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Substance Name: p-Nitrophenyl-O-ethyl ethylphosphonate [JAN]
RN: 546-71-4
UNII: H39MRI1X2O
InChIKey: XXUJMEYKYHETBZ-UHFFFAOYSA-N

Note

  • A reversible organophosphorus cholinesterase inhibitor. It also affects the presynaptic membrane and inhibits membrane postsynaptic cholinergic receptors. The compound had former use as a miotic.

Molecular Formula

  • C10-H14-N-O5-P

Molecular Weight

  • 259.1966
 

Classification Codes

  • Cholinergic Agents
  • Cholinesterase Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Neurotransmitter Agents
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Names and Synonyms

Name of Substance

  • Armin
  • p-Nitrophenyl-O-ethyl ethylphosphonate [JAN]

MeSH Heading

  • Armin

Synonyms

  • 4-06-00-01319 (Beilstein Handbook Reference)
  • Armin (ester)
  • Armine
  • Arminum
  • BRN 1990082
  • Ethoxy-4-nitrophenyloxyethyl-phosphineoxide
  • Ethyl-4-nitrophenyl ethylphosphonate
  • Ethylphosphonic acid ethyl p-nitrophenyl ester
  • p-Nitrophenyl-O-ethyl ethylphosphonate
  • UNII-H39MRI1X2O

Systematic Names

  • Ethyl p-nitrophenyl ethylphosphonate
  • Phosphonic acid, ethyl-, ethyl p-nitrophenyl ester

Registry Numbers

CAS Registry Number

  • 546-71-4

FDA UNII

  • H39MRI1X2O

Other Registry Number

  • 8053-54-1

System Generated Number

  • 0000546714

Structure Descriptors

InChI

1S/C10H14NO5P/c1-3-15-17(14,4-2)16-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3

InChIKey

XXUJMEYKYHETBZ-UHFFFAOYSA-N

Smiles

CCOP(=O)(CC)Oc1ccc(cc1)[N+](=O)[O-]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1862ug/kg (1.862mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) Pharmazie. Vol. 35, Pg. 806, 1980.
mouse LD50 intravenous 250ug/kg (0.25mg/kg)   Russian Pharmacology and Toxicology Vol. 42, Pg. 106, 1979.
mouse LD50 subcutaneous 250ug/kg (0.25mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 2, Pg. 411, 1968.
mouse LD50 unreported 460ug/kg (0.46mg/kg)   Pharmaceutical Chemistry Journal Vol. 3, Pg. 508, 1969.
rat LD50 intravenous 250ug/kg (0.25mg/kg) LUNGS, THORAX, OR RESPIRATION: BRONCHIOLAR CONSTRICTION

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Farmakologiya i Toksikologiya Vol. 42, Pg. 299, 1979.
rat LD50 subcutaneous 230ug/kg (0.23mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 2, Pg. 411, 1968.