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TBPS^[1]
Names


Preferred IUPAC name 4-tert-Butyl-2,6,7-trioxa-1λ⁵-phosphabicyclo[2.2.2]octane-1-thione
Identifiers
CAS Number	70636-86-1
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL485673
ChemSpider	94586
KEGG	C19930
PubChem CID	104781
CompTox Dashboard (EPA)	DTXSID7058464
InChI InChI=1S/C8H15O3PS/c1-7(2,3)8-4-9-12(13,10-5-8)11-6-8/h4-6H2,1-3H3 Key: VTBHBNXGFPTBJL-UHFFFAOYSA-N
SMILES CC(C)(C)C12COP(=S)(OC1)OC2
Properties
Chemical formula	C₈H₁₅O₃PS
Molar mass	222.24 g·mol⁻¹
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Extremely toxic
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	53 μg/kg (mice)^[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

TBPS (tert-butylbicyclophosphorothionate) is a bicyclic phosphate convulsant.^[3] It is an extremely potent GABA receptor antagonist.^[4]^[5]

References

^ "tert-Butyl bicyclo[2.2.2]phosphorothionate".
^ 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. doi:10.1016/0041-008x(79)90323-5. PMID 452023.
^ Trifiletti, Rosario R; Snowman, Adele M; Snyder, Solomon H (1984). "Solubilization and anionic regulation of cerebral sedative and convulsant receptors labeled with [³⁵S] tert-butylbicyclophosphorothionate (TBPS)". Biochemical and Biophysical Research Communications. 120 (2): 692–9. doi:10.1016/0006-291x(84)91311-1. PMID 6329179.
^ Atack, J R; Ohashi, Y; McKernan, R M (2009). "Characterization of [35S]t-butylbicyclophosphorothionate ([35S]TBPS) binding to GABAA receptors in postmortem human brain". British Journal of Pharmacology. 150 (8): 1066–74. doi:10.1038/sj.bjp.0707186. PMC 2013908. PMID 17339834.
^ Im, Wha Bin; Pregenzer, Jeffrey F; Thomsen, Darrel R (1994). "Effects of GABA and various allosteric ligands on TBPS binding to cloned rat GABAA receptor subtypes". British Journal of Pharmacology. 112 (4): 1025–30. doi:10.1111/j.1476-5381.1994.tb13185.x. PMC 1910256. PMID 7952860.

See also: Receptor/signaling modulators; GABA_A receptor positive modulators; GABA metabolism/transport modulators

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

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

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