ContaminantDB: Parathion

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (17)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:10 UTC

Update Date

2026-03-26 18:34:49 UTC

Accession Number

CHEM000135

Identification

Common Name

Parathion

Class

Small Molecule

Description

Parathion is a highly toxic cholinesterase inhibitor that is used as an acaricide and as an insecticide, generally applied by spraying, most often to cotton, rice, and fruit trees. Also called parathion-ethyl or diethyl parathion, parathion is an organophosphate compound. As parathion is highly toxic to non-target organisms, its use is banned or restricted in many areas. (14)

Contaminant Sources

Clean Air Act Chemicals
FooDB Chemicals
HPV EPA Chemicals
IARC Carcinogens Group 2B
IARC Carcinogens Group 3
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Ester
Food Toxin
Metabolite
Organic Compound
Organophosphate
Pesticide
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Diethyl p-nitrophenyl thiophosphate	ChEBI
Diethyl parathion	ChEBI
DNTP	ChEBI
Ethyl parathion	ChEBI
O,O-Diethyl O-(4-nitrophenyl) thiophosphate	ChEBI
O,O-Diethyl O-(p-nitrophenyl) thiophosphate	ChEBI
O,O-Diethyl O-p-nitrophenyl phosphorothioate	ChEBI
Phosphorothioic acid, O,O-diethyl O-(4-nitrophenyl) ester	ChEBI
Thiophos	ChEBI
Diethyl p-nitrophenyl thiophosphoric acid	Generator
O,O-Diethyl O-(4-nitrophenyl) thiophosphoric acid	Generator
O,O-Diethyl O-(p-nitrophenyl) thiophosphoric acid	Generator
O,O-Diethyl O-p-nitrophenyl phosphorothioic acid	Generator
Phosphorothioate, O,O-diethyl O-(4-nitrophenyl) ester	Generator
Alkron	HMDB
Alleron	HMDB
American cyanamid 3422	HMDB
Aphamite	HMDB
Aqua 9-parathion	HMDB
Aralo	HMDB
Bladan	HMDB
Bladen	HMDB
Corothion	HMDB
Corthione	HMDB
Danthion	HMDB
Deoxynucleoside 5'-triphosphate	HMDB
Diethyl 4-nitrophenyl phosphorothionate	HMDB
Diethyl O-p-nitrophenyl phosphorothioate	HMDB
Diethyl O-p-nitrophenyl phosphorothioic acid	HMDB
Diethyl p-nitrophenyl thionophosphate	HMDB
Diethyl para-nitrophenol thiophosphate	HMDB
Diethyl-p-nitrophenyl monothiophosphate	HMDB
Diethylparathion	HMDB
Drexel parathion 8E	HMDB
Durathion	HMDB
Ecatox	HMDB
Ethlon	HMDB
Ethyl parathion (O,O-diethyl-O-p-nitrophenylthiophosphate)	HMDB
Etilon	HMDB
Foliclal	HMDB
Folidol	HMDB
Folidol e e 605	HMDB
Folidol e605	HMDB
Folidol oil	HMDB
Fosfermo	HMDB
Fosferno	HMDB
Fosferno 50	HMDB
Fosfex	HMDB
Fosfive	HMDB
Fosova	HMDB
Fostern	HMDB
Fostox	HMDB
Gearphos	HMDB
Genithion	HMDB
Kolphos	HMDB
Kypthion	HMDB
Lethalaire g-54	HMDB
Lirothion	HMDB
Murfos	HMDB
Niran	HMDB
Nitrostygmine	HMDB
Niuif-100	HMDB
Nourithion	HMDB
O,O-Diethyl-O-(p-nitrophenyl)thionophosphate	HMDB
Oleofos 20	HMDB
Oleoparaphene	HMDB
Oleoparathion	HMDB
OMS 19	HMDB
Orthophos	HMDB
p-Nitrophenol O-ester with O,O-diethylphosphorothioate	HMDB
p-Nitrophenol O-ester with O,O-diethylphosphorothioic acid	HMDB
PAC	HMDB
Pacol	HMDB
Panthion	HMDB
Paradust	HMDB
Paramar	HMDB
Paramar 50	HMDB
Paraphos	HMDB
Parathene	HMDB
Parathion-e	HMDB
Parawet	HMDB
Parthion	HMDB
Penncap e	HMDB
Pestox plus	HMDB
Pethion	HMDB
Phoskil	HMDB
Phosphemol	HMDB
Phosphenol	HMDB
Phosphorothioate	HMDB
Phosphorothioic acid	HMDB
Phosphorothioic acid O,O-diethyl-O-(4-nitrophenyl) ester	HMDB
Phosphostigmine	HMDB
Rhodiasol	HMDB
Rhodiatox	HMDB
Rhodiatrox	HMDB
Selephos	HMDB
Sixty-three special e.c	HMDB
Soprathion	HMDB
Stabilized ethyl parathion	HMDB
Stathion	HMDB
Strathion	HMDB
Sulfos	HMDB
Super rodiatox	HMDB
T-47	HMDB
Thiomex	HMDB
Thionspray no.84	HMDB
Thiophos 3422	HMDB
Tiofos	HMDB
Vapophos	HMDB
Viran	HMDB
Vitrex	HMDB
Thiofos	HMDB
Parathion, ethyl	HMDB

