Phorate (CED0008715)

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:19 UTC

Update Date

2026-08-23 22:56:37 UTC

Accession Number

CHEM000197

Identification

Common Name

Phorate

Class

Small Molecule

Description

Phorate is an exogenous liquid compound with the formula C7H17O2PS3 and an average molecular weight of 260.38 g/mol. Phorate belongs to the dithiophosphate o-esters, a subclass of organic dithiophosphoric acids and derivatives within the organic compounds. It functions as an agrochemical, biocide, acaricide, and biological insecticide (PMC4179059). Biologically and chemically, it acts as an inhibitor of acetylcholinesterase (EC 3.1.1.7) and cholinesterase (EC 3.1.1.8) (PMC4179059). Its recorded protein targets include acetylcholinesterase (ACHE), cholinesterase (BCHE), retinoic acid receptor alpha (RARA), cytochrome P450 1A1 (CYP1A1), and one other protein. The compound is found in or released from 40 recorded sources. These include electrical and electronic equipment such as antennas, amplifiers, colour television systems, auxiliary devices, adjustable resistors, and 22 others. In building and construction, it is associated with ceilings, floors, roofs, stairs and ramps, and sunshades awnings or outside screens, among others. Household cleaning and consumer product sources include soap detergents, perfumes within detergents and soaps, cigar cigarettes, and tobacco smoke filters. Additionally, it is found in food, food processing and cookware sources, specifically fish processing, food preservation, and molasses and the treatment of molasses.

Contaminant Type

Ester
Ether
Human Neurotoxin
Organic Compound
Organophosphate
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
O,O-Diethyl S-(ethylthio)methyl phosphorodithioate	ChEBI
O,O-Diethyl S-[(ethylsulfanyl)methyl] dithiophosphate	ChEBI
O,O-Diethyl S-ethylmercaptomethyl dithiophosphate	ChEBI
Phosphorodithioic acid, O,O-diethyl S-((ethylthio)methyl) ester	ChEBI
Thimet	ChEBI
O,O-Diethyl S-(ethylthio)methyl phosphorodithioic acid	Generator
O,O-Diethyl S-[(ethylsulfanyl)methyl] dithiophosphoric acid	Generator
O,O-Diethyl S-[(ethylsulphanyl)methyl] dithiophosphate	Generator
O,O-Diethyl S-[(ethylsulphanyl)methyl] dithiophosphoric acid	Generator
O,O-Diethyl S-ethylmercaptomethyl dithiophosphoric acid	Generator
Phosphorodithioate, O,O-diethyl S-((ethylthio)methyl) ester	Generator
PHoric acid	HMDB
PHate	HMDB
PHic acid	HMDB
Thimet 10g	HMDB
Thimet 10-g	HMDB
Thimet 10 g	HMDB

Chemical Formula

C₇H₁₇O₂PS₃

Average Molecular Mass

260.377 g/mol

Monoisotopic Mass

260.013 g/mol

CAS Registry Number

298-02-2

IUPAC Name

O,O-diethyl {[(ethylsulfanyl)methyl]sulfanyl}phosphonothioate

Traditional Name

rampart

SMILES

CCOP(=S)(OCC)SCSCC

InChI Identifier

InChI=1S/C7H17O2PS3/c1-4-8-10(11,9-5-2)13-7-12-6-3/h4-7H2,1-3H3

InChI Key

BULVZWIRKLYCBC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dithiophosphate o-esters. These are o-ester derivatives of dithiophosphates, with the general structure RSP(O)(O)=S (R = organyl group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic dithiophosphoric acids and derivatives

Sub Class

Dithiophosphate O-esters

Direct Parent

Dithiophosphate O-esters

Alternative Parents

Substituents

Dithiophosphate o-ester
Dithiophosphate s-ester
Dialkylthioether
Sulfenyl compound
Thioether
Organothiophosphorus compound
Organic oxygen compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organic thiophosphate (CHEBI:38764 )
organothiophosphate insecticide (CHEBI:38764 )
Organophosphorus insecticides (C18690 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Biological Roles

Chemical Roles

Organoleptic Effects

Not Available

Physical Properties

State

Liquid

Appearance

Phorate is a clear pale-yellow liquid with a skunk-like odor. (1)

Experimental Properties

Property	Value
Melting Point	-43.7°C
Boiling Point	188 °C at 2 torr 118-120 °C at 0.8 torr
Solubility	0.05 mg/mL at 25 °C [MARTIN,H & WORTHING,CR (1977)]

