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TBPO^[1]
Names

Preferred IUPAC name 4-tert-Butyl-2,6,7-trioxa-1λ⁵-phosphabicyclo[2.2.2]octan-1-one
Other names t-Butyl-bicyclophosphate
Identifiers
CAS Number	61481-19-4
3D model (JSmol)	Interactive image
ChemSpider	39799
PubChem CID	43673
CompTox Dashboard (EPA)	DTXSID80977049
InChI InChI=1S/C8H15O4P/c1-7(2,3)8-4-10-13(9,11-5-8)12-6-8/h4-6H2,1-3H3 Key: CNBZOKKOTFTYLW-UHFFFAOYSA-N
SMILES CC(C)(C)C12COP(=O)(OC1)OC2
Properties
Chemical formula	C₈H₁₅O₄P
Molar mass	206.178 g·mol⁻¹
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Extremely toxic
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	36 μg/kg (mice)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.^[2]

Some sources claim that TBPO is as toxic as VX.^[3]

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.

^ Zhao, C.; Hwang, S. H.; Buchholz, B. A.; Carpenter, T. S.; Lightstone, F. C.; Yang, J.; Hammock, B. D.; Casida, J. E. (27 May 2014). "GABAA receptor target of tetramethylenedisulfotetramine". Proceedings of the National Academy of Sciences. 111 (23): 8607–8612. Bibcode:2014PNAS..111.8607Z. doi:10.1073/pnas.1407379111. PMC 4060666. PMID 24912155.
^ Milbrath, Dean S.; Engel, Judith L.; Verkade, John G.; Casida, John E. (February 1979). "Structure-toxicity relationships of 1-substituted-4-alkyl-2,6,7-trioxabicyclo[2.2.2.]octanes". Toxicology and Applied Pharmacology. 47 (2): 287–293. Bibcode:1979ToxAP..47..287M. doi:10.1016/0041-008x(79)90323-5. PMID 452023.
^ Gupta RC (2015). Handbook of toxicology of chemical warfare agents (2nd ed.). Amsterdam: Elsevier/Academic Press. pp. 228–229. ISBN 9780128004944. OCLC 433545336.

v t e Convulsants
GABA receptor antagonists	Bicuculline Bicyclic phosphates (TBPS, TBPO, IPTBO) BIDN Chlorophenylsilatrane Cicutoxin Cloflubicyne Coriamyrtin Dihydropicrotoxinin DMCM EBOB Endosulfan FG-7142 Fipronil Flurothyl Gabazine Oenanthotoxin Pentylenetetrazol Phenylsilatrane Picrotoxin p-CN-TBOB p-NCS-TBOB RDX TBOB Tetramethylenedisulfotetramine Thujone Trimethylolpropane phosphite Tutin
GABA synthesis inhibitors	3-Mercaptopropionic acid 4-Deoxypyridoxine Allylglycine Crimidine Decaborane Ginkgotoxin Isoniazid Pentaborane Thiocarbohydrazide Toxopyrimidine
Glycine receptor antagonists	Coriamyrtin Dendrobine Picrotoxin Strychnine Tutin
Glutamate receptor agonists	AMPA Domoic acid Kainic acid NMDA Quisqualic acid Tetrazolylglycine
Convulsant barbiturates	CHEB Diberal (DMBB) McN-481
Other	2,2,3,3-Tetrafluoropropyl trifluoromethyl ether Bromocamphor Camphor FAZ-4 Fluoroethyl fluoroacetate MC-2973 Methionine sulfoximine Methyl fluoroacetate Nitrocyclohexane Thebaine

v t e Neurotoxins
Animal toxins	Batrachotoxin Bestoxin Birtoxin Bungarotoxin Charybdotoxin Conotoxin Fasciculin Huwentoxin Poneratoxin Saxitoxin Tetrodotoxin Vanillotoxin Spooky toxin (SsTx) Epibatidine Zetekitoxin AB Dendrotoxin
Bacterial	Botulinum toxin Tetanospasmin
Cyanotoxins	Anatoxin-a Guanitoxin BMAA Saxitoxin
Plant toxins	Aconitine Bicuculline Penitrem A Picrotoxin Strychnine Tutin Rotenone Ginkgotoxin Cicutoxin Oenanthotoxin Thujone Volkensin Veratridine
Mycotoxins	Ibotenic acid Muscarine Muscimol
Pesticides	Fenpropathrin Tetramethylenedisulfotetramine Bromethalin Crimidine Methamidophos Endosulfan Fipronil Phenylsilatrane Chlorophenylsilatrane Sulfuryl fluoride Mipafox Schradan Dimefox
Nerve agents	Cyclosarin EA-3148 Novichok agent Sarin Soman Tabun VE VG VM VP VR VX GV EA-3990 EA-4056 T-1123 Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) Fluorotabun Chinese VX EA-2192
Bicyclic phosphates	TBPS TBPO IPTBO
Cholinergic neurotoxins	Acetylcholine mustard Catecholine Choline mustard Ethylcholine mustard Hemicholinium mustard
Psychoactive drugs	Alcohol Nitrous oxide
Other	Dimethylcadmium Dimethylmercury Toxopyrimidine IDPN Tetraethyllead