Chemical Formula

C₁₀H₁₄NO₅PS

Average Molecular Mass

291.261 g/mol

Monoisotopic Mass

291.033 g/mol

CAS Registry Number

56-38-2

IUPAC Name

O,O-diethyl O-4-nitrophenyl phosphorothioate

Traditional Name

bladen

SMILES

CCOP(=S)(OCC)OC1=CC=C(C=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C10H14NO5PS/c1-3-14-17(18,15-4-2)16-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3

InChI Key

LCCNCVORNKJIRZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenyl thiophosphates. These are organothiophosphorus compounds that contain a thiophosphoric acid O-esterified with a phenyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic thiophosphoric acids and derivatives

Sub Class

Thiophosphoric acid esters

Direct Parent

Phenyl thiophosphates

Alternative Parents

Substituents

Phenyl thiophosphate
Nitrobenzene
Phenoxy compound
Nitroaromatic compound
Thiophosphate triester
Monocyclic benzene moiety
Benzenoid
C-nitro compound
Organic nitro compound
Organic oxoazanium
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

C-nitro compound (CHEBI:27928 )
organic thiophosphate (CHEBI:27928 )
organothiophosphate insecticide (CHEBI:27928 )
Organophosphorus insecticides (C06604 )
an aryl dialkyl phosphate (PARATHION )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Physical Properties

State

Liquid

Appearance

White crystals.

Experimental Properties

Property	Value
Melting Point	6.1°C
Boiling Point	Not Available
Solubility	0.011 mg/mL

Predicted Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	3.76	ALOGPS
logP	3.32	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	-9.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	70.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	71.68 m³·mol⁻¹	ChemAxon
Polarizability	26.77 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03fr-1390000000-256208006a2b1561db1b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-01p9-0090000000-fe8742077ddcdaa84280	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-0190000000-af44a385ea22b6326819	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000l-1940000000-218556da13b43e16e2bf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-01vo-2910000000-4a40f241595d8b5628d0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-01vo-4900000000-c58ec980fa6b4210133c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-01ox-6900000000-80ce5f0f59ebc4a62681	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-01ox-6900000000-0ae225ae5aa0b11161e3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-01p9-0090000000-699baba652581ceae2be	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-000l-1940000000-15d927af1afee2c09028	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-0190000000-13506519f0e449b52678	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-01vo-2910000000-e81debcb63112f1a8187	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-01vo-4900000000-697208a779d2fefe32fd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-1090000000-e7daa1435a3c8202b8dc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00lr-1090000000-0ee220c0c9ec67d726bb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004j-9720000000-be163305078ac89a7681	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0390000000-3cdf27289e65564f2028	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0490000000-9b32c86de4c27c33c405	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000f-1940000000-6f5772e73d0e7958d6cb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-9585d70a69dd82c677f0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01pc-0090000000-7f509a774ae9d3a5ac84	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9340000000-b44b4f76ff61f463d2db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-f2d3ba63a2de010595cf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0290000000-b84c6ef99ca616492499	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006t-7910000000-fc58d956a883b5d8b5ca	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a74-8940000000-4bf55c77de23f747eb80	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral(14) ; inhalation (14) ; dermal (14).

Mechanism of Toxicity

Parathion is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

Metabolism

Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.

Toxicity Values

LD50: 2 mg/kg (Oral, Rat) (16) LD50: 6800 ug/kg (Dermal, Rat) (16) LD05: 3600 ug/kg (Intraperitoneal, Rat) (16) LD50: 6 mg/kg (Intramuscular, Rat) (16) LC50: 84.0 mg (Inhalation, Rat) (4)

Lethal Dose

7143 mg/kg for an adult human. (17)

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (13)

Uses/Sources

Parathion is an insecticide and acaricide that is generally applied by spraying, most often to cotton, rice, and fruit trees. (14)

Minimum Risk Level

Not Available

Health Effects

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Symptoms

Parathion exposure can result in headaches, convulsions, poor vision, vomiting, abdominal pain, severe diarrhea, unconsciousness, tremor, dyspnea, and finally lung-edema as well as respiratory arrest. (14)

Treatment

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0001355

FooDB ID

FDB022574

Phenol Explorer ID

Not Available

KNApSAcK ID