Bicyclic Phosphate

Bicyclic phosphate is a class of organophosphate compounds that are used as flame retardants, stabilizers and antioxidants. They are also used in spectroscopic studies.^[1]^[2]

Some bicyclic phosphates, such as TBPS, TBPO and IPTBO, are highly toxic. They have toxicity comparable to nerve agents. However, they are not acetylcholinesterase inhibitors.^[1] They act as GABA receptor antagonists and have potent convulsant effects.^[2]^[3]^[4]

References

^ ^a ^b Bellet, E. M.; Casida, J. E. (14 December 1973). "Bicyclic Phosphorus Esters: High Toxicity without Cholinesterase Inhibition". Science. 182 (4117): 1135–1136. Bibcode: 1973Sci...182.1135B. doi: 10.1126/science.182.4117.1135. PMID 4356280. S2CID 9462533.
^ ^a ^b Gupta, Ramesh C., ed. (2009). Handbook of toxicology of chemical warfare agents (1st ed.). London: Academic Press. ISBN 9780123744845.
^ BOWERY, N. G.; COLLINS, J. F.; HILL, R. G. (17 June 1976). "Bicyclic phosphorus esters that are potent convulsants and GABA antagonists". Nature. 261 (5561): 601–603. Bibcode: 1976Natur.261..601B. doi: 10.1038/261601a0. PMID 934303. S2CID 4184150.
^ Ellison, D. Hank (2007). Handbook of chemical and biological warfare agents (2nd ed.). Boca Raton, Fla.: CRC. ISBN 9780849314346.

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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 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
Other	Dimethylcadmium Dimethylmercury Toxopyrimidine IDPN Tetraethyllead