TBPS

TBPS[1]
Names
Preferred IUPAC name
4-tert-Butyl-2,6,7-trioxa-1λ5-phosphabicyclo[2.2.2]octane-1-thione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
  • 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
  • CC(C)(C)C12COP(=S)(OC1)OC2
Properties
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):
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).

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

  1. ^ "tert-Butyl bicyclo[2.2.2]phosphorothionate".
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.