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Details

Stereochemistry ACHIRAL
Molecular Formula C10H14NO6P
Molecular Weight 275.195
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PARAOXON

SMILES

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

InChI

InChIKey=WYMSBXTXOHUIGT-UHFFFAOYSA-N
InChI=1S/C10H14NO6P/c1-3-15-18(14,16-4-2)17-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C10H14NO6P
Molecular Weight 275.195
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Paraoxon is an odorless, reddish-yellow oil. Paraoxon is an aryl dialkyl phosphate where both the alkyl groups are ethyl and the aryl group is 4-nitrophenyl. It is a cholinesterase or acetylcholinesterase (AChE) inhibitor. It is an organophosphate oxon, and the active metabolite of the insecticide parathion. Paraoxon is one of the most potent acetylcholinesterase-inhibiting insecticides available, around 70% as potent as the nerve agent sarin, and so is now rarely used as an insecticide due to the risk of poisoning to humans and other animals. Exposure to Paraoxon can cause rapid, severe organophosphate poisoning with headache, sweating, nausea and vomiting, diarrhea, loss of coordination, and death. Paraoxon is on the Hazardous Substance List because it is cited by DOT and EPA. Parathion is converted in the body in part to paraoxon, a strong inhibitor of the enzyme acetyl cholinesterase. Upon inhibition of this enzyme in the tissues, acetylcholine, the substance responsible for transmission of nerve impulses in much of the nervous system, accumulates, producing an initial overstimulation and subsequent blockage of nerve stimuli. Paraoxon was once used as an opthamological drug against glaucoma.

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
Male Wistar rats received an intraperitoneal (i.p.) injection of one of three doses of paraoxon (0.3, 0.7, or 1mg/kg) or corn oil as vehicle (1ml/kg). he cortical glial glutamate transporters (GLAST and GLT-1) were up-regulated in animals treated with 0.7mg/kg of paraoxon, but down-regulated in 1mg/kg group. Neuronal glutamate transporter (EAAC1) was unchanged in 0.7mg/kg treated rats, while reduced in 1mg/kg group. No significant difference was found in the mRNA and protein expression of EAAC1 in animals intoxicated with 0.3mg/kg of paraoxon. Paraoxon (1mg/kg) resulted in an up-regulation of Bax and down-regulation of Bcl2 mRNA levels in the rat cerebral cortex.
Route of Administration: Intraperitoneal
Substance Class Chemical
Record UNII
Q9CX8P80JW
Record Status Validated (UNII)
Record Version