Isopropyl methylphosphonic acid

Diisopropyl methylphosphonate is rapidly absorbed following oral administration in animals and is widely distributed throughout the body. Two metabolites of diisopropyl methylphosphonate are isopropyl methylphosphonic acid (IMPA) and methylphosphonic acid (MPA). Excretion of these metabolites in animals occurs primarily through the urine. 

EPA. 1992. Health advisory for isopropyl methylphosphonic acid (IMPA). U.S. Environmental Protection Agency, Office of the Assistant Administrator for Water. NTIS No. PB92-232149. 

Hoskin FCG. 1956. Some observations concerning the biochemical inertness of methyl phosphonic and isopropyl methylphosphonic acids. Can J Biochem Physiol 34 743-746. 

IMPA IT-SIMS isopropyl methylphosphonic acid ion-trap secondary ion mass spectometry... 

G.A. Sega, B.A. Tomkins and W.H. Griest, Analysis of methylphosphonic acid, ethyl methylphos-phonic acid and isopropyl methylphosphonic acid at low microgram per liter levels in groundwater, J. Chromatogr. A, 790, 143-152 (1997). 

D. Noort, A.G. Hulst, D.H.J.M. Platenburg, M. Polhuijs and H.P. Benschop, Quantitative analysis of O -isopropyl methylphosphonic acid in serum samples of Japanese citizens allegedly exposed to sarin estimation of internal dosage, Arch. Toxicol., 72, 671-675 (1998). 

The hydrolytic displacement method was applied to four victims killed in the Tokyo subway attack (two died immediately and two later in hospital). Isopropyl methylphosphonic acid was identified at levels sufficient for full scan mass spectra to be obtained using a benchtop quadmpole mass spectrometer (46). Methylphosphonic acid was also identified. Some two years later, methylphosphonic acid... 

Sarin is metabolized to isopropyl methylphosphonic acid (IMPA) and excreted by the kidneys (Little et al, 1986). Approximately 50% of soman is converted to free pina-colyl-methylphosphonic acid within 1 min in mice. The half-life of this metabohte is less than 1 h (Reynolds et al,... 

In addition, due to the reversibility of the binding reaction of sarin and soman to CarbE, it appears that CarbEs are involved in metabolic detoxification of these agents to their corresponding nontoxic metabolites isopropyl methylphosphonic acid (IMPA) and pinacolyl methylphosphonic acid (PMPA) (Jokanovic et al, 1996). 

FIGURE 52.1. Metabolic detoxification of warfare nerve agents tabun, sarin, soman, and VX in mammals in vivo. Chemical names of metabolites are EDMPA - ethyl dimethylaminophosphoric acid, IMPA - isopropyl methylphosphonic acid, PMPA - pinacolyl methyl-phosphonic acid, EMPA - ethyl methylphosphonic acid, and MPA - methylphosphonic acid. 

Evans, R.A., Jakubowski, E.M., Muse, W.T., Matson, K., Hulet, S.W., Mioduszewski, R.J., Thomson, S.A., Totura, A.L., Retmer, J.A., Crouse, C.L. (2008). Quantification of sarin and cyclosarin metabolites isopropyl methylphosphonic acid and cyclohexyl methylphosphonic acid in minipig plasma using isotope-dilution and liquid chromatography-time-of-flight mass spectrometry. J. Anal. Toxicol. 32(1) 78-85. 

Under acidic conditions, hydrogen fluoride (HF) and isopropyl methylphosphonic acid (IMPA) are formed which further hydrolyze to produce methylphosphonic acid (MPA) and isopropanol. Under alkahne condition, methylfluorophosphonic acid (MFPA) and isopropyl alcohol are initially formed which further hydrolyze to produce MPA and HF ... 

FIGURE 19.2 Hydrolysis pathway of sarin (GB), soman (GD), and cyclosarin (GIO hydrolysis pathway of nerve agents proceeds through the alkyl methylphosphonic acids, isopropyl methylphosphonic acid (IMPA), pinacolyl methylphosphonic acid (PMPA), and cyclohexyl methylphosphonic acid (CMPA) to methylphos-ponic acid (MPA). Analysis of the alkyl methylphosphonic acids allows identification of the parent agent, while assay of MPA is nonspecific. 

Agent GB isopropyl methylphosphonic acid methylphosphonic acid... 

GB hydrolyzes first through the loss of fluoride, producing isopropyl methylphosphonic acid (IMPA) and hydrofluoric acid, and second, more slowly through the loss of the isopropanol to produce MPA (Rosenblatt et al, 1995 MacNaughton and Brewer, 1994 Kingery and... 

Isopropyl methylphosphonic acid (IMPA) C4H11PO3 1832-54-8 Hydrolysis of GB... 

In the case of sarin-inhibited ChE, the phos-phyl moiety has also been displaced as isopropyl methylphosphonic acid using trypsin digestion and alkaline phosphatase (Nagao et al., 1997 Matsuda et al., 1998). 

Very high levels of isopropyl methylphosphonic acid 0 PrMPA) and methylphosphonic acid (MPA) were detected in the urine of a Matsumoto casualty with low blood AChE activity and rendered unconscious (Nakajima et al., 1998). Urine was collected over a 7-day period. Estimated concentrations of t PrMPA declined from 760 ng/ml to 10 ng/ml and MPA from 140 ng/ml to below the LOD. A crude estimate of the total exposure was 2.8 mg. i. PrMPA was also detected in urine collected over 7 days from casualties of the Tokyo attack (Minami et al., 1997). Concentrations were not reported but the estimated exposures were 0.13-0.25 mg... 

Large amounts of 0-isopropyl methylphosphonic acid were found in blood and nrine of victims of the terrorist attacks with sarin in Matsumoto and Tokyo. Until recently, it was assnmed that hydrolysis of phosphofluoridates in plasma and tissues of mammals proceeds exclusively by cleavage of the P F bond. For example, treatment of C( )P( )- P-soman with rat plasma or liver homogenate did not lead to any conversion of PMPA into the secondary hydrolysis product methylphosphonic acid (MPA). Ramachandran observed that the primary hydrolysis product of DF P, i.e., 0,0-diisopropyl P-phosphoric acid, is not metabolized after s.c. admiiustration to mice. Rather, the product was excreted unchanged into urine. However, Nakajima et al. reported that MPA was detected (in urine) until the third day after hospitalization of a victim of the terrorist attack with sarin in Matsumoto. This discrepancy needs further investigation. 

Hydrogen fluoride Isopropyl alcohol Isopropyl methylphosphonic acid Methylphosphonic acid... 

N -butylphosphonic acid, phenylphosphonic acid, ethyl methylphosphonic acid, ethyl methylthiophosphonic acid, isopropyl methylphosphonic acid, pinacolyl methylphosphonic acid, dimethyl phenylphosphonate in 16 min Methylphosphonic acid, ethylphosphonic acid, CZE... 

Imperial Chemical Industries isopropyl methylphosphonic acid impurities removal system... 

---