TBPO
{{Chembox
| ImageFile = TBPO.svg
| ImageSize = 120px
| PIN=4-tert-Butyl-2,6,7-trioxa-1λ5-phosphabicyclo[2.2.2]octan-1-one
| OtherNames= t-Butyl-bicyclophosphate
| Section1 = {{Chembox Identifiers
| CASNo = 61481-19-4
| ChemSpiderID = 39799
| PubChem = 43673
| StdInChI=1S/C8H15O4P/c1-7(2,3)8-4-10-13(9,11-5-8)12-6-8/h4-6H2,1-3H3
| StdInChIKey = CNBZOKKOTFTYLW-UHFFFAOYSA-N
| SMILES = CC(C)(C)C12COP(=O)(OC1)OC2
}}
| Section2 = {{Chembox Properties
| C=8|H=15|O=4|P=1
}}
| Section3 = {{Chembox Hazards
| MainHazards = Extremely toxic
| LD50 = 36 μg/kg (mice)
}}
}}
TBPO is an extremely toxic bicyclic phosphate convulsant and GABA receptor antagonist. It is the most toxic bicyclic phosphate known, with an {{LD50}} of 36 μg/kg in mice.{{cite journal |last1=Milbrath |first1=Dean S. |last2=Engel |first2=Judith L. |last3=Verkade |first3=John G. |last4=Casida |first4=John E. |title=Structure-toxicity relationships of 1-substituted-4-alkyl-2,6,7-trioxabicyclo[2.2.2.]octanes |journal=Toxicology and Applied Pharmacology |date=February 1979 |volume=47 |issue=2 |pages=287–293 |doi=10.1016/0041-008x(79)90323-5 |pmid=452023|bibcode=1979ToxAP..47..287M }}
Some sources claim that TBPO is as toxic as VX.{{Cite book|title=Handbook of toxicology of chemical warfare agents|last=Gupta|first=Ramesh Chandra | name-list-style = vanc |publisher=Elsevier/Academic Press|year=2015|isbn=9780128004944|edition= 2nd|location=Amsterdam|pages=228–229|oclc=433545336}}
Synthesis
The synthesis is equivalent to the synthesis of IPTBO while the triol is produced by the condensation between 3,3-dimethylbutyraldehyde and formaldehyde analogous to the synthesis of trimethylolpropane.
See also
References
{{reflist}}
{{Convulsants}}
{{Neurotoxins}}
{{GABA receptor modulators}}
Category:GABAA receptor negative allosteric modulators
{{Neurotoxin-stub}}