IMP-pNP
sarin analogue. Less toxic but giving the same adduct close to parathion methyl parathion. Also inhibits fatty acid amide hydrolase (FAAH not analpha beta hydrolase) and monoacylglycerol lipase (MAGL)
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
Monoglyceridelipase_lysophospholip
Structure :
6H18
Protein :
human-ACHE
human-CEL
human-MGLL
References (17)
| Title : Imidazole as a Pendant Reactivation Ligand Increases Efficacy Scope for Reactivation and Resurrection of Organophosphorus-Inhibited\/Aged Cholinesterases by Quinone Methide Precursors - Lovins_2026_ACS.Chem.Neurosci__ |
| Author(s) : Lovins AR , Miller KA , Homoelle RK , Hoover HJ , McElroy CA , Callam CS , Hadad CM |
| Ref : ACS Chem Neurosci , : , 2026 |
| Abstract : |
| PubMedSearch : Lovins_2026_ACS.Chem.Neurosci__ |
| PubMedID: 41712538 |
| Title : Serine Hydrolase Targets of a Sarin Surrogate Anticholinesterase and Oxime Mediated Reactivation in Rat Brain - Price_2026_Toxicol.Sci__ |
| Author(s) : Price CY , Meek EC , Ross MK , Chambers JE |
| Ref : Toxicol Sci , : , 2026 |
| Abstract : |
| PubMedSearch : Price_2026_Toxicol.Sci__ |
| PubMedID: 41818676 |
| Title : Non-oxime reactivators of organophosphate-inhibited cholinesterases - Knittelova_2025_Arch.Toxicol__ |
| Author(s) : Knittelova K , Kohoutova Z , Prchalova E , Musilek K , Malinak D |
| Ref : Archives of Toxicology , : , 2025 |
| Abstract : |
| PubMedSearch : Knittelova_2025_Arch.Toxicol__ |
| PubMedID: 40317339 |
| 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 : 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 : 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 |