IMP-pNP
sarin analogue. Less toxic but giving the same adduct close to parathion methyl parathion
General
Type : Organophosphate, Surrogate OP, Nerve Agent G-series, pNP, Derivative of Sarin
Chemical_Nomenclature : 1-[methyl(propan-2-yloxy)phosphoryl]oxy-4-nitrobenzene
Canonical SMILES : CC(C)OP(=O)(C)OC1=CC=C(C=C1)[N+](=O)[O-]
InChI : InChI=1S\/C10H14NO5P\/c1-8(2)15-17(3,14)16-10-6-4-9(5-7-10)11(12)13\/h4-8H,1-3H3
InChIKey : YSHVIWJFWCEDSQ-UHFFFAOYSA-N
Other name(s) : 4-Nitrophenyl 2-propylmethylphosphonate || BRN 2220854 || Isopropyl p-nitrophenyl methylphosphonate || P-Nitrophenyl isopropyl methylphosphonate || 4-nitrophenyl propan-2-yl methylphosphonate || 4-nitrophenyl isopropylmethylphosphonate || ST50983466 || NIMP || Isopropyl (4-nitrophenyl) methylphosphonate
Target
Families : IMP-pNP ligand of proteins in family
ACHE
Cholesterol_esterase
Structure :
6H18
Protein :
human-ACHE
human-CEL
References (14)
| Title : Premature aging and neuropathic behaviours induced by an acute low-dose exposure to a sarin surrogate - Champault_2025_Toxicology_519_154327 |
| Author(s) : Champault A , Leterrier S , Bel R , Knoertzer J , Soyer A , Goutal S , Baati R , Francois S , Tournier N , Dal Bo G , Thibault K |
| Ref : Toxicology , 519 :154327 , 2025 |
| Abstract : |
| PubMedSearch : Champault_2025_Toxicology_519_154327 |
| PubMedID: 41173233 |
| Title : Characterization and comparison of respiratory toxicity induced by sublethal poisoning to two organophosphorus compounds: a pesticide and a sarin structural analog in mice - Hanak_2025_Toxicology__154276 |
| Author(s) : Hanak AS , Femy F , Berriche A , Reymond C , Rotiel T , Madi M , Jaffre N , Calas AG , Dal Bo G , Thibault K |
| Ref : Toxicology , :154276 , 2025 |
| Abstract : |
| PubMedSearch : Hanak_2025_Toxicology__154276 |
| PubMedID: 40902968 |
| Title : Long-Term Anxiety-like Behavior and Microbiota Changes Induced in Mice by Sublethal Doses of Acute Sarin Surrogate Exposure - Francois_2022_Biomedicines_10_ |
| Author(s) : Francois S , Mondot S , Gerard Q , Bel R , Knoertzer J , Berriche A , Cavallero S , Baati R , Orset C , Dal Bo G , Thibault K |
| Ref : Biomedicines , 10 : , 2022 |
| Abstract : |
| PubMedSearch : Francois_2022_Biomedicines_10_ |
| PubMedID: 35625901 |
| Title : Effects of novel brain-penetrating oxime acetylcholinesterase reactivators on sarin surrogate-induced changes in rat brain gene expression - Dail_2021_J.Biochem.Mol.Toxicol__e22755 |
| Author(s) : Dail ME , Brino MLM , Chambers JE |
| Ref : J Biochem Mol Toxicol , :e22755 , 2021 |
| Abstract : |
| PubMedSearch : Dail_2021_J.Biochem.Mol.Toxicol__e22755 |
| PubMedID: 33682265 |
| Title : Persistent brainwave disruption and cognitive impairment induced by acute sarin surrogate sub-lethal dose exposure - Angrand_2021_Toxicology__152787 |
| Author(s) : Angrand L , Takillah S , Malissin I , Berriche A , Cervera C , Bel R , Gerard Q , Knoertzer J , Baati R , Kononchik JP , Megarbane B , Thibault K , Dal Bo G |
| Ref : Toxicology , :152787 , 2021 |
| Abstract : |
| PubMedSearch : Angrand_2021_Toxicology__152787 |
| PubMedID: 33887375 |
| Title : X-ray structures of human bile-salt activated lipase conjugated to nerve agents surrogates - Touvrey_2019_Toxicology_411_15 |
| Author(s) : Touvrey C , Courageux C , Guillon V , Terreux R , Nachon F , Brazzolotto X |
| Ref : Toxicology , 411 :15 , 2019 |
| Abstract : |
| PubMedSearch : Touvrey_2019_Toxicology_411_15 |
