IPTBO
From Wikipedia, the free encyclopedia
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| Names | |
|---|---|
| Preferred IUPAC name
4-(Propan-2-yl)-2,6,7-trioxa-1λ5-phosphabicyclo[2.2.2]octan-1-one | |
| Other names
4-Isopropylbicyclophosphate | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C7H13O4P | |
| Molar mass | 192.151 g·mol−1 |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
Extremely toxic |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
180 μg/kg (mice)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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IPTBO (isopropylbicyclophosphate, also IPPO[2]) is a bicyclic phosphate convulsant.[3] It is an extremely potent GABA receptor antagonist that can cause violent convulsions in mice.[4][5]
IPTBO is found among a group of highly toxic bicyclic phosphates. Generally, bicyclic phosphates disrupt chloride ion flow through GABA receptors, causing CNS overstimulation and lethal convulsions within minutes. IPTBO has these effects when injected, inhaled, or ingested and is one of the more toxic types of this antagonist.[6]
Derivatives of IPTBO are used in spectroscopic studies and as flame retardants, vinyl resin stabilizers, and antioxidants (due to their ability to terminate oxidation reactions). It had also previously been used as plane engine lubricant, and contributed to "aerotoxic syndrome".[7]
Generally speaking, toxic phosphorus esters are used as insecticides or chemical weapons (such as DFP), but unlike most phosphorus esters, IPTBO doesn't inhibit acetylcholinesterase, despite this is highly toxic like similar phosphorus esters.[8] IPTBO and other similar compounds are all derivatives of 2,6,7-trioxa-phospabicyclo[2,2,2]octane, with the most toxic ones having four alkyl groups substituted. The prominence of this compound is still a subject of research and the structural similarity of this compound to adenosine 3',5'-monophosphate (i.e. cyclic AMP) and its ability to poison via a mechanism different from that of any other known organophosphorus toxicant makes it a topic of interest in research.[9][7]
Synthesis
IPTBO can be synthesized through many reaction paths. All synthesis routes are described to start with an isopropyl triol (an isopropyl group with three hydroxyl groups attached to the stem) and the addition of a phosphorus reagent that must be "caged," i.e. surrounded by oxygen molecules.[9] This specific experiment studied the chemical attribution markers for various preparation methods of IPTBO. The myriad ways in which to produce the IPTBO also lead to the production of many different side products, some of which may contain impurities or degradation products. Known attribution factors can be used to mark a recovered substance to a production method, which can be helpful in forensic studies. There are 5 primary production methods for IPTBO. They all start with a triol group, but differ in the phosphorus-containing compounds.