Predicted Properties

Property	Value	Source
Water Solubility	0.037 g/L	ALOGPS
logP	3.71	ALOGPS
logP	3.16	ChemAxon
logS	-3.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	68.95 m³·mol⁻¹	ChemAxon
Polarizability	27.46 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-004i-8690000000-389dad16a59caffc79a8	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0bt9-4930000000-536940f69767dcfa3259	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03fr-9410000000-edd61bd6bf01829ee071	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03fr-9100000000-9231513319c344a8e4a0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-1890000000-2773b2f8dd4dd604b399	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-06si-7950000000-9aac6c50700b539fd079	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00m0-2910000000-996ded89e76694fe1689	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01t9-9560000000-e1ae6dcd5627a1573a5d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00b9-5900000000-a2feb285263c94a0fdd5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-9000000000-39d4ad61034257710be6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0590000000-176c82bfdacfb604a119	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zfr-0910000000-53991a594f0917a1db89	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-2910000000-8f1600d8f0b4bb436a5f	Not Available	View Spectrum
MS	MS Spectrum	splash10-004i-9200000000-982f1838d1ab58fda966	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Phorate 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.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Symptoms of acute oral exposure may include blurred vision, headache, inability to concentrate, fatigue, nausea, diarrhea, irregular heart and respiration rates, tremors, excessive sweating, confusion and convulsions. Death can occur at high doses due to respiratory arrest or lung constriction. Symptoms resulting from phorate inhalation or skin contact may occur from a few minutes up to 12 hours after exposure. Workers chronically exposed to organophosphates have shown slow thinking, memory defects, irritability, delayed reaction time, and anxiety. Symptoms included a lowering of the heart rate. (1)

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.

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
1.0	mg/kg	Not Available	Rat	LD50	Oral	experimental	L1186
3.5	mg/kg	[3.5:6.59]	Mouse	LD50	Oral	experimental	L1186
20.0	mg/kg	Not Available	Guinea pig	LD50	Oral	experimental	L1186
5.7	mg/kg	Not Available	Rat	LD50	Dermal	experimental	L1186
5.2	mg/kg	Not Available	Rabbit	LD50	Dermal	experimental	L1186
20.0	mg/kg	[20:30]	Guinea pig	LD50	Dermal	experimental	L1186
11.0	mg/m3	Not Available	Rat	LC50	Inhalation	experimental	L1186

