Phenylsilatrane

Phenylsilatrane is a convulsant chemical which has been used as a rodenticide.[1][2] Phenylsilatrane and some of its analogs with 4-substituents of H, CH3, Cl, Br, and CSi(CH3)3 are highly toxic to mice. They have been observed in the laboratory to inhibit the 35S-tert-butylbicyclophosphorothionate (TBPS) binding site (GABA-gated chloride channel) of mouse brain membranes.[3]

Phenylsilatrane
Names
Preferred IUPAC name
(TBPY-5-23)-8-Phenyltetrahydro-4H-4λ5-8,4-(epoxyethano)[1,3,2]oxazasilolo[3,2-b][1,3,2]oxazasilol-4-ylium-8-uide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.016.603
PubChem CID
UNII
InChI
  • InChI=1S/C12H17NO3Si/c1-2-4-12(5-3-1)17-13(6-9-14-17,7-10-15-17)8-11-16-17/h1-5H,6-11H2
    Key: LDOWJVBCZRHOKX-UHFFFAOYSA-N
SMILES
  • C1C[N+]23CCO[Si-]2(O1)(OCC3)C1=CC=CC=C1
Properties
Chemical formula
 C12H17NO3Si
Molar mass 251.357 g·mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. Voronkov MG (1966). "Silatranes: Intra-Complex Heterocyclic Compounds of Pentacoordinated Silicon" (pdf). Pure and Applied Chemistry. 13 (1–2): 35–60. doi:10.1351/pac196613010035.
  2. Lukevics E, Ignatovich L, Khokhlova L, Belyakov S (1997). "Synthesis, Structure, and Toxicity of Arylgermatranes". Chemistry of Heterocyclic Compounds. 33 (2): 239–241. doi:10.1007/BF02256767.
  3. Horsham MA, Palmer CJ, Cole LM, Casida JE (1990). "4-Alkynylphenylsilatranes: Insecticidal Activity, Mammalian Toxicity, and Mode of Action". Journal of Agricultural and Food Chemistry. 38 (8): 1734–1738. doi:10.1021/jf00098a023.


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