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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, (Z)-

SMILES

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

InChI

InChIKey=RGCLLPNLLBQHPF-HJWRWDBZSA-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
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
acetylcholinesterase of hen brain
2
Target ID: acetylcholinesterase of hen brain
Inhibitor
8297
 2.9 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
[Toxicology and pharmacology of a new systemically active insecticide of the phosphate ester series, Phosphamidon (2-chloro-2-diethylcarbamoyl-1-methylvinyl dimethyl phosphate)].
1960
Chemical and physical properties of phosphamidon.
1971
Toxicology of phosphamidon.
1971
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 Sep-Oct
Different responses of E:Z-isomers of pesticides in liquid chromatography-electrospray ionization-mass spectrometry.
2010 Jul

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 Fri Dec 15 15:54:36 UTC 2023
Edited
by admin
on Fri Dec 15 15:54:36 UTC 2023
Record UNII
HQ7958Q90Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHOSPHAMIDON, (Z)-
Common Name English
PHOSPHAMIDON, CIS-
Common Name English
PHOSPHORIC ACID, (1Z)-2-CHLORO-3-(DIETHYLAMINO)-1-METHYL-3-OXO-1-PROPEN-1-YL DIMETHYL ESTER
Systematic Name English
(Z)-2-CHLORO-2-DIETHYLCARBAMOYL-1-METHYLVINYL DIMETHYL PHOSPHATE
Systematic Name English
PHOSPHAMIDON, Z ISOMER
Common Name English
Code System Code Type Description
CAS
23783-98-4
Created by admin on Fri Dec 15 15:54:36 UTC 2023 , Edited by admin on Fri Dec 15 15:54:36 UTC 2023
PRIMARY
PUBCHEM
3032604
Created by admin on Fri Dec 15 15:54:36 UTC 2023 , Edited by admin on Fri Dec 15 15:54:36 UTC 2023
PRIMARY
FDA UNII
HQ7958Q90Z
Created by admin on Fri Dec 15 15:54:36 UTC 2023 , Edited by admin on Fri Dec 15 15:54:36 UTC 2023
PRIMARY
EPA CompTox
DTXSID601030915
Created by admin on Fri Dec 15 15:54:36 UTC 2023 , Edited by admin on Fri Dec 15 15:54:36 UTC 2023
PRIMARY
NIH
NCATS
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