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TBPS

From Wikipedia, the free encyclopedia
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).
Chemical compound

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

See also

[edit ]

References

[edit ]
  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.
Ionotropic
GABAA Tooltip γ-Aminobutyric acid A receptor
GABAA Tooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABAB Tooltip γ-Aminobutyric acid B receptor
Animal toxins
Bacterial
Cyanotoxins
Plant toxins
Mycotoxins
Pesticides
Nerve agents
Bicyclic phosphates
Cholinergic neurotoxins
Psychoactive drugs
Other
GABA receptor antagonists
GABA synthesis inhibitors
Glycine receptor antagonists
Glutamate receptor agonists
Convulsant barbiturates
Other
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