| PubMedID: 30359675 |
| Gene_locus related to this paper: human-CEL |
| Title : The inhibition, reactivation and mechanism of VX-, sarin-, fluoro-VX and fluoro-sarin surrogates following their interaction with HuAChE and HuBuChE - Chao_2018_Chem.Biol.Interact_291_220 |
| Author(s) : Chao CK , Balasubramanian N , Gerdes JM , Thompson CM |
| Ref : Chemico-Biological Interactions , 291 :220 , 2018 |
| Abstract : |
| PubMedSearch : Chao_2018_Chem.Biol.Interact_291_220 |
| PubMedID: 29920286 |
| Title : Comparison of inhibition kinetics of several organophosphates, including some nerve agent surrogates, using human erythrocyte and rat and mouse brain acetylcholinesterase - Coban_2016_Toxicol.Lett_248_39 |
| Author(s) : Coban A , Carr RL , Chambers HW , Willeford KO , Chambers JE |
| Ref : Toxicol Lett , 248 :39 , 2016 |
| Abstract : |
| PubMedSearch : Coban_2016_Toxicol.Lett_248_39 |
| PubMedID: 26965078 |
| Title : Novel brain-penetrating oximes for reactivation of cholinesterase inhibited by sarin and VX surrogates - Chambers_2016_Ann.N.Y.Acad.Sci_1374_52 |
| Author(s) : Chambers JE , Meek EC , Chambers HW |
| Ref : Annals of the New York Academy of Sciences , 1374 :52 , 2016 |
| Abstract : |
| PubMedSearch : Chambers_2016_Ann.N.Y.Acad.Sci_1374_52 |
| PubMedID: 27153507 |
| Title : Testing of novel brain-penetrating oxime reactivators of acetylcholinesterase inhibited by nerve agent surrogates - Chambers_2013_Chem.Biol.Interact_203_135 |
| Author(s) : Chambers JE , Chambers HW , Meek EC , Pringle RB |
| Ref : Chemico-Biological Interactions , 203 :135 , 2013 |
| Abstract : |
| PubMedSearch : Chambers_2013_Chem.Biol.Interact_203_135 |
| PubMedID: 23123249 |
| Title : Synthesis and in vitro and in vivo inhibition potencies of highly relevant nerve agent surrogates - Meek_2012_Toxicol.Sci_126_525 |
| Author(s) : Meek EC , Chambers HW , Coban A , Funck KE , Pringle RB , Ross MK , Chambers JE |
| Ref : Toxicol Sci , 126 :525 , 2012 |
| Abstract : |
| PubMedSearch : Meek_2012_Toxicol.Sci_126_525 |
| PubMedID: 22247004 |
| Title : Asymmetric fluorogenic organophosphates for the development of active organophosphate hydrolases with reversed stereoselectivity - Amitai_2007_Toxicology_233_187 |
| Author(s) : Amitai G , Adani R , Yacov G , Yishay S , Teitlboim S , Tveria L , Limanovich O , Kushnir M , Meshulam H |
| Ref : Toxicology , 233 :187 , 2007 |
| Abstract : |
| PubMedSearch : Amitai_2007_Toxicology_233_187 |
| PubMedID: 17129656 |
| Title : Enhanced stereoselective hydrolysis of toxic organophosphates by directly evolved variants of mammalian serum paraoxonase - Amitai_2006_FEBS.J_273_1906 |
| Author(s) : Amitai G , Gaidukov L , Adani R , Yishay S , Yacov G , Kushnir M , Teitlboim S , Lindenbaum M , Bel P , Khersonsky O , Tawfik DS , Meshulam H |
| Ref : Febs J , 273 :1906 , 2006 |
| Abstract : |
| PubMedSearch : Amitai_2006_FEBS.J_273_1906 |
| PubMedID: 16640555 |
| Title : New safe method for preparation of sarin-exposed human erythrocytes acetylcholinesterase using non-toxic and stable sarin analogue isopropyl p-nitrophenyl methylphosphonate and its application to evaluation of nerve agent antidotes - Ohta_2006_Pharm.Res_23_2827 |
| Author(s) : Ohta H , Ohmori T , Suzuki S , Ikegaya H , Sakurada K , Takatori T |
| Ref : Pharm Res , 23 :2827 , 2006 |
| Abstract : |
| PubMedSearch : Ohta_2006_Pharm.Res_23_2827 |
| PubMedID: 17096183 |