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Substance Name: EPN
RN: 2104-64-5
UNII: 9Y6HP0HYA8
InChIKey: AIGRXSNSLVJMEA-UHFFFAOYSA-N

Note

  • An organothiophosphorus cholinesterase inhibitor that is used as an insecticide and as a acaricide.

Molecular Formula

  • C14-H14-N-O4-P-S

Molecular Weight

  • 323.308
 

Classification Codes

Classification Codes

  • Acaricide
  • Agricultural Chemical
  • Cholinergic Agents
  • Cholinesterase Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Insecticide
  • Insecticides
  • Neurotransmitter Agents
  • Pesticides
  • Reproductive Effect

Superlist Classification Codes

  • Threshold Planning Quantity (TPQ) = 100/10000 lb
  • TWA 0.1 mg/m3 inhalable fraction; skin; Not classifiable as a human carcinogen; BEI
  • TWA 0.5 mg/m3; skin

Names and Synonyms

Name of Substance

  • EPN

MeSH Heading

  • Phenylphosphonothioic acid, 2-ethyl 2-(4-nitrophenyl) ester

Synonyms

  • 4-16-00-01089 (Beilstein Handbook Reference)
  • AI3-17798
  • Benzenephosphonic acid, thiono-, ethyl-p-nitrophenyl ester
  • Benzenephosphothionic acid, ethyl-4-nitrophenyl ester
  • BRN 2542580
  • Caswell No. 454
  • EINECS 218-276-8
  • ENT 17,798
  • EPA Pesticide Chemical Code 041801
  • EPN
  • EPN 300
  • ESA
  • Ethoxy-4-nitrophenoxyphenylphosphine sulfide
  • Ethyl (p-nitrophenyl)thionobenzenephosphonate
  • Ethyl p-nitrophenyl benzenethionophosphonate
  • Ethyl p-nitrophenyl benzenethiophosphate
  • Ethyl p-nitrophenyl benzenethiophosphonate
  • Ethyl p-nitrophenyl phenylphosphonothioate
  • Ethyl p-nitrophenyl thionobenzenephosphate
  • Ethyl p-nitrophenyl thionobenzenephosphonate
  • Ethyl p-nitrophenylthiobenzene phosphonate
  • Ethyl-p-nitrophenylthionobenzenephosphate
  • HSDB 4049
  • Kasutop Dust
  • MAPJ
  • Meidon 15 Dust
  • NSC 404840
  • NSC 8943
  • O-(4-Nitrophenyl) O-ethyl phenyl thiophosphonate
  • O-Aethyl-O-(4-nitro-phenyl)-phenyl-monothiophosphonat
  • O-Aethyl-O-(4-nitro-phenyl)-phenyl-monothiophosphonat [German]
  • O-Ethyl O-(4-nitrophenyl) benzenethionophosphonate
  • O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate
  • O-Ethyl O-(4-nitrophenyl)benzenethionophosphonate
  • O-Ethyl O-(p-nitrophenyl) benzenethiophosphonate
  • O-Ethyl O-(p-nitrophenyl) phenylphosphonothioate
  • O-Ethyl O-(p-nitrophenyl) phenylphosphonothionate
  • O-Ethyl O-p-nitrophenyl phenylphosphonothiolate
  • O-Ethyl O-p-nitrophenyl phenylphosphorothioate
  • O-Ethyl phenyl p-nitrophenyl thiophosphonate
  • O-Ethyl phenylphosphonothioic acid O-(4-nitrophenyl) ester
  • O-Ethyl-O-((4-nitro-fenyl)-fenyl)-monothiofosfonaat
  • O-Ethyl-O-((4-nitro-fenyl)-fenyl)-monothiofosfonaat [Dutch]
  • O-Ethyl-O-p-nitrofenylester kyseliny fenylthiofosfonove
  • O-Ethyl-O-p-nitrofenylester kyseliny fenylthiofosfonove [Czech]
  • O-Ethyl-O-p-nitrophenylphenylphosphonothioate
  • O-Etil-O-((4-nitro-fenil)-fenil)-monotiofosfonato
  • O-Etil-O-((4-nitro-fenil)-fenil)-monotiofosfonato [Italian]
  • OMS 219
  • Phenol, p-nitro-, O-ester with O-ethyl phenyl phosphonothioate
  • Phenylphosphonothioic acid O-ethyl O-(4-nitrophenyl) ester
  • Phenylphosphonothioic acid O-ethyl O-p-nitrophenyl ester
  • Phenylthiophosphonate de O-ethyle et O-4-nitrophenyle
  • Phenylthiophosphonate de O-ethyle et O-4-nitrophenyle [French]
  • Phosphonothioic acid, phenyl-, O-ethyl O-(4-nitrophenyl) ester
  • Phosphonothioic acid, phenyl-, O-ethyl O-(p-nitrophenyl) ester
  • PIN
  • Santox
  • Tsumaphos
  • UNII-9Y6HP0HYA8

