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Parathion methyl

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Parathion methyl
Names
IUPAC name O,O-Dimethyl-O-p-nitrophenylphosphorothioate
Other names Azophos, Methyl parathion, O,O-Dimethyl O-4-nitrophenyl phosphorothioate, O,O-Dimethyl-p-nitrophenylthionophosphate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.005.501 Edit this at Wikidata
EC Number
  • 015-035-00-7
PubChem CID
RTECS number
  • TG0175000
UNII
UN number 2783
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H10NO5PS/c1-12-15(16,13-2)14-8-5-3-7(4-6-8)9(10)11/h3-6H,1-2H3Key: RLBIQVVOMOPOHC-UHFFFAOYSA-N
  • InChI=1/C8H10NO5PS/c1-12-15(16,13-2)14-8-5-3-7(4-6-8)9(10)11/h3-6H,1-2H3Key: RLBIQVVOMOPOHC-UHFFFAOYAW
SMILES
  • COP(=S)(OC)Oc1ccc(cc1)(=O)
Properties
Chemical formula (CH3O)2P(S)OC6H4NO2
Molar mass 263.2 g/mol
Appearance White to tan, crystalline solid or powder
Odor pungent, garlic-like
Density 1.36 g/mL (20°C)
Melting point 37 °C; 99 °F; 310 K
Boiling point 143 °C; 289 °F; 416 K
Solubility in water 0.006% (25°C)
Vapor pressure 0.00001 mmHg (20°C)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards reactive with strong oxidizers and water
Lethal dose or concentration (LD, LC):
LD50 (median dose) 67 mg/kg (rat, dermal)
10-25 mg/kg (male rat, oral)
24 mg/kg (female rat, oral)
NIOSH (US health exposure limits):
PEL (Permissible) none
REL (Recommended) TWA 0.2 mg/m
IDLH (Immediate danger) N.D.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Parathion methyl, or methyl parathion, is an organophosphate insecticide, possessing an organothiophosphate group. It is structurally very similar to parathion-ethyl. It is not allowed for sale and import in nearly all countries around the world, while a few allow it under subject to specified conditions only.

Applications

Parathion methyl is used as an insecticide on crops, including cotton.

Trade names

Penncap-M, Metacide

Safety

People can be exposed to parathion methyl in the workplace by breathing it in, getting it on their skin, swallowing it, or getting it in their eyes. Since it is an acetylcholinesterase inhibitor, symptoms of exposure to parathion methyl include irritated eyes and skin, nausea and vomiting, abdominal pain, diarrhea, salivation, feeling weak and tired, headache, runny nose, tightness in the chest, blurry vision, pupil constriction, irregular heartbeat, muscle twitches (fasciculation), and difficulty breathing.

In the United States, the Occupational Safety and Health Administration (OSHA) has not set a legal limit (permissible exposure limit) for parathion methyl exposure in the workplace. The National Institute for Occupational Safety and Health (NIOSH) has set a recommended exposure limit (REL) of 0.2 mg/m over an 8-hour workday.

Classifications and restrictions

Parathion methyl has been restricted for many years. It is classified as Extremely Hazardous (Ia) by the World Health Organization and it is classified as Severely Hazardous by the Rotterdam Convention. It is not allowed for sale and import in nearly all countries around the world, while a few allow it under subject to specified conditions only.

References

  1. ^ NIOSH Pocket Guide to Chemical Hazards. "#0427". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ "Skin notation profile: Methyl Parathion" (PDF). NIOSH.
  3. ^ "Methyl Parathion". 1988 OSHA PEL Project Documentation. NIOSH. 28 September 2011.
  4. "Methyl Parathion (Penncap-M) - Chemical Profile 4/85". Cornell.edu.
  5. Journal of Toxicology and Environmental Health B Critical Review (2003): Methyl parathion: a review of health effects., PubMed
  6. CABI Plantwise: Plantwise Pesticide Red List
  7. WHO (2010): The WHO Recommended Classification of Pesticides by Hazard, p5, IPCS
  8. Rotterdam Convention: Annex III Chemicals
  9. Annex III Chemicals: Methyl-parathion (Emulsifiable concentrates (EC) at or above 19.5% active ingredient and dusts at or above 1.5% active ingredient), Rotterdam Convention
Acetylcholine metabolism and transport modulators
Enzyme
(modulators)
ChATTooltip Choline acetyltransferase
AChETooltip Acetylcholinesterase
BChETooltip Butyrylcholinesterase
Transporter
(modulators)
CHTTooltip Choline transporter
VAChTTooltip Vesicular acetylcholine transporter
Release
(modulators)
Inhibitors
Enhancers
See also
Receptor/signaling modulators
Muscarinic acetylcholine receptor modulators
Nicotinic acetylcholine receptor modulators
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