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Details

Stereochemistry ACHIRAL
Molecular Formula C10H19ClNO5P
Molecular Weight 299.688
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PHOSPHAMIDON, (E)-

SMILES

CCN(CC)C(=O)C(\Cl)=C(\C)OP(=O)(OC)OC

InChI

InChIKey=RGCLLPNLLBQHPF-CMDGGOBGSA-N
InChI=1S/C10H19ClNO5P/c1-6-12(7-2)10(13)9(11)8(3)17-18(14,15-4)16-5/h6-7H2,1-5H3/b9-8+

HIDE SMILES / InChI
Molecular Formula C10H19ClNO5P
Molecular Weight 299.688
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Phosphamidon is an organophosphorus insecticide widely used in agriculture, which consists of two isomers Z and E. Phosphamidon is highly toxic to mammals and was shown to inhibit acetylcholinesterase in the brain of the hen.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
acetylcholinesterase of hen brain
2
Target ID: acetylcholinesterase of hen brain
Inhibitor
8504
 2.9 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Different responses of E:Z-isomers of pesticides in liquid chromatography-electrospray ionization-mass spectrometry.
2010-07
Persistence of residues of the insecticide phosphamidon on and in oranges, lemons, and grapefruit, and on and in orange leaves and in dried citrus pulp cattle feed.
1973-09-01
Chemical and physical properties of phosphamidon.
1971
Toxicology of phosphamidon.
1971
[Toxicology and pharmacology of a new systemically active insecticide of the phosphate ester series, Phosphamidon (2-chloro-2-diethylcarbamoyl-1-methylvinyl dimethyl phosphate)].
1960

Sample Use Guides

In Vivo Use Guide
The LD50 value of phosphamidon p.o. for hens was 9 mg/kg
Route of Administration: Oral
In Vitro Use Guide
Phosphamidon (PSM) was a potent inhibitor of acetylcholinesterase (AChE), with an I50 of 2.9 microM and second-order rate constant (ka) of 1.2 x 10(4) M-1 min-1 at 37 degrees C. PSM-inhibited AChE aged rapidly (t1/2 = 1.9 h).
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:13:43 GMT 2025
Edited
by admin
on Mon Mar 31 18:13:43 GMT 2025
Record UNII
54VR7A0BQD
Record Status Validated (UNII)
Record Version
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Name Type Language
PHOSPHAMIDON, (E)-
Common Name English
PHOSPHAMIDON, E ISOMER
Preferred Name English
PHOSPHORIC ACID, (1E)-2-CHLORO-3-(DIETHYLAMINO)-1-METHYL-3-OXO-1-PROPEN-1-YL DIMETHYL ESTER
Systematic Name English
PHOSPHAMIDON, TRANS-
Common Name English
(E)-2-CHLORO-2-DIETHYLCARBAMOYL-1-METHYLVINYL DIMETHYL PHOSPHATE
Systematic Name English
Code System Code Type Description
PUBCHEM
3033834
Created by admin on Mon Mar 31 18:13:43 GMT 2025 , Edited by admin on Mon Mar 31 18:13:43 GMT 2025
PRIMARY
FDA UNII
54VR7A0BQD
Created by admin on Mon Mar 31 18:13:43 GMT 2025 , Edited by admin on Mon Mar 31 18:13:43 GMT 2025
PRIMARY
CAS
297-99-4
Created by admin on Mon Mar 31 18:13:43 GMT 2025 , Edited by admin on Mon Mar 31 18:13:43 GMT 2025
PRIMARY
EPA CompTox
DTXSID5058357
Created by admin on Mon Mar 31 18:13:43 GMT 2025 , Edited by admin on Mon Mar 31 18:13:43 GMT 2025
PRIMARY
NIH
NCATS
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