Systematic Names

  • O-Ethyl O-4-nitrophenyl phenylphosphonothioate
  • Phosphonothioic acid, phenyl-, O-ethyl O-(4-nitrophenyl) ester

Superlist Names

  • EPN
  • O-Ethyl O-(p-nitrophenyl) phenylphosphonothioate

Registry Numbers

CAS Registry Number

  • 2104-64-5

FDA UNII

  • 9Y6HP0HYA8

System Generated Number

  • 0002104645

Structure Descriptors

InChI

1S/C14H14NO4PS/c1-2-18-20(21,14-6-4-3-5-7-14)19-13-10-8-12(9-11-13)15(16)17/h3-11H,2H2,1H3

InChIKey

AIGRXSNSLVJMEA-UHFFFAOYSA-N

Smiles

c1([P@@](Oc2ccc([N+](=O)[O-])cc2)(OCC)=S)ccccc1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 2370ug/kg (2.37mg/kg)   ASTM Special Technical Publication. Vol. (680), Pg. 157, 1979.
cat LD50 skin 45mg/kg (45mg/kg) BEHAVIORAL: ATAXIA

PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
Toxicology Letters. Vol. 1000(Sp,
chicken LD50 intraperitoneal 17mg/kg (17mg/kg)   Bulletin of Environmental Contamination and Toxicology. Vol. 18, Pg. 534, 1977.
chicken LD50 oral 5mg/kg (5mg/kg)   Journal of Environmental Science and Health, Part B: Pesticides, Food Contaminants, and Agricultural Wastes. Vol. 17, Pg. 611, 1982.
dog LD50 oral 20mg/kg (20mg/kg)   Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 478, 1966.
dog LDLo intraperitoneal 35mg/kg (35mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 112, Pg. 29, 1954.
duck LD50 oral 3mg/kg (3mg/kg)   Toxicology and Applied Pharmacology. Vol. 20, Pg. 57, 1971.
duck LD50 skin 400mg/kg (400mg/kg)   Toxicology and Applied Pharmacology. Vol. 47, Pg. 451, 1979.
guinea pig LD10 intraperitoneal 14mg/kg (14mg/kg)   Toxicology and Applied Pharmacology. Vol. 8, Pg. 259, 1966.
mouse LD50 intraperitoneal 8400ug/kg (8.4mg/kg)   Indian Journal of Biochemistry and Biophysics. Vol. 15, Pg. 336, 1978.
mouse LD50 oral 12200ug/kg (12.2mg/kg)   Agricultural and Biological Chemistry. Vol. 26, Pg. 257, 1962.
mouse LD50 skin 348mg/kg (348mg/kg)   Agricultural and Biological Chemistry. Vol. 26, Pg. 257, 1962.
mouse LD50 subcutaneous 22900ug/kg (22.9mg/kg)   Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 25, Pg. 635, 1978.
pigeon LD50 oral 4210ug/kg (4.21mg/kg)   ASTM Special Technical Publication. Vol. (680), Pg. 157, 1979.
quail LD50 oral 5mg/kg (5mg/kg)   Toxicology and Applied Pharmacology. Vol. 20, Pg. 57, 1971.
rabbit LD50 skin 30mg/kg (30mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: OTHER CHANGES
Quarterly Bulletin--Association of Food and Drug Officials of the United States. Vol. 16, Pg. 3, 1952.
rabbit LDLo intraperitoneal 20mg/kg (20mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 112, Pg. 29, 1954.
rat LC50 inhalation 106mg/m3/1H (106mg/m3) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

PERIPHERAL NERVE AND SENSATION: FASCICULATIONS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
National Technical Information Service. Vol. OTS0570820,
rat LD50 intraperitoneal 7200ug/kg (7.2mg/kg)   Advances in Pest Control Research. Vol. 4, Pg. 117, 1961.
rat LD50 oral 7mg/kg (7mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 112, Pg. 29, 1954.
rat LD50 skin 25mg/kg (25mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT
Toxicology and Applied Pharmacology. Vol. 2, Pg. 88, 1960.
rat LD50 unreported 7mg/kg (7mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 128, Pg. 289, 1960.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 36 deg C   EXP
log P (octanol-water) 4.78 (none)   EXP
Water Solubility 3.11 mg/L 23 EXP
Vapor Pressure 9.50E-07 mm Hg 25 EXP
Henry's Law Constant 4.44E-07 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 7.47E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.