED, INSERT A CUFFED ENDOTRACHEAL TUBE PRIOR TO GASTRIC INTUBATION. KEEP VICTIM'S HEAD BELOW LEVEL OF STOMACH DURING GASTRIC INTUBATION AND LAVAGE ... . KEEP VICTIM'S HEAD TURNED TO THE LEFT. /ORGANOPHOSPHATE PESTICIDES/

Non-Human Toxicity Values · 2 Einträge

LD50 Rat oral 5.4 mg/kg

LD50 Rat albino male oral 9 mg/kg /Amiton acid oxalate/

Regulatorische Informationen

CERCLA Reportable Quantities · 1 Eintrag

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Amiton is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.

DHS Chemicals of Interest (COI) · 4 Einträge

o,o-Diethyl S-[2-(diethylamino)ethyl]phosphorothiolate

30.00

2.2

Chemical Weapons/Chemical Weapons Precursors chemical material that, if stolen or diverted, can be converted into weapons using simple chemistry, equipment, or techniques.

Sicherheitsdaten

ridadr
3018
Toxizität
LD50 orally in rats: 5.4 mg/kg (Frawley)
hazard_class
6.1(a)
packing_group
I
Giftige Stoffe Daten
78-53-5(Hazardous Substances Data)

For more Antidote and Emergency Treatment (Complete) data for AMITON (8 total), please visit the HSDB record page.