Phenylsilatrane

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	2097-19-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	4321483 ;
ECHA InfoCard	100.016.603
PubChem CID	5147995;
UNII	694OD9N65R ;
CompTox Dashboard (EPA)	DTXSID1062176 ;
	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

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]

References[edit]

^ 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.
^ 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.
^ 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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[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.

[1]

[2]

[3]

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

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	2097-19-0^Y
3D model (JSmol)	Interactive image
ChemSpider	4321483^Y
ECHA InfoCard	100.016.603
PubChem CID	5147995
UNII	694OD9N65R^Y
CompTox Dashboard (EPA)	DTXSID1062176
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

Phenylsilatrane

See also[edit]

References[edit]