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
10	Insecticides	Agriculture & land management	Not Available
233	Brushes	Personal care & cosmetics	Not Available
495	Ceilings	Building & Construction	Not Available
497	Floors	Building & Construction	Not Available
499	Roofs	Building & Construction	Not Available
500	Stairs And Ramps	Building & Construction	Not Available
501	Sunshades Awnings Or Outside Screens	Building & Construction	Not Available
502	Sunshades Awnings Or Outside Screens	Building & Construction	Not Available
504	Adjustable Resistors	Electrical & Electronic Equipment	Not Available
505	Amplifiers	Electrical & Electronic Equipment	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
507	Auxiliary Devices	Electrical & Electronic Equipment	Not Available
509	Colour Television Systems	Electrical & Electronic Equipment	Not Available
511	Conductors Or Conductive Bodies Characterised By The Conductive Materials	Electrical & Electronic Equipment	Not Available
513	Cores Yokes Or Armatures	Electrical & Electronic Equipment	Not Available
514	Discharge Lamps	Electrical & Electronic Equipment	Not Available
516	Electric Hearing Aids	Electrical & Electronic Equipment	Not Available
517	Electric Switches	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
519	Electrodes	Electrical & Electronic Equipment	Not Available
520	Emergency Protective Devices	Electrical & Electronic Equipment	Not Available
521	Fixed Capacitors And Their Manufacture	Electrical & Electronic Equipment	Not Available
523	Gas Filled Discharge Tubes With Solid Cathode	Electrical & Electronic Equipment	Not Available
524	Hybrid Capacitors	Electrical & Electronic Equipment	Not Available
525	Line Transmission Systems	Electrical & Electronic Equipment	Not Available
526	Loudspeakers	Electrical & Electronic Equipment	Not Available
527	Magnets	Electrical & Electronic Equipment	Not Available
529	Power Cables	Electrical & Electronic Equipment	Not Available
530	Radio Transmission Systems	Electrical & Electronic Equipment	Not Available
531	Relays	Electrical & Electronic Equipment	Not Available
532	Selectors	Electrical & Electronic Equipment	Not Available
533	Sparking Plugs	Electrical & Electronic Equipment	Not Available
535	Superconducting Magnets And Superconducting Coils	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
545	Food Preservation	Food, food processing & cookware	Not Available
546	Molasses And Treatment Of Molasses	Food, food processing & cookware	Not Available
551	Processing Fish	Food, food processing & cookware	Not Available
556	Cigar Cigarettes	Household cleaning & consumer products	Not Available
561	Perfumes Within Detergents And Soaps	Household cleaning & consumer products	Not Available
563	Soap Detergents	Household cleaning & consumer products	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
578	Making Cigars	Industrial manufacturing & chemical processing	Not Available
579	Manufacture Of Iron Or Steel	Industrial manufacturing & chemical processing	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
581	Paper Making Machines	Industrial manufacturing & chemical processing	Not Available
583	Anchoring Equipment	Marine, shipping & aquaculture	Not Available
592	Marine Propulsion Or Steering	Marine, shipping & aquaculture	Not Available
596	Acaricides	Agriculture & land management	Not Available
597	Chemosterilants	Agriculture & land management	Not Available
598	Fertiliser Distributors	Agriculture & land management	Not Available
600	Herbicides And Algicides	Agriculture & land management	Not Available
601	Lawn Mowers	Agriculture & land management	Not Available
602	Molluscicides	Agriculture & land management	Not Available
603	Nematocides	Agriculture & land management	Not Available
604	Pest Attractants	Agriculture & land management	Not Available
605	Pest Repellants	Agriculture & land management	Not Available
606	Plant Growth Regulators	Agriculture & land management	Not Available
607	Rodenticides(1)	Agriculture & land management	Not Available
608	Rodenticides	Agriculture & land management	Not Available
609	Aftershave	Personal care & cosmetics	Not Available
610	Aftersun Products	Personal care & cosmetics	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
613	Depilatories	Personal care & cosmetics	Not Available
614	Essential Oils Or Perfumes	Personal care & cosmetics	Not Available
615	Eye Makeup Products	Personal care & cosmetics	Not Available
617	Lip Care Products	Personal care & cosmetics	Not Available
618	Lip Makeup Products	Personal care & cosmetics	Not Available
620	Card Games	Recreation & sports surfaces	Not Available
622	Game Accessories	Recreation & sports surfaces	Not Available
630	Toys	Recreation & sports surfaces	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available
642	Footwear	Textiles, leather & furnishings	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available
649	Pins Clothes	Textiles, leather & furnishings	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available
652	Ropes	Textiles, leather & furnishings	Not Available
653	Sewing	Textiles, leather & furnishings	Not Available
655	Slide Fasteners	Textiles, leather & furnishings	Not Available
656	Snap Fasteners	Textiles, leather & furnishings	Not Available
657	Surface Finishing Of Leather	Textiles, leather & furnishings	Not Available
662	Yarns Or Threads	Textiles, leather & furnishings	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Acetylcholinesterase	P07140	Drosophila melanogaster	Predicted (SEA)	0.700643
Click to view 3D structure	1-deoxy-D-xylulose-5-phosphate synthase	B7UJP3	Escherichia coli O127:H6 (strain E2348/69 / EPEC)	Predicted (SEA)	7.78492
Click to view 3D structure	Lysophosphatidic acid receptor 2	Q9HBW0	Humans	Predicted (SEA)	1417.25
Click to view 3D structure	Lysophosphatidic acid receptor 3	Q9UBY5	Humans	Predicted (SEA)	737.544
Click to view 3D structure	Diacylglycerol acyltransferase/mycolyltransferase Ag85C	P9WQN9	Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)	Predicted (SEA)	309.061
Click to view 3D structure	Carbamate kinase	O97438	Giardia intestinalis	Predicted (SEA)	4.12601
Click to view 3D structure	Monoglyceride lipase	O35678	Mus musculus	Predicted (SEA)	4196.54
Click to view 3D structure	Fatty-acid amide hydrolase 1	O08914	Mus musculus	Predicted (SEA)	5070.79
Click to view 3D structure	Cannabinoid receptor 1	P47746	Mus musculus	Predicted (SEA)	4458.58
Click to view 3D structure	Lysophosphatidic acid receptor 1	Q92633	Humans	Predicted (SEA)	5473.11
Click to view 3D structure	Acetylcholinesterase	P21836	Mus musculus	Predicted (SEA)	6443.04
Click to view 3D structure	Autotaxin	Q13822	Humans	Predicted (SEA)	5816.12
Click to view 3D structure	Gasdermin-D	P57764	Humans	Predicted (SEA)	9.34191
Click to view 3D structure	Gasdermin-D	Q9D8T2	Mus musculus	Predicted (SEA)	9.34191
Click to view 3D structure	Lysophosphatidic acid receptor 6	P43657	Humans	Predicted (SEA)	106.653
Click to view 3D structure	Sphingosine-1-phosphate lyase 1	Q8CHN6	Rattus norvegicus	Predicted (SEA)	108.833
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	7683.02
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	7646.43
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	7726.22
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	7692.83
Click to view 3D structure	Histidine biosynthesis bifunctional protein HisB	P06987	Escherichia coli O26:H11 str. CFSAN001629	Predicted (SEA)	265.077
Click to view 3D structure	Cholinesterase	P06276	Humans	Predicted (SEA)	7751.99
Click to view 3D structure	Carbonic anhydrase 7	P43166	Humans	Predicted (SEA)	7714.78
Click to view 3D structure	Carbonic anhydrase 14	Q9ULX7	Humans	Predicted (SEA)	7635.37
Click to view 3D structure	Monoglyceride lipase	Q99685	Humans	Predicted (SEA)	7554.33
Click to view 3D structure	Acetylcholinesterase	P22303	Humans	Known	Not Available
Click to view 3D structure	Cholinesterase	P06276	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 1A1	P04798	Humans	Known	Not Available
Click to view 3D structure	Retinoic acid receptor alpha	P10276	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Known	Not Available