DƯỢC LÍ Goodman & Gilman's The Pharmacological Basis of Therapeutics 12th, 2010

Table 10–1
Chemical Classification of Representative Organophosphorus Compounds of Particular Pharmacological or
Toxicological Interest
General formula
Group A, X = halogen, cyanide, or thiocyanate leaving group; group B, X = alkylthio, arylthio, alkoxy, or aryloxy leaving
group; group C, thionophosphorus or thio-thionophosphorus compounds; group D, quaternary ammonium leaving group.
R 1
can be an alkyl (phosphonates), alkoxy (phosphorates) or an alkylamino (phosphoramidates) group.
GROUP STRUCTURAL FORMULA COMMON, CHEMICAL, AND OTHER NAMES COMMENTS
A i-C 3 H 7 O O
DFP; Isoflurophate; Potent, irreversible
P
diisopropyl fluorophosphate
inactivator
i-C 3 H 7 O
(CH 3 ) 2 N
C 2 H 5 O
i-C 3 H 7 O
CH 3
P
P
F
O
CN
O
F
CH 3 CH 3
CH 3 C C
CH 3
O
H
CH 3
O
P
F
Tabun
Ethyl N-
dimethylphosphoramidocyanidate
Sarin (GB)
Isopropyl
methylphosphonofluoridate
Soman (GD)
Pinacolyl
methylphosphonofluoridate
Extremely toxic “nerve gas”
Extremely toxic “nerve gas”
Extremely toxic “nerve gas”;
greatest potential for
irreversible action/
rapid aging
B C 2 H 5 O O
Paraoxon (MINTACOL), E 600 Active metabolite of
P
O,O-Diethyl O-(4-nitrophenyl)-
parathion
C 2 H 5 O O NO 2
phosphate
CH 3 O O
Malaoxon
Active metabolite of
P
O,O-Dimethyl S-
malathion
CH 3 O S CHCOOC 2 H 5
(1,2-dicarboxyethyl)-
phosphorothioate
CH 2 COOC 2 H 5
C C 2 H 5 O S
Parathion Agricultural insecticide,
P
O,O-Diethyl O-
resulting in numerous
C 2 H 5 O O NO 2
(4-nitrophenyl)-
cases of accidental
phosphorothioate
poisoning; phased
out in 2003.
CH 3 Diazinon, Dimpylate
Insecticide; use limited
C 2 H 5 O S
O,O-Diethyl O-
to non-residential
P
N
(2-isopropyl-6-methyl-
agricultural settings
C 2 H 5 O O
CH 3
N CH 4-pyrimidinyl) phosphorothioate
CH 3
(Continued )